Transcript Red Wine and its Cardiovascular Effects

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 30
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
OCH 3
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
n
OH
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
R1
OH
HO
•Inhibit enzymes
from breaking down
collagen
•Supports existing
collagen structures
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
n
OH
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.