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R E S V E R A T R O L

(The data are from the Natural Medicine Database, PubMed, Wikipedia and 3d Chemistry)

CHEMISTRY

Resveratrol (3,5,4'-trihydroxy-trans-stilbene) is a phytoalexin produced naturally by several plants as defense against pathogens such as bacteria or fungi.

See a 3D mobile model of the molecule at http://www.3dchem.com/molecules.asp?ID=277#

RESVERATROL IN NATURE

Resveratrol is primarily found in red wine, red grape skins, purple grape juice, mulberries, and in smaller amounts in peanuts (1).

Other sources include eucalyptus (Eucalyptus wandoo, Eucalyptus sideroxylon), spruce (Picea excelsa), and Bauhinia racemosa

Polygonum cuspidatum (Hu Zhang), the roots of which are used in Chinese and Japanese traditional medicine and considered to be one of the richest sources of trans-resveratrol (2)

RED WINE

The trans-resveratrol content of wine is highly dependent on grape type, climate, and practices used to make the wine. White wines have very low trans-resveratrol concentrations. They have only about 1% to 5% the quantity found in red wines (3). Pinot Noir consistently has the highest concentrations of trans-resveratrol, regardless of climate. Wine prepared from Pinot Noir grapes average 5.13 mg resveratrol per liter (3)

Other red wines, including Cabernet Sauvignon, produced in cold, humid climates, such as Bordeaux and Canada, have higher trans-resveratrol content than those produced in hot, dry climates.

BIOLOGY

In the intestine most of the resveratrol is conjugated before absorption and is therefore found in the plasma primarily in glucuronidated and sulfated forms (4). Only a small amount of free resveratrol is absorbed directly;

When resveratrol supplements are taken orally peak plasma levels are reached in 0.5 to 1.5 hours (5). At low doses (<0.3 mg/kg), over 50% of the resveratrol is excreted in the urine within 24 hours. With higher doses (>1 mg/kg), about 25% is excreted in the urine within 24 hours (6).

The half-life of resveratrol is 2.9 to 8.9 hours.

ORAC Value

The ORAC value of trans-resveratrol is estimated to be about 3000 per 100mg.

HEALTH EFFECTS

Inflammation

Trans-resveratrol has antioxidant, anti-inflammatory, and antimutagenic activity (7) Resveratrol has anti-inflammatory activity, likely due to inhibition of cyclooxygenase-1 (COX-1) and COX-2, hydroperoxidases, 5-lipoxygenase (8)

Resveratrol also seems to decrease the activity of inflammatory cytokines (6126). In vitro, resveratrol appears to be more selective for COX-1. It appears inactivate COX-1, but only weakly inhibits COX-2 (15140,15148). Some evidence suggests that resveratrol is a more potent anti-inflammatory agent than NSAIDs such as aspirin, ibuprofen, or indomethacin (9).

In animal models, intra-articular injections of resveratrol decreases inflammation and reduces cartilage destruction (10).

In animal models of colitis, resveratrol reduces colonic damage, decreases inflammation by reducing neutrophil infiltration, cytokine levels, and inflammatory prostaglandins. Resveratrol also appears to enhance colonic cell apoptosis (11).

Resveratrol inhibits the replication of herpes simplex virus. Although the mechanism of this action is not fully known, exposure to resveratrol within one hour of cellular infection appears to be most effective in arresting viral growth. This suggests that resveratrol reduces production of proteins needed to regulate viral proliferation (12).

In vitro, resveratrol appears to inhibit Chlamydia pneumoniae (13). Systemic dissemination of Chlamydia has been suggested as a possible cause of atherosclerosis and heart disease. Some research speculate that resveratrol's activity against Chlamydia could wine's cardiovascular benefits.

Resveratrol also reduces interleukin-1 (IL-1), IL-8, and granulocyte macrophage-colony stimulating factor (GM-CSF) released from alveolar macrophages isolated from smokers (14) This suggests that resveratrol might have a role in reducing inflammation in chronic obstructive pulmonary disease.

