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PSMA 411 – AREA 2 THREE MAJOR REGIONS OF THE CELL
PHARMACEUTICAL BIOCHEMISTRY I. Nucleus: round and centrally place structure that
controls the various activities of the cell.
BIOCHEMISTRY II. Cell membrane/ plasma membrane: outer covering
― science concerned w/ the chemical basis of life of the cell that encloses the cytoplasm.
― biochemical reaction needs to occur in proper order, III. Cytoplasm: contains different organelles, jelly like
if not in order it may lead to disease. matrix within a cell that contains various organelles.
― chemical constituents of living cells and with the
reactions and processes they undergo. CELL MEMBRANE
― a study of the compounds and processes associated − AKA PLASMA MEMBRANE or PLASMA LEMMA
with living organisms − The outermost structure of the cell that decides its
― “BIOS” – life contour is the cell membrane.
▪ BIOMOLECULES: general term referring to − The control for entry and exit of substances inside
organic compounds which are essential to life. the cell.
→ Nucleic acids ▪ FLUID MOSAIC MODEL – This is most accurate
→ Proteins model today. It is used to describe cell structure
→ Carbohydrates of cell membrane. It indicates that the cell
→ Lipids membrane is not solid but a fluid and has a
flexible and a similar consistency of vegetable oil.
CELL It contains different molecules that embedded or
― Basic unit of life, responsible for carrying out all the present in phospholipid bilayer.
chemical activities, and reactions that are necessary − SEMIPERMEABLE – it only selects or permits certain
to sustain life. molecules to pass thru the cell membrane
― collection of cells → TISSUE
― collection of tissue → ORGAN COMPONENTS OF CELL MEMBRANE
― collection of organs → ORGAN SYSTEM PHOSPHOLIPIDS
― collection of organ system → ORGANISM → Main component of cell membrane
→ It occurs as bilayer
3 MOLECULAR COMPOSITIONS → Hydrophilic head (polar/ water loving) - outside
Water 70-75% » Phosphate
Organic Nucleic Acids = 7-10% » Choline
Molecules Proteins=10-20% » Glycerol
25-30% Carbohydrates = 2-5% → Hydrophobic tail (non-polar)– inside
Lipids = 3% » Fatty acids
Inorganic Trace Elements (ions) GLYCOPROTEIN
Molecules Na, K, Ca, Mg =>1% → Embedded in cell membrane
▪ Proteins: most abundant organic biomolecules inside → Important for cell signaling and attachment
the cell and human body. → Compose of carbohydrate + protein
▪ Carbohydrates: most abundant biomolecule in the GLYCOLIPIDS
environment or in the earth. → Important for cell signaling and attachment
→ Compose of carbohydrate + lipid
PARTS OF THE CELL CHOLESTEROL
→ Controls the fluidity and rigidity of the cell
membrane
→ The amount of cholesterol determines the
consistency of the cell membrane.
↓ fluid consistency = ↑ rigid less fluid consistency
ARACHIDONIC ACID
CYTOPLASM → Polyunsaturated fatty acids composed of: consist of
20 Carbon
→ Exist in ester form (phospholipid bilayer)
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→ Via the action of the enzyme called the » 1 pair is for sex chromosome
phospholipase A2 it is converted into free XX – female
arachidonic acid- important in the synthesis of XY – male
eicosanoids.
→ Eicosanoids: 20 carbon compound which has a CHROMATIN VS CHROMOSOME VS CHROMATIDS
localized effects in the body. (E.g., prostaglandin,
thromboxanes and prostacyclin)

Some specie the outermost layer is composed of cell

wall. Different type of organism is consisting of
different type of component.
▪ CELL WALL: more rigid compare to cell membrane

ORGANISM MEMBRANE/WALL STEROL PRESENT

PLANTS Cellulose Phytosterol → CHROMATIN: untangled form of DNA which it is
Cell wall B-Sitosterol wrapped around a protein which is called (histone
Peptidoglycan protein)
BACTERIA
(protein+ → CHROMOSOME: form of DNA during cell division,
Cell wall oligosaccharide) the chromatin will condense to form a dense rod-like
FUNGI Ergosterol structure
Chitin (Target of
→ CHROMATID: ½ of a chromosome
Cell wall antifungal agent)

NUCLEUS CHROMOSOMAL DISORDERS

− “CONTROL center of the cell” ANEUPLOIDY: Any abnormality in the number of
chromosomes of an individual. This usually happens in
− It contains genetic information, and the blueprint of
chromosomal mutation when entering cell division of the
life which is DNA.
cell or error in cell division.
» DNA → contains the instruction needed to grow
▪ TRISOMY 21/ DOWN SYNDROME:
develop and survive
» There are triplicate copies of chromosome 21.
− Information center of the eukaryotic cell.
» There is distinct physical features or facial
− Only present in eukaryotic cells
features, impaired cognitive ability, and
» Prokaryotic cell: nucleoid (w/o NM)
infertility
− It is mainly concentrated in the form of ▪ TRISOMY X/ XXX SYNDROME:
CHROMOSOMES – carry hereditary information, » Usually occurs in females.
coiled » There is additional X-chromosome, and is called
“superfemale syndrome”.
COMPONENTS OF NUCLEUS » Causes impaired cognitive development, distinct
NUCLEAR MEMBRANE physical features, infertility and shorter lifespan
→ refers to the outermost layer of the nucleus compared to normal individual.
→ barrier of the nucleus ▪ KLINEFELTER SYNDROME:
→ consist of double phospholipid membrane and » Usually occurs in male individuals, they will
phospholipid bilayer have triple sex chromosome.
→ It contains nuclear pores, to allow the passage of » XXY, there will be addition X chromosome
large molecules. » It is biologically male with female secondary
NUCLEOLUS characteristics such as enlargement of breast,
→ Site of ribosome assembly gynecomastia, widening hips, and less body hair.
→ where the enzymes synthesis in DNA na RNA » They will have cognitive impairment and
→ aka NUCLEAR MATRIX infertility.
CHROMOSOMES
→ Threadlike cellular structures where it contains ORGANELLES
hereditary information or genetic information. − a specialized subunit within a cell that has a specific
→ HUMANS: 23 pairs of chromosomes (46 in total) function
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− They are suspended in the cytoplasm → Responsible for oxidation or metabolism of fatty
❖ CYTOPLASM: located between cell membrane acids
and nucleus.
❖ PROTOPLASM: cytoplasm + nucleus ZELLWEGER SPECTRUM DISORDER
❖ CYTOSOL: liquid where organelles suspend in ▪ ZELLWEGER’S SYNDROME
cytoplasm » Absence or reduction of number of functional
peroxisomes.
COMPONENTS OF ORGANELLES » Low amount of peroxisomes.
MITOCHONDRIA » There will be build up of ROS and fatty acids that
→ It has an inner and outer membrane which consists can damage brain, liver, and kidney.
of proteins and phospholipids. An organelle with a » Also known as cerebrohepatorenal syndrome.
double membrane. » Adrenoleukodystrophy damage the white matter
→ “Powerhouse of the cell” of the brain and impairs the adrenal glands
→ It contains energy metabolizing enzymes » Children may show delayed development but not
→ Where ATP is produced have vision and hearing problems until adulthood
▪ CARDIOLIPIN: molecule present in mitochondria » Most severe form
which is a unique phospholipid which is localized ▪ NEONATAL ADRENOLEUKODYSTROPHY
and synthesize in inner mitochondrial membrane » Medium severity
that plays a role in different metabolic reaction ▪ INFANTILE REFSUM DISEASE
that occur inside the mitochondria. » Least severe form
▪ ATP – energy currency of the cell
▪ CRISTAE – “folds in the inner membrane” of CHARACTERISTIC OF ZELLWEGER SYNDROME
mitochondria, which increase the surface area of 1. Hypothermia
mitochondria, if there is increase surface area 2. Seizures
there will be also increase ATP generation. 3. Hearing loss
LYSOSOMES 4. Vision loss
→ called as ‘SUICIDAL BAGS’ of the cell 5. Distinctive Facial Features
→ sacs that contain digestive enzymes, they digest
worn out or non-usable cell structures
ENDOPLASMIC RETICULUM
→ lysosomal enzymes digest the molecules brought
→ Fluid-filled cisterns
into the cell by phagocytosis. (Cell Eating)
→ If it undergoes homogenization, it forms
→ Also known as “DEMOLITION SITES” and
MICROSOMES, where we can locate oxidative
“SCAVENGER OF THE CELL”
enzymes in SMOOTH MICROSOMES
PEROXISOMES
▪ Rough E.R.
→ Are also small vesicles surrounded by a membrane. » Attached ribosomes
→ They are also called as MICROBODIES. » are involved in Protein synthesis
→ They contain enzymes for H2O2 (hydrogen » Ribosomes are present
peroxide) metabolism. ▪ Smooth E.R.
→ Contains oxidase enzymes » Responsible for Lipids synthesis, lipid
▪ OXIDASE ENZYMES: important enzymes that is metabolism and detoxification.
responsible for different from oxidation » Ribosomes are NOT present
reactions that occurs inside the cell. GOLGI APPARATUS
→ Useful in cellular detoxification because uses O2 to → Stack of flatted sacks, “packagers of the cell”
detoxify harmful substance such as ROS (Reactive → Their primary action is to modify and package
Oxygen Species). They convert ROS into the less protein. The attachment of carbohydrate molecule
toxic hydrogen peroxide. or formation of glycoprotein.
▪ If hydrogen peroxide is accumulated in the cell, → are well developed in cells, which are involved in
it can cause toxic effect in our cellular structures SECRETION
→ Contains catalase → Involved in glycosylation and sulfation of proteins
▪ Catalase can convert H2O2 to H2O+O2 (non-
toxic)
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RIBOSOMES NUCLEIC
BIOMOLECULE PROTEIN CARBOHYDRATE LIPID
ACIDS
→ Very small macromolecular complexes composed of Nucleotides
BUILDING Amino Fatty Pentose Sugar
rRNA and proteins responsible in protein synthesis BLOCKS acids
Monosaccharide
acids Nitrogenous base
(translation) on mRNA templates. Phosphate

→ There function is to translate information encoded

Peptide Ester
Glycosidic
BONDS Phosphodiester
mRNA into polypeptide chains of amino acid which Amide
Ether bond
Phosphodieste
bond r bond
make up the proteins. Triglyceride
→ Example of nucleoprotein. Starch,
Glycogen Glycerol +fatty
▪ NUCLEOPROTEIN: composed of Protein+ Nucleic EXAMPLE
Pepsin,
hemoglo
acids DNA,
RNA
Acids (ribosomal RNA) bin
Waxes
Alcohol+ fatty
acids
CHARACTERISTIC ANIMAL CELL PLANT CELL
Round Rectangular
SHAPE CARBOHYDRATES
(irregular) (Cell wall)
― They are considered to be polyhydroxyketones or
CELL WALL Absent polyhydorxyaldehydes
Cellulose: primary Present
(Cell membrane) ― Their simple building blocks is called
component
PLASTIDS monosaccharide.
Present ― Primary source of energy
Manufacture and None
(chloroplast)
storage of food ― Polyhydroxy compounds with aldehyde, ketone or
1 or more 1 an alcohol.
VACUOLE (Vesicle or sac ― General Formula: (CH2O) n= hydrates of carbon
(Single large
Primary use for responsible for
vacuole for storage ― Most abundant organic molecule in nature
storage storage of waste
of water) ― Source of Energy:
and nutrients)
▪ 1g Lipids: 9kcal
CELLS ▪ 1g Carbo: 4kcal
PROKARYOTE EUKARYOTE ▪ 1g Alcohol: 7kcal
NO true nucleus TRUE nucleus
Mitochondria, FUNCTIONS OF CARBOHYDRATES
NO membrane bound STORAGE FORM OF FUEL
Lysosomes, ER, Golgi
organelles ― primary source of energy
apparatus
30 + 50s = 70s
Targets of antimicrobials which
also important in protein
40s + 60s = 80s
synthesis of bacteria.
Buys AT 30s
CELS at 50s
Bacteria, archaea ▪ Starch – storage form of energy in plants
Archaea: Live in extreme Plants, Animals, Fungi ▪ Glycogen – storage form of energy in animals, it can
conditions be converted to glucose (reversible)

POP QUIZ!
Example: We have been starve for a long period of time
What is the large ribosomal subunit of Candida albicans?
there is low blood glucose level there will be no energy
ANSWER: 60s (fungi)
receive by our cells and tissues. The glycogen stored in
our liver it will undergo glycogenolysis , the glycogen
BIOMOLECULES
will be metabolize into glucose. This will increase the
CARBOHYDRATES
blood glucose level there will be energy for our cells and
LIPIDS tissues.
VITAMINS ENZYMES
NUCLEIC ACIDS
PROTEINS STRUCTURAL ELEMENTS
− PROTEOGLYCAN - Complex molecule, more
carbohydrate compares to protein component. It is
consisting of protein and carbohydrate. Important
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structural component of tissues such as cartilage and ▪ It blocks the enzymes that
tendons. breaks down cartilage
− GLYCOPROTEIN - consist of protein and Dermatan sulfate: It is
carbohydrates. It is predominantly more protein consisting of L-iduronic acid + N
-acetyl-D- galactosamine. It is
than carbohydrate component responsible in wound repair,
and blood coagulation.
Heparan sulfate: It is composed
of D-glucuronic acid + D-
glucosamine. It plays important
role in blood coagulation,
involve in inflammatory
response and cell
differentiation.
Heparin: It is an anticoagulant
▪ PROTEOGLYCAN composed of L-iduronic acid+
― Molecule containing heteropolysaccharide + D-glucosamine. It is used in the
peptide (core protein). treatment of clots and
» Heteropolysaccharide thrombosis.
→ Molecules composed of several or many Hyaluronic acid: It is composed
monosaccharides. It contains more than of glucuronic acid+ N-acetyl-
one type of monosaccharide in its structure glucosamine. It used as skeletal
joint lubricant; it does not
→ It is in form of GAGS (glycosaminoglycans) contain sulfate. It retains
or also known as mucopolysaccharide water in order to keep tissues
well lubricated and moist.
Keratan sulfate: It is composed
of repeating unit of D-galactose
+ N-acetylglucosamine 6
sulfate. It is found in cartilage
and cornea. The only
glycosaminoglycan that does
not contain a sugar acid.

▪ GLYCOSAMINOGLYCANS OTHER FUNCTIONS OF CARBOHYDRATES

― Composed of repeating disaccharide units 1. LUBRICANT OF SKELETAL JOINTS
» Consist of 1 SUGAR ACID and 1 AMINO SUGAR ― e.g., Chondroitin Sulfate and Hyaluronic Acid
» The two-sugar acid present in in them is they are both used in the treatment of arthritis.
Glucuronic acid and Iduronic acid. 2. MAJOR COMPONENT OF BACTERIAL CELL WALLS
» The two amino sugar presents in them is N- AND SOFT CELL COATS IN ANIMAL TISSUES
acetyl glucosamine and N -acetyl ― bacterial cell is composed of complex molecules

galactosamine. called peptidoglycan.

― Chitin

EXAMPLE OF GLYCOSAMINOGLYCANS PRESENT IN OUR 3. PROVIDE ADHESION BETWEEN CELLS

BODY − E.g., Hormonal activation of cells, immune
Chondroitin sulfate: consist of system mediation through cytokines
repeating unit of D- glucuronic − Glycoconjugates: class of carbohydrates that
acid + N -acetyl-D- provides adhesion between cells
galactosamine.
▪ acts as skeletal joint
4. TRANSPORT FUNCTIONS
lubricant, use to prevent and − Biochemical Transport)
treat arthritis. It keeps − E.g., Transferrin for Fe transport, Ceruloplasmin
cartilage healthy by for Cu Transport
absorbing fluid particularly
water into the connective
− TRANSFERRIN: glycoprotein, responsible for the
tissue. transport of iron.
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− CERULOPLASMIN: glycoprotein, responsible for BIOSYNTHESIS
transport of the copper ions.
5. CONFER BIOLOGIC SPECIFICITY ON ANIMAL CELL
SURFACE
― They can establish identity base on specific cell
― Different blood type can be distinguished base
on the certain carbohydrate molecules that are
present in the surface of the red blood cells.

DIFFERENT BLOOD TYPES BASED ON SUGAR

MOIETIES PRESENT/ABSENT.

O-Antigen: glycolipids or sphingolipids

GLUCONEOGENESIS
» Ceramide + Sugar (oligosaccharide)
» Ceramide contains sphingosine (18 C-amino alcohol) and fatty − Formation of glucose from nonhexose precursors.
acids − It is a chemical reaction which converts pyruvate into
» Oligosaccharide present are glucose, galactose, N-acetyl- glucose
galactosamine, and galactose- fructose
− Important precursors in order to form glucose. The
following are the starting materials.
▪ Lactate
▪ Pyruvate
A-Antigen: glycolipids or sphingolipids ▪ Glycerol
» Oligosaccharide presents contains the glucose, galactose, N-
acetyl-galactosamine, galactose-fructose and additional N-
▪ Amino Acids: starting materials
acetyl-galactosamine sugar unit − GLYCOLYSIS: this is the inverse of gluconeogenesis
glucose is being broken down to pyruvate

B-Antigen: glycolipids or sphingolipids

» Oligosaccharide present are glucose, galactose, N-acetyl-
galactosamine, galactose-fructose and additional galactose
sugar unit

6. SUPPLY PRECURSORS FOR SYNTHESIS OF VITAL

BIOLOGIC SUBSTANCES
− Enzymes – glycoprotein (E.g., pepsin, pancreatic
ribonuclease, deoxyribonuclease)
− Hormones – FSH (Follicle Stimulating Hormone),
TSH (Thyroid Stimulating Hormone)
CARBOHYDRATES (CH2O) n
− Precursors of DNA, RNA and ascorbic acid
▪ Aldehyde alcohol – ALDOSES
▪ DNA (deoxyribose) and RNA (ribose):
▪ Ketone alcohol – KETOSES
contains the pentose sugar.
▪ Ascorbic acid is synthesized from hexoses
from fructose or glucose. IS IT AN ALDOSE OR KETOSE?

Answer: Aldose Answer: Ketose

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5 Pentose Ribose, xylulose
Gluc, Fruc, Mann,
6 Hexose Psicose, Sorbose,
Tagatose
7 Heptose Sedoheptulose
9 Nonose Neuraminic acid
▪ Simplest ALDOSE: GLYCERALDEHYDE
▪ Simplest KETOSE: DIHYDROCYACETONE (keto triose)
Answer: Aldose Answer: Ketose
/ulose: this indicates a FUNCTIONAL GROUP PRESENT (ALDOSE/KETOSE)
ketose sugar → ALDOSE for “aldo”
▪ ALDOSE: The carbonyl is located in C1. → KETOSE for “keto”
→ Glucose → Most natural sugars exist as D-ISOMER
▪ KETOSE: Carbonyl group is position at any carbon ▪ Penultimate carbon: 2nd to the last carbon, the
except C1 position of the OH group
→ Fructose ▪ OH GROUP – right → D-sugar
▪ OH GROUP-left → L-sugar
CLASSIFICATION OF CARBOHYDRATES
ACCORDING TO STRUCTURE
MONOSACCHARIDE
(Simplest unit) CRYSTALLINE
DISACCHARIDE (sweet)
(2 monosaccharide units)
OLIGOSACCHARIDE
(2-10 monosaccharides units)
POLYSACCHARIDE FIBROUS
(No taste)
(More than 10, numerous
monosaccharide units)
▪ Glycosidic bond - bond present in a monosaccharide in
order to form disaccharide, oligosaccharide or
polysaccharide

A. MONOSACCHARIDE
− The simplest unit of carbohydrate because they can
no longer be hydrolyzed further. RING STRUCTURE FORMED
− The simplest sugar; building block of carbohydrates → Monosaccharides containing 4 or more carbon
− Contains 3-10 carbon atoms, can contain single atoms tend to have cyclic structures.
polyhydroxy aldehyde and single polyhydroxy
ketones.

