BIOCHEMISTRY

BSN1
PREPARED BY: INO JAVIER

Lesson 5: Lipids

● 3 types of fatty acids according to the length of the

Lipids hydrocarbon chain:
● Organic compound found in living organisms (organic: o Long-chain (C12 to C26): INSOLUBLE
because these molecules mainly contain carbon and o Medium-chain (C8 to C10)
hydrogen, and then there are atoms that are bonded to them) o Short-chain (C4 to C6): have some solubility
● Merely a carboxylic acid with long hydrocarbon chains (10-30
C)
o Carboxylic acids: blue in image (C,O,O,H)
● Lipids also has hydrocarbon chains (black). Chains mainly
have 10-30 carbons but lipids has only 12-18 carbons
o Unlike some carbohydrates which can be dissolve in
water like disaccharides, lipids are insoluble in
water because they are non-polar compounds
o The only time that they can be dissolve is in non-
polar organic solvents like: alcohol, gasoline and
kerosine. Two types of Fatty Acids
● Insoluble in water ● SATURATED
● Soluble in non-polar organic solvents ● UNSATURATED
o Monounsaturated
o Polyunsaturated

B. Fatty Acids: Saturated

● Carbon chain with C-C bonds are all single bonds

C. Fatty Acids: Unsaturated

A. Structure
● Monounsaturated Fatty acid
● Lipids do not have a common structural features that serves o Carbon chain with one C-C double bond
as the basis for defining such compounds

● Polyunsaturated Fatty acid

o Carbon chain with two or more C-C double bonds

FATTY ACIDS
● Naturally occurring monocarboxylic acids with linear carbon
chain
● Classified according to the length of the hydrocarbon chain:
● Have even number of carbon atoms o Numbering starts from the other end of -COOH
o When you count the number of Carbons in fatty
acids, you start from the Carboxylic end.

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 o Every point of the zigzag lines, represents one (1) DIFFERENCE OF SATURATED AND UNSATURATED FA:
carbon. saturated vs. unsaturated
● Structural notation indicates number of C atoms
o 18:3 (18 carbons with 3 double bonds) - only single bonds - at least one double bond
(monounsaturated) (polyunsaturated)
- more H bonded to C - Less H bonded to C

● The reason why its called:

TYPES OF POLYUNSATURATED FATTY ACIDS:
● Omega (w) - 3 fatty acid Saturated: it is saturated with hydrogen (presence of hydrogen);
o Unsaturated fatty acid with its endmost double bond Since saturated fatty acids only have single bond, both ends that
3 carbon atoms away from it methyl end. are available in carbon.
o The methyl here is the CH3 Unsaturated: have less hydrogen bonded to carbon.

I. FATTY ACIDS: PHYSICAL PROPERTIES

● WATER SOLUBILITY
o The ability of these fatty acids to be dissolve in
water
o Long-chain fatty acids are insoluble in water
o Short-chain fatty acids have some level of solubility
(because of the presence of carboxylic acid which
are polar in nature; they are attracted to water)
▪ The shorter the hydrocarbon chain, the
more polar it is.
● Zigzag structure or Natta Projection
o While hydrocarbon chains are non-polar
● 3 types of omega 3 fatty acids o Short chain acids: Acetic Acid, Propionic Acid
o ALA: a-Linolenic acid - has 3 double bonds (found and Butyric acid.
mainly in plant oils) essential fatty acid
o EPA: Eicosapentanoic acid - 5 double bonds
(found in fish/seafood)
o DHA: Docosahexonoic acid - 6 double bonds
(found in fish/seafood) also present in brain

● Omega (w) - 6 fatty acid

o Unsaturated fatty acid with its endmost double bond
six carbon atoms away from it methyl end ● MELTING POINTS
o Purpose: o Depends upon the following:
▪ LA, AA and DPA Generally contribute to ▪ Length of carbon chain
the structure and function of cell
▪ Degree of saturation
membrane
▪ Plays part in gene regulation and gene
expression
o 3 types:
▪ LA: Linoleic acid - 2 double bonds; most
abundant in the food that we eat and in our
body. Essential fatty acids because it can
be used to synthesized AA and DPA.
▪ AA: Arachidonic acid - 4 double bonds;
abundant in brain and important for normal
brain development in fetus and infants.
▪ DPA: Docosapentanoic acid - 5 double EXPLANATION:
bonds/
o STEARIC ACID: saturated fatty acid and has long
carbon chain , so you see in the image that the
amount of heat or temperature you need in order to
melt it is high (70 degree c)
o Whereas saturated fatty acids like olic acid (1
double bond), linoleic acid (2 double bonds) and
linolenic acid (3 double bonds) they need only low
heat.
o These 3 examples of unsaturated fatty acids are
liquid in room temperature and already melted in
room temperature

