17 Lipids - Structure and Biological Significance

17 Lipids - Structure and Biological Significance - Lipids:...

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Lipids: Structure and Biological Significance HNFE 3025 Fall 2009
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Classification of Biologically Important Lipids Non-esterified Fatty acids – Saturated fatty acids – Unsaturated fatty acids (MUFA, PUFA, n-3 and n-6, trans) Glycerolipids – Mono-, di- and triacylglycerols Glycerophospholipids – Lecithin Glycoglycerolipids Sphingolipids Isoprenoids (carotenoids, retinoids) Biological waxes Sterols (cholesterol, hormones, bile acids) Eicosanoids Other lipids 2
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Fatty Acids – Simplest of all Lipids Almost invariably an even number of C atoms From 2-40 carbon atoms, but more commonly 12-22 C atoms Short chain FAs have 6 or fewer C atoms Medium chain FAs have 8-14 C atoms Long chain FAs (LCFA) have more than 14 C atoms Classification Saturated: no carbon to carbon double bonds Unsaturated with one or more double bonds One double bond – monounsaturated (MUFA) Two or more double bonds – polyunsaturated (PUFA) FFA – free fatty acids (aka NEFA) are found in plasma ~0.5-1.0 mM bound to blood protein albumin 3
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Fatty Acid Structure Carboxylic (-COOH) end and methyl (-CH 3 ) end Hydrophilic, polar end (carboxylic end) Hydrophobic, nonpolar end Unsaturated FAs are typically in cis configuration Affects molecular configuration trans – linear cis – folding or kinking configuration 4 Fig. 5-1, p. 132
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Fatty Acid Nomenclature Two shorthand notation systems Delta (Δ) System Denotes chain length and number of double bonds Lists position of all double bonds Omega (ω) System Denotes chain length and number of double bonds Gives position of first double bond from the methyl end Scientific names Trivial names 5
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Shorthand Naming Systems 6 Fig. 5-2, p. 133 Trivial name Scientific name: 9,12-octadecadienoic acid
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Trivial Names Dominate Trivial, shorthand and scientific names for some common FAs in human nutrition 7 Laurate 12:0 Dodecanoic acid Myristate 14:0 Tetradecanoic acid Palmitate 16:0 Hexadecanoic acid Stearate 18:0 Octadecanoic acid Palmitoleate 16:1 Δ 9 9-Hexadecenoic acid Oleate 18:1 Δ 9 9-Octadecenoic acid
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Common PUFAs 8 Linoleate 18:2 ∆ 9 ,1 2 ( 9,12-Octadecadienoic acid) Arachidonate 20:4 ∆ 5 ,8 ,1 1 ,1 4 (5,8,11,14-Eicosatetraenoic acid) Docosahexaneoic acid (DHA) 22:6 ∆ 4 ,7 ,1 0 ,1 3 ,1 6 ,1 9 Eicosapentaenoic acid (EPA)
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This note was uploaded on 03/23/2010 for the course HNFE 3025 taught by Professor Mwhulver during the Spring '10 term at Virginia Tech.

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17 Lipids - Structure and Biological Significance - Lipids:...

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