CAN BE CLASSIFIED ACCORDING TO:

NUMBER OF CARBON ATOMS
→ Glucose = Aldohexose (aldehyde + 6C)
→ Fructose = Ketohexose (ketone+ 6C) ▪ FURANOSE: the ring structure resembles to furan, it
→ Aldopentose = (Aldehyde + 5C) contains five atom rings it contains, 4 carbon atoms
→ Ketotetrose = (Ketone + 4C) and one oxygen rings. (pentoses)
» E.g.: Ribose
# of Carbon Category name Examples ▪ PYRANOSE: six atom rings composed of five carbons
Glyceraldehyde and one oxygen atoms. (hexoses)
3 Triose
Dihydroxyacetone » E.g.: Glucose
4 Tetrose Erythrose
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The ring structure form by the interaction of which is hydrolyzed and produces equal
penultimate OH group (2nd to the last OH group). If it amounts of glucose and fructose.
reacts with the carbonyl group of the monosaccharide it OTHER NAMES OF FRUCTOSE:
will now form ring structure. » Levulose (levorotatory/ left / counterclockwise)
» Fruit Sugar
MONOSACCHARIDE EXAMPLES:
A. GLUCOSE D. GALACTOSE
→ ALDOHEXOSE → ALDOHEXOSE
→ Primary carbohydrate we utilized in order to → C4 epimer of glucose
produce energy. Because our body contains a lot of → Gal → Glu (Glucose -1- phosphate) →Glycogen
metabolizing enzymes that could break down ▪ GALT: galactose-1-phosphate uridyltransferase.
glucose into different energy producing molecules. It is the responsible enzyme from converting
→ When there is high amount of glucose in the blood it galactose into glucose-1-phosphate.
is called hyperglycemia. → GALACTOSEMIA
→ GLYCOGENESIS: if the glucose in the blood undergo ▪ A condition in which a person is unable to
to this it will form glycogen it will be stored in our metabolize galactose into glucose.
liver and muscles as a form of energy in our body. ▪ There is accumulation of galactose in the blood
→ TWO HORMONES CONTROLLING IT: and other parts of the body most especially in
▪ Insulin: it decreases blood glucose levels, by the BRAIN and EYE.
increasing the uptake of glucose by the different » BRAIN: neuronal damage, brain damage
cells and tissues in the body. » EYE: cataract that may lead to blindness.
▪ Glucagon: it increases blood glucose levels ▪ If a person is deficient in GALT enzyme
OTHER NAMES OF GLUCOSE: → CHEMICAL TEST:
» Blood sugar – naturally found in blood ▪ Mucic acid Test → (+) crystal formation/ppt
 NORMAL SUGAR: >99 mg/dL at a fasting state lactose
 PREDIABETIC SUGAR: 100-126 mg/dL » It is also known as galactaric acid test.
 DIABETIC SUGAR: >126 mg/dL Because the product of this reaction will be
» Physiologic sugar galactaric acid or mucic acid.
» Grape sugar » Sugars that result positive into this test
» Dextrose includes: galactose, disaccharides with
» Corn sugar galactose and disaccharides lactose.
» D-glucopyranose OTHER NAMES OF GALACTOSE:
» Brain Sugar (Galactocerebroside): a glycolipid which
B. XYLOSE contains a galactose sugar. It acts as an important
→ ALDOPENTOSE component of myeline sheath.
→ Obtain by boiling the Corn cob + diluted acid → Myelin sheath: a protective covering of neurons
→ Diagnostic agent for intestinal absorption that ensure rapid transmission of nerve impulses.
malabsorption
OTHER NAMES OF XYLOSE: Wood sugar SYMPTOMS AND MANIFESTATION OF GALACTOSEMIA
❖ Rapidly absorbed in the small intestine
C. FRUCTOSE ✓ Brain damage
→ KETOHEXOSE ✓ Cataracts→ lead to blindness
→ Sweetest Sugar ✓ Jaundice
→ CHEMICAL TEST: ✓ Enlarged liver
▪ Seliwanoff’s Test → (+) Cherry Red Complex/ ✓ Kidney damage
Precipitate ✓ If a galactosemic infant is given milk,
» It distinguishes between aldose and ketose unmetabolized milk sugars build up and damage
sugar. It will give positive result to ketoses. the liver, eyes, kidneys and brain.
→ Sources of Fructose: → Soy based milk: alternative milk for infants
▪ Sucrose (hydrolysis) → glucose + fructose with galactosemia.
▪ Invert sugar → a mixture of equal amounts of
glucose and fructose. A sucrose boiled with acid
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I. Ribose: pentose sugar present in RNA.

II. Deoxyribose: pentose sugar present in DNA.
E. MANNOSE o it lacks oxygen in C2
→ ALDOHEXOSE
→ C2 epimer of glucose REDUCING PROPERTY
→ USES: ❖ 3 aldehyde and 3 ketone functional group
▪ Prevents UTI ❖ REDUCING PROPERTY: It is present in all types of
▪ Mannitol → Osmotic diuretic (IV) monosaccharide
» A product of reduction of mannose ❖ REDUCING OR NON-REDUCING SUGAR: property for
» IV Mannitol (OSMOTIC DIURETIC) is given to disaccharide.
 Example of reducing disaccharide is;
patient when there is an increase
intracranial pressure and intraocular A. Maltose
pressure. This is mainly cause of fluid B. Lactose
 Example of non-reducing disaccharide is;
overload in our head or eyes.
» Oral Mannitol (LAXATIVE) A. Sucrose
❖ NON-REDUCING SUGAR : is considered in all
→ CHEMICAL TEST:
polysaccharide
▪ Ozasone Test → (+) NEEDLE shaped crystal or
Broomstick
» It produces crystals called Ozasone. TEST REAGENT RESULT
Fehling’s Test Fehling’s A –
» Main reagent of this test is phenyl (1) Copper Sulfate
hydrazine  Oxidizing agent
Reducing sugar+
» Monosaccharide → phenyl hydrazine → CuSO4 → Cu20 Fehling’s B –
forms Ozasone Crystals (Cupric Oxide) (1) Rochelle’s Salt
 It prevents the (+) BRICK RED
» A test specifically used for mannose,
because it is the only one that produces (VD GEROA) precipitation of PPT
copper as copper
insoluble Ozasone with phenyl hydrazine. It hydroxide or
cupric hydroxide
produces precipitate. Cu(OH)2.
» The Ozasone have specific shape when
observe in microscope. (2) NaOH
 make sugar more
sensitive to the
The following are the shape of the Ozasone of some oxidizing agent
sugars.
Benedict’s Test (1) CuSO4
▪ Needle shaped Crystal → MANNOSE  reacts with sodium
▪ Sunflower shaped → MALTOSE Cupric→cuprous ion
citrate to form
▪ Powder puff shaped or hedgehog shape → LACTOSE copper citrate (+) BRICK RED
(2) Na2CO3
▪ Rhombic like → GALACTOSE A traditional test of PPT
 alkalinizing agent
glucose in the urine
(3) Sodium Citrate
(urinalysis).
 reacts with CuSO4 Represents the reduce
F. RIBOSE to form copper copper ions in the
It is more
→ ALDOPENTOSE advantageous
citrate form of cuprous oxide.
→ Component of nucleotides compare to Fehling’s
(4) Copper Citrate
 main oxidizing
▪ Nucleotides: building block of nucleic acids. Test. It is because the
agent
stability of the
Sugar present in RNA and DNA. reagent.
→ Important sugar for genetics formation (1)Silver nitrate
Tollen’s Test
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 AgNO3+NH3→ OXIDATION OF SUGARS
Also known as Silver- Diamine Silver (I) ❖ Aldonic acids –
Mirror Test. It is a oxide (main
qualitative laboratory oxidizing agent aldehyde→ COOH
test used to that would react (+) SILVER
distinguish between on the reducing
MIRROR
aldehydes and ketone. sugar)

Aldehydes is easily Ag+1→ Ag0 (reduced Represents the

oxidized to form valence means aldehyde
carboxylic acids by the reduction reaction)
used of silver ion. ❖ Uronic acids - primary
alcohol is being
oxidized
Trommer’s Test

It involves treating the Alkaline solutions of

sample of simple acid copper sulphate +
such as sulfuric acid. strong acid
❖ Saccharic acids - both
Hydrolyzed
(+) RED aldehyde and 1°
oligosaccharide into
monosaccharide
alcohol
units. That reacts to
copper sulfate to
produce the reduced
copper.

More sensitive to
disaccharide (much)
and oligosaccharide.
Addition of sulfuric B. DISACCHARIDE
acid will hydrolyzed ― Form from glycosidic bond (ether bond)
disaccharide into A) SUCROSE
monosaccharide unit.
Alkaline solution of ▪ Non reducing sugar
Nylander’s Test
bismuth subnitrate ▪ GLU+ FRU
(+3)
▪ C6H12O6 + C6H12O6 → C12H22O11
(1) Rochelle’s Salt ▪ Demulcent: forms soothing protective film over
(+) BLACK
(2) KOH a mucus membrane relieving minor pain and
(3) Bismuth subnitrate
 Main oxidizing
inflammation
agent ▪ Contained in Simple syrup NF → 85% w/v in
 Bi3→Bi0 (black concentration
ppt)
(4) KOH Other name of Sucrose: Table sugar
Sources of Sucrose:
Barfoed’s Test (1) Cupric acetate in o Saccharum officinarum (sugar cane)
Acetic Acid +H2O→
Cu(OH)2 (when heat it o Beta wilgaris (sugar beet)
Differentiating test will form copper oxide o Acer saccharum (sugar maple)
for monosaccharide CuO)
and disaccharide (+) RED
 Copper oxide :
main oxidizing B) MALTOSE
It only produces
positive result for (+)
agent in the ▪ Reducing sugar
reaction.
monosaccharide.  When reducing
▪ GLU+ GLU (alpha -1-4- glycosidic bond)
sugar is added: ▪ Product of partial hydrolysis of starch
CuO→Cu2O (Brick Other name of Maltose:
red ppt)
o Malt sugar
o Beer sugar
Formation of maltose from 2 Glucose units
 PHARMACEUTICAL BIOCHEMISTRY 11
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 TREATMENT: Via the action of bacteria
the lactulose will be converted into acetic
and lactic acids making the colon acidic.
This will increase the elimination of basic
ammonia.
▪ Poorly absorbed and has laxative effect
▪ Brands: Lilac®, Dupholac®, Movelax®

C. OLIGOSACCHARIDE

SUGAR SUGAR UNITS

In order to form a disaccharide there will be form of dehydration RAFFINOSE Gal + Glu + Fru
reaction between two saccharide units between the glycosidic Sources:
bond . The formation of water will form a by product water and it ▪ Beans
▪ Cabbage
will form a linkage (ether bond) in a two glucose unit which is an
▪ Brussels
oxygen atom.
MALTOTRIOSE Glu + Glu + Glu
Alpha-1,4-glycosisdic bond:
o Alpha: represents the orientation of the oxygen in 1st glucose unit SUCRALOSE Glu + Fru + Gal
→ DOWNWARD ▪ Zero calorie or non nutritive
artificial sweetener
▪ 600x sweeter than sugar for
diabetic patient
C) TREHALOSE ▪ Brand name: Splenda°
▪ Non reducing sugar GENTIANOSE Glu + Glu + Fru
▪ GLU+ GLU (alpha-1-1-glycosidic bond) ▪ Plant metabolite
▪ Obtain from seaweed, yeast and ergot. ▪ Produce by gentian plant
▪ Hydrolyzable sugar like
substance with slightly sweet
D) LACTOSE taste
▪ Reducing sugar
▪ GLU+ GAL D. POLYSACCHARIDE
▪ Metabolized by the enzyme lactase. HOMOGLYCANS HETEROGLYCAN
 Low lactase will have lactose intolerance. (homopolysaccharide) (heteropolysaccharide)
 Lactase converts lactose into it 1 component 2 or more component
monosaccharide units (glucose + galactose).If Glucosan (glucose) o Gums
there is low lactase the lactose will stay in o Starch o Mucilage
colon. This will now cause GI distress, o Glycogen
diarrhea, and flatulence. o Dextran
▪ Metabolized by lactic acid bacteria to produce o Cellulose
methane, CO2, and fatty acids. Inulin (fructose)
Other name of Lactose: Milk sugar o Fructusan

E. LACTULOSE A) STARCH
▪ alkaline rearrangement of lactose → important inactive pharmaceutical ingredient
▪ FRU + GAL used as diluent, binder and disintegrant.
▪ It is freely absorb, it will directly go in large AMYLOSE AMYLOPECTIN
intestine. o linear o Branching (every 25 units)
o composed of 250 to 300 D- o consists of 1000 or more
▪ Bacteria in the colon metabolize the disaccharide
glucopyranose units glucose units
to acetic and lactic acids . It will create acidic o linked by α -1, 4 glucosidic o α-1,4 linkages, α -1,6
environment in the colon that is used in Hepatic bonds (branch)
encephalopathy. o more soluble in water than o Less water soluble of the
 Hepatic Encephalopathy : a condition of amylopectin starch
o Amylose + iodine = deep o amylopectin + iodine = blue-
raise in ammonia and waste toxins in the blue complex violet or purple color
brain because of liver damage. o Constitute 20% of starch o Constitute 80% of starch
 PHARMACEUTICAL BIOCHEMISTRY 12
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ENZYMES INVOLVE IN METABOLISM OF STARCH ― Diagnostic agent for kidney function. It can be
❖ Alpha -amylase (α -1,4-glucan 4- glucanohydrolase) used in order to measure the GFR of a patient
― an enzyme present in pancreatic juice and ― The fructose unit is being connected by
saliva, hydrolyzes starch by a random splitting beta-1, 2 glycosidic bonds
of α -1,4- glycosidic linkages ― Cannot be digest by the body
 amylopsin- alpha amylase found in
pancreatic juice E) CHITIN
 ptyalin- alpha amylase found in saliva ― Homopolymer of N-acetyl-B-D-glucosamine
― END-PRODUCT: glucose, maltose, amylopectin ― Aminated glucose
― It is present in human, animals, plants and ― Major components of exoskeleton of arthropods
microbes such as crabs and shrimps etc.
❖ ß- Amylase (α- 1,4-glucan maltohydrolase) ― Important cell wall in fungi
― Produces its effect by removing maltose units ― USES IN ANIMALS:
from the nonreducing ends of polysaccharide 1. Acts as a protective barrier
molecules. ― USES IN INDUSTRY:
― END-PRODUCT: is nearly pure maltose. 1. Fertilizer
― Only present in microorganism and plants 2. Food additive as flavorant
― An enzyme involves in fruit ripening 3. Emulsifying agent
4. Help to lower cholesterol level by
Why it is sweeter when the fruit ripens? decreasing cholesterol absorption.
✓ This is because of catalytic action of beta-amylase in fruit . The beta-
amylase in plants converts starch in maltose . Maltose is sweeter compare
to starch. F) DEXTRAN
― sucrose [transglucosylase enzyme system
B) GLYCOGEN (dextran sucrase)] → dextran
― major stored carbohydrate for animals ❖ Leuconostoc mesenteroides
― the glucose unit present in the linear part/long  lactic acid bacteria that can convert sucrose
chain of glycogen are being connected together to dextran
by alpha 1,4 in every 8-10 units there is branching  Able to secrete dextran sucrase the enzyme
of glucose units connected by alpha 1,6 glycosidic capable of converting sucrose to dextran.
bonds. ❖ Streptococcus mutans
― stored in muscles and liver: high energy  A bacteria cause dental plaque.
requirement in muscles  Able to secrete dextran sucrase the enzyme
― used during fasting capable of converting sucrose to dextran.
― GLYCOLYSIS: glycogen → glucose ― Dextran
 compose of glucose units (alpha 1,6
C) CELLULOSE glycosidic bonds)
― β 1, 4 glycosidic bond  10% solution = adjunct in the treatment of
― A Glucosan, contains glucose only shock. Used as plasma expander which
― cellobiose: disaccharide unit composed of two increases plasma in the blood, BV and where
glucose units, that are being connected together it is use in hypotension or low blood pressure
by β 1, 4 glycosidic bond (hypovolemic shock).
― most abundant carbohydrate in nature ― Iron Dextran injection (hematinic)
― important component of cell wall in plants.  Sterile solution →Fe (OH) 3 + partially
― we cannot digest cellulose and cellobiose hydrolyzed dextran
because we lack enzymes that are capable of  Used to treat ammonia
breaking their β 1, 4 glycosidic bonds. ― Dextrin:
 a class of low molecular carbohydrates
D) INULIN produce from a partial hydrolysis of starch
― Fructusan  Use as an adhesive, stiffening agent in
― A polysaccharide composed of repeating surgical cast , diluent, binder, and thickening
fructose unit agents in tablets and suspension.
 PHARMACEUTICAL BIOCHEMISTRY 13
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VISUAL PROJECTIONS OF CARBOHYDRATES
❖ There are three ways to present the structures of
carbohydrate:
1. Fischer Projection
2. Haworth Projection
3. Conformational Formulas

A. FISCHER PROJECTION
― Developed by German chemist Emil Fischer in the
1800s, when printing techniques could handle Rules :
only lines (not wedges) (1) anomeric carbon: a carbon with a carbonyl group.
 Alpha-D-glucose: C1 -DOWNWARD
― 2 dimensional representation of a 3D molecule
 Beta-D-glucose: C1-UPWARD
using vertical and horizontal lines. BUDA
― The carbon chain is usually drawn vertically with Beta Up, Down Alpha
a C1 at the top. (2) Placement of OH group: if in the Fischer projection it is in the ;
 OH- right→ DOWNWARD
― A way of writing structures in which the
 OH- left→ UPWARD
stereochemistry of a molecule can still be
determine.
C. CONFORMATIONAL STRUCTURES
❖ “Boat” and “chair” forms
― It includes bond angle for the molecule. The
actual bond angles of the molecule is being
represented.
― Sugars can be “boat” or “chair” forms but they
are different of bond angle in the cyclic structure.
― CHAIR is more stable conformation of sugar than
We can determine the type of isomer base on the structure, we can identify
if it is D-isomer or L-isomer based on the placement of penultimate OH- BOAT.
group or the 2nd to the last carbon in a molecules.
RIGHT →D ISOMER
LEFT →L ISOMER
The ring structure is being represented by a long bond that will connect to
the carbon no. 1 with the penultimate carbon.

 QUESTION: D or L SUGAR?

ISOMERS
o Compounds with the same molecular formula but
with different structures.
o 2 main classes:
― Constitutional Isomers: differ by bonding
arrangement
B. HAWORTH PROJECTION ― Stereoisomers: have same molecular formula,
― The ring structure of the sugars they are bonding arrangement of atoms, but differ in
represented by this. spatial arrangement.
― Developed by the English chemist Walter
Norman Haworth STEREOISOMER
― Represents the 2 dimension and that depicts 3D o Also known as configurational isomers
structure of cyclic form of saccharide. o Compounds wherein the atoms are connected in
the same way, but differ in how it’s arranged in
3 dimensional space.
 PHARMACEUTICAL BIOCHEMISTRY 14
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CHIRAL MOLECULES
o 4 different attachments or one that has four
different groups attached to it. It cannot be
superimposed on its mirror image
o Any substance that has a chiral center possess
handedness.
o Chiral Carbon/ Center: it has four different D-RIBOSE and L-RIBOSE→Enantiomers (mirror)
groups of atoms attached to it. They have an L-RIBOSE and D-ARABINOSE→ Diastereomer (not mirror)
optical activity and can exist as an enantiomer.
❖ Epimer
― Diastereomers that differ ONLY in the
configuration at a single chiral carbon atom

A. ENANTIOMERS
― Stereoisomers that are non-superimposable
images of each other
― Chirality is a property of an enantiomer.
― Van’t hoff rule→ a mathematical formula that ANOMER
determines the number of possible polymer a ― The only carbon in the molecule that is bonded
monosaccharide can have. to two oxygen atoms, usually carbon 1.
 FORMULA: 𝟐𝒏 ― The carbon on which this occurs is therefore
 N= no. of chiral centers called an anomeric carbon.
N= 3
𝟐𝟑 = 𝟖 𝒑𝒐𝒔𝒔𝒊𝒃𝒍𝒆 𝒔𝒕𝒆𝒓𝒆𝒐𝒊𝒔𝒐𝒎𝒆𝒓

D-RIBOSE
N=4 REACTIONS OF MONOSACCHARIDES
𝟐𝟒 = 𝟏𝟔 𝒑𝒐𝒔𝒔𝒊𝒃𝒍𝒆 𝒔𝒕𝒆𝒓𝒆𝒐𝒊𝒔𝒐𝒎𝒆𝒓𝒔
1. Cyanohydrin formation
✓ Also known as the ‘Kiliani Fischer’ synthesis
✓ An organic chemical reaction by an aldehyde or
ketone with a cyanide anion or a nitrile to form
a cyanohydrin.
✓ A reaction used to increase the number of
carbons of a sugar or increases carbon chain
length of sugar.
B. DIASTEREOMER ❖ CYANOHYDRIN: a chemical specie in which there
― differ in some stereocenter but are NOT MIRROR is cyanide group and an OH group is attach to a
image single atom.
― Stereoisomers that are not enantiomers/mirror
images of each other.
 PHARMACEUTICAL BIOCHEMISTRY 15
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 Half as sweet as sucrose
 used as an humectant in toothpaste
 use in mints and chewing gums
 If it undergoes to dehydration reaction → sorbitan
a component of tweens and spans, use as an
emulsifying agents/ surfactants
2. Ruff Degradation ❖ MANNITOL
✓ Removal of 1 carbon atom from molecule of an  Reduction product of mannose
aldose  Obtain in Fraxinus ornus or manna plants
✓ Shortens the carbon chain by 1 carbon  Used as an oral (Laxative) and IV (osmotic diuretic)
✓ Opposite of cyanohydrin formation ❖ GLYCEROL
 Ex. D-glucose(6C) →D-arabinose(5C)  obtain in reaction of glyceraldehyde
3. Lobry de Bruyn Degradation  Use as an humectant
✓ Interconversion or transformation from aldose  when it undergoes nitration→ nitroglycerine (anti-
to ketose or from ketose to aldose, this process angina drug)
will then perform unsaturated alcohol  Synonymous to glycerin
 Aldose →unsaturated alcohol →ketose ❖ GALACTOSE
 Aldose alcohol ketose  Reduction product is GALACTITOL.
4. Osazone reaction → Galactitol: responsible for cataract formation
✓ The carbonyl group of Aldose will be linked to - 7. Phosphorylation
Phenylhydrazine ✓ Addition of phosphate group to the sugar
✓ product of the linkage is crystal called molecule
OSAZONE. ✓ The hydroxyl groups of monosaccharide can
react with inorganic oxyacids (phosphoric
acids) to form inorganic esters.
✓ Enzyme: hexokinase

5. Oxidation reaction
✓ addition of oxygen to a molecule or the removal
of hydrogen from a molecule.
The glucose is converted in glucose-6-phosphate via the
✓ This will produce a sugar acid
enzyme hexokinase.

