Resveratrol Resveratrol Seven-generation sustainability Category="Chemopreventive agents"

Overview

Resveratrol is a polyphenolic Phytoalexin which is produced in plants with the help of the Enzyme stilbene synthase, and which has anti-fungal properties. It is found in the skins of certain red grapes, in peanuts, blueberries, some pines (Scots Pine, Eastern White Pine) and the roots and stalks of Japanese knotweed (hu zhang in China) and giant knotweed. Resveratrol was first isolated from an extract of the Peruvian Legume Cassia quinquangulata in 1974. It is now available as a mass-produced nutritional supplement but not as a therapeutic agent (though it is now registered as an investigational drug). The supplement, first sourced as ground dried red grape skins, has shifted somewhat to include certain of the knotweeds as a raw material.

Resveratrol is often referred to as a Nutraceutical, along with other bioactive plant compounds that are being studied for potential clinical applications such as Curcumin, EGCG and Silibinin, among others.

The amount of resveratrol in food substances varies greatly. Red wine contains approximately 5 mg/L, depending on the grape variety, whilst white wine has much less - the reason being that red wine is fermented with the skins, allowing the wine to absorb the resveratrol, whereas white wine is fermented after the skin has been removed.

Chemical & physical properties

Resveratrol
Chemical nameResveratrol
Chemical formulaC14H12O3
Molecular weight228.25 g/mol
Melting point
Boiling point
Density
CAS number501-36-0
SMILESC1(=CC(=CC(=C1)O)CCC2=CC=C(C=C2)O)O
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Disclaimer and references

Names/Synonyms

Trans-3,5,4'-trihydroxystilbene; 3,4',5-stilbenetriol; trans-resveratrol and (E)-5-(p-hydroxystyryl)resorcinol

It exists as two structural isomers: cis- (Z) and trans- (E), with the trans-isomer shown in the image. Trans-resveratrol can undergo isomerisation to the cis form when heated or exposed to UV irradiation.

General

At room temperature resveratrol is a solid white powder with a slight yellow cast to it. It is soluble in Ethanol at ~50 mg/mL, in DMSO at least 16 mg/mL and is only very slightly soluble (warming required) in water at ~3 mg/100 mL.

Resveratrol research

Activities & mechanisms of action

Resveratrol has Antioxidant properties, and as a constituent of Red wine it has been implicated in the “French paradox” that the incidence of Coronary heart disease is relatively low in southern France despite high dietary intake of saturated fats. Resveratrol interferes with all three stages of Carcinogenesis - initiation, promotion and progression. Experiments in various Cell types and isolated subcellular systems In vitro implicate a multitude of mechanisms in the pharmacological activity of resveratrol. These mechanisms include inhibition of the Transcription factor NF-kB, cytochrome P450 isoenzyme CYP1A1, androgenic actions and expression and activity of Cyclooxygenase (COX) enzymes. Resveratrol has been shown to induce Fas/ Fas ligand mediated Apoptosis, P53 and cyclins A, B1 and cyclin-dependent kinases cdk 1 and 2, furthermore it possesses Antioxidant and anti-angiogenic properties. Due to these discoveries resveratrol is currently being investigated extensively as a Cancer chempreventive agent.

The mechanisms of resveratrol's apparent effects toward life extension are not fully understood. It was believed to have longevity-enhancing properties by acting as a CR-mimetic, but this has since been shown not to be true.

Experiments from the laboratory of David Sinclair at Harvard were published in the journal Nature claiming that resveratrol significantly extends the "lifespan" of Yeast. Dr. Sinclair then founded Sirtris pharmaceuticals to capitalize on the hype surrounding resveratrol as an anti-aging drug. Only the trans-form is capable of activating the mammalian SIRT1 Gene In vitro; it is also the form predominately found in red grape skin (red wine).

Resveratrol has also been seen to increase the potency of some antiretroviral drugs In vitro. Recent research at Ohio State University indicated that resveratrol inhibits the development of cardiac Fibrosis.

Metabolism of resveratrol

In humans resveratrol rapidly undergoes phase II conjugation, both Glucuronidation and sulphation at multiple sites on the molecule.

References

Gescher AJ, Steward WP. Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: a conundrum. Cancer Epidemiol Biomarkers Prev. 2003;12(10):953-957.

External links