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m2 Biochem
m2 Biochem
HYDROLYZABLE LIPIDS
Fatty Acids
• MONOUNSATURATED
o (Monoethenoid,
monoenoic) acids
containing double bond
• POLYUNSATURATED
Omega-n Nomenclature:
o (polyethenoid, polyenoic)
alternative nomenclature applied in human
acids containing two or
nutrition
more double bonds
n = the carbon at which the first double
bond occurs in the carbon chain • EICOSANOIDS
(beginning at the end of the chain
o Derived from eicosa- (20
containing methyl group) 22
Linolenic acid is called an omega-3 acid, because carbon) polyenoic fatty
of the position of the first C=C in the nonpolar acids
chain. o Arachidonic acid is the
major precursors
-Prostanoids
-Leukotrienes (LTs )
-Lipoxins (LXs)
PROSTANOIDS
Humans require omega-3 linolenic acid o Are part of a family of biologically active
Essential FA lipids derived from the twenty-carbon
Precursor in the synthesis of eicosapentaenoic essential fatty acids or eicosanoids;
acid (EPA) and docosahexaenoic acid (DHA) o Relates to the products of the
cyclooxygenase pathway
PHYSICAL and PHYSIOLOGIC PROPERTIES OF FATTY
o Prostanoic acid as the central structural
ACIDS
element
• MELTING POINT o Three main groups ▫
Prostaglandins (PGs)
–of even numbered carbon fatty
Prostacyclins (PGIs)
acids:
Thromboxanes (TXs)
o increases with chain
length
o decreases according to
unsaturation
• TRIACYLGLYCEROL
– containing three saturated fatty
acids of 12 C or more is solid at
body temperature
o 18:2 fatty residues are
liquid at body
temperature to below 0°C
• MEMBRANE LIPIDS
THROMBOXANES
• Cyclopentane ring interrupted with an oxygen
atom;
• The two major thromboxanes are
thromboxane A2 and thromboxane B2
• Its role is in clot formation (thrombosis)
An unsaturated triacylglycerol:
General Features
B. GLYCOLIPIDS
Phosphoacylglycerols
• CHOLINE LYSOPHOSPHOLIPIDS
– important in nervous transmission,
as acetylcholine, and as a store of – Are intermediates in the
labile methyl group metabolism of phosphoglycerols
– Important in the metabolism and
• DIPALMITOYL LECITHIN interconversions of phospholipids
– Effective surface-active agent (lysophosphatidylcholine)
– Major constituent of the – Found in oxidized lipoproteins
surfactant preventing adherence, and can promote atheroschlerosis
due to surface tension, of the Sphingomyelins
inner surfaces of the lungs.
– Absence: Respiratory distress – Sphingomyelins do not contain a
syndrome glycerol backbone, they have a
sphingosine backbone instead.
PHOSPHATIDYLETHANOLAMINE (Cephalin) and – Sphingomyelins do not contain an
PHOSPHOTIDYLSERINE (tissues) ester; their single fatty acid is bonded
– Ethanolamine or serine replaces to the backbone by an amide bond.
choline
– PHOSPHOTIDYLSERINE (tissues) –
Serine replaces choline
PHOSPHATIDYLINOSITOL
PLASMALOGENS
• Precursor of second messenger
• 10% of the phospholipids of the
• Inositol is present as
brain and muscle
stereoisomer, myoinositol
• Resemble
• Phosphatidylinositol 4,5-
phosphatidylethanolamine (ether
biphosphate important
linked)
constituent of the cell membrane
• Alkyl radical is an unsaturated
phospholipids and cleaved into
alcohol
diacylglycerol and inositol
• Choline, serine or inositol ---- may
triphosphate (internal signals or
be substituted for ethanolamine
second messenger)
CARDIOLIPIN
• bisphosphatidyl glycerol
• Is an important component of the
inner mitochondrial membrane,
where it constitutes about 20% of
the total lipid
• It serves as an insulator and
stabilizes the activity of protein
SPHINGOMYELINS
• Distributed in every tissue of the body
• Found in large quantities in brain
o – Nervous tissues (brain)
and nerve tissues
o – Plasma membrane – cell
• Yields fatty acid, phosphoric acid,
surface carbohydrates
choline, and a complex amino
• Glycosphingolipids
alcohol, sphingosine
o – Major glycolipids in animal
tissues
o – Ceramide + sugar
• GALACTOSYLCERAMIDE
o – Major sphingolipid of brain
& other nervous tissue, C24
fatty acids
• GANGLIOSIDES
• Are complex glycosphingolipids
derived from glucosylceramide
that contain in addition one or
more molecules of a sialic acid
• NEURAMINIC ACID
Derived Lipid
• Fatty acids
• Glycerol
GLYCOLIPIDS (GLYCOSPHINGOLIPIDS)
• Steroids •Two important classes of steroid hormones include
• Other alcohols sex hormones and adrenal cortical steroids.
• Fatty aldehydes
•The female sex hormones are estrogens and
• Ketone bodies
progestins.
• Hydrocarbons, Lipid-soluble
vitamins •The male sex hormones are called androgens.
• Hormones * Acylglycerols,
cholesterol, and cholesteryl ester Steroid Hormones Female Sex Hormones: Estrogens
are uncharged, so are termed •The estrogens estradiol and estrone control
NEUTRAL LIPIDS development of secondary sex characteristics,
NON-HYDROLYZABLE LIPIDS regulate the menstrual cycle, and are made in the
ovaries.
Focus on Health & Medicine Cholesterol
Steroids
Steroid Hormones
Vitamin A
Vitamin D
Aldosterone
PEROXIDATION
ANTIOXIDANTS
CLASSES OF ANTIOXIDANTS
• Preventive antioxidants
o reduce the rate of chain initiation.
Catalases and Peroxidases –
glutathione peroxidase
(reacts with ROOH) –
Selenium – EDTA, DTPA
(Chelators of metal ions)
• Chain-breaking antioxidants