Red Wine and its Cardiovascular Effects

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Red Wine and its Cardiovascular Effects

• By Mary C. Lawrence

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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
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How Antioxidants Work

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

Auto-oxidation R3CH O-O
R3COOH R3CO-OH 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

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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

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Wine Antioxidants

• Phenolic Acids

• Gallic acid

• Benzoic acid

Flavonols

• Quercetin

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Wine Antioxidants cont.
Anthocyanins

• Malvidin

• Cyanidin

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Wine Antioxidants cont.
Condensed Tannins
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Wine as a cholesterol detoxifier

• antioxidants help inhibit the oxidation and
  cytotocicity of low-density lipoprotiens

Taken from www.kumc.edu
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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)
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How LDL is Oxidized
Taken from www.kumc.edu
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How Atherosclerotic Lesions Occur in Arteries
Taken from www.kumc.edu
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Atherosclerotic Lesion cont.
Taken from www.kumc.edu
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Anticoagulant activity
Anthocyanosides

• Protective role on collagen structures
• Inhibit enzymes from breaking down collagen
• Supports existing collagen structures

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Anticoagulant Activity cont.
Proanthocyanidins

• Protect single layer cells of capillaries
• Reinforce collagen structures

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Vascular Relaxation
Quercitin Condensed Tannins

• Both have been shown to relax smooth muscle
  surrounding rat aortic rings
• Both believe to involve the NO-cGMP pathway

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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
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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

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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

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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-Dependen
t 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/healt
h/carper_archive/951203eat_smart_grapes.html Fess
enden, 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.
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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-Ca
lixto, 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.