Resveratrol

Resveratrol is a naturally occurring phytoalexin produced by some higher plants in response to injury or fungal infection. Phytoalexins are chemical substances produced by plants as a defense against infection by pathogenic microorganisms, such as fungi. Epidemiological, in vitro and animal studies suggest that a high resveretrol intake is associated with a reduced incidence of cardiovascular disease, and a reduced risk for cancer. Resveratrol is touted by nutritionists and biochemists because of its potential as an anticancer and cardioprotective compound.

Resveratrol belongs to the phytoalexin class of phytochemicals and functions as a moderate antioxidant, quenching free radical damage linked to several cancers. The compound has also demonstrated anti-inflammatory properties that help it to block reactions associated with the cancer process.

Resveratrol, which is also known as 3,4',5 trihydroxystilbene and 3,4',5-stilbenetriol, exists in cis- and trans-stereoisomeric forms. Resveratrol is the parent molecule of a family of polymers called viniferins. Cis- and trans-resveratrol occur naturally as do their glucosides. Resveratrol-3-O-beta-D-glucoside is also known as piceid, and the respective cis- and trans-glucosides are called cis-piceid and trans-piceid. The molecular formula of resveratrol is C14H12O3 and its molecular weight is 228.25 daltons.

Some benefits of resveratrol include:
1) Powerful antioxidant. Antioxidants are substances that can neutralize free radicals, which are highly reactive compounds that, if left unchecked, can lead to cellular damage. Free radicals are believed by some experts to be a major culprit in heart disease, cancer, and aging itself.
2) The study conducted by Dr. Pezzuto showed that resveratrol was effective against the progression of cancer. Most impressively, it was effective in all the major stages of cancer -- the initiation, promotion, and progression.
3) Resveratrol has been shown to help lower bad cholesterol (LDL), and, therefore, may be a potent nutrient in preventing cardiovascular disease. It has also shown to reduce the clumping of platelets. Thus, such conditions as atherosclerosis and heart attacks, which are often caused by arterial blockages, may potentially be reduced by this potent substance.

Resveratrol has several activities that may account for its possible cardioprotective action. These include inhibition of the oxidation of low-density lipoprotein (LDL), inhibition of smooth muscle cell proliferation and inhibition of platelet aggregation. Resveratrol has also been found to reduce the synthesis of lipids in rat liver and to inhibit the production of proatherogenic eicosanoids by human platelets and neutrophils. Resveratrol's antioxidant activity may play an important role in its possible cardioprotective action. Above, was mentioned its ability to inhibit the oxidation of LDL. Resveratrol also has been found to exert a strong inhibitory effect on superoxide anion and hydrogen peroxide production by macrophages stimulated by lipopolysaccharides or phorbol esters. It also has been demonstrated to decrease arachidonic acid release induced by lipopolysaccharides or phorbol esters, or by exposure to superoxide or hydrogen peroxide. It has hydroxyl-radical scavenging activity and has recently been found to possess glutathione-sparing activity. Resveratrol's possible phytoestrogenic activity may also contribute to its possible cardioprotective action. Resveratrol appears to act as a mixed agonist/antagonist for estrogen receptors alpha and beta. It has been found to bind estrogen receptor beta and estrogen receptor alpha with comparable affinity but with 7,000-fold lower affinity than estradiol. Resveratrol differs from other phytoestrogens, which bind estrogen receptor beta with higher affinity than they bind estrogen receptor alpha. Resveratrol also shows estradiol antagonistic behavior for estrogen receptor alpha with some estrogen receptors. It does not show estradiol antagonistic activity with estrogen receptor beta. Resveratrol's possible antiproliferative activity also may be accounted for in several different ways. Resveratrol's antioxidant activity was discussed above. It also has antimutagenic activity, as illustrated by its dose-dependent inhibition of the mutagenic response induced by treatment of Salmonella typhimurium strain TM677 with 7,12-dimethylbenz(a)anthracene (DMBA). Resveratrol has been found to inhibit cellular events associated with tumor initiation, promotion and progression. It has been found to inhibit cyclooxygenase (COX) activities in different cancer models, suggesting an effect at the level of tumor promotion. It has also been found to reverse tumor-promoter-induced inhibition of gap-junctional intracellular communication in rat epithelial cells. Inhibition of gap-junctional intracellular communication is an important mechanism of tumor promotion. Resveratrol has demonstrated inhibition of growth of several cancer cell lines and tumors, suggesting that it has an inhibitory effect on cancer promotion/progression. It has been found to inhibit ribonucleotide reductase, DNA polymerase, the transcription of COX-2 in human mammary epithelial cells and the activity of ornithine decarboxylase. Ornithine decarboxylase is a key enzyme of polyamine biosynthesis, which is enhanced in tumor growth. Resveratrol has also been found to induce phase II metabolizing enzymes which are involved in the detoxification of carcinogens, to upregulate apoptosis, to inhibit the progression of cancer by inducing cell differentiation and to inhibit protein kinase D and possibly protein kinase C. Recently, resveratrol has been shown to inhibit both NF-kappaB activation and NF-kappaB-dependent gene expression via its ability to inhibit IkappaB kinase activity, the key regulator of NF-kappaB activation. This appears to upregulate apoptosis.

Synonyms: trans-3,4',-5-trihydroxystilebene
Molecular Formula: C14H12O3
Molecular Weight: 228.2
CAS Number: 501-36-0
Appearance: Off-white Powder
Purity by HPLC: Minimum 98%
Solubility: Clear faint yellow solution at 50Mg/Ml in acetone.
Packing Nt.W:500g/Al drum, with the inner aluminum foil package
Storage: The product is stable stored at 4 C and in a dampproof, airtight, lightresistant area for at least two years.