resveratrol

3,4',5-Stilbenetriol;

trans-Resveratrol;

(E)-5-(p-Hydroxystyryl)resorcinol (E)-5-(4-hydroxystyryl)benzene-1,3-diol Identifiers CAS number 501-36-0 SMILES [show] Oc2ccc(C=Cc1cc(O)cc(O)c1)cc2 InChI [show] 1/C14H12O3/c15-

12-5-3-10(4-6-12)

1-2-11-7-13(16)9-

14(17)8-11/h1-9,15-

17H/b2-1+ ChemSpider ID 392875 Properties Molecular formula C14H12O3 Molar mass 228.25 Appearance white powder with

slight yellow cast Solubility in water 0.03 g/L Solubility in DMSO 16 g/L Solubility in ethanol 50 g/L Except where noted otherwise, data are given for

materials in their standard state

(at 25 °C, 100 kPa)

Infobox references The cis-isomer of resveratrol

Resveratrol is a phytoalexin produced naturally by several plants when under attack by pathogens such as bacteria or fungi. Resveratrol has also been produced by chemical synthesis[1] and is sold as a nutritional supplement derived primarily from Japanese knotweed. Resveratrol has been shown at times to extend the life span of yeast and mice.[2] In mouse and rat experiments, anti-cancer, anti-inflammatory, blood-sugar-lowering, chelating and other beneficial cardiovascular effects of resveratrol have been reported. Most of these results have yet to be replicated in humans. In the only positive human trial, extremely high doses (3–5 g) of resveratrol in a special proprietary formulation have been necessary to significantly lower blood sugar.[3] Resveratrol is found in the skin of red grapes and is a constituent of red wine, but apparently not in sufficient amounts to explain the French paradox that the incidence of coronary heart disease is relatively low in southern France despite high dietary intake of saturated fats.[4] Contents [hide] 1 Physiological effects 1.1 Life extension 1.2 Cancer prevention 1.3 Athletic performance 1.4 Neurodegenerative disease 1.5 Radiation protection 2 Pharmacokinetics 2.1 Adverse effects and unknowns 3 Mechanisms of action 4 Chemical and physical properties 5 Plants and foods 5.1 Content in wines and grape juice 5.2 Content in selected foods 6 Supplementation 7 Related compounds 8 See also 8.1 Other articles 9 References 10 Further reading 11 External links //

Physiological effects

Life extension

The groups of Howitz and Sinclair reported in 2003 in the journal Nature that resveratrol significantly extends the lifespan of the yeast Saccharomyces cerevisiae.[5] Later studies conducted by Sinclair showed that resveratrol also prolongs the lifespan of the worm Caenorhabditis elegans and the fruit fly Drosophila melanogaster.[6] In 2007, a different group of researchers was able to reproduce Sinclair's results with C. elegans,[7] but a third group could not achieve consistent increases in lifespan of D. melanogaster or C. elegans.[8] However, a large scale study of the effects of resveratrol on lifespan in D. melanogaster and C. elegans, by the Gems and Partridge labs (which are not financially