Lipids Introduction and their Nomenclature
- 1. Introduction to Lipids and Nomenclature Course: Principles of Biochemistry By; M. Sheraz Yasin Lecturer, Institute of Biochemistry and Biotechnology, University of Veterinary and Animal Sciences, Lahore.
- 2. LIPIDS • DEFINITION • CLASSIFICATION (STRUCTURAL AND FUNCTIONAL) • FUNCTIONS OF DIETARY LIPIDS • CHEMICAL NATURE OF FATTY ACIDS • NOMENCLATURE – Saturated Fatty acids – Unsaturated Fatty acids • Positional and geometric isomerism - Essential Fatty acids
- 3. DEFINITION Heterogeneous group of organic compounds which are • relatively insoluble in water, • but soluble in organic solvents such as ether, benzene and chloroform.
- 4. CLASSIFICATION:( STRUCTURE) 1. Simple Lipids a. Fats & Oils (TRIGLYCERIDES) F.A. esters with Glycerol ( Triacyglycerols ) b. Waxes F.A. esters of long chain mono- hydroxy alcohols (Cetylpalmitate)
- 5. CLASSIFICATION:( STRUCTURE) Contd 2. Complex Lipids a. Phospholipids (contain phosphate group) Glycerophospholipids Alcohol is Glycerol (e.g.phosphatidylcholine) Sphingophospholipids Alcohol is sphingosine (C18 amino alcohol) b. Glycolipids Contain F.A, Sphingosine and Carbohydrate c. Other Complex Lipids Sulfolipids, Aminolipids, Lipoproteins
- 6. CLASSIFICATION (Contd) 3. PRECURSOR & DERIVED LIPIDS F.A, Alcohols & Aldehydes 4. MISCELLANEOUS LIPIDS Fat Soluble Vitamins, Carotenoids,Steroids (Cholesterol, Steroid hormones, Bile Salts) Eicosanoids
- 7. CHOLINE
- 8. BILE SALTS A B C D (cholesterol)
- 9. CLASSIFICATION (Functional) LIPIDS • FATTY ACIDS • TRIGLYCERIDES • PHOSPHOLIPIDS • SPHINGOLIPIDS FUNCTIONS • Metabolic fuel; component of several other classes of lipids • Main storage form of fatty acids and chemical energy • Components of membranes; sources of arachidonic acid, inositol trisphosphate (IP3), and diglyceride (DAG) for Signal Transduction • Components of membranes; Imp. in signal transduction
- 10. CLASSIFICATION (Functional) Contd • CHOLESTEROL • BILE SALTS • Component of membranes; precursor of bile salts and steroid hormones • Lipid digestion and absorption; main product of cholesterol metabolism
- 11. FUNCTIONS CONTD • STEROID HORMONES • EICOSANOIDS Prostaglandins, Thromboxanes, Leukotrienes • VITAMINS A,D,E,K • Intracellular signals that regulate gene expression in target cells • Regulators of physiological /immunological functions. Local hormones • Vision; calcium metabolism; antioxidants; blood coagulation
- 12. FUNCTIONS OF DIETARY FATS 1. Concentrated sources of energy 9 Kcal/g vs.4 Kcal/g for carbohydrates and proteins 2. Carriers of fat-soluble vitamins A,D,E,K 3. Sources of Essential Fatty Acids Linoleic acid 18:2 n-6 (w6) α- Linolenic acid 18:3 n-3(w 3) 4. Impart taste and flavor to foods
- 13. FATTY ACIDS • Monocarboxylic • Usually straight-chain having even number (2-26) of carbon atoms • Most common are C12-C22 • Short-Chain (2-4 C atoms) • Medium- Chain (6-10 C atoms) • Long-Chain (12-20 C atoms) • Very long-Chain (C22 and above)
- 14. Saturated Fatty Acids Most Commonly occurring are • Myristic Acid (14:0) • Palmitic Acid (16:0) • Stearic Acid (18:0) Since the carboxylic group is ionized at physiological pH, they exist as carboxylate ion e.g. palmitate CH3 (CH2)14-COOH CH3(CH2)14-COO- + H+ pKa 4.8
- 15. UNSATURATED FATTY ACIDS Contain carbon to carbon double bonds. MUFA • Mono-unsaturated (1 double bond) OLEIC ACID 18:1 ( high concentrations in olive oil ) PUFA • Polyunsaturated (> 1 double bond ) LINOLEIC ACID, 18:2 α-LINOLENIC ACID, 18:3 ARACHIDONIC ACID 20:4