6. Reduction reactions
8. Glycoside formation
✓ Reduction means the addition of
✓ GLYCOSIDE a general term for monosaccharide
hydrogen to a molecule or the
acetals. When they are in a form of a ring
removal of oxygen from a
structure they are considered to be
molecule.
hemiacetals.
✓ if as sugar is being REDUCED, the
✓ Hemiacetal – the carbon is bonded both the
product will be sugar ALCOHOL
hydroxyl group and ether group.
✓ If ketones is REDUCED it will form a
 If a hemiacetal reacts with an alcohol in the
secondary ALCOHOL.
presence of an acid it will form an acetal.
✓ The resulting product is a polyol or
✓ Acetal- contains two ether functional group,
sugar alcohol (alditol)
when it is a monosaccharide acetal it is a
glycoside.
 Glucose = sorbitol (glucitol) - toothpaste
 Mannose = mannitol (osmotic diuretic)
 Fructose = mannitol or sorbitol
❖ SORBITOL
 obtain in berries from mountain ash
 PHARMACEUTICAL BIOCHEMISTRY 16
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Tauber’s (+) Bright Reddish Purple
Aminoguanidine

Differentiate ketose and aldose

(+) ketose

Reagent: aminoguanidine
Bial’s Orcinol Test (+) Blue Green

Differentiate pentoses from

9. Amino Sugar Formation hexoses. The pentoses reacts
✓ Amino is an amino derivative of with orcinol to have positive
result
monosaccharide OH in C2 is replace by an (+) pentoses -blue green
amino group. (-) hexoses-muddy brown ppt
✓ If one of the hydroxyl groups of a
monosaccharide is replaced with an amino OTHER TESTS:
group, an amino sugar is produced. 1. Seliwanoff’s Test
✓ The amino sugars can be modified in our body Differentiate ketose from aldose.
Ketose : (+) deep red
by n-acetylation reaction which they can be Aldose: faint red
(e.g n-acetyl-glucosamine, n-acetyl-galactosomine and n-
acetyl-mannosamine)
✓ They are important components of proteoglycans and
glycolipids.
(+) deep red

Tollen’s Test
Test for reducing sugar
GENERAL TESTS FOR CARBOHYDRATES
Diamine silver (I) ion
CHEMICAL TEST POSITIVE RESULT reduced into silver
Molisch Test (+) Purple Ring at the (+) aldoses
Junction General test for aldehydes
General test for carbohydrates. It (two layers)
can also be called as alpha- . (+) silver
naphthol reaction/ test.

Reagent: alpha-naphthol Moore’s Test

Anthrone Test (+) green/blue green Test Reducing sugar
Reagent: strong alkali (NaOH), it will
color react in reducing sugar to form free
General test for Carbohydrates , aldehyde. It will polymerized in
it detects the presence of order to form a resin.
hydroxymethylfurfural and Odor: caramel-like odor
methyl furfural .These are (+) Brown
dehydration products of
monosaccharides. It is Keller-Killiani
dehydrated via the action of Detects the presence of deoxy
sulfuric acid. They are react with sugar.
anthrone in order to have the
positive result.
(+) reddish brown layer at
Sulfuric acid: dehydrating agent the junction of two liquids
Tauber’s Benzidine test (+) Cherry Red Fehling’s Test
Test for reducing sugars
Identification test for pentose (+) Cuprous oxide
sugars (ribose, xylose)
(+) brick RED ppt
Reagent: Benzidine in glacial
acetic acid

II. LIPIDS
 PHARMACEUTICAL BIOCHEMISTRY 17
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― Class of a heterogenous group of compounds, which 1. Controls the fluidity or consistency of cell
are more related by their physical than by their membrane
chemical properties.  long and saturated FA in phospholipid
❖ SIMILAR PHYSICAL CHARACTERISTIC bilayer more rigid cell membrane
 Non-polar 2. Synthesis of important biomolecule such as
 Hydrophobic synthesis of phospholipids, cholesterol,
 liposoluble lipoproteins and eicosanoids.
― MAJOR SOURCE OF ENERGY in the body. 3. Protects certain organs . The Omega 3 is an
― Considered to be single type of molecule. example of beneficial fatty acid.
― They are not considered as polymer , because they  Omega 3: protects the liver from
are not made-up of repeating unit. There is no specific accumulating fats
structural unit. SATURATED: BuCaCaCaLaMyPaStAr
UNSATURATED: OLLA
FATTY ACIDS
Saturated Unsaturated
Functions of Lipids (single bond) (double bond)
1. Act as a coenzyme Solid at room temperature Liquid at room temperature
2. Important for homeostasis Butyric (Butter)→ 4C Oleic→ 18C: 1 (C9)
 maintaining stable internal environment Caproic (Goat)→ 6C Linoleic (omega 6)→ 18C:2 (C0, C12)
suitable for sustaining life. Caprylic (Goat)→ 8C Linolenic→ 18C: 3 (C9,C12,C15)
3. Temporary source of energy, when there is low Capric (Goat)→ 10C Arachidonic → 20C:4
Lauric → 12C (C5,C8,C11,C14)
carbohydrate intake. Myristic → 14C  Eicosatetraenoic acid
 1 g of fat/lipid→ 9kcal of energy Palmitic → 16C  Precursor or eicosanoids
4. Serves as an thermal insulator Stearic → 18C (leukotrienes, prostaglandins,
thromboxane)
 Helps us trap heat in the body since fat Arachidic → 20C
Lignoceric → 24C
are not good conductor of heat. ESSENTIAL UNSATURATED FA
5. Precursors of hormone → steroid hormone o Docosahexaenoic acid (DHA)/
cervonic acid 22: 6
▪ plays an important role in brain
FATTY ACIDS development of infant.
▪ Exists freely in the body in their unesterified form and ▪ Plays an important role in
immunity of infant that secreted in
fatty acyl esters the breast milk
▪ Consists of hydrophobic hydrocarbon chain with a
terminal carboxyl group o Eicosapentaenoic acid (EPA) :
▪ Long chain carboxylic acids. They also usually contain 20:5
▪ An omega 3 fatty acid. Good for the
even number of atoms (16-20C). heart and improves overall
 Made from acetyl coA (2C molecule) cardiovascular health.
▪ Fish oils
▪ They can be saturated of unsaturated

Two Types of Fatty Acid

TYPES OF FATTY ACIDS BONDS
1. Essential FA
Type of Fatty Acids Double bonds Diagram
― Cannot be synthesize by our body and
Saturated 0
we must obtain them from our diet
(E.g. Steric acid)
o Linoleic Acid (omega 6)
Monosaturated 1
o Linolenic Acid (omega 3) (E.g. Oleic acid)
2. Non Essential FA Can exists as Cis+ trans
― Our body is capable of producing them , isomer

we don’t need to get them from our o

diet. Polysaturated
(E.g. Linolenic acids) >1
o Palmitic acid Can exists as Cis+ trans
o Stearic acid isomer
Functions of Fatty Acids CIS-hydrogen atom attach
to carbon double bond
same side
 PHARMACEUTICAL BIOCHEMISTRY 18
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TRANS- hydrogen atom 2. Melting points are influenced by both carbon chain
attach to carbon double
bond on different side and degree of unsaturation
o They have ore linear ⚫ ↑# of carbons = ↑ melting point
structure and ↑IMF ⚫ Saturated fatty acids = ↑ melting point
↑melting point
o Worst type of fats it is ⚫ ↑# of double bond = ↑ degree of unsaturation
not easy to dissolve. = ↓ melting point
⚫ ↑ IMF ↑LDF ↑MP

3. Saturated fatty acids are solid in room temperature

4. Unsaturated fatty acids are liquid in room
TYPES OF FATTY ACIDS CONFIGURATION temperature
Saturated
FATTY ACID SYNTHESIS
Monosaturated

Polysaturated

(done na ‘to, remember na

lang the structure)

Triacylgycerol: also known as

Triglycerol, and Triglyceride.
▪ An ester of glycerol + 2 or BUILDING BLOCK OF FA: acetyl-CoA, an energy
more fatty acids
▪ an important form of generating molecule.
energy and in regulation Where?: It happens in cytosol. The liquid portion of
of temperature.
cytoplasm in which organelles are suspended.
Phospholipid: The most
abundant type of lipid in cell
membrane. They give the METABOLISM
structural integrity of the cell
membrane
Steroids:
▪ Hydrophobic and
insoluble in water.
▪ They don’t resemble the
usual type of lipid. They
have 4 loose rings.
▪ CPP nucleus: defining
structure
▪ CHOLESTEROL: most
common steroid present
in the body.
Glycolipid:
▪ Complex molecule
composed of
carbohydrate and lipids
▪ It plays in establishing
identity of cell.
▪ Play a role in cellular
recognition and cell to cell
communication.

CHARACTERISTIC OF FATTY ACIDS

1. Fatty acids have low water solubility (lipophilic)
⚫ ↑# of carbons = ↓nonpolar↓ water solubility
 PHARMACEUTICAL BIOCHEMISTRY 19
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Triglyceride via the enzyme Lipase it is being converted into ― ↑ length of fatty acids ↑high molecular weight
a glycerol + FA → glucose 3 phosphate which can be ↑ high saponification value
converted into glucose. ― Determines in soap making property of oil ↑
saponification value ↑ suitable for soap making
The fatty acids will undergo oxidation reaction (beta- 3. Iodine Number
oxidation) that will be converted into acetyl CoA KREB ― the number of grams of iodine absorbed, under
CYCLE in order to produce energy (ATP). prescribed conditions, by 100 grams of
The Glucose via glycolysis and further oxidation reaction substance
can also be converted into pyruvate and oxidized by Acetyl ― measure degree of unsaturation. More double
CoA KREB CYCLE to produce energy (ATP). bonds.
― ↑high iodine number ↑degree of unsaturation
BETA OXIDATION HAPPENS WHERE? Organelles that have ― Other physical constants such as melting point,
an oxidizing enzymes such as in peroxisomes and specific gravity, and refractive index also served
mitochondria. as identity, purity and quality tests
❖ Drying oil - suitable in oil painting > 120
e.g linseed oil, cod liver oil
KETONE BODIES ❖ Semi drying oil - between 100-120
 considered to be by products of beta oxidation. e.g cottonseed oil, sesame oil
 It has distinct characteristic of unpleasant smell ❖ Non drying oil - <100
and very volatile. e.g olive oil , almond oil
 They can also be converted into acetyl-CoA. That TYPE OF LIPIDS
will be enter in KREB CYCLE that will produce 1. SIMPLE LIPIDS
energy (ATP). FATS WAXES
 It happens when we have a low carbohydrate Esters of 3 F.A + Glycerol esters of high molecular
intake. Other names: weight of fatty acids with
 Ketogenic Diet: ↑ fat intake ↓ carbohydrate Triglycerides long chain alcohol
intake. The fat via the action of lipase undergo Triacylglycerides
beta oxidation to have KREB CYCLE will produce Triacylglycerol
ketone bodies.
1. Acetone ✓ Protect internal organ
2. Acetoacetic acid from shock and injury
3. B-hydroxybutyric acid Functions: Protection, Insulation, Energy

PHYSICAL CONSTANTS: DIFFERENT TESTS FOR LIPIDS 2. COMPOUND LIPIDS

1. Acid Value or Acid number ▪ Lipid + another type of molecule
― the number of milligrams of potassium hydroxide a) Phospholipids
required to neutralize the free fatty acids in 1 g ― Important component of cell membrane and
of the substance neurons, and considered to be most abundant
― ideal acid value must be low lipids present in the body
― indicates the free fatty acids present in oil. Chemical composition of phospholipids:
― ↑Acid Value ↑number hydrolysis of oil I. Glycerol/Sphingosine (Platform molecule)
2. Saponification Value II. 1 or more Fatty acids
― the number of milligrams of potassium hydroxide III. Phosphate
required to neutralize the free fatty acids and IV. Organic molecule → Alcohol
saponify the esters contained in 1 g of the
substance GLYCEROPHOSPHOLIPIDS SPHINGOPHOSPHOLIPIDS
― measure the characteristics of fatty acid Chemical composition: Chemical composition:
― measure of the average mol. weight or chain ▪ Glycerol ▪ Sphingosine
length of all FA present in oil. ▪ 2 Fatty acids ▪ 1 Fatty acid
― ↓length of fatty acids ↓ low molecular weight ▪ Phosphate ▪ Phosphate
↓ low saponification value ▪ Organic molecule → ▪ Organic molecule →
Alcohol Alcohol
 PHARMACEUTICAL BIOCHEMISTRY 20
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o Lecithin → Choline o Sphingosine 18c amino glucosylceramide or glucoseramide, galactosyl
o Cephaline → Ethanolamine alcohol
ceramide or galactocerebroside
✓ The fatty acid is connected to 3. Cytolipins : a type of globoside : ceramide +
✓ Made up of ester bond sphingosine via amide bond and neutral oligosaccharide. It has an immunological
the phosphate via the ester
bond and the alcohol connected properties, it has important role in immune
to the phosphate via ester bond. response.
TYPES OF SPHINGOLIPIDS
1. Ganglioside
❖ Organic molecule +choline= ― compounds related to cerebrosides that
Lecithin: phosphatidylcholine sphingomyelin
 used as an antioxidant contain sphingosine, long- chain fatty acids,
 It is found in all cell
 also used in treating membrane and structural hexoses (usually galactose or glucose), and
memory disorders e.g component of the myelin neuraminic acid or sialic acid.
dementia and Alzheimer’s sheath . (protective insulating
of the neurons that allow
― They occur in the surfaces of neurons and
disease.
 Present in brain tissues.
electrical impulses to transmit present in gray matter of the brain
quickly and efficiently along
 Found in soy bean and egg neurons and nerve cell) ― ↑ Ganglioside → TAY SACH’S DISEASE
yolk.  Other name is GM2 gangliosidosis,
 It is not an essential hexosaminidase deficiency and
Niemann - Pick disease –
nutrient, it is synthesize in  sphingomyelinase sphingolipidosis .
our body in liver. deficiency, accumulation
 A deficiency of enzymes hexosaminidase. It
sphingomyelin in brain and
blood will produce harmful is an enzyme responsible for the metabolism
effects. Symptoms includes or degradation of ganglioside.
Cephaline: mental retardation,
phosphatidylethylnolamine spasticity, ataxia and  Accumulation of ganglioside in the brain
 compose of glycerol with 2 death. will produce a toxic effects in nerves that will
fatty acids an phosphate group  sphingomyelinase capable
attached by an alcohol
lead to brain damage.
of breaking down
ethanolamine sphingomyelin 2. Cerebroside
 found in liver and heart tissue ― Very abundant in our brain, makes up the 7% of
 involve in blood clotting
brain mass.
― Galactosylceramide: important component in
myelin sheet (efficient nerve transmission) :
b) Sphingolipids  1st ceramide to be discovered by
― They serve as structural component of cell Johann Thudichum.
membrane which they maintain the integrity, cell ― contain carbohydrate (galactose or glucose),
signaling/ cell to cell communication, immunological one fatty acid and sphingosine, but no
functions and important components of neurons. phosphoric acid or glycerol.
Chemical composition of sphingolipids ― Ceramide+ 1 monosaccharide (galactose or
⚫ Sphingosine glucose)
⚫ 1 Fatty acid ― The fatty acid present is stearic acid.
⚫ Phosphate (not usually present) ― CHEMICAL TEST: Lassaigne’s Test : used to
⚫ Organic molecule → Ceramide detect cerebroside
 core structure of sphingolipids ― ↑ Cerebroside → GAUCHER’S DISEASE
 a molecule compose of 1 sphingosine molecule and 1  A metabolic condition where there is
fatty acid molecule.
accumulation of glucocerebroside in
 Linked with an amide bond
 Sphingosine is attached by an R group it determines the body due to deficiency of
the type of sphingolipids. glucocerebrosidase. This will lead to
organ damage, neurological damage
or brain disorders, and
hepatosplenomegaly. It can cause
multiple organ damage.
1. Ganglioside : ceramide + charge oligosaccharide ― DIAGNOSTIC TEST: Beta-Glucosidase
(n-acetyl neuraminic acid or sialic acid) Leukocyte Test an enzymatic test use in the
2. Cerobroside : ceramide+ 1 monosaccharide diagnosis of Gaucher’s disease.
(glucose or galactose) it can be called as 3. Cytolipins
 PHARMACEUTICAL BIOCHEMISTRY 21
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⚫ contain fatty acids, sphingosine, glucose and build- up in wall of arteries it delivers the plaque
galactose. back into the liver. There will be low risks of
⚫ Usually they have immunological properties atherosclerosis, heart attack, and stroke.
⚫ A type of globoside (ceramide+ neutral ― It is also known as Good cholesterol.
oligosaccharide)
⚫ It has immunological properties , important STEROIDS
role in immune response. ❖ Basic nucleus: CPPP
CYCLOPENTANOPERHYDROPENANTHRENE
LIPOPROTEINS RING
 Lipid molecules which are complex with proteins
 They are transport proteins and responsible for
transporting cholesterol and triglycerides
throughout the body.
 They carry endogenous lipids
Density Triglycerides
Protein increases
 It is made up of multiple ring structure.
 It contains four fused rings
Increases o 3 →6 membered rings
o 1→ 5 atom ring
o C17 →determines the type of
1. Chylomicrons steroid molecule
― Present and produced on intestines
▪ OH : testosterone
― Least dense, least amount of protein
▪ C=O-CH2OH: cortisone
― has the highest amount of Triglycerides
1. STEROLS:
― Transfer fats from the intestine→liver→skeletal
― A subgroup of steroid which contains the OH
muscles→ adipose tissue group
2. Very Low Density Lipoprotein (VLDL) ― Cholesterol lowering substances
― Slightly higher density than chylomicrons, high
a) Cholesterol
TAG  sterol present in the cell membrane of the
― Synthesized in liver
animals.
― It is type of bad cholesterol, because it transports
 It is not an essential nutrient.
fats from the liver → different cells and tissues  Important function:
 wall of arteries → “plaque” o Precursor to steroid hormone
atherosclerosis . There is an increase o Used in the synthesis of bile acids,
chance that there will be heart attack lipoproteins and Vit D.
and stroke of patients. b) Phytosterol- plants sterol
3. Intermediate Low Density Lipoprotein (IDL) c) Ergosterols- fungi sterol
― Denser than VLDL, low TAG, more Protein
d) Stigmasterol- sterol obtain from soybean. It is
― It transports fats (cholesterol) from the liver →
also called as Wulzen anti-stiffness factor , it is
different tissues of the body. used to reduces the muscle stiffness and treat
― High amount will cause atherosclerosis , heart
rheumatoid arthritis.
attack and stroke.
4. Low Density Lipoprotein (LDL)
― It transports fats (cholesterol) from the liver →
different tissues of the body.
― Bad cholesterol.
5. Density Lipoprotein (HDL)
― Highest density , highest amount of protein
SYNTHESIS OF CHOLESTEROL IN THE BODY
― Lowest amount of Triglycerides
― Responsible to deliver unused fats from the
tissues→ liver. When there is an excess fats
 PHARMACEUTICAL BIOCHEMISTRY 22
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 Three classes of estrogen depending on
structure:
❖ Estrone-ketone
+Acetyl coA
❖ Estradiol-alcohol
❖ Estratriol- alcohol
c. Progesterone
– makes the uterus for the implantation of a
fertilized ovum and upholds the
The thiolase will convert Acetyl coA → Acetoacetyl CoA it will be react maintenance of pregnancy
with another molecule of Acetyl coA to form HMG coA (3-hydroxyl-3 – Responsible for thickening of
methyl glutaryl-coA) via the enzyme HMG coA synthase .
ENDOMETRIUM
The HMG coA will be converted into → Mavelonic acid via the enzyme – Important hormone in pregnancy
HMG coA reductase . This conversion is considered to be the rate limiting – Aid in presecretory
step of cholesterol synthesis. This is targeted by anti cholesterol drugs or
d. Human chorionic gonadotropin
the STATINS (HMG coA reductase inhibitor).
― It is not a steroid but an example of sex
2. SEX HORMONES hormone but a glycoprotein.
― Group of sterols that are release by the gonads. ― increases when a patient is pregnant.
― ↓ LOW SEX HORMONES = HYPOGONADISM ― it is produced by the placenta
a. Androgens ― It is detected by the pregnancy test
 are a groups of sex hormones that include ― It is excreted in the urine
testosterone and others. ― In male when you take pregnancy test and
 Generally referred to as “male hormones” it turns out positive: it will indicates cancer
because men have higher levels than women such as testicular cancer and prostate
 Testosterone is important for the cancer.
development of the secondary male 3. BILE ACIDS
characteristics . It is produce in the gonads ▪ Essential for the digestion of food, especially for
(testes). It functions as solubilization of ingested fats
o Maintains bone density ▪ Cholecystokinnin – a hormone produe in small
o Fat distribution intestine responsible to have contraction of
o Muscle strength blood vessel to release BILE ACIDS
o Mass ▪ “Emulsifying agents”
o RBC production ▪ It synthesize from cholesterol
o Sperm production ▪ 1/3 of the daily produce cholesterol is converted
o Sex drive in males by the bile acids.
b. Estrogen ▪ They are produce and synthesize in the liver and
 include estradiol and others and are referred stored in the gall bladder.
to as “female hormones” because women
have higher levels. PRIMARY BILE ACID SECONDARY BILE ACID
 Natural carcinogen : increase risk for breast ▪ Cholic Acid ▪ Lithocholic Acid
cancer . In high amount can increase chances ▪ Chenodeoxycholic ▪ Deoxycholic Acid
Acid ▪ Chemically modified
of getting cancer. primary bile acid
▪ from cholesterol an no
 Its functions is to chemical modification ▪ Formed by gut bacteria
present in colon
o help in development and but gut bacteria
maintenance of the secondary
female sex characteristics ❖ Cholecystokinin
o develop and maintain uterus and  A hormone produce in small intestine,
vagina responsible for stimulating the contraction of
o aids in presecretory development of pancreas ang gall bladder.
mammary gland  There is an increase secretion of digestive
o it acts as a growth hormone to uterine enzymes
smooth muscle cells during 4. VITAMIN D
pregnancy. ― Fat soluble vitamin – steroidal in nature
 PHARMACEUTICAL BIOCHEMISTRY 23
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▪ Vitamin D2 – ergocalciferol (fungi) Membrane lipids
▪ Vitamin D3 – cholecalciferol (animal, humans)
― “ Sunshine vitamin “
― Function: Calcium absorption
― Deficiency: fragile bones
▪ Rickets - Child
▪ Osteomalacia – Adult
 Our liver produce inactive form of vitamin D : 7-
dehydrocholesterol that will migrate to the skin Eicosanoid came from membrane lipids or fatty acids came from
if it come in contact with the UV light →25- phospholipid bilayer. They are in ester form with phosphate group via the
hydroxycholesterol →kidneys →calcitriol action of phospholipase A2, they will be converted in 3-arachidonic acid or
eicosatetraenoic acid. Via two enzymatic pathway can be converted int
(active form of vitamin D) different types of eicosanoids;
 It maintain and regulate the calcium levels in our ❖ COX PATHWAY: it uses enzymes cyclooxygenase where it convert
body and it also aids in calcium absorption. arachidonic acid →PGH2 common precursor to other types of
eicosanoids that will be converted into PGI2, prostacyclin, thromboxanes
and other prostaglandins.
5. COTICOSTEROIDS  COX 1: Constitutive isoform of cyclooxygenase enzyme. It is
― It is produce by the adrenal glands responsible for generating prostaglandins that are involve in the
protection of gastrointestinal mucosa.
GLUCORCOTICOIDS MINERALOCORTICOIDS  COX 2: Inducible isoform more involve in the formation of
⚫ Secreted by Zona ⚫ Secreted by Zona prostaglandins that mediate in inflammation , pains and trigger.
IMPORTANT FUNCTIONS OF DIFFEREENT TYPE OF PROSTAGLANDIN
fasciculata of Adrenal glomerulosa of  Prostacyclin (PGI2)- inhibit platelet activation, potent
gland Adrenal gland vasodilator
⚫ Cortisone & ⚫ Aldosterone  Thromboxane- produce by platelets in which they promote
o Increases Na and water platelet aggregation
Hydrocortisone GENERAL FUNCTION OF PROSTAGLANDINS
o natural anti-inflammatory retention
o Responsible in regulation K, 1. Responsible for inflammatory response (pain, fever)
o Regulate protein and 2. Inhibit secretion gastric juice
carbohydrate metabolism Na, balance
o It also increases the excretion 3. Increase the production of the protective mucus layer of
Desoxycorticosterone/Desoxycortone stomach. If COX-1 is inhibited if we take non-selective NSAID there will
― Restore and maintain the of the potassium ions.
be decrease amount of prostaglandin in production of protective mucus
balance of sodium and layer of our stomach. This will increase the risk of ulcer.
potassium in the body. 4.It is responsible for relaxation and contraction of certain
― Drug used in Addison’s smooth muscles.
disease or renal  MISOPROSTOL Cytotec®: analog of PGE1 used as an oxytocic.
insufficiency. It may be used for uterine contraction, induced labor, and
postpartum hemorrhage. This drug is used by some
individuals as an abortion.
❖ LOX- PATHWAY
6. EICOSANOIDS (20C)  Leukotrienes: an eicosanoid responsible for inflammatory
and sensitivity reactions. They are usually found in
― Eicosanoids are 20-Carbon compound responsible leucocytes. (PIC) Platelet aggregation, Inflammatory
for localized effects in the body. Response and Chemotaxis – movement of organism
― It is also known as local hormones. response to chemical stimulus.
― The term “eikos” comes from the Greek word GENERAL TESTS FOR LIPIDS
1. Salkowski Test  Test for Cholesterol
which means “20”. Their precursor is 20 carbon  POSITIVE RESULT: Production of
unsaturated fatty acid which is the Arachidonic green fluorescence in the acid
Main reagent: H2SO4 layer.
acid.
― The true hormones enter the circulatory system
such as blood stream in order to produce their 2. Liebermann Burchard  Test for Cholesterol
effects. Whereas the eicosanoids it has localized  POSITIVE RESULT: formation of
bluish-green color
effects does not enter into blood stream. Main reagent: Acetic acid-sulfuric
― All of our cells produce eicosanoids EXCEPT RBC; acid mixture

