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LIPIDS

LIPIDS. Extracted from living Tissue. Soluble in Nonpolar Solvents. contain High ratio of C:O. C : O(+N) ratios. Glucose: C 6 H 12 O 6 1:1 Stearic Acid: C 18 H 36 O 2 9:1 cholesterol: C 27 H 46 O 27:1 Phenylalanine: C 9 H 11 NO 2 3:1

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LIPIDS

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  1. LIPIDS Extracted from living Tissue Soluble in Nonpolar Solvents contain High ratio of C:O C : O(+N) ratios Glucose: C6H12O6 1:1 StearicAcid: C18H36O2 9:1 cholesterol: C27H46O 27:1 Phenylalanine: C9H11NO2 3:1 Asparagine: C4H8N2O3 0.8:1

  2. LIPID FUNCTIONS Structure ―Biological Membranes phospholipids (phosphoglycerides) Energy Reserve―Triglycerides (fats/oils) Chemical Signals ―some hormones, prostaglandins, leukotrienes Many cellular lipids are esters made from the combination of an alcohol group (glycerol & sphingosine) and one or more Fatty acids.

  3. Olic Acid = C18 monounsaturated Stearic Acid = C18 saturated natural unsaturated fatty acids are ‘cis’ isomers

  4. HO-C HO-C HO-C HO-C O O O O Ω3 Ω6 polyunsaturated Stearic (saturated) C18 fatty acids Oliec (monounsaturated) Linoleic Linolenic

  5. O -C-R O -C-R' O -C-R'' = = = CH2-O CH-O CH2-O Triglyceride (fat or oil) esters formed between alcohol (glycerol) and 3 fatty acids CH2-OH | CH-OH | CH2-OH glycerol O || HO — C— R fatty acid + 3x triglyceride

  6. Animal fats have more saturated fatty acids while vegetable oils contain a higher degree of unsaturated fatty acids. Animals lack the enzymes to insert more than 1 C=C.

  7. H O || HO-C O || HO-C H-H O || HO-C H Hydrogenation changes unsaturated to saturated Linear – like saturated ↑LDL/HDL cholesterol Trans Fatty Acids

  8. cis oleic linoleic trans oleic linolenic

  9. SOAP O _ || O - C _ Soap is prepared by the base (NaOH or lye) hydrolysis of fat. This produces a solid sample comprised of glycerol + the salt of various fatty acids. When dissolved the fatty acid salts dissociate, and the ‘soap’ ions form a micelle structure. Na+ Salt of fatty acid

  10. Micelle Structure H2O out Nonpolar

  11. dirt & grime Soap Action add heat & agitate .....

  12. Soap Action add heat & agitate .....

  13. Soap Action cease mechanical disruption .... micelles reform spontaneously & trap dirt : dirt is ‘soluble’

  14. O _ || O - C _ The molecular ion below would form which of the following structures when dispersed in water? a) micelle b) lipid bilayer c) cell membrane d) precipitate Na+ Salt of fatty acid

  15. + - O -C-R'' O -C-R O -C-R' O -P-O-CH2-CH2-NR3+ O -C-R' O -C-R = = = = = = CH2-O CH-O CH2-O CH2-O CH-O CH2-O = O- Triglyceride (fat or oil) esters formed between alcohol (glycerol) and 3 fatty acids Phosphoglycerides Contain a phosphate ester. The phosphate also forms an ester with an amino alcohol. (e.g. ethanolamine R = H, choline R = CH3, or serine)

  16. The molecular ion above would form which of the following structures when dispersed in water? a) micelle b) lipid bilayer c) cell membrane d) precipitate Lipid Bilayer cross section

  17. Lipid bilayers in an aqueous solution • would best be defined as which of the • following types of structure …. • Rigid • Fluid

  18. H2O in H2O in Nonpolar solvent Phosphoglyceridesspontaneously form vesicles in water. H2O out

  19. What type of molecule will most readily pass through a vesicle? a) a slightly soluble nonpolar molecule b) a soluble polar molecule c) an ion d) none of the above will penetrate a vesicle Diffusion of polar & ionic molecules through vesicles is slow. Na+ Nonpolar Glucose

  20. OH | C - C = C O | C - N - C O | || + C - O - P - O - C - C - NR3 | O- Sphingomyelin A sphingolipid and a phospholipid

  21. OH | C - C = C O | C - N - C | C OH O OH C HO OH Cerebroside O - a glycolipid

  22. Prostaglandins are regulatory lipid molecules. They are similar to hormones but typically act within the same tissue type rather than being transported to the site to the site of action through the circulatory system. Prostaglandins are involved in blood clotting, inflammation response, gastric acid secretion, etc. They are synthesized from the membrane lipid, arachidonic acid. Aspirin is an inhibitor of prostaglandin synthesis and has multiple effects including.. reduce inflammation response, and inhibit blood clotting. However, aspirin can also cause damage to the stomach lining.

  23. Steroid Hormones

  24. Arachidonic Acid Derivatives as Signaling Lipids • Enzymatic oxidation of arachidonic acid yields • Prostaglandins (inflammation and fever) • Thromboxanes (formation of blood clots) • Leukotrienes (smooth muscle contraction in lungs)

  25. O -C-R O -C-R' O -C-R'' = = = Today’s topics: Lipids – soluble in nonpolar solvents Triglycerides – Fats and Oils Soap and micelle structures Phosphoglycerides vesicles and membranes The molecule shown below is …… a) fatty acid b) triglyceride c) common to membrane structures d) none of the above CH2-O CH-O CH2-O

  26. HO-C O The molecule shown below is …… a) saturated b) omega-3 c) both of the above d) none of the above The molecule shown below is …… a) stearic acid b) oleic acid c) linoleic acid d) linolenic acid The molecule shown below is …… a) harmful in your diet b) better for you than trans fats in your diet c) both of the above d) none of the above

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