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 o If the fatty acid has a long hydrocarbon chain [ A ] ENERGY STORAGE LIPIDS: TRIGLYCERIDE
and if its saturated, it will have a high melting
point ● AKA triacylglycerol
o If it is unsaturated and has short or medium ● major energy storage material (concentrated in adipocytes)
carbon chain, its melting point is lower than ● Condensation reaction - process of forming larger molecule
room temperature. and water is released in the process
● BENDING ● Triglyceride is an ester of glycerol
o Number of “Bends” in a fatty acid: o Ester - Organic compound that is formed when an
▪ Increases as the number of double bonds alcohol (gycerol) and a fatty acids joins together to
increases release water
▪ Less packing occurs
▪ Melting point is lower
▪ Tend to be liquid at room temperature

● Two types:
1. Simple triglyceride: glycerol + 3 identical FA
molecules
2. Mixed triglyceride: glycerol + more than 1 kind of FA

EXPLANATION:
o First is straight chain so it is saturated FA
o The 3 are bending so they are unsaturated FA
▪ Because of their double bonds, they have
the ability to bend
▪ Ex:
● Olic acid has 1 double bond so it
can be bend once
● Linoleic acid has 2 double bonds
so it can be bend twice
● Oils and fats
● Linolenic acid has 3 double
bonds so it can be bend thrice
saturated vs. unsaturated

- high melting point - low melting point

- solid at room temp - liquid at room temp
- mostly animal-derived - mostly plant-derived fats
fats

Explanation:
▪ If melting point is lower you tend to be
liquid at room temperature
● Triglyceride as energy source
II. CLASSIFICATION OF LIPIDS
● BIOCHEMICAL FUNCTION Dietary Considerations
o Energy-storage lipids ● Typical Filipino diet contains too much fat
o Membrane lipids ● Philippines (2020) - deaths due to ischaemic heart or CHD
o Emulsification lipids diseases were the leading cause of death)
o Messenger lipids o 99.700 cases (17.3% of the total deaths)
o Protective-coating lipids
● SAPONIFICATION Good Fats VS Bad Fats
o Lipids that can be saponified
o Lipids that cannot be saponified ● Saturated fats: bad
● Monounsaturated fats: good
● Polyunsaturated fats: good

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 Triglycerides: Chemical Reactions
[ B ] MEMBRANE LIPIDS: PHOSPHOLIPIDS
● Hydrolysis
o reaction between the triglyceride and water; water ● 3 SUB TYPES:
is used to break triglyceride (fat or oil) Lysis (break o phospholipids
apart) o Sphingophospholipids (glycolipids)
o Cholesterol

PHOSPHOLIPIDS
● play important roles in cell signaling, vesicle trafficking, and
membrane fluidity
● Polar lipids that contains ff:
o One or more fatty acids
o An alcohol unit
o A phosphate group
o A platform molecule

● Saponification
o soap making process; hydrolysis in basic solution
(sodium hydroxide: base) Breaks carbon to oxygen
(use potassium hydroxide = softer or liquid soap)
(sodium hydroxide = hard soap)
▪ LYE - sodium hydroxide and potassium
hydroxide

● Glycerophospholipids (ester bonds)

o contain two fatty acids and a phosphate group
bonded to a glycerol molecule and an alcohol
bonded to the phosphate group

● Hydrogenation
o conversion of liquid oils into solid or semi-solid fats

o alcohol attached to the phosphate group is usually

o Advantages: one of 3 amino alcohols:
▪ increases melting point ▪ Choline (Phosphatidylcholines)
▪ Decreases rate of oxidation (longer shelf ▪ Ethanolamine
life) ▪ Serine
o Components of cell membrane
o amphiphatic (both polar and non-polar)

● Trans fats
o increase the level of LDL (low-density lipoprotein)
cholesterol in the body
o LDL cholesterol enters the arteries where it builds
up plaque ----> athereosclerosis

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● Sphingophospholipids
o Contain the following: o CEREBROSIDES
▪ One fatty acid ▪ simplest sphingoglycolipids
▪ One phosphate group ▪ contain one monosaccharide unit
(glucose/galactose)
▪ Sphigosine molecule
▪ occur primarily in the brain (7% of dry
▪ An alcohol mass)
o Sphingosine: 18-carbon monounsaturated alcohol
o Participate in tissue development, cell recognition
and adhesion, and act as a receptor for toxins

o GANGLIOSIDES
▪ complex sphingoglycolipids
▪ contain a branched chain of up to 7
monosaccharide units
▪ occur in the gray matter of the brain and
myelin sheath

o Sphingomyelins
▪ the alcohol attached to the phosphate
group is choline (alcohol); myelin sheat

▪ C27 with a hydrocarbon tail. A steroid

nucleus, and a hydroxyl group
▪ A steroid
● Fused ring system of three 6-
membered rings and one 5-

