Dr.

Eman Shaat
Professor
of Medical Biochemistry and Molecular Biology

Lipid chemistry
Lecture 2 (23 slides)
L/O/G/O
*Simple lipids:Triacylglycerols
*Derived lipids: Monoacylglycerol & diacylglycerol.
*Complex lipids: Glycero-phospholipids

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Derived & associated lipids

They include:
1. Fatty acids.
2. Glycerol.
3. Alcohols (other than glycerol).
4. Monoacylglycerol & diacylglycerol.
5. Steroids (sterols, steroid hormones, bile acids).
6. Carotenoids.
7. Fat Soluble vitamins (D, E, K, A).
Definition:
• They are either derived from simple and compound
lipids by hydrolysis (1,2,3,4) or associated with lipids
(5,6,7) and they possess the general physical
characteristics of lipids.

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Monoacylglycerol; monoglycerides (MAG; MG)
Diacylglycerol; diglycerides (DAG; DG)
Triacylglycerol; triglycerides (TAG; TG)

Lipase

Lipase

Lipase

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Diacylglycerol; diglycerides (DAG; DG)
• MAG & DAG are intermediate in TG metabolism.
• DAG acts as signal molecule.
• MAG is more polar than DAG, however TG are hydrophobic.

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 II. Complex lipids
1. Phospholipids
A. Glycerophosphlipids:
i. Phosphatidic acid.
ii. Lecithin (phosphatidyl choline) & Dipalmitoyl
lecithin.
iii. Cephalin (phosphatidyl ethanolamine).
iv. Phosphatidyl Serine.
v. Phosphatidyl inositol.
vi. Diphosphatidyl glycerol or Cardiolipin.
L/O/G/O Vii. Plasmalogens.

B. sphingophospholipids
1. Sphingomyelin.
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II- Complex lipids
1.Phospholipids.
Structure: (alcohol + FA + P +/- Base)
• Their amount remains constant even in starvation (constant
element of fat).
• They can be hydrolysed by phospholipases.
Function:
• major constituents of all cell membranes.
• components of bile.
• signal mediators.
• components of lung surfactant.
• components of lipoproteins

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II- complex lipids
1.Phospholipids.

Properties:
• They are amphipathic
lipids that contain both
polar and non polar part in
the same molecule.
• They form micelles in water
which are involved in
solubilization of lipids in
intestinal lumen helping their
digestion and absorption.
• Liposomes.

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8
II- complex lipids
1.Phospholipids. A. Glycerophospholipids :
• The fatty acids present in phosphoglycerides are: one
mostly saturated in the 1st position of glycerol, the 2nd
is unsaturated fatty acid. Both are high fatty acids.
• Phospholipids because they have phosphoryl bases as
polar, hydrophilic, heads (ionizable heads) in addition to
their hydrocarbon non polar hydrophobic tail are
considered (amphipathic ).
G
L
FA1 Saturated FA
Non-polar tail
Y
unsaturated FA
Non-polar tail
FA 2 C
E
R
O
L
P Base/OH
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Head - polar
 II- complex lipids
1.Phospholipids. A. Glycerophospholipids :
O
Each glycerophospholipid
includes O H2C O C R2
 a polar region:
Pi, & the group (X) are R1 C O CH O
polar head H2C O P O X
 non-polar hydrocarbon
O
tails of fatty acids (R1, R2). glycerophospholipid

Amphipathic
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II- complex lipids
1.Phospholipids. A. Glycerophospholipids
Name and Formula Name of Phospholipid

ethanolamine phosphatidylethanolamine
- OCH2 CH2 N H2 (cephalin)

choline phosphatidylcholine
+ (lecithin)
- OCH2 CH2 N ( CH3 ) 3
serine phosphatidylserine
-
- OCH2 CHCO2
+
N H3
OH OH
inositol
-O Phosphatidyl inositol
OH
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OH
OH
II- complex lipids
1.Phospholipids. A. Glycerophospholipids
Types of Glycerophospholipids
i. Phosphatidic acid:
G
• it is the precursor of all L
FA1
glycerophospholipids. Y
• It is present mainly as FA 2 C
E
intermediate compound R
during the synthesis of O
phosphoglycerols and TG. L
P
• It occurs in very small
amounts in the cell.
• It has no base.
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II- complex lipids
1.Phospholipids. A. Glycerophospholipids :
Tail - nonpolar
ii. Lecithin saturated FA
(phosphatidyl choline): G
FA1
• It is the most L
Y
abundant
FA 2 C
phosphoglyceride in E
animals. unsaturated FA R
O
• The base here is L P Choline
choline.
• It is present in the
animal’s cell Head-polar
membrane.

