Red Wine and its Cardiovascular Effects

Red Wine and its Cardiovascular Effects

By: Mary C. Lawrence

Why the interest in red wine?

“French Paradox”

Loaded with natural health aids Cholesterol Detoxifier

Anticoagulant

Artery Relaxant

Lowest rate of cardiac disease mortality

Fairly high intake of saturated fatty acids

How Antioxidants Work

• Saturated fats and oils contain many double bonds or 30 hydrogen which are easily targeted for auto-oxidation

• 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

Auto-oxidation

R3CH + O-O R3COOH

R3CO-OH R3CO + OH

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 Phenolic Acids

Flavonols

OH

OH

OH

COOH

•Gallic acid

O

O

O

H

O

H

O

H

O

H

O

H

•Quercetin

•Benzoic acid

C

O

O

H

H

H

H

Wine Antioxidants cont.

O

O

H

O

H

O

H

O

H

O

C

H

3

O

C

H

3

Anthocyanins

•Malvidin

•Cyanidin

O

O

H

O

H

O

H

O

H

O

H

H

Wine Antioxidants cont.

O

O

H

O

H

O

H

R

O

H

O

H

O

O

H

O

H

O

H

O

H

O

H

H

n

O

O

H

O

H

O

H

O

H

O

H

H

Condensed Tannins

Wine as a cholesterol detoxifier• antioxidants help inhibit the oxidation and cytotocicity of low-density lipoprotiens

Taken from www.kumc.edu

LDL Uptake into cells1. LDL binds to receptor

2. Receptor-LDL complex internalized by endocytosis3. 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 activityAnthocyanosides

•Protective role on collagen structures

•Inhibit enzymes from breaking down collagen

•Supports existing collagen structures

O

O

H

O

H

R1

O

H

O

H

R2

Anticoagulant Activity cont.

Proanthocyanidins

•Protect single layer cells of capillaries

•Reinforce collagen structures

Vascular RelaxationQuercitin Condensed Tannins

•Both have been shown to relax smooth muscle surrounding rat aortic rings

• Both believe to involve the NO-cGMP pathway

O

O

O

H

O

H

O

H

O

H

O

H

O

O

H

O

H

O

H

R

O

H

O

H

O

O

H

O

H

O

H

O

H

O

H

H

n

O

O

H

O

H

O

H

O

H

O

H

H

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

ReferencesAndriambeloson, 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.