Chemical Name: trans-3,5,4'-Trihydroxystilbene;3,4',5-Stilbenetriol;trans-Resveratrol;(E)-5-(p-Hydroxystyryl)resorcinol (E)-5-(4-hydroxystyryl)benzene-1,3-diol
Molecular Formula:C₁₄H₁₂O₃

Mol. Wt.:228.24

Molecular Structure:

Chemical and physical properties of Resveratrol

Resveratrol (3,5,4'-trihydroxystilbene) is a polyphenolic phytoalexin. It is a stilbenoid, a derivate of stilbene, and is produced in plants with the help of the enzyme stilbene synthase. It exists as two geometric isomers: cis- (Z) and trans- (E), with the trans-isomer shown in the top image. The trans- form can undergo isomerisation to the cis- form when exposed to ultraviolet irradiation. Trans-resveratrol in the powder form was found to be stable under "accelerated stability" conditions of 75% humidity and 40 degrees C in the presence of air. Resveratrol content also stayed stable in the skins of grapes and pomace taken after fermentation and stored for a long period.

Acetyl-resveratrol

CAS No.: 42206-94-0

Chemical Name: 5-[(1E)-2-[4-(acetyloxy)phenyl]ethenyl]-1,3-Benzenediol diacetate; 3,4',5-Triacetoxy-trans-stilbene; 3,5,4'-Tri-O-acetylresveratrol; trans-Resveratrol triacetate

Molecular Formula:C₂₀H₁₈O₆

Mol. Wt.: 354.35

Molecular Structure:

Chemical and physical properties of Acetyl-resveratrol

Acetyl-resveratrolis a derivative of the Resveratrol (trans-). The resveratrol’s Hydroxyls are replaced by acetyls. Acetyl –resveratrol is called prodrug on medicinal chemistry. Acetyl-resveratrol is more stable than trans-resveratrol. When absorbed, it returns to resveratrol under action of metabolism. Scientists have started analyzing these naturally occurring analogs to determine why it is they seem to be so biologically active and important. What they found was that among these analogs, acetylated phenolics exhibited a higher level of activity that is attributed to faster absorption and greater cellular uptake. The existence of these acetylated phenolic compounds in natural sources has been established in many recent studies and the comparative data is being studied extensively. So far the naturally occurring acetylated derivatives of Resveratrol have been identified in plants and specifically, triacetylated resveratrol has been found in marine invertebrates.

Resveratrol(trans-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 and is sold as a nutritional supplement derived primarily from Japanese knotweed. In mouse and rat experiments, anti-cancer, anti-inflammatory, blood-sugar-lowering 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 proprietary formulation have been necessary to significantly lower blood sugar. 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. Experiments have shown that resveratrol treatment extended the life of fruit flies, nematode worms and short-lived fish but it did not increase the life span of mice.

The Resveratrol (trans-) and Acetyl-resveratrol used in dietary supplements is derived primarily from the roots of Polygonum cuspidatum. Resveratrol was originally isolated by Takaoka from the roots of white hellebore in 1940, and later, in 1963, from the roots of Japanese knotweed. However, it attracted wider attention only in 1992, when its presence in wine was suggested as the explanation for cardioprotective effects of wine. Resveratrol is also found in many kinds of plants and foods, such as in grape (primarily in the skin, and in muscadine grape also in the seeds), in red wine — the reason being that red wine is fermented with the skins, allowing the wine to absorb the resveratrol, in the fruits of the mulberry (esp. the skin), in bluberries and bilberries, and ect..

Japanese knotweed (Polygonum cuspidatum)is a perennial species with spreading rhizomes and numerous reddish-brown, freely branched stems. Its root is much richer in resveratrol than any other plant known, and now is the primarily natural source of resveratrol.

Benefits

Anti-oxidant

Life extension

Cancer prevention (Anti-cancer)

Anti-diabetic property (Activate AMPK, Blood sugar lowering)

Beneficial cardiovascular effects

Anti-inflammatory effects

Supplementation As a result of extensive news coverage, sales of supplements greatly increased in 2006, despite cautions that benefits to humans are unproven.

Pharmacokinetics

The most efficient way of administering resveratrol in humans appears to be buccal delivery that is without swallowing, by direct absorption through the inside of the mouth. When one mg of resveratrol in 50 mL solution was retained in the mouth for one min before swallowing, 37 ng/ml of free resveratrol were measured in plasma two minutes later. This level of unchanged resveratrol in blood can only be achieved with 250 mg of resveratrol taken in a pill form.

Mechanisms of action

The mechanisms of resveratrol's apparent effects on life extension are not fully understood, but they appear to mimic several of the biochemical effects of calorie restriction.

Resveratrol interferes with all three stages of carcinogenesis — initiation, promotion and progression.

Resveratrol was reported effective against neuronal cell dysfunction and cell death, and in theory could help against diseases such as Huntington's disease and Alzheimer's disease.Again, this has not yet been tested in humans for any disease.

Research at the Northeastern Ohio Universities College of Medicine and Ohio State University indicates that resveratrol has direct inhibitory action on cardiac fibroblasts, and may inhibit the progression of cardiac fibrosis.

Resveratrol also significantly increases natural testosterone production from being both a selective estrogen receptor modulator and an aromatase inhibitor.

In December 2007, work from Irfan Rahman's laboratory at the University of Rochester demonstrated that resveratrol increased intracellular glutathione levels via Nrf2-dependent upregulation of gamma-glutamylcysteine ligase in lung epithelial cells, which protected them against cigarette smoke extract induced oxidative stress.

Safety, Adverse effects and unknowns

Long term effects of using resveratrol are as of yet unknown. While the health benefits of resveratrol seem promising, one study has theorized that it may stimulate the growth of human breast cancer cells, possibly because of resveratrol's chemical structure, which is similar to a phytoestrogen. However, other studies have found that resveratrol actually fights breast cancer. Some studies suggest that resveratrol slows the development of blood vessels, which suppresses tumors, but also slows healing. Citing the evidence that resveratrol is estrogenic, some retailers of resveratrol advise that the compound may interfere with oral contraceptives and that women who are pregnant or intending to become pregnant should not use the product, while others advise that resveratrol should not be taken by children or young adults under eighteen, as no studies have shown how it affects their natural development. A small study found that a single dose of up to 5 g of trans-resveratrol caused no serious adverse effects in healthy volunteers.

Dosage

• The typical dose is 500-1200mg per day (usually in 2-3 doses throughout the day).
• Consult physicians for different condition specifics.

GNI’s Resveratrol Features and Benefits:

Resveratrol is one of GNI's most competitive products, with many advantages as list in the following, produced as our patent-pending process and know-how technology from Polygonum cuspidatum roots.

• Produced with pure water only

• High purity: over 99%

• Low Emodin content

• NO solvent - residual free

• Pesticide-free

• Crystal white in appearance

• High anti-bacteria, and longer shelf life