do not produce eicosanoids , prostaglandins , 3. Osmic Test  Test for prosthetic groups of
LIPIDS
prostacyclin and thromboxanes.  Non-lipid components of lipid
― They have a very short half life. molecules
 E.g phospholipid: phosphate
BIOSYNTHETIC PATHWAY OF EICOSANOIDS  Test for CHOLINE
4. Rosenheim’s test
 It will give positive result for
Lecithin, and sphingomyelin.
 PHARMACEUTICAL BIOCHEMISTRY 24
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10. Proteins are one of the major components of
III. PROTEINS biological membrane
― “Proteios” means “primary” or “holding first place” ― glycoprotein
or “of first importance”. It is one of the most AMINO ACIDS
important biomolecule in the body. ― building block of protein
― Most abundant biomolecule present in the body ― They are joined together by amide bond or peptide
― G.J Mulder - coined the word protein bond.
― Complex, organic nitrogenous substances with very ― The letters or alphabet of our body. It has a same
high molecular weight. It is consist of repeating function when it comes to alphabet because the
monomers. sequence and the type of letters, determine what
― Found in all plant and animal cells. type of word is produce. While in amino acids it
― Consisting largely or entirely of alpha-amino acids depends on the sequence and type of amino acids of
united in peptide linkage. (amide bond) one protein to determine what type of protein is
― CHON produce.
― 70% of our body are mainly build-up of proteins STANDARD AMINO ACID NONSTANDARD AMINO
ACID
BIOMEDICAL IMPORTANCE OF PROTEINS  20 amino acids that makes up  Amino acids that have been
proteins chemically modified
1. Enzymatic catalysts – speed up chemical reaction
 Amino acids that are not  Amino acids that are not used in
2. Transport and storage chemically modified protein synthesis
― Hemoglobin: function in oxygen molecules in the  It is also known as primary and  It is always derived in
body normal amino acid. primary amino acid
― Transferrin : transport of iron EXAMPLES:
1. Proline →hydroxylation reaction
― Myoglobin: found in muscle, store oxygen in →5-hydroxyproline or 4-
EXAMPLES:
muscle cell hydroxyproline. Depending on the 1. 5-hydroxyproline
attachment of OH group. Used in 2. 4-hydroxyproline
3. Coordinated motion – muscle contraction 3. gamma-carboxyglutamate it is
the synthesized of collagen
― Actin 2. Glutamic acid synthesized by glutamic acid. It is
not used in protein synthesis but
― Myosin rather in blood clotting.
4. Mechanical support
― Collagen : most abundant protein in the body,
considered to be the structural component of
skin, bones, tissues, tendons, and blood vessels.
They provide structure, strength and support.
― Keratin : nails and hair
5. Immune protection – antibodies are derived from
proteins (GAMMAGOBULIN)
― Antibodies
6. Generation and Transmission of Nerve
― Neurotransmitters are derived from amino acid ALPHA AMINO ACID- the amino group and carboxyl
 Serotonin- derived from amino acid group are attached to the alpha carbon.
tryptophan. It is considered as happy
hormone and a vasoconstrictor. BETA AMINO ACID-
7. Control of Growth and Differentiation
― Repressor proteins- essential for orderly growth
and differentiation of cell.
8. Cell Signaling
― Glycoproteins- found in the surface of cell
membrane. Important in cell to cell signaling.
― Receptors -in a form of glycoproteins Central Carbon It is also known as chiral center
9. Hormones Optically active
Except glycine it lacks chiral center
― insulin, thyrotropin , somatotropin/GH, Basic functional group which has a tendency to
Amino Group
luteinizing hormones, follicle stimulating accept hydrogen ion (proton) then it will become
hormone (FSH). positive charge.
 PHARMACEUTICAL BIOCHEMISTRY 25
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Carboxyl Group Capable of releasing hydrogen ions ATHEROSCLEROSIS,
Hydrogen Atom KESHAN DISEASE.
Side chain Keshan Disease:
Alpha Carbon Carbon adjacent to the carboxyl  Cardiomyopathy
group associated with
Amino acids selenium deficiency.
 are also called as Zwitterions where is has two functional  It particularly affects
groups which one has a positive charge and the other has children and women
a negative charge.
of child bearing age
 also called as amphoteric molecules they can acts as both
base and as an acid
 L-amino acids are more common in nature. It is based on
the position of the amino group in order tell if it D or L
isomer.
 L-left
 D-right
ESSENTIAL NON-ESSENTIAL
 not metabolized in the body.  metabolized in the body. It is not
It must be obtain by the diet required to be obtain in our diet.
1. Histidine 1. Alanine
2. Isoleucine 2. Arginine DIFFERENT TYPES OF AMINO ACIDS
3. Leucine 3. Asparagine A. ACIDIC AMINO ACIDS
4. Lysine 4. Aspartic acid
5. Methionine 5. Cysteine
1. GLUTAMATE
6. Phenylalanine 6. Glutamic acid ― antagonized by drugs of abuse such as ketamine
7. Threonine 7. Glutamine (dissociate anesthetic) and phencyclidine
8. Tryptophan 8. Glycine
9. Valine 9. Proline (hallucinogen-Angel dust)
10. Selenocysteine ― Major neurotransmitter in the brain. It has a
11. Serine stimulant activity.
12. Tyrosine
 21st amino acid ― Common ingredient in brain GLUTAPHOS®
― It is usually seen in Monosodium Glutamate
 Structural analog of
(MSG).
cysteine amino acid
 If selenium , replace with  Chinese Restaurant Syndrome: a toxicity
sulfur it will be the of MSG and glutamate. It may cause
symptoms of CNS stimulation such as
structure of cysteine.
 It is not include in 20 headache and seizure.
Amino Three- Single Use in the
SELENOCYSTEINE standard amino acid. It is Examples letter letter
acids synthesis of……
not represented by code code
codon.  CNS Excitatory
neurotransmitter
o The three nucleotides 1. Glutamic Glu E  1st isolated in
that represent a acid/ wheat gluten
 Excess glutamic will
specific amino acid glutamate result in seizure.
 Bacterial Cell Wall
during translation.
 It plays an important role
2. Aspartic Asp D  Aspartame
in our body. (aspartic acid

 It is present in the active acid +Phenylalanine) :

artificial
site of REDOX enzymes. ACIDIC sweetener
 Impairment of AMINO 200X sweeter
than sugar.
selenoproteins. This are ACIDS  Used by
proteins made in diabetic
selenocysteine. This will patient.
 Brand name
result in detrimental EQUAL®
effects in our body that Classified as polar charge amino acids. It usually
will lead to contain acidic functional group. Their side chain or R-
TUMORIGENESIS, group contains carboxylic groups. They are also called
 PHARMACEUTICAL BIOCHEMISTRY 26
PSMA 411
as charge amino acids because their side chain with
carboxylic group releases hydrogen it can produce a
negative charge.
NEGATIVELY CHARGED AT PHYSIOLOGICAL PH

The R chain DIAMINO ACID GUIANIDINIUM

contains ION
IMIDAZOLE  Very basic
molecule
RING  most basic amino
2. BASIC AMINO ACIDS acid
Amino Examples Three- Single Use in the synthesis  CHEMICAL TEST:
letter letter of……  Sakaguchi Test
acids (+) red color
code code
 Histidine when it formation
Basic 1. Histidine His H  RGT: naphthol
undergoes
amino decarboxylation. 1. HISTAMINE
acids →HISTAMINE- ― formed by the decarboxylation of histidine.
endogenous
amine ― It is also a powerful vasodilator,
responsible for bronchoconstriction and increases gastric acid
the symptoms of
secretion.
allergic reaction
2. Arginine Arg R  It can also be ― secreted by mast cells as a result of allergic
It is used as converted → reactions or trauma
food NITRIC OXIDE-
supplement for potent
patients uses vasodilator.
vasodilators as
part of their
therapy.
E.g: Angina,
Erectile
Dysfunction
3. Lysine Lys K  Use in the 3. AROMATIC AMINO ACIDS
synthesis of Amino Examples Thre Singl Description Amino acids
CARNITINE. It is a acids e e- Use in the
supplement used letter
letter synthesis of…….
to loose weight. It code
code
helps in the
Phe F Nonpolar
conversion of
fatty acids into essential
energy. It is a amino acids,
molecule which Phenylalanin via the action
e of
transports fatty
acids in our cells phenylalanine
Aromati hydroxylase
into the c → tyrosine
mitochondria. amino
Tyr Y Polar  fumaric acid,
Beta oxidation of acids  adrenaline
fatty acids can  (catecholamine
1st isolated
occur inside from cheese s e.g.
mitochondria. "tyros" norepinephrine
It is classified as polar charged amino acids. Their Tyrosine cheese , epinephrine,
Contains dopamine)
side chain contains a basic functional group phenol found in  Tyramine
 Melanin (anti
POSITIVELY CHARGED AT PHYSIOLOGICAL PH group large skin cancer)
quantities in Via the action of
casein. tyrosinase →
Present in melanin
the milk.
DEFICIENCY OF
TYROSINASE is
called ALBINISM
Tryptophan Trp W Nonpolar
 Niacin (vit b3)
 Serotonin
only amino  Melatonin
acid that
HISTIDINE LYSINE ARGININE
contains
 PHARMACEUTICAL BIOCHEMISTRY 27
PSMA 411
indole Tryptophan
→Serotonin→
nucleus Melatonin

Hartnup’s disease
 inability to
absorb
tryptophan
 characterized
by pellagra-like
symptoms 3D’s
(Dementia,
Dermatitis,
Death)
 similar to vit B3
deficiency
symptoms.

It can be classified as polar or non-polar. These are

amino acids with benzene ring.

Phenylalanine Tyrosine Tryptophan

(Phenylalanine hydroxylase)
hydroxylation
Derived from amino  It has a Phenolic  Indole ring
structure alanine ring.  Hopkins-Cole Test it
 Millon’s Test : reacts with the indole
confirmatory ring of the tryptophan.
test for Tyrosine.
It specifically
detects the
phenol ring. 4. SULFUR CONTAINING AMINO ACIDS
 General test: Xanthoproteic test detects the presence of aromatic rings Amino Acids Examples Three- Single Amino acids
RGT: HNO3 (+) yellow ppt letter - Use in the
code letter synthesis
code of…….
BIOSYNTHETIC PATHWAY OF CATHECOLAMINES
Methionine Met M  Start codon
(AUG-
methionine)
 synthesis in
carnitine
Sulfur
Cysteine Cys C  important in
containing disulfide
amino linkages
 GSH
acids  dimer of
Cystine
Lead Acetate cysteine-
Test: It will consist of two
react with sulfur cysteine
in order to molecules
produce →PbS link by
(+) black PPT disulfide bond
that
undergoes
dehydrogenation
reaction.