- 16. STRUCTURE OF SATURATED FATTY ACIDS
- 17. POSITIONAL AND GEOMETRIC ISOMERISM IN UNSATURATED FATTY ACIDS
- 18. POSITIONAL AND GEOMETRIC ISOMERISM IN UNSATURATED FATTY ACIDS • cis configuration mostly present in naturally occurring fatty acids • cis double bond causes a bend. Therefore the hydrocarbon chain cannot be packed as tightly as in trans fatty acids • Melting points of fatty acids with cis double bonds are lower than the corresponding trans fatty acids
- 19. POSITIONAL AND GEOMETRIC ISOMERISM IN UNSATURATED FATTY ACIDS (CONTD) MELTING TEMPERATURE Stearic acid 18:0 69oC Elaidic acid 18:1 trans ∆9 44oC Oleic acid 18:1cis ∆9 13oC Trans Fatty acids, unlike Cis isomers, increase plasma cholesterol levels ( total and LDL ) and decrease HDL-cholesterol Current concerns about trans fatty acid intake and attempt to ↓ their dietary intake
- 20. NOMENCLATURE Fatty acids Common (trivial) names Systematic names (derived from parent hydrocarbons) • Saturated fatty acids end with anoate Palmitate is hexadecanoate • Unsaturated fatty acids end with enoate The position of the double bond (counting from the –COOH toward CH3 group) and its geometric configuration (cis or trans) is indicated The palmitoeate will be called cis- ∆9 –hexadecenoate.
- 21. NOMENCLATURE (CONTD) There are 2 systems to number the position of carbon to carbon double bonds 1. The ∆ system, according to which one starts counting from carboxyl carbon as C1 and goes toward the methyl carbon e.g. Palmitoleate will be called 16:1 ∆9 10 9 C O O 10 9 C O O CH3 ω carbon or nth carbon 1 2 3 α β
- 22. NOMENCLATURE (CONTD) 2. The ω- (or n- ) system which starts counting from the CH3 carbon as C1. The position of the first double bond is indicated e.g. palmitoleate will be 16: 1 ω-7 (n-7) 1 CH3 ω carbon or nth carbon 7 8 C O O
- 23. ESSENTIAL FATTY ACIDS • Linoleic acid 18:2 ∆9,12 or 18 :2 ω -6 (n- 6) • α-Linolenic acid 18 :3 ∆9,12 ,15 or 18:3 ω-3 (n-3) • These fatty acids cannot be synthesized by the human body and therefore have to be provided in the diet. • Insufficient amounts in the diet result in EFA Deficiency (very rare) infants: scaly dermatitis, growth retardation Also present in CYSTIC FIBROSIS patients (Vignette 2)
- 24. Other Important PUFA’S • Arachidonic Acid 20:4 ω -6 Present in animal tissues A common precursor of eicosanoids • Eicosapentaenoic Acid 20:5 ω -3 Present in fish oils. Also a precursor of different class of eicosanoids • Docosahexaenoic acid 22:6 ω -3 Present in fish oils • Omega 3 fatty acids are important components of developing brain and retina
- 25. Heath benefits of ω-3 Fatty acids • Higher intakes associated with low risk of cardiovascular disease • Higher intakes can reduce the risk of sudden heart attacks in individuals with cardiovascular disease • Reduce blood triglyceride levels • May be helpful in treatment of depression and other psychiatric diseases • May reduce joint tenderness and requirements of anti-inflammatory medications in patients with arthritis
- 26. Contd • Members of different families of PUFA (ω3, ω6, ω7, ω9) Member of one family cannot be converted into another family 20:4 ω -6 22:5 ω-3 • Members of the same family can be chain elongated and desaturated 18:2 ω -6 20:4 ω -6 C2+ 2∆ S Linoleic Acid Arachidonic Acid 18:3 ω-3 α-Linolenic Acid * the additional double bonds are always added towards the carboxyl end (not towards the methyl end) of the pre- existing double bonds.
- 28. Lippincott’s
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