Lipids Function
and Structure
Lipid
I. THE MOLECULAR STRUCTURE OF
LIPIDS
Unlike the proteins, nucleic acids, and
polysaccharides, lipids are not polymers
They are quite small molecules.
The predominance of hydrocarbon chains
(CH2-CH2-CH2--) in their structure, lipids have a
hydrophobic, which explain why they are
insoluble or only poorly soluble in water
They are readily solible in non polar solvent
solvent such as ether, chloroform, and benzene
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cis
3 2 1
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Lipid
DEFINISI
composed of carbon, hydrogen, and
oxygen but have many more hydrogens
than oxygens. Different types of lipids
include the neutral lipids ( fats and oils ),
the phospholipids, steroids, and waxes.
Kelompok heterogen senyawa yang
memiliki sifat tidak larut dalam air; larut
dalam senyawa non polar (eter,
kloroform, benzene)
lemak, minyak, wax, dll
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Lipid
Lipid
Berdasarkan muatan
Neutral Lipid
TG
Kolesterol/ester
Polar lipid
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A. CLASSIFICATION
There are many different methods of classifying
lipids.
In this chapter used classification of lipids and
the biologic functions
FATTY ACIDS
TRIACYLGLYCEROL (triglyceride)
KETONE BODIES
PHOSPHOGLYCERIDES (Phospholipid)
SPHINGOLIPIDS
EIOCOSANOID (Prostaglandins,Thromboxanes,
Leucotrienes)
CHOLESTEROL
STEROID HORMONES
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FATTY ACIDS
A. Nature and Nomenclature
Fatty acids are water-insoluble long-chain
hydrocarbon with one carboxyl group at
the end/beginning of the chain, which may
be saturated or unsaturated (Table 10.1
list some biologically important fatty acids)
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1. Saturated fatty acids (SFA) do not have
double bonds in the chain
Nomenclature.
The systematic name gives the number of carbons,
with the suffix anoic (IND=ANOAT).
Palmitic acid, for example, has 16 carbons and has
the systematic name hexadecanoic acid
Structure
The general formula of saturated fatty acids is CH 3(CH2)n-COOH
Where n specifies the number of methylene groups
between the methyl and carboxyl carbons
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2. Unsaturated Fatty acids have one or more
double bonds
Nomenclature.
The most commonly used system for designating the
position of double bonds in an unsaturated fatty acid
is the delta () numbering system.
(1). The terminal carboxyl carbon is designated
carbon number 1, and the double bond is given the
number of the carbon atom on the carboxyl side of
the double bond.
For example:
Palmitoleic acid has 16 carbons and has a double
bond between carbons 9 and 10. It is designated as
16:1 9 or 16 : 1 :9
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(2) The systematic name gives the number
of carbon atoms,the number of double
bonds, and bears thesuffic enoic
Palmitoleic acid is cis- 9-hexadecenoic acid;
linoleic acid, which has 18 carbons and two
double bonds, is (i.e, all double bond are cis)
cis- 9- 12
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Structure.
Double bonds in naturally occurring Fatty
acids are always in a cis
H H
CH2 C C CH2
cis
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B. SOURCES
Non essential Fatty acids
Essential fatty acids
The melting point of fatty acids is related to chain length and degree of unsaturation.
The longer the chain length, the higher the melting point, and the greater the number of double bonds the lower the melting point
C. PHYSICAL PROPERTIES
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TRIACYLGLYCEROLS : FATS
Structure
Triglycerides or triacylglycerols are triesters
of glycerol and three fatty acids.
The general formula is shown here
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Function
The long hydrocarbon chains of fatty acids
are extraordinarily efficient for energy
storage. In fact, storage of fatty acids in
organism is largely in the form of
triacylglycerols, or fats.
Fatty acids are converted to triglycerides
for transport between tissues and for
storage of metabolic fuel.
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a. The main stores are the fat deposit in fats cells
(adipocytes)
b. Triglycerides have several advantages
(1) Triglycerides are light (less than water). They
complete combustion to CO2 and water release 9
kcal/g as opposed to 4 kcal/g for carbohydrate.
(2)Triglycerides present no osmotic problems to the
cell even when stored in large amounts, because
they are water insoluble.
[Link] of fatty acids. The fatty acids are used by
most tissues, with the exeption of the brain .
Utilization of glycerol. The glycerol, which cannot be
used by adipose tissue cells, is picked up by the liver
as a substrate for gluconeogenesis.
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KETONE BODIES
Keton bodies are small, water soluble,
potential units of acetate: acetone,
acetoacetate and -Hydroxybutirate, all of
which are formed from fatty acids (and
amino acid catabolism):
1. Synthesis of ketone bodies are limited,
for example, in fasting and in starvation
2. During starvation, keton bodies are the
source of fuel
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PHOSPHOLIPIDS
A. FUNCTION
Phospholipids are the major lipid constituent of
cellular membranes and occur in high
concentration in the lipids of glandular organs,
blood plasma, egg yolk.
40 % of the lipids in the erythrocyte membrane
over 95 % of the lipids in the inner
mitochondrial membrane, only about 20% the
inner mitochondrial membrane are cardiolipin,
a phosphoglyceride
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B. STRUCTURE OF PHOSPHOGLYCERIDE
Phosphoglycerides are triesters of
glycerol 3-phosphate
O
CH2 O C R1
O
R2 C O CH
O
CH2 O C R3
O
O
CH2 O C R1
R2 C CH
CH2 O P OH
OH
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Glycerophospholipid Structure
O
CH 2 O C R 1
O
O
CH O C R 2
R 3 O P O CH 2
OH
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C CLASSIFICATION OF PHOSPHOGLYCERIDE
1. Phosphatidylcholine (lecithin)
2. Phosphatidylethanolamine (a cephalin)
3. Phosphatidylserine
4. Phosphatidylinositol
5. Cardiolipin
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D. PROPERTIES OF PHOSPHOGLYCERIDES
1.
