Red Wine and its Cardiovascular Effects By: Mary C. Lawrence Why the interest in red wine? French Paradox Lowest rate of cardiac disease mortality Fairly high intake of saturated fatty acids Loaded with natural health aids Cholesterol Detoxifier Anticoagulant Artery Relaxant How Antioxidants Work Saturated fats and oils contain many double bonds or 3 0
hydrogen which are easily targeted for auto-oxidation Auto-oxidation R3CH + O-O R3CO-OH R3COOH R3CO + OH Auto-oxidation leads to hydroperoxides which can dissociate rapidly because the RO-OR bond dissociation energy is ~35 kcal/mol which is lower than most bonds How Antioxidants Work cont. Antioxidants inhibit auto-oxidation of the free radical groups
Antioxidants are usually phenol compounds (aromatic ring with -OH group attached) Phenols make good radical scavengers because the radical products are resonance-stabilized so they are then non-reactive compare to other radicals O O O O O Wine Antioxidants COOH
Phenolic Acids HO Gallic acid OH OH COOH Benzoic acid H H H
OH Flavonols OH HO O Quercetin OH OH O Wine Antioxidants cont.
Anthocyanins OCH3 OH HO O OCH3 Malvidin OH OH OH OH
HO O Cyanidin H OH OH Wine Antioxidants cont. R OH HO Condensed Tannins
O OH OH OH OH OH HO O H OH OH
OH n OH HO O H OH OH Wine as a cholesterol detoxifier antioxidants
help inhibit the oxidation and cytotocicity of lowdensity lipoprotiens Taken from www.kumc.edu LDL Uptake into cells 1. LDL binds to receptor 2. Receptor-LDL complex internalized by endocytosis 3. Fusion with lysosomes--LDL hydrolyzed 4. Regulatory actions Taken from Stryer Ed. 2 (p. 472)
How LDL is Oxidized Taken from www.kumc.edu How Atherosclerotic Lesions Occur in Arteries Taken from www.kumc.edu Atherosclerotic Lesion cont. Taken from www.kumc.edu Anticoagulant activity Anthocyanosides Protective role on
collagen structures Inhibit enzymes from breaking down collagen Supports existing collagen structures R1 OH HO O R2 OH OH Anticoagulant Activity cont.
Proanthocyanidins Protect single layer cells of capillaries Reinforce collagen structures Vascular Relaxation Quercitin Condensed Tannins R OH HO OH OH
O OH OH OH OH HO O OH HO O
OH OH O H OH OH OH n OH HO
O H OH OH Both have been shown to relax smooth muscle surrounding rat aortic rings Both believe to involve the NO-cGMP pathway NO-cGMP Pathway Known that the intracellular messenger for NO is guanylate cyclase-which catalyzes cGMP
cGMP then leads to an increase in protein kinase G phosphorylation and smooth muscle relaxation Taken from www.kumc.edu Differences in wine Red versus white wine Red wine fermented with grape stems and skins White wines show lesser vascular relaxation effects Thick versus thin skinned grapes Flavonol content higher in thick skin -quercetin glycosides accumulate in skins
Grapes left on vine longer have higher flavonol levels--skins usually thicker The Future? ActiVin--nutritional ingredient manufactured by Inter Health Natural extract of red grape seeds, contains high amounts of flavonoids Powerful inhibitor of free radical induced lipid peroxidation References Andriambeloson, Emile, Celine Magnier, Gisele Haan-Archipoff, Annelise Lobstein, Robert Anton Alain Beretz, Jean Claude Stoclet, and Ramaroson Andriantsitohaina. Natural Dietary Polyphenlolic Compounds Cause Endothelium-Dependent Vasorelaxation in Rat Thoracic Aorta Journal of Nutrition: 1998 Dec; 128(12): 2324-33. Carper, Jean. The Ways of Wine are Rosy. USA Weekend Online. Internet 1-3 Dec. 1995. Available:
http://www.usaweekend.com/health/carper_archive/951203eat_smart_grapes.html Fessenden, Ralph J. and Joan S.Fessenden. Organic Chemistry. 4th Edition. Brooks/Cole Publishing Company. 1990. Fitzpatrick, David P., Steven L. Hirschfield, and Ronald G. Coffey. Endothelium-dependent vasorelaxing activity of wine and other grape products. American Journal Of Physiology 265 (1993): H774-H778. Flesch, Markus, Andreas Schwarz, and Michael Bohm. Effects of red and white wine on endothelium-dependent vasorelaxation of rat aorta and human coronary arteries. American Journal of Physiology 275 (1998): H1183-H1190. References cont. Ghiselli, Andrea, Mirella Naradini, Alessandro Baldi, and Cristina Scaccini. Antioxidant Activity of Different Phenolic Fractions Separated form an Italian Red Wine. Journal of Agricultural and Food Chemistry 46(2) (1998): 361-367. McDonald, Morag S., Mark Hughes, Jennifer Burns, Michael E. J. Lean, David Matthews, and Alan Crozier. Survey of the Free and Conjugated Myricetin
and Quercetin Content of Red Wines of Different Geographical Origins. Journal of Agriculture and Food Chemistry 46(2) (1998): 368-375. Resveratrol and Red Grape Skin Extract and Grape Seed Extract. Online. Internet. 22 Feb. 1999. Available: http://www.healthxl.com/resveratrol.html Saura-Calixto, Fulgencio. Antioxidant Dietary Fiber Product: A New Concept and a Potential Food Ingredient. Journal of Agriculture and Food Chemistry 46(10) (1998): 4303-4306. The Secret of the French Paradox. ACTIVIN Online. Internet 22 Feb. 1999. Available: http://www.uaslabs.com/activin.html Styer, Lubert. Biochemistry. 2nd Edition. W.H. Freeman and Company. 1981.
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