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LIPIDS II. Common Name. Systematic Name. Formula. Common source. CLASSIFICATION OF FATTY ACIDS PRESENT AS GLYCERIDES IN FOOD FATS. I. Saturated Fatty Acids. Butanoic. CH 3 (CH 2 ) 2 COOH. butterfat. Butyric. butterfat, coconut and palm nut oils. Caproic. Hexanoic.
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Common Name Systematic Name Formula Common source CLASSIFICATION OF FATTY ACIDS PRESENT AS GLYCERIDES IN FOOD FATS I. Saturated Fatty Acids Butanoic CH3(CH2)2COOH butterfat Butyric butterfat, coconut and palm nut oils Caproic Hexanoic CH3(CH2)4COOH CH3(CH2)6COOH coconut and palm nut oils, butterfat Caprylic Octanoic Capric coconut and palm nut oils, butterfat Decanoic CH3(CH2)8COOH Lauric Dodecanoic CH3(CH2)10COOH coconut and palm nut oils, butterfat Tetradecanoic coconut and Palm nut oil, most animal and plant fats Myristic CH3(CH2)12COOH Palmitic Hexadecanoic CH3(CH2)14COOH practically all animal and plant fats Stearic CH3(CH2)16COOH animal fats and minor component of plant fats Octadecanoic Arachidic Eicosanoic CH3(CH2)18COOH peanut oil
Common Name Systematic Name Formula Common source Arachidonic 5,8,11,14-Eicosatetraenoic C19H31COOH traces in animal fats II. Unsaturated Fatty Acids A. Monoethenoic Acids C17H33COOH plant and animal fats Oleic Cis 9-octadecenoic C17H33COOH animal fats Elaidic Trans 9-Octadecenoic B. Diethenoic Acids peanut, linseed, and cottonseed oils Linoleic 9,12-Octadecadienoic C17H31COOH C. Triethenoid Acids 9,12,15-Octadecatrienoic C17H29COOH linseed and other seed oils Linolenic Eleostearic 9,11,13-Octadecatrienoic C17H29COOH peanut seed fats D. Tetraethenoid Acids fish oils Moroctic 4,8,12,15-Octadecatetraenoic C17H27COOH
Common Name Systematic Name Formula Common source Arachidonic 5,8,11,14-Eicosatetraenoic C19H31COOH traces in animal fats Common and Systematic Names of Fatty Acids A. Monoethenoic Acids Cis 9-octadecenoic C17H33COOH plant and animal fats Oleic Trans 9-Octadecenoic C17H33COOH animal fats Elaidic B. Diethenoic Acids 9,12-Octadecadienoic C17H31COOH peanut, linseed, and cottonseed oils Linoleic C. Triethenoid Acids C17H29COOH linseed and other seed oils Linolenic 9,12,15-Octadecatrienoic 9,11,13-Octadecatrienoic C17H29COOH peanut seed fats Eleostearic D. Tetraethenoid Acids Moroctic 4,8,12,15-Octadecatetraenoic C17H27COOH fish oils
Biomedical importance of fatty acids: • Human body can synthesize various fatty acids with the exception of; • “linoleic” and “linolenic” acids; this is because body tissues cannot introduce double bonds beyond the Δ 9 position. • In contrast, plants are able to introduce double bonds at the Δ 12 and Δ 15 positions. • Therefore, linoleic acid and linolenic acid are considered as nutritionally essential fatty acids, • and must be supplied in a diet of plant origin or from animals that have consumed these plant fats.
1. Dietary ώ -3 fatty acids (in fish oil and plant fats) • can reduce serum triglycerides, thrombosis and • the risk of cardiovascular mortality. 2- ώ -6 fatty acids (in olive oil and corn oil) lower plasma cholesterol and protect against coronary heart disease. 3-Generally, a high ratio of polyunsaturated fatty acids to saturated fatty acids in the diet is a major factor to prevent coronary heart disease.
Eicosanoids: Prostaglandins, Leukotrienes, and Thromboxanes • Fatty acids which can’t be synthesized by the body are essential fatty acids • Linoleic acid is an essential fatty acid required to make arachadonic acid • Arachidonic acid (20 C) is the eicosanoid precursor • Eicosanoids are three groups of structurally related compounds • Prostaglandins • Leukotrienes • Thromboxanes
Prostaglandins • Potent biological molecules • They act like hormones in controlling the body’s processes • Structure • Synthesized from 20-carbon unsaturated fatty acids • Cyclic compounds including a 5-carbon ring • Names are based on ring substituents and number of side-chain double bonds • Made in most tissues • Exert their effects on cells that produce them and cells in the immediate vicinity
Biological Processes Regulated by Eicosanoids • Blood clotting • Thromboxane A2 stimulates constriction of blood vessels and platelet aggregation • Prostacyclin dilates blood vessels and inhibits platelet aggregation • Inflammatory response • Prostaglandins mediate aspects of inflammatory response • Reproductive system • Stimulation of smooth muscle by PGE2
Biological Processes Regulated by Eicosanoids • Gastrointestinal tract • Prostaglandins inhibit gastric secretion • Inhibition of hormone-sensitive lipases • Prostaglandins increase secretion of protective mucus • Kidneys • Prostaglandins dilate renal blood vessels • Results in increased water and electrolyte excretion • Respiratory tract • Leukotrienes promote the constriction of bronchi • Prostaglandins promote bronchodilation
Aspirin and Prostaglandins Aspirin inhibits prostaglandin synthesis by acetylating cyclooxygenase, an enzyme necessary for prostaglandin synthesis
Test your understanding 1- Fatty acids are • Soluble in water • Esters of long chain alcohol • Saturated hydrocarbons • Long chain carboxylic acids • None of the above
Test your understanding 2- Saturated fatty acids are those: • Containing no carbon carbon double bonds. • Contain carbon carbon double bond. • Mainly solid at room temperature. • Both b and c. • Both a and c. 3- Unsaturated fatty acids are those: • Containing no carbon carbon double bonds. • Contain carbon carbon double bond. • Liquid at room temperature. • Both b and c. • Mainly solid at room temperature.
Test your understanding 4- Arachidonic acid is a: • 20:1 Δ 5 fatty acid • 20:2 Δ 5,14 fatty acid • 20:3 Δ 5,8,11,14 fatty acid • 20:4 Δ 5,8,11,14 fatty acid • 20:5 Δ 5 fatty acid
Test your understanding 5- Linoleicacid is a polyunsaturated fatty acids, that means: • It has no double bond • It is solid at room temperature • It has one double bond • It is nonessential fatty acid • It is liquid at room temperature
Test your understanding 6- Regarding prostaglandins all of the following is true except: • Synthesized from arachidonic acid • Increase secretion of gastric protective mucus • Dilate renal blood vessels • Stimulate platelets aggregation • Mediate aspects of inflammatory response