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 II- complex lipids
1.Phospholipids. A. Glycerophospholipids :
Dipalmitoyl lecithin :
• in this phosphlipid position 1,2 of G palmitic
glycerol are occupied by palmitate. L
Y
• This phospholipid is the major lipid
palmitic C
components of lung surfactants E
(The extracellular fluid lining the alveoli). R
• Surfactants serve to decrease surface O
tension of the fluid layer therefore L P Choline
prevent alveolar collapse.
Infant respiratory distress syndrome:
• caused by lack of surfactant.
• commonly suffered by premature babies
born before 28–32 weeks of gestation.

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II- complex lipids
1.Phospholipids. A. Glycerophospholipids :
iii. Cephalin (phosphatidyl G
FA1
L
ethanolamine): Y
• It is another abundant C
phosphoglycerides which is
FA 2 E
R
also found in animal cell
O
membranes.
• The base is ethanolamine.
L
P ethanolamine

• Cephalin is one of the

important blood clotting G
FA1
factors. L
Y
C
iv. Phosphatidyl Serine: FA 2 E
• It is cephalin-like and present in R
membranes and many tissues. O

• It plays a role in apoptosis.

L
P Serine 15
II- complex lipids
1.Phospholipids. A. Glycerophospholipids :
v. Lipositol (phosphatidyl
O
inositol ):
• The polar head here is the cyclic O H2 C O C R2
hexose sugar alcohol inositol R1 C O CH O
(myoinositol).
H2 C O P O
• It is a membrane lipid.
• (phosphatidyl inositol 4,5- O H
bisphosphate is an important OH OH
constituents of cell membrane H OH
OH H
phospholipid → upon stimulation
phosphatidyl- H H
by a suitable hormone → it is inositol
cleaved into diacylglycerol and H OH
inositol triphosphate, both act as
internal signals or second
messenger). 16
v. Lipositol (phosphatidyl inositol ):
O

O H2 C O C R2
DAG
R1 C O CH O

H2 C O P O
 Inositol-tri-P
O H

OH P
OH
H OH
OH H
phosphatidyl-
Phosphatidyl inositol H H
inositol
4,5-bisphosphate
H P
OH
II- complex lipids
1.Phospholipids. A. Glycerophospholipids :
vi. Diphosphatidyl glycerol or Cardiolipin
• It is composed of 2 molecules of phosphatidic acid attached to a
glycerol molecule.
• Cardiolipin is present in large amounts in the inner membrane of
mitochondria. It is essential for mitochondrial function. ↓↓
cardiolipin, → mitochondrial dysfunction in aging & heart failure.

G FA1 G
P L
L L
O
Y Y
R

FA 2 C C
E
E E
C
FA 2
R R
Y
O O
L
L P L FA1
G
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II- complex lipids
1.Phospholipids. A. Glycerophospholipids :
Vii. Plasmalogens:
Structure: they resemble phosphatidyl ethanolamine but possess an
ether link on the sn-1 carbon instead of the ester link found in
acylglycerols.
• Typically, the alkyl radical is an unsaturated alcohol.
• Somtimes, choline, serine, or inositol may be substituted for
ethanolamine.
Site: Plasmalogens are found in numerous human tissues, with
particular in nervous, immune, and cardiovascular systems.
Present in high concentration in myelin sheath.
Function: they can protect mammalian cells against the damaging
effects of reactive oxygen species.
• they have been implicated as being signaling molecules.
Possible disease links: ↓↓ plasmalogens in the brain in Alzheimer
disease, Parkinson's disease.
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II- complex lipids
1.Phospholipids. A. Glycerophospholipids :

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Phospholipase classes
1. Phospholipase A
 Phospholipase A1: cleaves the sn-1 acyl chain.
 Phospholipase A2: cleaves the sn-2 acyl chain, releasing
arachidonic acid.
2. Phospholipase B: cleaves both sn-1 and SN-2 acyl chains; this
enzyme is also known as a lysophospholipase.
3. Phospholipase C: cleaves before the phosphate, releasing
diacylglycerol and a phosphate-containing head group.
4. Phospholipase D: cleaves after the phosphate, releasing
phosphatidic acid and an alcohol.

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Phospholipase classes

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 O
Lysolecithin
O H2 C O C R1
Phospholipase A2
• is secreted by the pancreas. R2 C O C H O
•It hydrolyzes the ester linkage
between the fatty acid & the hydroxyl CH 2O P O X
on C2 of phospholipids.
phospholipid O
Cobra venoms contain
Phospholipase A2. These venoms, Phospholipase A2 H2 O
injected into the blood, produce O
lysophospholipids that:
 disrupt cell membranes H2 C O C R1 O
lyse blood cells
HO C H O + R2 C O
 neurotoxic effect (degeneration
of the nerve terminal and skeletal
CH 2O P O X
muscle).
Thank you O
Best wishes lysophospholipid
Lysophospholipid fatty23acid