5. BRANCHED-CHAIN AMINO ACIDS

 PHARMACEUTICAL BIOCHEMISTRY 28
PSMA 411
Amino Examples Three Single - structure secondary
Acids letter letter alcohol
code code
Leucine Leu L Important sites of
Branche carbohydrates
d -chain Glutamine Gln Q
amino
acids
R-isobutyl
Isoleucine Ile I
Aliphatic
Non-Polar
Amino
Acids Contains amide
derivative group
Sec-butyl
 important in
Valine Val V ammonia
detoxification

GSH
Isopropyl branch polar uncharge
Examples Three Singl Structure Amino acids Asparagine Asn N
letter e- Use in the
code letter synthesis
code of……. 1st amino acid
Glycine Gly G  only non-chiral  CNS inhibitory discovered
amino acid NT during 1806
 simplest Contains amide
“Glykos”
amino acid derivative group
-sweet
 Collagen
 GSH (glutamate+  important in
cysteine + glycine)
ammonia
 antagonized
detoxification
by strychnine
(inhibits the
inhibitory NT- polar uncharge
seizure)
Proline Pro P “imino acid” collagen

Cysteine SH thiol : can be considered as polar

Alanine Ala A methyl- Bacterial uncharged amino acids
group cell wall
Methionine

6. POLAR UNCHARGE AMINO ACIDS

Polar Three- Single - Use in the
Uncharged letter letter synthesis of…
Amino Acids code code
Important sites of
Serine Ser S carbohydrates
primary alcohol
Important in
glycosylation
reactions

Threonine Thr T

Involve in
glycosylation
reactions
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

INTRODUCTION TO PHARMACOGNOSY MICROORGANISM

Streptomyces griseus
PHARMACOGNOSY 1st aminoglycoside discovered
⎯ formed from two Greek words Streptomycin Only aminoglycoside used for TB
 Pharmakon (drug) Most ototoxic aminoglycoside
 Gnosis/gignosco (study) DOC: Tularemia
⎯ First coined by Johann Adam Schmidt, a Swiss Penicillin Penicillium notatum
Botanist; Venia; 1811. Erythromycin Streptomyces species
⎯ Introduced by C.A. Seydler in his work Analecta Bacitracin Bacillus subtilis
Pharmacognostica (1815)
⎯ covered all information on medicines from natural HISTORY
sources. name derived from the Wife of a
 Plants Cinchona
Spanish Viceroy of Peru
 Animals Clay models of human body and
 Microorganisms early writings in the medicinal
 Inorganic source Babylonians
effects of many plants
⎯ an applied science that deals with the biologic, clay tablets
biochemical, and economic features of natural Embalming: with the use of
drugs and their constituents. oleogum resin (Myrrh) – also an
⎯ embraces a knowledge of the: astringent
 History: Clay Tablets (Babylonians), Paper Ancient
Ebers Papyrus: Famous old
scroll/Ebers Papyrus (Egyptians) Egyptians
document written in 1500bc;
 Distribution: what altitude can the plant found in the tomb of mummy;
grow paper scrolls
 Cultivation: control growth for mass Georg Ebers discovered the Ebers papyrus
production, temperature, humidity, or the De materia Medica Libri cinque
amount of sunlight required by a plant Father of Pharmacognosy
 Collection: collecting of parts Aloe: mentioned in the book that
 Selection is used to treat burns
 Preparation Belladonna (Atropa belladonna –
Atropine): “beautiful lady” used by
PLANT SOURCE Cleopatra; mydriasis (dilation of
Digitalis lanata pupil); adverse effect can cause
(Lanoxin®): A positive inotropic temporary blindness
Digoxin
agent that increases the force of Ergot (Claviceps purpurea):
contraction lysergic acid diethylamine (LSD);
Digitalis purpurea has a hallucinogenic property
Digitalis Pedanios
has long half-life than digoxin • Ergotamine
Papaver somniferum Dioscorides
(Avamingant®): migraine
Morphine
Opium poppy attack
Sambong Blumea balsamifera • Ergonovine: oxytocic
Colchicum autumnale agent, uterine contraction
Colchicine
Used for acute gout Colchicine (Colchicum
ANIMAL SOURCE autumnale): for acute gout
Porcine: Pancreas of hog/pig (Sus Opium: stone of immortality
scrofa) (Paracelsus); most important and
Bovine: pancreas of cow (Bos most abundant constituent of
taurus) morphine
Insulin A/E: allergic reaction • Morphine: analgesic for
Eli Lilly: first manufacturing “more pain”
company who used DNA Hippocrates Father of Medicine
Recombinant Technology – Human Aristotle focused his studies on ANIMALS
Insulin (Humulin®) Paracelsus focused his studies on PLANTS
Urokinase human urine Christianus
Conjugated Aenotheus Analecta Pharmacognostica (1815)
uterus of a pregnant MARE
estrogen Seydler
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

Father of Pharmaceutical INERT CONSTITUENTS

Compounding → NO definite pharmacologic activity
Described the method of preparing → Plants: cellulose, lignin, suberin, cutin, starch,
Claudius
formulas containing plant and albumin, coloring agent
Galen
animal drugs → Animals: keratin, chitin, muscle fiber,
• Extraction connective tissue, collagen, glycogen
• Antidotaria & Receptaria ▪ Chitin: Invertebrate
• Galenical Pharmacy ▪ Glycogen: stored in liver
Johann Adam Lehrbuch der Materia medica
Schmidt (1811) SECONDARY PLANT SUBSTANCES
Carolus → Constituents that are EXTRACTED,
Father of Taxonomy
Linnaeus CRYSTALLIZED and PURIFIRED for therapeutic
India Vedas use
China Pen T’sao → 3 principal factors that influence:
▪ Heredity (genetic composition):
Isolated induced both qualitative and
Name Profession quantitative changes
Substance
Quinine: alkaloid; ▪ Ontogeny: stage of development
antimalarial drug  Marijuana (Cannabis
Joseph French sativa/ruderalis/indica):
Caffeine: alkaloid;
Caventou Pharmacist Cannabidiol (young leaves –
CNS stimulant and
diuretic no hallucinogenic property),
Pierre French Cannabinol (mature leaves –
Codeine has hallucinogenic property by
Robiquet Pharmacist
Friedrich German THC or Tetrahydrocannabinol)
Morphine ▪ Environment: produce variations in
Serturner Pharmacist
Rudolf German Hyoscyamine secondary plant
Brandes Pharmacist Noscapine  Senna: has a glycosidic
Rudolf constituent called sennosides;
German has a cathartic property
Brandes and Atropine
Philipp Geiger
Pharmacists  Square rice paddles: wetlands
Salicin: from
Johannes German EXTRACTION
willow bark
Buchner Pharmacist
Nicotine → Menstruum: solvent
American → Marc: undissolved portion of the drug that
Carl Koller Cocaine remains after the extraction process
Surgeon
LSD: Most active
Albert Swiss and most specific GEOGRAPHIC SOURCE AND HABITAT
Hoffman Scientist psychotomimetic → Indigenous: Plants growing in their NATIVE
agent countries
→ Naturalized: Plants grown in a FOREIGN land or
DEFINITION OF TERMS in a locality other than their native countries
ACTIVE CONSTITUENTS ▪ Datura stramonium: introduced into
→ Responsible for therapeutic effect US from Europe
→ Single chemical substance (Glycosides,
ETHNOBOTANY
terpenoids, steroids, alkaloid, peptides) or
mixtures of principles (gums, fixed oils, fats, → A broad term referring to the study of plants by
volatile oils, resins, and resin combination) humans

Single Chemical Substance or Mixture of Principles ETHNOMEDICINE

1. Lavender oil – mixture of principles (volatile oil) → Refers to the use of plants by humans as
2. Senna – single entity (glycoside) medicine
3. Coconut oil – mixture of principles (fixed oil)
4. Psyllium – mixture of principles (gum) TRADITIONAL MEDICINE
5. Morphine – single entity (alkaloid) → the sum total of all non-mainstream medical
practices, “western” medicine
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

PHARMACOPOEIA 4. Some natural products contain compounds that

→ book containing direction for the identification demonstrate little or no activity themselves but
of samples and the preparation of compound which can be modified by chemical or biological
medicines methods to produce potent drugs not easily
obtained by other methods.
DRUG BIOSYNTHESIS OR BIOGENESIS − Baccatin III → Taxol
→ study of biochemical pathways leading to the
formation of secondary constituents used as TAXONOMY – science of naming organisms and
drugs their correct integration into the existing system of
nomenclature
PRIMARY Papaver somniferum L.
PRODUCT
CONSTITUENT indicates the botanist who
Carbohydrates Glycoside, gums, mucilages provided the first scientific
Fats Fixed oils, volatile oils, fats, waxes L. description of the species and
Proteins Alkaloids, terpenoids (terpene) Taxonomy who assigned the
botanical name.
EXTRACTIVES (DERIVATIVES) Papaver a group of species, in this case
→ term deals with the principle constituents that (GENUS) poppies, which are closely related
found in natural substances by many methods somniferum
sleep producing
like extraction, distillation etc. (SPECIES)
Papaveraceae a group of genera sharing certain
NATURAL PRODUCT (FAMILY) traits
→ chemical compound or substance produced by CORRECT TAXONOMY:
a living organism found in nature that usually Papaper somniferum L.
has a pharmacological or biological activity for Papaver somniferum L.
use in pharmaceutical drug discovery and drug
design. CRUDE DRUGS
→ It can be: → Vegetable or animal drugs that consist of
▪ Entire organism (plant, animal, natural substances that have been undergone
organism) only the processes of collection and drying.
▪ Part of an organism (leaf, flower, an
isolated gland or other organ) Preparation of Crude Drugs
▪ Extract or an exudate of an organism 1. Collection
▪ Isolated pure compounds
− For the small-scale basis
→ Tadenan: used for benign prostatic hyperplasia
− Unripe: protopectin
− Just Ripe: pectin
Types of Drugs Derived From Plants
− Over Ripe: pectic acid
1. Herbal drugs: derived from specific parts of a
2. Harvesting
medicinal plant
− Proper time for harvesting is particularly
2. Compounds: isolated from nature
important because the nature and the
3. Nutraceuticals, or functional foods
quantity of the constituents vary greatly
according to the season
VALUE OF NATURAL PRODUCTS
− Can be mechanical or manual (for potent
→ Compounds from natural sources play 4
drugs)
significant roles in modern medicine
3. Drying
1. They provide a number of extremely useful drugs − removes the sufficient moisture in the
that are difficult, if not impossible, to produce plants to ensure good quality and prevent
commercially by synthetic means molds from growing
2. Natural sources also supply basic compound that 4. Curing
may be modified slightly to render them more − Modified drying method. Used to enhance
effective or less toxic the property of an active ingredient.
3. Their utility as prototypes or models for synthetic 5. Garbling
drugs possessing physiologic activities similar to − the final step in the preparation of a crude
the originals drug. It consists of the removal of
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

extraneous matter, such as dirt. The final EVALUATION OF CRUDE DRUGS

step of preparation of crude drug. Test (+) result
6. Packaging pink-red color
Anthraquinone Borntrager’s in the
DRUG PACKAGING MATERIAL glycosides test ammoniacal
ALOE goat skin (lower) layer
COLOPHONY kerosene tins Honeycomb
Froth test
ASAFOETIDA well closed container froth
Saponin
SENNA, VINCA pressed & baled Capillary tube
glycosides −
test
MOLECULAR PHARMACOGNOSY Hemolysis test −
→ A science dealing with the study of Liebermann-
Green color
classification, identification, cultivation, and Burchard test
Cardiac
protection of crude drugs and production of Kedde Test Violet
glycosides
effective elements at molecular level Keller-Killiani
Reddish brown
→ Study objects: animal sources and herbal drugs test
Cyanophore
Guignard test Red coloration
EVALUATION OF CRUDE DRUGS glycoside
(1) Organoleptic
(2) Microscopic COLOR REACTION TESTS
(3) Biologic Halphen’s test Cottonseed oil
(4) Chemical Baudouin test Sesame oil
(5) Physical Serger’s test Vegetable oils
Millon’s test Olive oil
1. ORGANOLEPTIC SPECIFIC CHEMICAL TESTS
− evaluation by means of the organs of sense Van Urk’s rgt Ergot
and includes the macroscopic appearance Vitali’s test Tropane
of the drug, its odor and taste, occasionally Murexide test Purine bases
the sound or “snap” of its fracture, and the
Lead acetate Gums
“feel” of the drug to the touch.
− False taste: creation of our mind of what
ANALYSIS OF VEGETABLE AND ANIMAL DRUGS
something tastes like.
Analytical detection of PURITY of crude
pharmacognosy drugs
2. BIOLOGIC ASSAY
depends on the absence of
− Assays on living animals as well as on intact Purity
foreign matter
or exercised organs often indicate the
sum total of the characteristics
strength of the drug or its preparations.
Quality that would make up a product.
External and internal
3 Main Types of Biological Assay Methods
characteristics
• Toxic: rats
debasement of an article
• Symptomatic: chicken egg, duck egg
Adulteration It can be determined while
• Tissue methods: use in anti-cancer drug
performing chemical tests.
TEST ANIMALS
CAUSE OF ADULTERATION
Mice phenol coefficient 1. Erroneous adulteration caused by sharing of
Turtles Cardiovascular drugs similar features or absence of distinguishable
Rabbits Insulin, Tubocurarine characters
Rats Corticotrophin inj, Vasopressin 2. Intentional substitution of high value material by
Cat Glucagon inj inexpensive substances
Chicken Oxytocin 3. Misuse caused by sharing of similar common
Pigeon Digoxin, digitalis names
4. Historical use of local substitutes
3. CHEMICAL TEST
− best method of determining the official CONDITIONS OF ADULTERATION
potency. Inferiority sub standard
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

Spoilage due to attack of microorganisms SHAPE DESCRIPTION EXAMPLES

Deterioration Impairment in quality of drug When the bark is
addition of one article to another FLAT removed from the
Quillaia
Admixture through ignorance, carelessness or large trees and
Arjuna
an accident dried under
intentional or deliberate kind of pressure
Sophistication
adulteration When the bark is
when an entirely different article is removed from the
Substitution sold or used in placed of one CURVED small branches due
Wild cherry
required to shrinkage of soft
Cassia
tissues, forming
CLASSIFICATION OF DRUGS concavity of the
Acc. to their morphology – flowers, part of bark inner side
Acc. to the taxonomy RECURVED If the concavity is
Acc. to their therapeutic application Kurchi
outside the bark
Acc. to their chemical constituents
When the
1. ACCORDING TO THEIR MORPHOLOGY shrinkage of the Ashoka
CHANNELED
a) Flower tissues is to a Cinchona
− Modified shoot meant for production of greater extent and Ledgeriana
seeds it forms a deep Cassia
− Examples: Rose, Saffron, pyrethrum, trough or channel
Flower buds – Clove QUILL
− Calyx: outermost whorl, generally green, One edge of the bar Cascara
group of sepals covers the other Cinnamon
− Corolla: Second whorl Either white or
bright colored. Group of petals DOUBLE
− Gynoecium: Third circle female part QUILL If both the edges of
Java
− Androecium: Fourth whorl male part the bark roll
Cinnamon
independently

COMPOUND One quill of the

QUILL bark is put inside
Cinnamon
the other quill; man
made
BARK LAYERS
CORK Phellem
Phellogen (it
CORK-
produces cork
CAMBIUM Periderm
cells/phelloderm
SECONDARY
phelloderm
CORTE

b) Barks c) Woods
− Cascara − tissues produced by cambium on inner side
− Cinnamon: dried
− Willow − Innermost central region of dicot
− Cinchona stem or root
− Sassafras: dried root bark − Non-functioning
Heart
− Nonliving
wood
SHAPES IN BARKS − Dark colored due to tannins,
(Duramen)
− Dependent on the method adopted for its pigments, gums, and resins
preparation − Gives mechanical support
− Depends on type of incision − E.g. Sandal woods
− Extent of any subsequent shrinkage
 Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

− Outer region of the wood tamarind

Umbelliferae/
− Function: conducts water and Asafoetida,
Sapwood Umbelliflorae
apiaceae
caraway,
food material to plant (Cremocarp
(Laburnum) fennel
− Lighter in color Fruit)
− E.g. Quassia Contortae Apocynaceae
Rauwolfina,
vinca
Solanaceae/
UNDERGROUND STRUCTURES (STEMS) Belladonna,
Tubiflorae asteridae
datura,
Ginger, turmeric, (Cymose
Grow horizontally Flowers)
capsicum
RHIZOME rhubarb, male
under the soil
fern, orris
Swollen Potato, jalap, b) Plant Family
TUBER underground aconite, − Distinguished characteristics
structure dioscorea
Garlic, onion, FAMILY NAME OTHER NAME EXAMPLES
Specialized Sunflower
BULB sqill, tunica
underground shoot family,
(paper-like_
Underground Mugwort, Milk
Saffron, Asteraceae Compositae thistle
CORM modification of
colchicum, gabi (silymarin) –
stems
discovered by US
2. ACCORDING TO THEIR MORPHOLOGY NIH
Betel nut
Arecaceae Palame
PART OF PLANT DRUG Coconut
Linseed, nutmeg, nux vomica, Cassia fistula
Seed Caesalpinaceae Golden shower
mustard
Entire plant or Ephedra, cannabis, cochineal, tree
organism cantharides Grains and
Gums Acacia Poaceae Graminae cereals, corn,
Latices Opium, papaya Rice
Dried juices Aloe Umbelliferae fruits anise,
Apiaceae
Extracts Catechu, agar, gelatin (cremocarp) fennel, caraway
Leaves Coca, senna, digitalis Solanaceae belladona,
Lemon, fennel, coriander, dried Asteridae (cymose Hyoscyamus,
Fruits flowers) Stramonium
unripe - pepper

3. ACCORDING TO THE TAXONOMY 4. ACCORDING TO THERAPEUTIC APPLICATION

a) Taxonomic Classification
− Consider the natural relationship of MIOTICS MYDRIATIC
PHYLOGENY among plants and animals Physostigmine
Atropine
Pilocarpine
CLASS ORDER FAMILY DRUG
I. Gymnospermae − Ephedraceae Ephedra 5. ACCORDING TO CHEMICAL CONSTITUENTS
II. Angiospermae
Rice
Graminae
Wheat
(Poaceae)
Maize
Monocotyledonae Aloe
Liliaceae
Colchicum
Cardamom
Zingeberaceae
Turmeric
Buchu
Rutales Rutaceae Orange
Lemon peel
Wild cherry Areca
Dicotyledonae
Rosales Rosacease Almond Ipil-ipil
Rose oil Niyog-niyogan
Glycyrhiza Santonin
Rosales Leguminosae
senna
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

a pair of carpels cremocarp fruits,

Umbelliferae pendent from a anise, fennel,
supporting axis. caraway
Alternate leaves,
belladona,
Solanaceae/ cymose flowers,
Hyoscyamus,
Asteridae fruits that are
Stramonium
capsules or berries
Peppermint,
Spearmint,
Square stems,
Thyme
Labiatae opposite leaves,
bilabiate flowers
ENGLISH NAME:
MINT FAMILY

Cremocarp fruit APIACEAE

Cymose flowers SOLANACEA
Bilabiate flowers LAMIACEAE
Citrus family RUTACEAE
Mint family LAMIACEAE (labiatae)
Sunflower family ASTERACEAE (compositae)
Palm family ARECACEAE (palmae)
Nightshade family ASTERIDAE (solanaceae)
Grains family POACEAE (graminae)
Legumes family FABACEAE (leguminosae)

Citrus family Calamansi

Mint family Peppermint, spearmint, thyme
Sunflower family Mugwort, milk thistle
Palm family Betel nut, coconut
Nightshade family Belladona, hyosyamus, datura
Grains family Corn, rice, wheat
Legumes family Sitaw, bataw, patani

Rununculaceae Aconitum, helleborus

Papaveraceae Saguinaria
Crassulaceae Subfamily of fabaceae
Apocynaceae Family with anti-cancer property

IRRITANT BULK-FORMING OSMOTIC

Antraquinone
Gums
glycosides
Lactulose
Cellulose
Castor oil
derivatives
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

CARBOHYDRATES 2 TYPES OF PHOTOSYNTHETIC REACTIONS IN GREEN

⎯ AKA Saccharides Cn(H2O)n PLANTS
⎯ Source of energy; polyhydroxy compound • LIGHT REACTIONS
 Aldehyde (Aldoses): terminal carbon o that actually convert electromagnetic
 Ketone alcohol (Ketoses): penultimate energy into chemical potential. It needs
carbon light to produce food.
⎯ Use as protein sparing, having carbohydrates • DARK REACTIONS
allows protein to do its job. o consists of the enzymatic reactions that
⎯ Even plants and animals can be a source of utilize the energy from the light reactions
carbohydrates. to fix carbon dioxide into sugar.
⎯ It also aids in digestion. o responsible for the fixing or reducing of
⎯ It is composed of carbon and hydrates. carbon dioxide into sugar (sucrose)
2H2O + CO2 + light →(CH2O) n + H2O +O2

CLASSIFICATION OF CARBOHYDRATES
1. Monosaccharides: compounds that cannot be
hydrolyzed to simpler sugars
2. Oligosaccharides: 2-10 sugar units
3. Polysaccharides: more complex, larger number;
can be hydrolyzed into small units
PHOTOSYNTHESIS
→ Carbon dioxide from human is need by the # OF CATEGORY
EXAMPLES USES
plant to produce carbohydrates. Then oxygen C NAME
made by the plant was need by human to live. Hydroxy
2 Diose
acetaldehyde
→ Starch: main source of carbohydrates in plants Cannot be found in
→ Glycogen: main source of carbohydrates in Glyceraldehyde
free-state
3 Triose
humans Dihydroxy
Simplest ketose
→ Sucrose: end-product, first sugar formed acetone
4 Tetrose Erythrose Not found in free state
during photosynthesis and the main transport
Can be found in
material nature as products of
Ribose
5 Pentose hydrolysis of
Xylulose
CALVIN CYCLE hemicelluloses, gums,
→ a process that plants and algae use to turn and mucilages
Glucose Most important
carbon dioxide from the air into sugar, the food 6 Hexose Fructose monosaccharides
autotrophs need to grow. Every living thing on Mannose found in plants
Earth depends on the Calvin cycle. Plants 7 Heptose Sedoheptulose
depend on the Calvin cycle for energy and 9 Nonose Neuramic acid
food.
→ Shows how carbon dioxide convert into SYNONYM DERIVED FROM
energy. Obtained by controlled
→ Carbohydrates can be classified according to Grape
enzymatic hydrolysis of
its no. of carbons. D-glucose starch (polysaccharides)
sugar
Homoglycan: same units
are hydrolyzed
From rigorous purification
Crystalline
of high conversion
Dextrose
hydrolysates
obtained by the
Liquid incomplete hydrolysis of
Glucose starch; controlled acid
hydrolysis of cornstarch
C4 epimer of glucose;
most absorbed in the
Brain
Galactose small intestine; Mucid
sugar
acid test (identification
test)
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