Cardiovascular ans Ishemia

Preliminary research suggests that chronic administration of resveratrol might improve myocardial function in models of myocardial ischemia (15).

Resveratrol significantly reduces lipid peroxidation and organ damage in animal models of ischemia-reperfusion (16).

Blood fluidity and Circulation

Trans-resveratrol also seems to interfere with blood coagulation and decrease platelet aggregation (17).

Cancer

Preliminary research in animal models suggests resveratrol might reduce the risk of cancer. It seems to inhibit tumor growth and promote apoptosis (18). The effect of resveratrol on cellular apoptosis differs depending on conditions. In some cases, it facilitates apoptosis and others it inhibits apoptosis.

In vitro, low concentrations of resveratrol inhibit hydrogen peroxide-induced apoptosis of human leukemia cells (19)

Resveratrol also inhibits growth and induces apoptotic cell death of breast cancer cell lines, medulloblastoma cell lines, and colorectal cancer cells in vitro (20).

Lifespan

Research in animals on a high-calorie diet shows that resveratrol can increase lifespan and improve other factors associated with a longer lifespan including increasing insulin sensitivity and decreasing insulin-like growth factor-1 (IGF-1) (21)

Alzheimer

Resveratrol might have a role in preventing Alzheimer's disease. In vitro, resveratrol prevents beta-amyloid petide-related reductions in glutathione. This suggests that resveratrol might prevent oxidative damage caused by beta-amyloid peptide (22).

Liver

Resveratrol also appears to decrease mortality in animal models of alcohol-related liver damage (23).

INTERACTION

Herbs

Theoretically, concomitant use of resveratrol with herbs that have anticoagulant or antiplatelet activity could increase the risk of bleeding in some people (24). These herbs include angelica, clove, danshen, feverfew, garlic, ginger, ginkgo, ginseng Panax, horse chestnut, red clover, turmeric, and others.

Pharmaceuticals

Resveratrol seems to have antiplatelet effects (26). Theoretically, taking resveratrol with other antiplatelet or anticoagulant drugs might increase the risk of bruising and bleeding. Some of these drugs include aspirin; clopidogrel (Plavix); nonsteroidal anti-inflammatory drugs (NSAIDs) such as diclofenac (Voltaren, Cataflam, others), ibuprofen (Advil, Motrin, others), naproxen (Anaprox, Naprosyn, others); dalteparin (Fragmin); enoxaparin (Lovenox); heparin; warfarin (Coumadin); and others.

Hormonal effect

Because resveratrol might have estrogenic effects (26), women with hormone sensitive conditions should avoid it.

REFERENCES

1 - Agri Res Svc: Dr. Duke's phytochemical and ethnobotanical databases. www.ars-grin.gov/duke )

2 - Soleas GJ, Diamandis EP, Goldberg DM. Resveratrol: a molecule whose time has come? And gone? Clin Biochem 1997;30:91-113.)

3 - Pervaiz S. Resveratrol: from grapevines to mammalian biology. FASEB J 2003;17:1975-85

4 - Boocock DJ, Faust GE, Patel KR, et al. Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol Biomarkers Prev 2007;16:1246-52.

5 - Goldberg DM, Yan J, Soleas GJ. Absorption of three wine-related polyphenols in three different matrices by healthy subjects. Clin Biochem 2003;36:79-87.

6 - Meng X, Maliakal P, Lu H, et al. Urinary and plasma levels of resveratrol and quercetin in humans, mice, and rats after ingestion of pure compounds and grape juice. J Agric Food Chem 2004;52:935-42.

7 - Jang M, Cai L, Udeani GO, et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997;275:218-20. ).

8 - Soleas GJ, Diamandis EP, Goldberg DM. Resveratrol: a molecule whose time has come? And gone? Clin Biochem 1997;30:91-113. 2948,12482,12484).

