LIPIDS The term lipid denotes a heterogeneous group of substances, associated with living systems, which have the

e common property of insolubility in non-polar solvents. fatty acids (RCOOH)

Some generalizations: 1. nearly all naturally occurring fatty acids have an even number of carbon atoms; most have between 12 and 20 in an unbranched chain 2. the most abundant are palmitic, stearic and oleic acids 3. the essential fatty acids are linoleic, linolenic and arachidonic acids 4. in most unsaturated fatty acids, the cis isomers predominate; trans isomers are rare 5. as the number of carbon atoms in a saturated fatty acid increases, its melting point increases 6. unsaturated fatty acids have lower melting points than do their saturated counterparts 7. the greater the degree of unsaturation in a fatty acid, the lower the melting point

Common fatty acids Designation 4:0 6:0 8:0 10:0 12:0 14:0 16:0 18:0 20:0 22:0 16:19 18:19 18:29,12 18:39,12,15 18:36,9,12 20:45,8,11,14 22:57,10,13,16,19 Molecular Formula C3H7COOH C5H11COOH C7H15COOH C9H11COOH C11H23COOH C13H27COOH C15H31COOH C17H35COOH C19H39COOH C21H43COOH C15H29COOH C17H33COOH C17H31COOH C17H29COOH C17H29COOH C19H31COOH C21H33COOH Common name Butyric acid Caproic acid Caprylic acid Capric acid Lauric acid Myristic acid Palmitic acid Stearic acid Arachidic acid Behenic acid Palmitoleic acid Oleic acid Linoleic acid -Linolenic acid -Linolenic acid Arachidonic acid Clupanodonic acid Systematic name Butanoic acid Hexanoic acid Octanoic acid Decanoic acid Dodecanoic acid Tetradecanoic acid Hexadecanoic acid Octadecanoic acid Eicosanoic acid Docosanoic acid 9-hexadecenoic acid 9-octadecenoic acid 9,12-octadecadienoic acid 9,12,15-octadecatrienoic acid 6,9,12-octadecatrienoic acid 5,8,11,14-eicosatetraenoic acid 7,10,13,16,19docosapentaenoic acid

Triacylglycerols
H O H C O C R1

H C O C R2 O H C O C R3 H O

hydrolysis yields glycerol and 3 fatty acids Phosphoacylglycerols (phospholipids)

H O H C O C R1

R2

C O C H O H O H C O P O X O
-

phosphatidylethanolamine phosphatidylcholine (lecithin) phosphatidylserine phosphatidylinositol

ethanolamine choline serine inositol

CH2CH2NH3
+

CH2CH2N (CH3)3

CH2CH(NH3 )COO
H OH H OH H OH OH H OH

phosphatidylglycerol

glycerol

CH2CH(OH)CH2OH

phosphatidic acid yields glycerol, 2 fatty acids and phosphoric acid on hydrolysis phosphoacylglycerols are important components of biological membranes

Waxes (RCOOR) esters of long chain carboxylic acids and long chain alcohols protective coatings for plants and animals

Sphingolipids
CH CH(CH2)12CH3 CHOH

CH CH(CH2)12CH3
CH CH(CH2)12CH3 CHOH CHNH2 CH2OH sphingosine

O CHNH C R

CHOH O CHNH C R CH2OH

a ceramide

O CH2OP O CH2CH2N (CH3)3 O

+

a sphingomyelin

occur in cell membranes in the nervous system Glycolipids contain a carbohydrate bound to an alcohol group of a lipid by a glycosidic linkage a ceramide is usually the parent compound for glycolipids In a cerebroside, a glycosidic bond is formed between the primary alcohol group of the ceramide and a sugar residue. Cerebrosides are found in cell membranes in brain and nerve cells.

CH CH(CH2)12CH3 CHOH O CHNH C R CH2

CH2OH

O
OH OH OH

Gangliosides are examples of glycolipids with a complex carbohydrate moiety containing more than 3 sugars, one of which is always sialic acid. They have net negative charges at neutral pH and are found in nerve tissues.

Steroids Cholesterol is a highly hydrophobic molecule, widespread in biological membranes especially in animals. It is a precursor of other steroids (e.g. steroid hormones, bile acids) and vitamin D. Cholesterol plays a role in atherosclerosis (condition in which large deposits block the blood vessels and lead to heart disease). Bile acids/salts synthesized in the liver from cholesterol principal pathway for the elimination of cholesterol from the body emulsify fats in the intestine, aid digestion and absorption of dietary fats Steroid hormones Hormones are substances produced by the endocrine glands of higher animals which are secreted into the blood and carried to all parts of the body where they regulate many metabolic functions of the organism by influencing the rate of synthesis of enzymes and other proteins, affecting the rate of enzyme catalysis, altering the permeability of cell membranes. Androgens (male sex hormones; the most important is testosterone which promotes normal growth of primary sex characteristics and the development of secondary sex characteristics) Estrogens (female sex hormones; changing rates of secretions of these hormones causes the periodic change in the ovaries and the uterus; estradiol, which is responsible for the development of secondary sex characteristics, is one of the most important estrogens) Progesterone (female sex hormones; synthesized in the ovaries from cholesterol, prepares the uterus wall to accept a fertilized egg and maintain pregnancy) Adrenocorticoid hormones Mineralocorticoids (e.g. aldosterone; affect H2O and electrolyte balance by stimulating renal Na+ absorption; overall effect is to retain Na+ and excrete K+) Glucocorticoids (e.g. cortisol; affect carbohydrate and protein metabolism; stimulate the process of gluconeogenesis by promoting the catabolism of proteins)

Fat-soluble vitamins Vitamin A (retinol) (site of primary photochemical reaction in vision) Vitamin E (tocopherol) (antioxidant; for prevention of muscular dystrophy) Vitamin K (required in blood clotting) Vitamin D (cholecalciferol) (involved in Ca and P metabolism; causes resorption of bone with release of Ca2+ and PO43- in the blood)

Prostaglandins - 20 C fatty acids synthesized in cell membranes from arachidonic acid - function to carry out messages that cells receive from hormones - have a wide range of physiological activities (e.g. control of blood pressure, stimulation of smooth muscle contraction, induction of inflammation, inhibition of aggregation of platelets) - aspirin, cortisone and other steroids inhibit prostaglandin synthesis and therefore have anti-inflammatory effects - Leukotrienes , like prostaglandins, are derived from arachidonic acid. These are found in white blood cells (leukocytes) and have 3 conjugated double bonds. They are known to constrict smooth muscle, especially in the lungs. - Thromboxanes, also derivatives of arachidonic acid, contain cyclic ethers as part of their structures. The most widely known member of the group (thromboxane A2) is known to induce platelet aggregation and smooth muscle contraction.