Mannose C2 epimer of glucose o Usually prepared by controlled acid

hydrolysis of cornstarch
SOURCES SYNONYMS o It is primarily used as one of excipients of
Table sugar, Invert sugar, dextrose.
Sugar cane Sucrose
Cane sugar, Beet sugar
Barley Maltose Malt, Beer sugar • CALCIUM GLUCONATE, CALCIUM GLUCEPTATE,
Grapes D-glucose Dextrose, Blood sugar AND CALCIUM LEVULINATE
Fungi Trehalose o It is used by patients with low calcium, it
Honey Fructose Levulose, Fruit sugar can be an electrolyte replenisher and
primary source of calcium.
MONOSACCHARIDES o Usual dose is 1-3 grams a day.
1. FRUCTOSE o Calcium Levulinate: from glucose via a
− Synonyms: Levulose, Fruit sugar cyanohydrin intermediate and levulinic
− Sources: acid
 Sweet fruits
 Honey: Inversion of aqueous • FERROUS GLUCONATE/FUMARATE
solutions of sucrose o It contains ferrous salt, and glucose.
 obtained from enzymatically o It is usually used by patients with iron
prepared high fructose syrup deficiency, or anemic.
 From the hydrolysis of inulin o Ferrous fumarate has greater salt content,
(polysaccharide) and used by pregnant women.
− Uses:
 Food for diabetic people cyclic form of levulose when it is
 In particular benefit for diabetic present in oligosaccharide or Fructofuranose
acidosis polysaccharides
 Ingredient in infant formulations Cyclic form of glucose Glucofuranose
Cyclic form of dextrose Glucopyranose
2. D-XYLOSE The only disaccharide that occurs
Sucrose
− Corn cobs, straw + Dilute acid abundantly in the free state in
Saccharose
− An aldopentose plants

From controlled enzymatic DISACCAHARIDES

Dextrates ⎯ Yields 2 monosaccharides molecules on hydrolysis
hydrolysis of starch
Usually prepared by
controlled acid hydrolysis of SYNONYMS SOURCES
corn starch Sugar cane, sugar beet,
Liquid glucose Sucrose Table sugar
Product obtained by the sugar maples
incomplete hydrolysis of Lactose Milk sugar Cow’s milk
starch. Barley (diastatic
Maltose Beer sugar
From rigorous purification of fermentation)
Crystalline dextrose Trehalose Ergot/fungi
high conversion hydrolysates
High-fructose Enzymatic breakdown of
Prepared by controlled Cellobiose
sweeteners or corn cellulose
enzymatic isomerization of Semi-synthetic sugar
syrups: contains
glucose. prepared by alkaline
90% fructose Lactulose
rearrangement of
PRODUCTS CONTAINING GLUCOSE lactose
• DEXTRATES
o Obtain by controlled enzymatic hydrolysis PRODUCT OF HYDROLYSIS
of starch. Lactulose Acetic acid + Lactic acid
o Used as an excipient for dextrose and for Sucrose Glucose + Fructose
pharmaceutical purpose. Lactose Glucose + Galactose
Maltose
• LIPID GLUCOSE Trehalose Glucose + Glucose
o Obtained by the incomplete hydrolysis of Cellubiose
starch.
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

Sophorose 3 Glucose Maltotriose

Primverose Glucose + Xylose
TETRASACCHARIDES
1. LACTOSE 1. STACHYOSE
− provides substrate from Lactobacilli o 2 Galactose + Glucose + Fructose
− tablet diluent, infant foods, inert diluent o Tubers of Stachys japonica, (Lamiaceae)
− Milk sugar
− Cow's milk is the fresh, unpasteurized, or Sugar rapidly absorbed in the small
Galactose
pasteurized milk of Bos taurus Linne (Fam. intestine
Bovidae), without modification C4 epimer of glucose Galactose
− Glucose + galactose = lactose C2 epimer of glucose Mannose
− A nutrient and a pharmaceutical necessity Used as diagnostic agent to evaluate
Xylose
− A tablet diluent intestinal absorption

SUGAR AND SUGAR-CONTAINING DRUGS PRODUCTS OF GLYCOLYTIC AND OXIDATIVE

Fat globules rise to the top upon METABOLISM
Cream • CHERRY JUICE
standing
Butter Union of fat globules o Succus cerasi
Buttermilk Liquid left o Liquid expressed from the fresh, ripe fruit
The milk left after separation of of Prunus cerasus Linne (Rosaceae)
Skimmed milk o It contains NLT 1% malic acid
the cream
Skimmed milk treated with rennin o Used in cherry syrup, flavored vehicle
Coagulum especially to those acidulous nature
(coagulating agent)
Proper treatment of the coagulum;
Cheese
coagulum + rennin • PLANT ACIDS
Liquid separated from the o Citric acid
Whey coagulum; contains lactose and o Lactic acid
inorganic salts o Tartaric acid
o Ferrous fumarate
2. LACTULOSE
− alkaline rearrangement of lactose • SUGAR ALCOHOLS
o Obtained from reduction of sugar
− Fructose + galactose = Lactulose
 Dulcitol
− poorly absorbed and most orally ingested
 Mannitol
lactulose reaches the colon unchanged
 Glucitol/ Sorbitol
− Bacteria in colon metabolize disaccharide
 Galactitol
to acetic and lactic acids (irritating agents)
 Xylitol: Compositae family
− laxative effect (10-20 g)
SUGAR ALCOHOLS
TRISACCHARIDES Brandy (from
a liquid containing
wine)
2 Glucose + not less than 92.3%
Gentianose Gentiana spp Whiskey (from
by weight,
Fructose Alcohol or fermented
corresponding to
Glucose + Fructose Manna from Ethanol
94.9% by volume,
malted grain)
Melezitose Rum (from
+ Glucose Larix of ethanol at
Glucose + Fructose Seed of fermented
Planteose 15.56ᵒC
+ Galactose Psyllium spp. molasses)
Isolated from
Galactose +
Raffinose Cotton seed manna Fraxinus
Fructose + Glucose ornus
Fraxinus Linne (Fam.
2 Galactose + Laxative
Manneotriose ornus, Oleaceae)
Glucose Mannitol or Diagnostic aid
Oleaceae ash Obtained by
D-mannitol and an osmotic
2 Rhamnose + Rhamnus reduction of
Rhaminose mannose
diuretic
Galactose infectoria
Rhamnose + 2 Glycodise of A hexahydric
Scillatriose alcohol
Glucose squill
that is not absorbed
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

from the ⎯ Dicarboxylic acids: Oxalic, Malonic, Succinic,

gastrointestinal Glutaric, Adipic, Pimelic, Suberic, Azelaic, Sebacic
tract (Oh My! Such Good Apple Pie, Sweet As Sugar)
Tastes
approximately
POLYSACCHARIDES
Hexitol – obtained half as sweet as
from the ripe sucrose;
⎯ polymers of monosaccharides (sugars)
Sorbitol or D- berries of mountain humectant ⎯ linked together through glycosidic (ether) linkages
glucitol ash,
Sorbus aucuparia Sorbitol + HOMOGLYCAN HETEROGLYCAN
(Fam. Rosaceae) mannitol = used Starch (Glucose units)
for urologic Glycogen Gums & Mucilage
irrigation Inulin (Fructose units) Glycosides
⎯ Note: Oxidation of sugar yields acid Cellulose
⎯ Glucose + H2O → Gluconic acid or Glucuronic acid
CLASSIFICATION BASED ON MONOMERS
PLANT ACIDS • HEXOSANS
• Lactic acid o Polymers of hexose
• Tricarboxylic acid o Examples:
• useful in buffering
Citric Isolated by  Glucosan: Starch, Dextrin,
systems
acid Scheele Glycogen, cellulose
• acidulant in
effervescent  Fructosan: Inulin
formulations  Mannosan: vegetable ivory
• It is obtained by the
lactic fermentation of • PENTOSAN
sugars or is prepared o Polymers of pentose
synthetically o E.g. Araban, Xylan
• used as an acidulant,
especially in infant POLYSACCHARIDES: HOMOGLYCAN
feeding formulas. 1. STARCH
• It is obtained by the − temporary storage form of photosynthetic
lactic fermentation of
products
sugars or is prepared
Lactic
synthetically
acid AMYLOSE AMYLOPECTIN
• used as an acidulant,
especially in infant Branching (every 25
Linear
feeding formulas. units)
Ethanedioic composed of 250 to 300 consists of 1000 or more
acid (C2H2O4) • Bleaching agent D-glucopyranose units glucose units
Oxalic
(anhydrous) • Common agent in linked by α -1, 4 α-1,4 linkages, α -1,6
acid
C2H2O4•2H2O permanganometry glucosidic bonds (branch)
(dihydrate)
more soluble in water
Succinic butanedioic insoluble
acid acid (C4H6O4)
than amylopectin
2- Amylose + iodine = deep amylopectin + iodine =
Malic Hydroxybutane blue complex blue-violet or purple
acid dioic acid
(C4H6O5) • USES OF STARCH
• a dicarboxylic acid o ingredient in dusting powder
obtained as a o a tablet filler, binder, and disintegrant
byproduct of the wine  Sodium starch glycolate: semi-
Dihydroxy industry synthetic material; sodium salt of
Tartaric
butanedioic • used as a substitute for
acid the carboxymethyl ether of starch
acid (C4H6O6) citric acid in buffer
 Pregelatinized starch: slightly
systems and in
effervescent soluble to soluble in cold water;
formulations table excipients
Fumaric • Ferrous fumarate: o Starch suspension: antidote for iodine
acid hematinic poisoning
o Branch (every 20-30 residues)
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

• HETASTARCH Hydroxyethylcellulose
Components of
o 6% solution = used as a plasma expander Methylcellulose
artificial tears
o adjunct therapy in treatment of shock Hydroxypropyl methylcellulose
caused by hemorrhage, burns, surgery,
sepsis, or other trauma CELLULOSE DERIVATIVES
o semi-synthetic material that is prepared in • Methylcellulose
SUSPENDING
such a manner that it is approximately 90% • Hydroxypropyl methylcellulose
AGENT
• Sodium carboxymethyl cellulose
of amylopectin
LOCAL • Oxidized cellulose and oxidized
HEMOSTATICS • regenerated cellulose
2. INULIN OR HYDROUS INULIN
BULK • Methylcellulose
− a D-fructofuranose polymer whose LAXATIVES • Sodium carboxymethylcellulose
residues are linked in linear fashion by β–
• a fibrous form of bleached,
2,1 bonds. regenerated cellulose.
− particularly abundant in taraxacum, inula PURIFIED
• It is used as a surgical aid and may
(elecampane), lappa (burdock root) RAYON
not contain more than 1.25% of
echinacea (cone flower), and chicory titanium dioxide
(succory or blue dandelion root).
− Compositae family 5. PYROXYLIN
− Diagnostic agent − used in the preparation of collodion and
flexible collodion,
• DEXTRAN − topical protectants.
o an α-1,6-linked polyglucan − 2 acids involved: Nitric acid & sulfuric acid
o sucrose [transglucosylase enzyme system − Synonym: Soluble GUN COTTON
(dextran sucrase) Leuconostoc
mesenteroides]> dextran • STARCH
o 10% solution = adjunct in the treatment of o Stored energy in plants
shock.
• GLYCOGEN
3. GLYCOGEN o Stored energy in animals
− Major form of stored carbohydrate in
animals The end product of the action
− Glucosan Maltose
of beta amylase on starch is
− Branch = every 8-10 residues Used in the evaluation of renal
Inulin
function.
4. CELLULOSE Used as Plasma volume Hetastarch and
− structural element expander Dextran
Most abundant polysaccharide
• PURIFIED COTTON Cellulose
in nature
o Gossypium hirsutum (Fam. Malvaceae) This enzyme affects the
o absorbent cotton synthesis of amylose fraction Transglycosylase
of starch
• POWDERED CELLULOSE
o self-binding tablet diluent and
disintegrating agent.

• MICROCRYSTALLINE CELLULOSE
o diluent in tablets

CELLULOSE DERIVATIVES USES/S

Pyrus malus
Self-binding tablet Rosaceae
Powdered Cellulose diluent and APPLE
Constituent/Use: Malic acid (antioxidant)
disintegrating agent Chemical name: 2- hydroxybutaendioic acid
Cellulose acetate phthalate enteric coating Vitis vinifera
binder and film Vitaceae
Hydroxypropylcellulose GRAPES
coating in tablet Constituent: D-glucose
Ethylcellulose
formulation Other name: dextrose and blood sugar
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

Solanum tuberosum Vermiform

Wormlike and is twisted into coils
Solanaceae/Asteridae tragacanth
POTATO
Constituent: Starch Tragacanth Shaped is like irregular tears (tear
Plant part used: Tuber sorts drop); Yellowish or brownish color
Saccharum offinarum The better grade comes from the
Ribbon gum
Poaceae/Graminae transverse incisions made with a knife
SUGAR and flake gum
Sugar component: sucrose in the main stem and older branches
CANE
Other name: table sugar, beet sugar, maple
sugar fetid odor; Forms discontinuous type of
Bos taurus Karaya gum
mucilage
Bovidae Most resistant hydrocolloid to acid
Sugar component: Lactose Tragacanth
MILK hydrolysis
Other name: Milk sugar Have a low viscosity and good stability
CHEESE: Milk formed from the mixture of Acacia
over the pH range of 2 to 10
coagulum & renin.
Apis mellifera GHATTI GUM OR INDIAN
Apidae TRAGACANTH
HONEY GUM
Sugar component: Fructose
Commercial grade of Colorless
Other name: Fruit sugar, Levulose
tragacanth Yellow (10 days),
No. 1 – almost colorless Pink (weeks),
POLYSACCHARIDES: HETEROGLYCAN and nearly translucent Brown (months)
1. GUMS No. 2 and No. 3 – have Characteristic odor and
− natural plant hydrocolloids more color and Opacity taste (acetic acid).
− anionic or non-ionic polysaccharides
− translucent, amorphous substances MARINE GUMS
− heterogenous in composition Brown Seaweeds
Sodium alginate
Algin Llaminaria
GUMS MUCILAGE Agar or Japanese Isinglas
Readily dissolved in water Form slimy masses Red Algae Carrageenan
Pathologic products Physiologic products Danish agar
USES
• Ingredients in dental • Gelating agents • Chondrus crispus
and other adhesives and • Suspending agents o Chondrus or Irish Moss
in bulk laxatives. • Stabilizers o an allusion to the cartilage like character of
• Tablet binders • Thickeners the dry thallus
• Emulsifiers
• Gigartina mamillosa
Shrub or
Synonym
Botanical
Constituent o Gigartina
Tree Source o an allusion to the fruit bodied that appear
Gum as elevated tubercles in the thallus
Astragalus Bassorin,
Tragacanth tragacanth,
gummifer Tragacanth
Goats horn
GERD TREATMENT
Acacia
Gum Acacia senegal Trade Dosage
(insol. In Arabin Producer Ingredients
arabic (Leguminosae) Name Form
alcohol)
Anogeissus Al(OH)3
Ghatti Powder
latifolia Mannitol
gum Gaviscon Ferring Chewing
(Combretaceae) Alginic acid
Tablet
Fam. Na bicarbonate
D-
Sterculiaceae AL(OH)3
galacturonic
Sterculia urens CaCO3
Karaya acid Liquid
Sterculia S. villosa Na alginate
gum
gum S. tragacntha
D- Na bicarbonate
Fam. Bixaceae
glucuronic
Cochlospermum
acid
gossypium

• TRAGACANTH
o The nature of the incision governs the
shape of the final product
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

OTHER NAME BOTANICAL SOURCE CONSTITUENT

MARINE GUMS
Extracted from brown seaweeds by the Mannuronic Acid
use of dilute alkali.  major component

Chief source: Macrocystis pyrifera Sodium alginate: a mixture of

ALGIN
Fam. Lessoniaceae beta D-sodium salts of
(Sodium alginate +
glucuronic acid (Na
alginic acid)
Other sources: glucuronate)
 Class Phaeophycea
 Ascophyllum, Ecklonia, Laminaria, Sodium salts of mannuronic
Nereocystis acid (Na mannuronate)
 Gelidium cartilagineum
(Gelidiaceae)
Japanese  Gracilaria confervoides (Linné) Agarose
AGAR
Isinglas (Sphaerococcaceae) Agaropectin
 Related red algae
(Rhodophycease)
CHONDRUS: derived from cartilage
GIGARTINA: derived from fruit body Gelating agent
1. K-carrageenan (Kappa)
CARRAGEENAN  Chondrus crispus (Linne) – 2. I-carrageenan (Iota)
Stackhouse
 Gigartina mamillosa Thickener, phlogistic agent
(Goodenough and Woodward) 3. L-carrageenan (Lambda)
 J. agardh (Fam. Gigartineceae)
Furcellaria fastigiata (Fam.
FURCELLARAN Danish agar
Furcellariaceae)
SEED GUMS
Plantago psyllium
P. indica Linne, P. arenaria
 Spanish or French psyllium seed
PLANTAGO SEED psyllium seed,
P. ovata (Forskal)
or plantain seed
 Blonde psyllium or Indian
plantago seed (Fam.
Plantaginaceae)
QUINCE SEED Cydonium Cydonia vulgaris (Fam. Rosaceae)
LOCUST BEAN “carob” pulp or Ceratonia siliqua Linne (Fam.
Galactomannan
GUM St. John’s bread Leguminosae)
Cyamopsis tetragonolobus (Fam. Galactomannan
GUAR GUM Guaran
Leguminosae) A-D-galatcose + B-Dmannose

MICROBIAL GUM SOURCE REMARKS

High molecular-weight microbial gum with
pseudoplastic properties (toothpaste & ointments)
XANTHAN GUM Xanthomonas campestris
The exocellular gum is recovered from the fermentation
broth by precipitation with isopropyl alcohol
Alpha-1,6-linked polyglucan
DEXTRAN Leuconostoc mesenteroides 10% solution can be used as an adjunct in the treatment
of shock.
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

PLANT EXTRACT SOURCE REMARKS

PECTIN  Pectin is a Greek word means “congealed or curdled”
Commercial pectin: contain  MW: ranges from 100,000 to 250,000
sugars or organic acids.  Chief component: Methoxylated Polygalacturonic
Pharmaceutic pectin: pure Obtained from the Acids
pectin to which no additions dilute acid extract  The main carbohydrate component is a linear 1,4-
have been made. of inner portion of linked D-galacturonan
the rind of citrus
fruits of from apple Uses:
Propectin: Pectin in fruit is pomace  Classified as protectant
found in an insoluble form. It  A suspending agent
is converted to the soluble KAOLIN + PECTIN =  An ingredient in may anti-diarrheal formulations
form by heating the fruit KAOPECTATE  As a colloidal solution, it has the property of
with dilute acid conjugating toxins and enhancing the physiologic
functions of the digestive tract through its physical and
chemical properties.