9 - Hwang D, Fischer NH, Jang BC, et al. Inhibition of the expression of inducible cyclooxygenase and proinflammatory cytokines by sesquiterpene lactones in macrophages correlates with the inhibition of MAP kinases. Biochem Biophys Res Commun 1996;226:810-8.

10 - Elmali N, Baysal O, Harma A, et al. Effects of resveratrol in inflammatory arthritis. Inflammation 2007;30:1-6.

11 - Martin AR, Villegas I, La Casa C, de la Lastra CA. Resveratrol, a polyphenol found in grapes, suppresses oxidative damage and stimulates apoptosis during early colonic inflammation in rats. Biochem Pharmacol 2004;67:1399-410

12 - Docherty JJ, Fu MM, Stiffler BS, et al. Resveratrol inhibition of herpes simplex virus replication. Antiviral Res 1999;43:145-55.

13 - Schriever C, Pendland SL, Mahady GB. Red wine, resveratrol, Chlamydia pneumoniae and the French connection. Atherosclerosis 2003;171:379-80.

14 - Culpitt SV, Rogers DF, Fenwick PS, et al. Inhibition by red wine extract, resveratrol, of cytokine release by alveolar macrophages in COPD. Thorax 2003;58:942-6.

15 - ) Mokni M, Limam F, Elkahoui S, et al. Strong cardioprotective effect of resveratrol, a red wine polyphenol, on isolated rat hearts after ischemia/reperfusion injury. Arch Biochem Biophys 2007;457:1-6

16 - Hascalik S, Celik O, Turkoz Y, et al. Resveratrol, a red wine constituent polyphenol, protects from ischemia-reperfusion damage of the ovaries. Gynecol Obstet Invest 2004;57:218-23.

17 - Wang Z, Huang Y, Zou J, et al. Effects of red wine and wine polyphenol resveratrol on platelet aggregation in vivo and in vitro. Int J Mol Med 2002;9:77-9.

18 - Jang M, Cai L, Udeani GO, et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997;275:218-20.

19 - Ahmad KA, Clement MV, Hanif IM, Pervaiz S. Resveratrol inhibits drug-induced apoptosis in human leukemia cells by creating an intracellular milieu nonpermissive for death execution. Cancer Res 2004;64:1452-9.

20 - Schneider Y, Vincent F, Duranton B, et al. Anti-proliferative effect of resveratrol, a natural component of grapes and wine, on human colonic cancer cells. Cancer Lett 2000;158:85-91.

21 - Baur JA, Pearson KJ, Price NL, et al. Resveratrol improves health and survival of mice on a high-calorie diet. Nature 2006;444:337-42.

22 - Ying-Shan Han,1 Wen-Hua Zheng,1 Stéphane Bastianetto,1 Jean-Guy Chabot,1 and Rémi Quirion1* Neuroprotective effects of resveratrol against β -amyloid-induced neurotoxicity in rat hippocampal neurons: involvement of protein kinase C. Br J Pharmacol. 2004 March; 141(6): 997–1005. Published online 2004 March 18. doi: 10.1038/sj.bjp.0705688.

23 - Bujanda L, Garcia-Barcina M, Gutierrez-de Juan V, et al. Effect of resveratrol on alcohol-induced mortality and liver lesions in mice. BMC Gastroenterol 2006;6:35.

24 - Soleas GJ, Diamandis EP, Goldberg DM. Resveratrol: a molecule whose time has come? And gone? Clin Biochem 1997;30:91-113.

25 - Pace-Asciak CR, Rounova O, Hahn SE, et al. Wines and grape juices as modulators of platelet aggregation in healthy human subjects. Clin Chim Acta 1996;246:163-82.

26 - Gehm BD, McAndrews JM, Chien PY, Jameson JL. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc Natl Acad Sci U S A 1997;94:14138-43

  

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