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Learning Objectives
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n Lipids (fats) include a diverse range of compounds that have nonpolar groups that make them relatively insoluble in water (hydrophobic)
n Simple lipids – FA, TG, Waxes n Compound lipids – Phospholipids, glycolipids, lipoproteins n Derived lipids - Sterols
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Diversity in structure leads to a diversity in biological function
n Non-polar lipids (fats) are the principal molecules for energy storage n Polar lipids (nitrogen and phosphorus containing) are components of biological membranes n The steroid class of lipids (cholesterol) is found in biological membranes and used as a precursor for many hormones n Miscellaneous lipids present only in minor quantities in the cell are involved as light-absorbing pigments (â-carotene, retinal), enzyme cofactors (vitamin K), signal molecules (prostaglandins), and electron carries (ubiquinone)
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Classes of Lipids
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Fatty acids are:
n Insoluble in water. n Saturated or unsaturated.
Fatty Acids
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Fatty Acid Formulas
n The formulas for fatty acids are written as condensed and line-bond formulas. For example caprylic acid with 8 carbon atoms can be written as: CH 3 —(CH 2 ) 6 —COOH CH 3 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —COOH O || CH 3 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —C—OH
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n The carbon atoms of an acid are numbered (or lettered with Greek lettering system, such as á, â, ã) either from the carboxyl group or from the carbon farthest removed from the carboxyl group (n or omega numbering system) n CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -COOH n 10 9 8 7 6 5 4 3 2 1 n 1 2 3 4 5 6 7 8 9 10 n ù ä ã â á
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Saturated – single bonds
Unsaturated – double bonds
R1 C C C C C R
R1 C C C C C R
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n A trans configuration, by contrast, means that the next two hydrogen atoms are bound to opposite sides of the double bond. n Animal fats and foods with partially hydrogenated vegetable oils can contain trans-fatty acids
n Increased consumption of partially hydrogenated vegetable oils is associated with increased risk of heart disease
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Saturated fatty acids have single C–C bonds.
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Components Common name Systematic name 1 formic methanoic 2:0 acetic ethanoic 3:0 propionic propanoic 4:0 butyric butanoic 5:0 valeric pentanoic 6:0 caproic hexanoic 8:0 caprylic octanoic 10:0 capric decanoic 12:0 lauric dodecanoic 14:0 mystiric tetradecanoic
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Components Common name Systematic name 16:0 palmitic hexadecanoic 16:1 (9) palmitoleic cis-9-hexadecenoic 18:0 stearic octadecanoic 18:1 (9) oleic cis-9-octadecenoic 18:1 (11) vaccenic cis-1-octadecenoic 18:2 (9,12) linoleic all cis-9,12- octadecadienoic 18:3 (9,12,15) linolenic all cis-9,12,15- octadecatrienoic 20:0 arachidic eicosanoic 20:4 (5,8,11,14) arachidonic all cis-5,8,11,14- eicosatetraenoic
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Saturated fatty acids have: n Molecules that fit closely together in a regular pattern. n Strong attractions between fatty acid chains. n High melting points that makes them solids at room temperature.
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Unsaturated fatty acids: n Have nonlinear chains that do not allow molecules to pack closely. n Have low melting points. n Are liquids at room temperature.
Unsaturated Fatty Acids
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linoleic acid cis -9, trans -11 CLA trans -11 18:
Double bonds: cis vs. trans
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linoleic acid cis -9, trans -11 CLA trans -11 18:
Double bond pairs: non-conjugated vs. conjugated
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The hydrogenation of oils
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n Humans are unable to synthesize fatty acids that have double bonds in the omega-3 or omega-6 positions
n Omega-3 EFAs n Eicosapentaenoic acid (EPA): coldwater fish n Docosahexaenoic acid (DHA): coldwater fish n Alpha-linolenic acid (ALA): flax, walnut, soybean oils
n Omega-6 EFAs n Linolenic acid (LA): animal fats, sunflower oil n Gamma-linolenic acid (GLA): sunflower oil
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The first double bond: n In vegetable oils is at carbon 6 (omega-6). n In fish oils is at carbon 3 (omega-3).
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n Mammals cannot synthesize the two main types of polyunsaturated fatty acids: the linoleic (omega-6) and linolenic (omega-3) n Essential fatty acid deficiency is characterized by dermatitis and poor wound healing n Most prostaglandins are synthesized from arachidonic acid (a linoleic acid derivative) n Lack of these prostaglandins causes some aspects of the essential fatty acid deficiency syndrome n A small daily intake of linolenic acid is recommended (this may be especially important when the nervous system is developing) n Docosahexaenoic acid (22:6n-3) – omega-3 fatty acid is needed for maximum development of the visual and central nervous systems during the neonatal period (it is present in large amounts in the retina and parts of the brain; it enhances the visual response and the function of certain domains in neural membranes)
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Prostaglandins have: n 20 carbon atoms in their fatty acid chains. n An OH on carbon 11 and 15. n A trans double bond at carbon 13.
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LDL
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HDL
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n When a cell responds to a stimulus, bioactive mediators (prostaglandins, thromboxanes, leukotrienes, and others) often are formed from the lipids contained in its membranes. n Thromboxanes regulate blood coagulation. n Leukotrienes play a role in allergic and inflammation responses. They were isolated from leukocytes (white blood cells).
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