Amphipatic
Phosphoglycerides possessing both
hydrophilic and hydrophobic groups
2. Amphoteric
Phosphoglycerides bering both negatively
charged and positively charged groups
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SPHINGOLIPIDS
The greatest concentration of sphingolipids
is found in the CNS, particularly in white
matter
Types of sphingolipids: sphingomyelin and
the glycosphingolipids.
All sphingolipids are derived from
sphingosine.
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A. SPHINGOMYELIN
Function. Sphingomyelin are the major
phospholipid component of membranes in
neural tissue
Structure. Sphingomyelin are the only
sphingolipids that contain phosphate and
have no sugar moiety
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Sphingosin
O
OH
CH3 (CH2)12 CH = CH C CH NH C R
CH2
O
Phosphic acid
Fatty acid
O = P OH
+
O CH2 CH2 N(CH3)3
Cholin
Sphingomyelin
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B. GLYCOSPHINGOLIPID
Sphingolipids that contain carbohydrate
moieties are known as glycosphingolipids
have been distinguished : cerebrosides and
Ganglioside
1. Cerebrosides are ceramides
monohexosides, the most important being
galactocerebroside and glucocerebroside.
Cerebrosides are found in neural tissue
membrane, particularly the myelin sheath .
2. Gangliosides are ceramide
oligosaccharides, they contain one or more
neuraminic residue
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Sia
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C. SPHINGOLIPIDOSES
There are a number of inherited genetic
disorders referred to as lipid storage
diseases in which there is a deficiency of
an enzyme.
For example : Gauchers disease,
Niemann-Pick disease and Tay-Sachs
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EICOSANOIDS
Eicosanoids are products of the
metabolism of the 20-carbonpoliunsaturated fatty acid arachidonic acid
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A. PROSTAGLANDINS
1. Structure .
Prostaglandins are analogs of prostanoic
acids
OH
COOH
Prostaglandin E1
OH
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2. Function
a. Prostaglandins are widely distributed in
tissues, but their role is not yet fully understood .
At very low concentrations prostaglandins have
been shown biologic activies, including:
(1) Smooth muscle contraction and relaction
(2) Gastric secretion
(3) Platelet aggregation
(4) Inflamatory response
(5) Response to trophic hormone (FSH & LH)
(6) Sodium and water retention by kidney
tubules
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B THROMBOXANES
1. Structure.
Thromboxanes are also analogs of
prostanoic acids, but they possess a sixmembered, oxygen containing ring
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2. Function
Thromboxane A2 (TX2) is produced by
platelets; it causes contraction of arteries
and platelet aggregation.
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STEROIDS
Steroids are lipids that contain four fused carbon
rings that form the steroid nucleus
cyclopentanoperhydrophenantrene
A.
Sterol are a class of steroid in the human
body
1. A hydroxyl group at carbon 3 (C-3)
2. An aliphatic chain of at least eight
carbons at C-17
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B. Cholesterol is the mayor sterol in the
human body.
1.
It is a structural component of cell
membranes and plasma lipoprotein
2. It is precursor from wich steroid
hormones and bile acids are synthesized
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a. Steroid hormones
(1) The steroid hormones produced in humans
are formed and secreted by the adrenal
cortex, the testis, the ovary, and the
placenta.
In addition, the steroid compound, 1,25dihydroxycholecalciferol is form in the kidney.
The structures are
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(2) The adrenal cortex produces hormones
with two kind of physiologic activities.
(a) The zona fasciculate of the adrenal
cortex primarily produces cortisol in humans,
they are glucocorticoid and cortisol
(b) The zona glomerulosa produces
mineralocorticoid, that is aldosteron, which
controls the reabsorption of Na+ in the
kidney.
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(3). Gonadal steroids
(a)Testis produced testosterone
CH3OH
CH3
Testosterone
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b. Bile acids
The predominant bile acids in humans are cholic,
chenodeoxycholic, deoxycholic, and lithocholic
acids (Figure 8-5)
1. Structure
a)
The bile acids are C-24 steroids and are
derived from cholesterol (a C-27 steroid) by
scissor of the side chain, which leaves:
(i) A C-24 carboxyl group with the loss of
three carbons
(ii) Saturation on 5 double bond of
cholesterol
(iii) Hydroxylation of the steroid nucleus
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b) Cholic and chenodeoxycholic acids are
formed in the liver from cholesterol and are
the primary bile acids.
Deoxycholic acids and lithocholic acids are
known as the secondary bile acids because
they are formed from the primary bile acids
c). The bile acids are conjugated to glycine or
taurine in the liver to form glycol or
taurocholate
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2. Function.
Continuos conversion of cholesterol to
bile acids prevents the excessive
accumulation of cholesterol in tissues.
Bile acids are secreted with faeces
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1. storage form of metabolic fuel
2. transport form of metabolic fuel
3. part of the outer coat between the body of
the organism and the environment, providing
protection in bacteria, plants, insects and
vertebrates
4. structural components of membranes n
neural system
5. Precursor of vitamins, hormons
6. Cell cignaling
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SELESAI
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