MEMBRANE LIPIDS: SPHINGOGLYCOLIPIDS

● Contain the following:
o A fatty acid
o A carbohydrate component
o Sphigosine molecule
o TWO TYPES:
▪ CEREBROSIDES
▪ GANGLIOSIDES

membered ring

MEMBRANE LIPIDS: CHOLESTEROL

● What does it do?
o precursor for other steroid-based lipids
o important in human cell-membranes, nerve tissue
and brain tissue
o important in chemical synthesis of various hormones
and vitamins essential for life
● CHOLESTEROL IN FOOD
o Liver synthesizes almost 1g of cholesterol everyday
o Cholesterol ingestion decreases biosynthetic
cholesterol production
o Animal food contains lots of cholesterol
o Plant food contains negligible amounts of
cholesterol

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 CELL MEMBRANE membrane proteins against a
concentration gradient.
● Up to 80% of plasma membrane is lipid material
● involves expenditure of cellular
● Lipid bilayer: nonpolar tails of phospholipids are in the middle energy
and polar heads are on the surface
● supplied by ATP molecules
● proteins involved are called
pumps

[ C ] EMULSIFICATION LIPIDS: BILE ACIDS

● EMULSIFIER
o substances that act as a stabilizer for emulsions,
preventing liquids that ordinarily don’t mix from
separating
● Cholesterol and Cell Membrane
o Cholesterol helps regulate membrane fluidity ● BILE ACID
(permeability) o steroid acids derived from cholesterol that functions
o Fits between fatty acid chains of the lipid bilayer as an emulsifying agent making dietary lipids soluble
in aqueous environment of the digestive tract
● Membrane Proteins
[ D ] MESSENGER LIPIDS
o Responsible for moving substances across the
membrane ● HORMONES
o Act as receptors that bind hormones and o biochemical susbtances produced by a ductless
neurotransmitters gland that has a messenger function
o Act as markers in processes by which different cells o some hormones are lipids:
recognize each other ▪ STEROID HORMONE - derivative of
cholesterol
▪ EICOSANOID - derivative of fatty acids

MESSENGER LIPIDS: STEROID HORMONES

● Two major classes:
o SEX HORMONES - control production and
secondary sex
o ANDRENOCORTICOID HORMONES - regulate
numerous biochemical processes in the body
● Transport Across Cell Membrane
o Various types of molecules are transported across ● SEX HORMONES
the cell membranes o classified into 3 major sub-classes:
o Three types of transport:
▪ Estrogen - female sex hormones
▪ Passive transport
▪ Androgens -male sex hormones
▪ Facilitated transport
▪ Progestogens - the preganancy hormones
▪ Active transport

1. PASSIVE TRANSPORT: DIFFUSION (passive: does ● ADRENOCORTICOID HORMONES

not need energy) o produced by the adrenal glands
o Types:
▪ process in which a substance moves
across a cell membrane from a region of ▪ MINERALOCORTICOIDS - salt and water
higher concentration to a region of lower balance
concentration ▪ GLUCOCORTICOIDS - control glucose
● no cellular energy expenditure metabolism and counteract inflammation
● only a few types of molecules
MESSENGER LIPIDS: EICOSANOIDS
can cross membranes by this
process (O2, N2, urea and ● Arachidonic acid (OMEGA 6 FA) (20:4) derivatives
ethanol) ● Have profound physiological effects at extremely low
● semi permeable (osmosis) concentrations
2. FACILITATED TRANSPORT ● Are hormone-like molecules
▪ process in which a substance moves ● Exert their effects in the tissues where they are synthesized
across a cell membrane, with the aid of a
● 3 principal types:
membrane protein, from a region of higher
o Prostaglandin
concentration to a region of lower
o Thromboxane
concentration.
o Leukotriene
● no cellular energy expenditure
● no specific protein carriers or
transporters are involved in the
process
3. ACTIVE TRANSPORT
▪ process in which a substance moves
across a cell membrane with the aid of

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 o PROSTAGLANDIN - (nakita sa prostate glands): CLASSIFICATION OF LIPIDS: SAPONIFICATION
involved in pain and inflammatory response
SAPONIFIABLE & NON-SAPONIFIABLE LIPIDS
(noceceptors: perceive and register pain signals)
(brain: hypothalamus)
● SAPONIFIABLE LIPIDS
o lipids that undergo saponification
o contain long chain carboxylic fatty acids that are
linked to an alcoholic functional group through an
ester linkage (FA + ALCOHOL --> ESTER BOND)

o THROMBOXANE - platelet aggregation that will

lead to blood clots (thrombocytes-platelets) o FA + LYE (process)
o (POTTASIUM AND SODIUM HYDROXIDE)
o FA + ALCOHOL
o FA + ESTER BONDS

● COMPONENTS IN ORDER FOR LIPIDS TO BE

SAPONIFIED :
o Fatty acid
o Alcohol
o Ester bonds

o LEUKOTRIENE - WBC (CHEMOTAXIS- migration

of cells to the WBC that releases leukotriene);

[ E ] PROTECTIVE-COATING LIPIDS
● monoester of a long-chain fatty acid and a long-chain alcohol

● plants: water repellents, honey