TREE/SHRUB SEED MARINE MICROBIAL PLANT EXTRACT

Ghatti gum Locust been
Danish agar
Acacia Cydonium Dextran
Carageenan Pectin
Tragacanth Psyllium Xanthan
Algin Agar
Karaya Guar gum

SYNONYMS USES
Gum tragacanth Used for treatment of gastric
Tragacanth Mastic gum
Goat’s horn ulcer
Acacia Gum Arabic Anti-diarrheal Pectin
Karaya gum Sterculia gum Karaya
Gum component of Movicol
Ghatti gum Indian gum Frangula
Agar Japanese isinglas Bulk forming laxatives Seed gums
Plantain seed Lambda
Plantago seed Phlogistic agent
Psyllium carrageenan
Cydonium Quince seed Matrix for immunodiffusion
Guar gum Guaran For electrophoresis
Carob pulp Chromatography Agar
Locust Bean gum
St. John's bread Gel in bacteriologic culture
Furcellaran Danish agar media
With pseudoplastic property
Xanthan gum
COMPONENTS (toothpaste and ointment)
Swelling property of
Bassorin A term referring to closely related
Tragacanth
Swelling property of Acacia Arabin hydrocolloids that are obtained from Carrageenan
various red algae or seaweeds. property
Soluble component
Tragacanthin Purified carbohydrate product obtained
Tragacanth
from the dilute acid extract of the inner
From inner rind of citrus Pectin
D-Galacturonic acid portion of the rind of citrus fruits or from
fruits apple pomace
Components of Karaya D-Galacturonic acid A purified carbohydrate product
gum D- glucuronic acid extracted from the brown seaweeds
Algin
Carrageenan Kappa, Iota, Lambda Macrosystic pyrifera by the use of dilute
Major component of Algin Mannuronic acid Alkali:
Agarosoe
Agar
Agaropectin
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

GLYCOSIDES CLASSIFICATION OF THE GLYCOSIDES BASED ON

⎯ Mixed acetals THE CHEMICAL NATURE OF THE AGLYCONE GROUP
⎯ Suffix “IN” A. Cardioactive Steroid group F. Flavonol group
⎯ Yield one or more sugars among the product of B. Anthraquinone group G. Alcohol group
hydrolysis C. Saponin group H. Aldehyde group
D. Cyanophore group I. Phenol group
⎯ Usually, mixed acetals in which the hydroxyl group
E. Glucosinolate Isothiocyanate J. Lactone
on the anomeric carbon atom is replaced by a group
moiety possessing a nucleophilic atom.
IDENTIFICATION TESTS
Components of Glycosides
Froth Test
• Aglycone, aglycon, or genin
Saponin Glycosides Hemolysis test
→ non sugar component of glycosides Capillary tube test
• Glycone Anthraquinone Glycosides Borntrager test
→ sugar component Cyanogenic glycosides Guignard test
Importance of Glycoside
✓ Regulatory
✓ Protective
✓ Sanitary functions of plants
✓ Therapeutic agents

A. CARDIAC GLYCOSIDES
− Related to steroids, CPPP (cyclopentanoperhydrophenanthrene) nucleus
− Sugar component is attached on the 3 positions of the CPPP nucleus
− 2 Aglycone
▪ Cardenolides - 5 membered ring
▪ Bufadienolides (discovered from BUFALIN isolated from the skin of toad) - 6 membered ring
− INOTROPIC AGENTS

CARDIAC GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENTS REMARKS
• Digitoxin
Foxlove Digitalis purpurea • Gitaloxin Most lipid soluble
• Gitoxin
DIGITALIS • Digoxin
• Desacetyl Polar, short-acting
Digitalis lanata
Grecian foxlove Lanatoside Used for rapid
scrophulariaceae
(deslanoside) digitalization
Conavallaria majalis
CONVALLARIA Lily of the valley • CONVALLATOXIN
LILIACEAE
Black Indian hemp Apocynum cannabinum
APOCYNUM • CYMARIN
Dogbane APOCYNACEAE
• Adonitoxin
Adonis vernalis
ADONIS Pheasant’s eye • CYMARIN
RANUNCULACEAE
• K-STOPHANTIN
CACTUS Night blooming Selenicereus grandiflorus
GRANDIFLORUS cereus CACTACEAE
Three Varieties
• Black: glycosidal,
cardiac stimulant
BLACK Helleborus niger (inotropic)
Christmas rose • HELLEBRIN
HELLEBORE RANUNCULACEAE • Green and White:
alkaloidal, cardiac
depressant; most
lipid soluble
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

• Cymarin (or
Strophantus kombe 3rd most important
kstrophanthidin)
STROPHANTHUS Strophantus hispiidus glycoside available in
• Ouabain (g-
APOCYNACEAE the market
Strophanthin)
Polar, short-acting
Used for rapid
• SCILLARE: A convert
Urginea maritima digitalization
SQUILL Squill bulb to scillarenin which
HYACINTHACEAE Use:expectorant
is more active
Red Variety:
RODENTICIDE
Nerium oleander
ADELFA Oleander • OLEANDRIN Genocide in Sri- lanka
APOCYNACEAE

GLYCOSIDES SOURCES
Adinotoxin Adonis
Hellebrin Black hellebore
Strophanthin/ouabain G-Strophanthoside Strophantus (K is beneficial) (G is toxic)
Scillaren Squill
Oleandrin Nerium oleander

B. ANTHRAQUINONE GLYCOSIDES
− Related to ANTHRACENE
− Use: Stimulant cathartics
− Identification test:
▪ Borntrager test
▪ Schonteten’s test: used often for anthranols (Green fluorescence)
− Source: Penicillium islandicum
− Orange compounds
− Upon hydrolysis, the aglycone portion consists of a di-, tri- or Tetrahydroxy Anthraquinone

ANTHRAQUINONE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENTS REMARKS
CASANTHRANOL
• CASCAROSIDE A & B: based on
optical isomers of BARBALOIN
• CASCAROSIDES C & D: based
on the optical isomer of
CHRYSALOIN
Rhamnus purshiana
CASCARA
Sacred bark CASANTHRANOL Found in LANE’S PILLS
SAGRADA Types of Anthracene
compounds
• Normal O-glycosides (basedon
emodin) about10-20%
• Aloinlike C-glycosides about
80-90%. Ex. Barbaloin and
deoxybabaloin (chrysaloin)
Components of OTC
FRANGULA Buckthorn bark Rhamnus frangula • Frangulins A & B product MOVICOL-
also contains karaya
Pharmaceutic acid for
compound Benzoin
Aloe barbadensis
Tincture
ALOES
• Aloin A: barbaloin Cathartic
CAPE ALOES Sabila Aloe ferox
• Aloin B: isobarbaloin Aloe vera gel- for
CURACAO ALOES Aloe Africana
burns, abrasions and
Aloe spicata
skin irritation,
inflammation, alopecia

Rheum officinale
RHUBARB Rheum • Rhein anthrones
Rheum palmatum
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

Chinese rhubarb Rheum emodi

Himalayan rhubarb Rheum webbianum
Indian rhubarb
• Aloe: emodin or rhein-
sennosides Blue green - B EST
• Sennosides A & B: a pair of GRADE
Alexandria senna Cassia acutifolia
stereoisomers whose Yellowish- poorest
SENNA Tinnevelly senna Cassia angustifolia
aglycones are rehin Cultivated on wet
FABACEAE
dianthrone (sennidin A and B) lands resemblin g
• Sennosides C & D: dimeric rice paddies
aglycone

CHRYSAROBIN DANTHRON or CHRYSARIN

− a mixture of neutral principles obtained from Goa powder − 1, 8 –DIHYDROXYANTHRAQUINONE
− Andira araroba − Cathartic
− used to extract chrysarobin (Hot benzene) − an important intermediate in the manufacture of
− Not employed as cathartic because it is too irritating to us anthralinand of alizarin and indanthrene dyestuffs
− Keratolytic: psoriasis, trichophytosis and chronic eczema

C. SAPONIN GLYCOSIDES
− form colloidal solutions in water that foam upon shaking – FROTH TEST
− They have a bitter, acid taste and drugs containing them are usually sternutatory and otherwise irritating to
the mucous membrane.
− Destroy red blood cells by hemolysis and are toxic especially to cold-blooded animals – HEMOLYSIS TEST
(Capillary tube test)
− Widely distributed in the plant kingdom
− USES: toxic to insects and mollusks, used to control schistosomiasis, fish poison & source of anti-inflammatory
agents

CHEMICAL CLASSES
− Diosgenin and botogenin - the most important plant steroids
− GLYCYRRHIZA
for the partial synthesis of steroid hormones
− DIOSCOREA
▪ From the genus of dioscorea
− GINSENG
− Hecogenin, manogenin, and gitogenin from species of
− AGAVE: moluscicide
AGAVE
− GUAVA: Psidium guajava
− Sitosterol from crude vegetable oil

SAPONIN GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENTS REMARKS
Glycyrrhiza glabra =
Spanish Licorice Mask the taste of bitter
G. glabra Linne. Var. drugs
LICORICE ROOT
Glandulifera = Russsian Used in Peptic ulcer
Licorice and Addison’s disease
FABACEAE
50 times as sweet as
sugar converted to the
aglycone glycyrrhetic
GLYCYRRHIZA acid (glycyrrhetinic
acid) + 2 molecules of
glucuronic acid
• Glycyrrhizin (Glycyrrhizic
acid)

USES:
• Increases fluid and
sodium retention
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

and promotes
potassium depletion
• CI: Patients with
cardiac failure and
hypertension should
avoid this drug
• Glycyrrhetic acid
Anti-inflammatory
(Aglycone portion of
agent
glycyrrhizin)
Best source of steroids.
• Dioscin → Diosgenin Major precursor of
Dioscorea floribunda
DIOSCOREA Mexican yam • BOTOGENEN AND glucocorticoids, oral
Dioscorea spiculifora
DIOSGENIN contraceptives and sex
hormones
• Tonic, stimulant,
diuretic, and
carminative
properties
• Performance and
• GINSENOSIDES endurance enhancer
Panax quinquefolius
• PANAXOSIDES • In the orient, it is
Linne.
GINSENG American ginseng • CHIKUSETSUSAPONINS used in the
Panax ginseng
• Ginsenosi de Rg1: one of treatment of anemia
ARALIACEAE
the major saponins diabetes, insomnia,
neurasthenia,
gastritis and,
especially, sexual
impotence
(aphrodisiac)

D. CYANOPHORE GLYCOSIDES
− Glycosides yielding hydrocyanic acid (HCN)
− ß- glucosidases
− Derivatives of mandelonitrile (benzaldehdyecyanohydrin)
− Detected by GUIGNARD TEST
− Enzyme: EMULSIN
− Found in ROSACEAE
Bitter Almonds Glycoside
Apricot Wild cherry Amygdalin
Linamarin
Cherries Linseed Leartrile
Phaseolunatin
Plum in kernels of apricot Patani bean Prunasin
− Both amygdalin and prunasin yield (R)- mandelonitrile as the aglycone
▪ R - going to the right – rectus
▪ S- going to the left - sinister
− Sambucus nigra liberates (S)- mandelonitrile as its aglycone

Steps in Hydrolysis of amygdalin

1. The molecule is hydrolyzed initially to liberate 1 molecule of glucose and 1 molecule of mandelonitrile glucoside.
2. The second molecule of glucose is liberated with formation of mandelonitrile.
3. The mandelonitrile then breaks down with the formation of benzaldehyde and hydrocyanic acid.

AMYGDALIN Amygdalase Glucose + prunasin

PRUNASIN Prunase Glucose + mandelonitrile
MANDELONITRILE Mandelonitrile lyase Benzaldehyde + HCN

CYANOPHORE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENTS REMARKS
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

USES:
• Flavored vehicle
Prunus serotina • PRUNASIN
Prunus Virginia especially in
WILD CHERRY Ehrhart (Dmandelonitrileglucoside)
Wild black cherry tree cough remedies
ROSACEAE • SCOPOLETIN- resin
• Sedative
• expectorant
Prunus armeniaca • LEATRILE (-)-MANDE
APRICOTS PITS linne • LONITRILE- beta-
ROSACEAE • GLUCURONoside

E. ISOTHIOCYANATE GLYCOSIDES
− Glucosinolates; enzyme myrosinase
− Group of bound toxins, like cyanogenic glycosides
− Major role in plants: Feeding deterrents against both insects and mammals
− Mustard family vegetables have been found to have anticarcinogenic properties

DISTRIBUTION
→ Mustard family (Brassicaceae) which includes:
▪ Oilseeds (rapeseed)
▪ Condiments (mustard and horseradish)
▪ Vegetables (broccoli, cabbage, and turnips)

Psidium guajava (MYRTACEAE)

→ Use in Vaginal wash after in giving birth and as antibacterial agent

LUPULIN
→ Humulone (alpha- acids)
→ Lupulone (beta-acids)
▪ Use in the manufacturing of beer
▪ Main compounds responsible for the bitterness of lupulin

AGAVE
→ the roots, sap, and juice of agave are used to make medicine. Agave has been taken by mouth for constipation,
indigestion, flatulence, jaundice, cancer, and diarrhea
→ to promote labor; and to promote urine production.
→ Moluscide

ISOTHIOCYANATE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENTS REMARKS
• Responsible for
lachrymator factor of
allium
• Alliin Enzyme: (+)- S-allyl-L
GARLIC Ajos Allium sativum • Derived from cysteine
cysteine sulfoxide) = Allicin
• Main component of
commercial garlic
powder
• Antibacterial
• Ajoene • Antihyperlipidemic
• Anti-thrombotic
• Sinalbin
White mustard Sinapis alba Brassica alba
• Acrinyl isothiocyanate
Sinapis nigra Brassica nigra • Sinigrin
Black mustard
Brown mustard • Allyl isothiocyanate

F. ALCOHOL GLYCOSIDES

ALCOHOL GLYCOSIDES
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

SYNONYMS BOTANICAL SOURCE CONSTITUENTS REMARKS

• Anti-rheumatic agent
natural forerunner of
aspirin
Salix purpurea • Salicin
WILLOW BARKS Principal products of
Salix fragilis • Populin (Benzoyl Salicin)
hydrolysis of salicin
• D-glucose and salicyl
alcohol
• D-glucose and saligenin

G. ALDEHYDE GLYCOSIDES

ALDEHYDE GLYCOSIDES
BOTANICAL
SYNONYMS CONSTITUENTS REMARKS
SOURCE
• Glycoside present in
PINE TREES • Coniferin the cambium sap of
pine trees
Mexican vanilla or Vera cruz
Vanilla • Vanillin is
• Best grade on the market methylprotocathechuic
• The pods frequently attain a aldehyde
length of 30-35 cm
Bourbon vanilla
VANILLA • It resembles the Mexican Vanilla palnifolia • Flavoring agent
variety but it is about two
thirds as long, blacker in • 4-hydroxy-3-
color, usually covered with a methoxybenzaldehyde
sublimate of needle shape
vanillin crystals and possess
a coumarin like odor
Tahiti vanilla
• a reddish brown in color and
about as long as the Mexican
variety but sharply
Vanilla tahitensis
attenuated and twisted in
ORCHIDACEAE
lower portion.
• The odor is somewhat
unpleasant and the variety is
less suitable for flavoring.
Vanilla splits or cuts
• Represent the more mature
fruits in which dehiscence
has taken place
• They cut into short lengths

H. PHENOL GLYCOSIDES

PHENOL GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENTS REMARKS
Acrtostaphylos uva-ursi • Antiseptic and astringent
• Arbutin
ERICACEAE urinary antiseptic
UVA-URS Bearberry
• Hesperidin • From citrus fruits
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

• Phloridzin • Root bark of rosaceous plants

Baptisia • Baptisin

Iris • Iridin

I. FLAVONOL GYCOSIDES
− The largest group among the naturally occurring phenolic compounds
− Examples: Rutin, quercitrin, hyperoside, vitexin
− Citrus bioflavonoids
▪ Hesperidin
▪ Diosmin
▪ Naringen
− Chalcones Flavonoid
▪ found in yellow flower pigments
▪ Chalcone: These compounds are termed nitrogenous anthocyanins which are responsible for the bright
colorations of flower and fruits of cactaceae
 Anthocyanin: VACUOLAR PIGMENT - red, pruple, blue black
 Betalanins: Red and Yellow tyrosine – derived pigment
 Leucoanthocyanins: Colorless
− Vitamin P or the Permeability factors - RUTIN and HESPERIDIN

J. LACTONE GLYCOSIDES

LACTONE GLYCOSIDES USES OF LACTONE GLYCOSIDES

• Coumarin: tonka bean • Fraxin: ash bark • Santonin • Anticoagulant: Tonka beans
• Skimmin: Japanese star • Scopolin: belladonna • Cantharidin • Aphrodisiac: Cantharides
anis • Limettin: Citrus fruits • Bishydroxycoumarol or • Anthelmintic: Santonin
• Aesculin: chestnut tree • Scopoletin: True dicumarol: Melilotus • Antispasmodic: Scopoletin
• Daphnin: mezereum camp tree officinalis • Repigmentation agent: Psolarens
• Viburnum (methoxsalen, trioxsalen)

LACTONE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENTS REMARKS

TONKA BEANS Dipteyx odorata • Coumarin • Anti-coagulant

Anthoxanthum odoratum
SWEET VERNAL
linne • Bishydroxycou marol or dicoumarol
GRASS
GRAMINAE
• First oral anticoagulant
Melilotus albus Mediscus
• The usual dose is 200 to 300 mg
Melilotus officinalis (linne)
SWEET CLOVER initially, then 25 to 200mg once a
lamarck
day, as indicated by the prothrombin
LEGUMINOSAE
time determinations
Galium triflorum
SWEET SCENTED
Michaux
BEDSTRAW
RUBIACEAE

Trifolium pratense linne

RED CLOVER
LEGUMINOSAE

• 0.6 to 1.0% the chief vesicating

Cantharis vesicatoria
principle of cantharedes
CANTHARIDES linne’ de geer • Cantharidin
• Uses: irritant, rubefacient,
MELOIDAE
aphrodisiac
Pharmaceutical Seminar 1 – AREA 2 (Pharmacognosy and Plant Chemistry)

• Topical: warts removal

• Photosensitizing coumarins
• Methoxalen, 8-
• Repigmentation agent for idiopathic
methoxypsoralen
PSORALENS UMBRELLIFERAE vitiligo (leukoderma) and for control
or Xanthotoxin
of symptomatic control of severe,
• Trioxalen
disabling psoriasis.
 PHARMACOGNOSY AND PLANT CHEMISTRY Part 3

PHARMACEUTICAL SEMINAR 1 (PSMA 411) midterm

GLYCOSIDES normal O- glycosides

(based on emodin)—
● mixed acetals
about 10-20%
● yield one or more sugars among the product of hydrolysis
● Suffix “-IN”
aloinlike C- glycosides
● Sugar component: Aglycone, aglycon, or genin
- about 80-90%
● Non-sugar component: Glycone
EX: Barbaloin and deoxy
● Importance: regulatory, protective sanitary, functions of plants, Therapeutic agents
barbaloin (chrysaloin)
Classification of the glycosides based on the chemical nature of the aglycone Component of OTC
group Rhamnus product MOVICOL
Frangula Buckthorn bark Frangulin A and B
● Cardioactive Steroid group ● Flavonol group frangula also contains
● Anthraquinone group ● Alcohol group karaya
● Saponin group ● Aldehyde group Aloes
● Cyanophore group ● Phenol group pharmaceutic aid
● Glucosinolate or Isothiocyanate group ● Lactone Curacao Aloe for
aloe barbadensis Compound Benzoin
Glycosides Identification test/s Tincture
● Froth test Cape aloe Aloe ferox Aloin A — barbaloin
Sabila
Saponin ● Hemolysis test Aloe africana Aloin B—isobarbaloin Cathartic
● Capillary tube test Aloe spicata Aloe vera gel - For
Anthraquinone ● Borntrager test Burns , Abrasions
and skin irritation,
Cyanogenic ● Guignard test
Inflammation,
Alopecia
1. Cardiac Glycosides
Rheum, Rheum
● Related to steroids, CPPP nucleus Chinese rhubarb, officinale;
● Sugar component is attached on the 3 position of the CPPP nucleus Rhubarb Himalayan R. palmatum; Rhein anthrones
● 2 aglycone Rhubarb, R. emodi;
○ cardenolides Indian Rhubarb R. webbianum;
○ bufadienolides (discovered from BUFALIN isolated from the skin of toad) Aloe-emodin or rhein –
● Inotropic agents sennosides Blue green —best
Alexandria
Glycosides Synonym Botanical source Constituent Remark Cassia acutifolia grade,
Senna
Digitoxin, Gitaloxin, Sennosides A&B– a Yellowish –
Foxglove Digitalis purpurea Most lipid soluble
Gitoxin pair of stereoisomers poorest
Senna
Digitalis Digoxin Polar, short- acting. whose aglycones are
Grecian Cassia
Digitalis lanata Desacetyl lanatoside Used for rapid dianthrone (sennidin A Cultivated on wet
foxglove Tinevelly Senna angustifolia
(deslanoside) digitalization and B) lands resembling
lily of the Convallaria majalis (Fabaceae) Sennosides C&D– rice paddies
Convallaria convallatoxin dimeric aglycone
valley (liliaceae)
Black indian Apocynum ● CHRYSAROBIN
Apocynum hemp, cannabinum cymarin ○ |s a mixture of neutral principles obtained from Goa powder
Dogbane (apocynaceae) ○ Abdira araroba
Pheasant’s Adonis vernalis Adonitoxin, cymarin, ○ used to extract chrysarobin Hot benzene
Adonis
eye (Ranunculaceae) K-strophanthin ○ not employed as cathartic because it is too irritating to use
Night Selenicereus ○ USE: Keratolytic - psoriasis, trichophytosis and chronic eczema.
Cactus ● DANTHRON or CHRYSARIN
blooming grandiflorus
grandiflorus ○ 1, 8 — DIHYDROXYANTHRAQUINONE
cereus (CACTACEAE)
3 varieties: ○ Cathartic
Black - glycosidal, ○ Is an important intermediate in the manufacture of anthralin and of alizarin
cardiac stimulant and indanthrene dyestuffs
Black Christmas Helleborus niger
Hellebrin (inotropic)
hellebore rose (Ranunculaceae) 3. Saponin glycosides
Green and White -
alkaloidal, cardiac ● form colloidal solutions in water that foam upon shaking — FROTH TEST
depressant ● They have a bitter, acrid taste and drugs containing them are usually sternutatory and
S. kombe and S. K. strophantoside 3rd most important otherwise irritating to the mucous membrane.
Strophanthus – hispidus G. strophanthin glycoside available in ● Destroy red blood cells by hemolysis and are toxic especially to cold- blooded animals
(apocynaceae) (ouabain) the market — HEMOLYSIS TEST
Scillaren-A – Use: expectorant ● Widely distributed in the plant kingdom
Urginea maritima ● toxic to insects and mollusks
Squill Squill bulb convert to scillarenin red variety:
(hyacinthaceae) ● used to control schistosomiasis
w/c is more active rodenticide
Nerium oleander ● fish poison
Adelfa Oleander Oleandrin Genocide in Sri lanka ● source of anti-inflammatory agents
(apocynaceae)
two chemical classes
2. Anthraquinone glycosides ● Steroid
○ Diosgenin and botogenin – the most important plant steroids for the partial
● related to anthracene synthesis of steroid hormones
● use: Stimulant cathartics ■ from the genus of Dioscorea
● Identification test: Borntrager test ○ Hecogenin, manogenin and gitogenin from species of Agave
○ Schonteten’s test is often used for anthranols (green fluorescence). ○ Sitosterol from crude vegetable oils
● Penicillium islandicum (SOURCE) ● Tripenoids
● orange red compounds Glycosides Synonym Botanical source Constituent Remark
● Upon hydrolysis, the aglycone portion consists of a di- , tri- or tetrahydroxy Glycyrrhizin
anthraquinone (Glycyrrhizic acid)
Glycosides Synonym Botanical source Constituent Remark - 50 times as sweet
Casanthranol as sugar.
Emodin- Cascarosides (Fabaceae) - Increases fluid mask the taste of bitter
Cascarosides A & B and Na retention drugs
—vasedon optical Glycyrrhiza glabra = and promotes K
isomers of barbaloin Licorice Spanish Licorice depletion increase foaminess in
Rhamnus Cascarosides C & D — Glycyrrhiza
Cascara Found in Lane’s root - Cl: Patients with beer
Sacred bark purshiana based optical isomers of G. glabra Linne. Var. cardiac failure
sagrada Pills
(Rhamnaceae) Chrysaloin glandulifera = Russian and hypertension Used in Peptic ulcer
Licorice Glycyrrhetic acid and addison’s dze
- aglycone portion
of glycyrrhizin
2 Types of Anthracene - Anti-inflammatory
compounds: agent

Go bobo!!! ❤ | 1
 D. floribunda Best source or steroids White Brassica Sinalbin
Dioscin ➞ Diosgenin Sinapis alba
major precursor of mustard alba Acrinyl isothiocyanate
Mexican
Dioscorea glucocorticoids, Oral Black Sinapis nigra Brassica Sinigrin
yam D. spiculifora Botogenen and
contraceptives and sex mustard Brown mustard nigra Allyl isothiocyanate
diosgenin
hormones
tonic, stimulant, 6. Alcohol glycosides
diuretic, and
● principal products of hydrolysis of Salicin
carminative
● Ginsenosides ○ D-glucose and Salicyl alcohol
properties.
Panax quinquefolius ● Panaxosides ○ D-glucose and saligenin
Linne. ● Chokusetsu Glycosides Synonym Botanical source Constituent Remark
Performance and
Saponins endurance enhancer Salicin Anti-rheumatic agent natural
American Salix purpurea forerunner of aspirin
Ginseng Willow bark
ginseng In the Orient, it is used Salix fragilis Populin
in the treatment of (benzoyl salicin)
anemia, diabetes,
Ginsenoside Rg1 - insomnia, 7. Aldehyde group
Panax ginseng
one of the major neurasthenia, gastritis, Glycosides Synonym Botanical source Constituent Remark
(Araliaceae) and, especially, sexual
saponins Mexican vanilla, (Orchidaceae) Vanillin is methyl
impotence Bourbon vanilla Vanilla planifolia protocatechuic
(aphrodisiac). Vanilla Flavoring agent
aldehyde
Vaginal wash after Tahiti vanilla V. tahitensis
Psidium guajava
Guava giving birth and as Glycoside present in
(myrtaceae)
antibacterial agent Pine trees Coniferin the cambium sap of
Agave Molluscicide pine trees
used in the ● lignin a by-product of the bulb industry
manufacture of beer ○ Most of the vanillin in commerce is made from lignin
Humulone (a-acids) ● Ethyl vanillin- a synthetic analog of vanillin is also used as flavoring agent
Lupulin
Lupulone(p-acids) main compounds Commercial varieties
responsible for the ● Mexican or Vera cruz vanilla
bitterness of lupulin ○ Best grade on the market
○ The pods frequently attain a length of 30- 35 cm
4. Cyanophore group / Cyanogenic glycosides ● Bourbon vanilla
● glycosides yielding hydrocyanic acid (HCN) ○ it resembles the Mexican variety but it is about two thirds as long, blacker in
● 𝛃-glucosidases color, usually covered with a sublimate of needle shape vanillin crystals and
○ derivatives of mandelonitrile (benzaldehyde cyanohydrin) possess a coumarin like odor
○ Detected by GUIGNARD TEST ● Tahiti vanilla
○ enzyme: EMULSIN ○ Is a reddish brown in color and about as long as the Mexican variety but
● Glycoside found in Rosaceae sharply attenuated and twisted in lower portion
○ bitter almonds, apricot,cherries, plum — amygdalin ○ the odor is somewhat unpleasant and the variety is less suitable for flavoring
○ in kernels of apricots — laetrile ● Vanilla splits or cuts
○ Wild Cherry — prunasin ○ represent the more mature fruits in which dehiscence has taken place
○ Linseed — linamarin ○ they cut into short lengths
○ Patani bean — phaseolunatin
● Both amygdalin and prunasin yield (R) - mandelonitrile as the aglycone 8. Phenol group
● Sambucus nigra liberates (S)- mandelonitrile as its aglycone Glycosides Synonym Botanical source Constituent Remark
(Ericaceae) Arbutin Antiseptic (urinary) and astringent
STEPS IN HYDROLYSIS OF AMYGDALIN
Arctostaphylos Hesperidin From Citrus fruits
● 1. The molecule is hydrolyzed initially to
Uva-ursi Bearberry uva-ursi Phloridzin root bark of rosaceous plants
liberate 1 molecule of glucose and 1
molecule of mandelonitrile glucoside. Baptisia Baptisin
● 2. The second molecule of glucose is Iris Iridin
liberated with the formation of
mandelonitrile. 9. Flavonoids
● 3. The mandelonitrile then breaks down with ● The largest group among the naturally occurring phenolic compounds
the formation of benzaldehyde and hydrocyanic acid. ● Examples
Glycosides Synonym Botanical source Constituent Remark ○ Quercetin — citrus bioflavonoids
○ Rutin — Hesperidin
Prunasin Uses:
Prunus ○ Hyperoside — Diosmin
(D-mandelonitrile Flavored vehicle
virginia and Prunus serotina ○ Vitexin — Naringen
Wild cherry glucoside) especially in cough
wild cherry Ehrhart (Rosaceae) ● Vitamin P or the Permeability factors — RUTIN and HESPERIDIN
Scopoletin - resin remedies
black tree ● Chalcones
Sedative expectorant
○ Flavonoid found in yellow flower pigments
Laetrile (-) –
Prunus armeniaca ○ These compounds are termed nitrogenous anthocyanins which are
Apricot pits mandelonitrile –
Linne. (Rosaceae) responsible for the bright colorations of flowers and fruits of Cactaceae
𝛃-glucuronoside
● Anthocyanin – Vacuolar pigment: red, purple, blue, black
● Betalains – red and yellow tyrosine-derived pigments
5. Glucosinolate or Isothiocyanate group ● Leucoanthocyanin – colorless
● enzyme myrosinase
● group of bound toxins, like cyanogenic glycosides. 10. Lactone
● Major role in plants: Feeding deterrents against both insects and mammals Glycosides Synonym Botanical source Constituent Remark
Distribution Tonka beans Dipteryx odorata Coumarin Anti-coagulant
● Mustard family (Brassicaceae) which includes: Anthoxanthum
○ Oilseeds (rapeseed) Sweet vernal Bishydroxycoumarol
odoratum Linne
○ Condiments (mustard and horseradish) grass or dicoumarol
(Gramineae)
○ Vegetables (broccoli, cabbage, and turnips) 1st oral anticoagulant.
● Mustard family vegetables have been found to have anticarcinogenic properties The usual dose is 200
Botanical Melilotus albus
Glycosides Synonym Constituent Remark to 300 mg initially,
source (Mediscus)
then 25 to 200 mg
Allin responsible for lachrymator Sweet clover M. officinalis (linne)
once a day, as
(+)–S-allyl-L-cysteine factor of allium lamarck,
indicated by
sulfoxide (Leguminosae)
prothrombin time
Derived from cysteine determinations.
Allicin main component of Sweet
Garlic Ajos A. Sativum commercial garlic powder Galium triflorum
scented
Michaux, (Rubiaceae)
bedstraw
Ajoene Antibacterial
Antihyperlipidemic Trifolium pratense
Anti-thrombotic Red clover
Linne’ (Leguminosae)

Go bobo!!! ❤ | 2
 0.6 to 1.0% the chief EFA-Omega 3 & 6 FAs
Spanish vesicating principle of ● Omega indicates the position of the first double bond from the methyl group
flies, cantharides ● The first point of unsaturation if next to the third Carbon (omega 3 FA) - Linolenic
Cantharis vesicatoria
russian ● The first point of unsaturation if next to the sixth Carbon (omega 6 FA) - linoleic
Cantharides Linne’ De Geer Cantharidin
flies, or Uses: irritant, ● Great significance on human nutrition and health Issues
(Meloidae)
blistering rubefacient,
flies aphrodisiac, warts Properties and Processes of lipids
removal (topical)
● Physical properties: Greasy, Lighter than water, Insoluble in water, and Soluble in
(Umbelliferae) photosensitizing
organic solvents
coumarins
● Hydrogenation – conversion of liquid oil to semi solid fats which are used as
Methoxsalen, cooking fats and shortening.
Repigmentation agent
8-methoxypsoralen, ● Saponification – production of soap
for idiopathic vitiligo
Psoralens or xanthotoxin ● Hydrolysis – alcohol + acid
(leukoderma) and for
● Oxidation – rancidity
control of
Trioxsalen ● Heating of oils – acrolein
symptomatic control
of severe, disabling
Different tests for lipids
psoriasis.
● Coumarin — tonka beans (anti-coagulant) ● Acid Value or Acid number
● skimmin — Japanese star anise ○ the number of milligrams of potassium hydroxide required to neutralize the
● aesculin — chestnut tree free fatty acids in 1 g of the substance
● daphnin — mezereum ○ indicates the amount of free fatty acids present in the oil
● fraxin — ash bark ● SaponificationValue
● scopolin — belladona
● Limettin — Citrus fruits ○ the number of milligrams of potassium hydroxide required to neutralize the
● Scopoletin — True camp tree (antispasmodic) free fatty acids and saponify the esters contained in 1 g of the substance
● Santonin — Artemisia cina (were formerly used as anthelmintic) ○ Triglyceride + 3 KOH (lipase) ➜ glycerol + 3 Ksalt
● Cantharidin — Blistering flies (aphrodisiac) ● Iodine Number
● Bishydroxycoumarol or dicumarol - Melilotus officinalis ○ the number of grams of iodine absorbed, under prescribed conditions, by 100
● Viburnum grams of substance -indicates the degree of unsaturation
● Psoralens (Methoxsalen, Trioxalen) – (repigmentation agent)
Iodine number of triglycerides
FAs # of double bond Iodine #
LIPIDS Palmitoleic acid 1 95
● consists of fixed oils, fats and waxes . Oleic acid 1 86
● Their primary function is food (energy) storage Linoleic acid 2 173
● Esters of long chain fatty acids and alcohols, or of closely related derivatives.
Linolenic acid 3 261
● Fats and fixed oils are obtained from either plants (olive oil, peanut oil) or animals
Arachidonic acid 4 320
(lard)
○ Fixed oil and fats differs only as to melting point ● Other physical constants such as melting point, specific gravity, and refractive index
○ Fatty or fixed oils – liquid at normal room temp (except cocoa butter) also served as identity, purity and quality tests
○ Fats – semi-solid or solid at ordinary temp (except cod liver oil)
● Triglycerides (through Esterification) classes of lipids based on its ability to absorb oxygen from air
● Drying oils
● Semi-drying oils
● Non drying oils

FIXED OILS
Methods of obtaining fixed oils of vegetable and animal origin
● Fixed oils and fats of vegetable origin are obtained by expression in hydraulic presses
○ ○ Virgin oil or a cold- pressed oil – if the expression is carried out in cold
○ Glycerol + 3 Fatty acids = Triglycerides ○ Hot pressed oil – if the expression is carried out in heat
● Sometimes organic solvents are used for extraction of oils.
FATTY ACIDS
Types of Fatty acids SATURATED FIXED OILS
● Saturated – no single bond present Source Botanical source Constituent Remark
● Unsaturated – one or more double bonds has the highest
○ Monounsaturated (one); polyunsaturated (2/more) saponification value and
Cocos nucifera Lauric and myristic
Coconut oil lowest iodine value
Classification of Fatty Acids present as glycerides in food fats (Arecaceae) acids
CN Systematic name Formula Common source Copra – endosperm
I. Saturated FA one of the world’s most
Elaeis guineensis
Butyric Butanoic CH3(CH2)2COOH butterfat Palm oil widely consumed edible
(Arecaceae)
Butterfat, coconut and oils, next to soybean oil
Caproic Hexanoic CH3(CH2)4COOH Palm kernel oil
palm nut oils
Caprylic Octanoic CH3(CH2)6COOH
coconut and palm nut oils, MONOUNSATURATED FIXED OILS
Capric Decanoic CH3(CH2)8COOH
butterfat Source Botanical source Constituent Remark
Lauric Dodecanoic CH3(CH2)10COOH
coconut and Palm nut oil, ● Trioleoylglycerol -
Myristic Tetradecanoic CH3(CH2)12COOH cathartic effect
most animal and plant fats
practically all animal & ● Emollient
Palmitic Hexadecanoic CH3(CH2)14COOH 45- 55% of fixed oil
plant fats ● plasticizer in flexible
20 % of protein
collodion
animal fats and minor substance (globulin,
Stearic Octadecanoic CH3(CH2)16COOH Ricinus communis ● Hydrogenated castor
component of plant fats Castor oil albumin,
(Euphorbiaceae) oil - stiffening agent
Arachidic Eicosanoic CH3(CH2)18COOH peanut oil nucleoalbumin,
● Ricinoleic acid is an
II. Unsaturated FA (Monoethenoic Acids ) glycoprotein and
ingredient in a vaginal
Oleic Cis 9-octadecenoic C17H33COOH Plants & animal fats Ricin - a toxic lectin
jelly for restoration
Elaidic Trans 9-octadecenoic C17H33COOH Animal fats and maintenance for
III. Unsaturated FA (Ethanoic Acids) vaginal acidity.
peanut, linseed, and one of the world’s most
Linoleic 9,12-Octadecadiencic C17H31COOH Olive oil Olea europea
cottonseed oils widely consumed edible
(sweet oil) (Oleaceae)
IV. Unsaturated FA oils, next to soybean oil
Linolenic 9,12,15-Octadecatrienoic C17H29COOH linseed and other seed oils 1. setting retardant for
Eleostearic 9,11,13-Octadecatrienoic C17H29COOH Peanut seed fats dental cements and in
V. Unsaturated FA Peanut oil Arachis hypogaea 45% fixed oil, 20% the preparation of
4,8,12,15 (arachis oil) (Fabaceae) protein and thiamine soaps, plasters and
Moroctic C17H27COOH fish oils liniments
-Octadecatetraenoic
Arachidonic 5,8,11,14-Eicosatetraenoic C19H31COOH traces in animal fats 2. salad oil

Go bobo!!! ❤ | 3
 Brassica campestris.
1. Non-drying WAXES
Rapeseed oil B. juncea, ● high molecular weight alcohol and long chain fatty acids
50% erucic acid 2. Solvent for IM
(Canola oil) B. napus ● PLANT WAX
injection
(Brassicaceae) ○ Jojoba oil – Liquid plant wax
○ Carnauba wax – myricyl cerotate
Grades of Purity OF Olive Oil ○ Bayberry wax
● Virgin oil – obtained by gently pressing the peeled pulp with greater pressure ● INSECT WAX
○ Beeswax – myricyl palmitate
● First Class or First Grade oil is pressed from crushed pulp with less pressure
○ Lac wax
● Second Grade of edible oil is pressed from crushed pulp with greater pressure. ● Spermaceti
Hand- picked olives are used, and the oil is obtained promptly before decomposition
produces fatty acids. Finally, the pulp, mixed with hot water, is pressed again Source source Remark
● Technical oil: or the pulp is extracted with Carbon Disulfide to obtain “Sulfur” Olive oil head of the sperm whale
of inferior quality. Spermaceti Physeter macrocephalus ● ingredient in cold creams
● The fallen, decomposed or refused leaves that are allowed to ferment furnish a low (Family Physeteridae)
grade “tournant oil” which contains large amounts of free fatty acids’ cetyl esters
Synthetic Spermaceti
wax
POLYUNSATURATED FIXED OILS ● mixture of solid alcohols consisting chiefly
Glycosides Synonym Botanical source Constituent Remark (not less than 90%) of cetyl alcohol or 1-
Cetyl Alcohol
Teel oil, Sesamolin effective synergist for hexadecanol
Sesamum indicum ● emulsifying aid and a stiffening agent
Sesame oil Benne oil, Sesamol pyrethrum Insecticides.
(Pedaliaceae) liquid wax expressed from
Gingily oil Baudoin test
Gossypium Gossypol against P. falciparum and E. Seeds of Simmondsia
Cottonseed Jojoba oil ● emollient
hirsutum histolytica chinensis
oil (Fam: Simmondsiaceae)
(Malvaceae). Halphen test
stigmasterol - precursor in the synthesis COMPONENTS:
of progesterone 1. myricyl palmitate (72 %)
Syn: Wulzen - A drying oil, with an 2. cerotic acid (14%)
anti-stiffness IODINE VALUE between 3. Hydrocarbons (12%)
Glycine soja factor 120-141 and is not useful Beeswax/ Apis mellifera (Fam. 4. Moisture
Soybean oil Yellow wax Apidae) 5. Pollen
(Fabaceae) as cooking oil
- The oil is used in the 6. Propolis (Bee glue)
manufacture of stiffening agent & ingredient in yellow
varnishes, insulators and ointment.
other products. base for cerates and plasters.
- flour sifted from bleached beeswax.
decorticated ground seed - Saponification cloud test – It is rapid,
Soybean reliable and expensive method of detecting
of Glycine soja
meal White wax the presence of certain adulterants of
- used to detect urea
nitrogen in blood serum natural beeswax.
- USES: Employed pharmaceutically in
● Almond oil – Prunus amygdalus (Fam. Rosaceae) ointments and cold creams.
● Apricot Kernel Oil – Prunus armeniaca
● Peach Kernel Oil – P. persica PROSTAGLANDINS
● Corn oil – solvent for _____, IM inj. ● Are C20 lipid metabolites formed in the body from essential, unsaturated fatty acids in
○ The oil-rich embryos (Often called GERMS) are separated by a FLOTATION the diet.
during the preparation of CORN STARCH. ● Apparently occur in all mammalian tissues, but they are present in low concentrations
● Safflower oil – Carthamus tinctorius Linne’ (Fam. Asteraceae)
● Sunflower oil – Helianthus annuus Linne’ (Family Asteraceae)
● Linseed oil — Flaxseed oil, Linum usitatissimum linne’ (Fam. Linaceae)
● Cod liver oil — Gadus morhua Linne (Gadidae)
● Ethiodized oil injection – an iodine addition product of the Ethyl ester of the fatty
acids of poppy seed oil.
○ Radiopaque and is used as a diagnostic aid in hysterosalpingography and
lymphography.

● Policosanol –lipid lowering found in sugar cane waste and leaves of alfalfa and
wheat ● Four classes of prostaglandins: A, B, E, and F
● Safflower oil – drying fixed oil expressed from Carthamus tinctorius and is
recommended for its cholesterol lowering properties. PG synonym Remark
● Glyceryl triacetate – antifungal (MOA: gradual release of acetic acid) PGF2a Dinoprost ● Uterine stimulant
● Lecithin – A substance obtained from Glycine soja which is used to control deranged (15S)-methyl PGF2a Carboprost ● IM injection
lipid and cholesterol metabolism PGE2 Dinoprostone ● vaginal suppository
● USES: vasodilator, inhibits platelet
● Theobroma oil Alprostadil aggregation, and stimulates
● Lanolin – (hydrous wool fat) 25 to 30% water. PGE1 Alprostadil intestinal and uterine smooth muscle
● palliative therapy to maintain temporarily
○ Water absorbable ointment base
neonates with patent ductus arteriosus
● Anhydrous lanolin — (wool fat) Nmt 0.25% water
● Undecylenic acid — antifungal
● Sodium Morrhuate - sclerosing agent

● Royal jelly – used for counteracting the effects of aging and for the treatment of
depression and dermatitis.
○ milky fluid produced by the salivary glands of worker bees
● Suet (Prepared Suet NF (1950)) – A purified internal fat of the abdomen of the
sheep, Ovis Aries which is used as ointment base.
● Lard NF X (1955)
○ Synonyms: Hogs Lard, Manteca, Grasa
○ Origin: fatty matter of the abdomen of the hog Suis scrofa (Suidae)
○ Use: ingredient in the preparation of ointment and cerates- emollient

Go bobo!!! ❤ | 4