Chemical structures of cis- ((Z)-resveratrol, left) and trans-resveratrol ((E)-resveratrol, right)
|Jmol 3D model||Interactive image|
|Molar mass||228.25 g·mol−1|
|Appearance||white powder with
slight yellow cast
|Melting point||261 to 263 °C (502 to 505 °F; 534 to 536 K)|
|Solubility in water||0.03 g/L|
|Solubility in DMSO||16 g/L|
|Solubility in ethanol||50 g/L|
|UV-vis (λmax)||304nm (trans-resveratrol, in water)
286nm (cis-resveratrol, in water)
|Safety data sheet||Fisher Scientific
|R-phrases||R36 (irritating to eyes)|
|S-phrases||S26 (in case of contact with eyes, rinse immediately with plenty of water and
seek medical advice)
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|23.2 µM (5.29 g)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced naturally by several plants in response to injury or when the plant is under attack by pathogens such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and senna.
Although it is used as a dietary supplement, there is no clear evidence that consuming resveratrol affects life expectancy or human health. However, one meta-analysis noted that high doses of resveratrol produce statistically significant reductions in systolic blood pressure.
- 1 Health effects
- 2 Adverse effects
- 3 Pharmacology
- 4 Chemistry
- 5 Occurrences
- 6 History
- 7 Research
- 8 Related compounds
- 9 See also
- 10 References
- 11 External links
There is no evidence of benefit from resveratrol in those who already have heart disease. A 2014 Chinese meta-analysis found that resveratrol supplementation at doses below 150 mg per day had no effect on blood pressure, whereas increasing the dose to above 150 mg per day could reduce systolic blood pressure.
Although limited human studies have shown resveratrol is well-tolerated, one clinical study of Alzheimer's disease patients showed there were side effects from daily intake of up to 2 grams, including nausea, diarrhea and weight loss.
One way of administering resveratrol in humans may be buccal delivery, that is without swallowing, by direct absorption through tissues on the inside of the mouth. When one milligram of resveratrol in 50 ml 50% alcohol/ water solution was retained in the mouth for one minute 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. However, the viability of a buccal delivery method is called into question due to the low aqueous solubility of the molecule. For a drug to be absorbed transmucosally it must be in free-form or dissolved. Resveratrol fits the criteria for oral transmucosal dosing, except for this caveat. The low aqueous solubility greatly limits the amount that can be absorbed through the buccal mucosa. Resveratrol that is attempted to be taken buccally was expected to pass through the mucous membrane of the mouth and be absorbed as an oral dose, however, the need to explore buccal delivery in future pharmaceutical formulations was expressed.
While 70% of orally administered resveratrol is absorbed its oral bioavailability is approximately 0.5% due to extensive hepatic glucuronidation and sulfation. Resveratrol given in a proprietary formulation SRT-501 (3 or 5 g), developed by Sirtris Pharmaceuticals, reached five to eight times higher blood levels. These levels did approach the concentration necessary to exert the effects shown in animal models and in vitro experiments.
In rats, less than 5% of the oral dose was observed as free resveratrol in blood plasma. There is a hypothesis that resveratrol from wine could have higher bioavailability than resveratrol from a pill.
Resveratrol gets extensively metabolized in the body, with the liver and lungs as the major sites of its metabolism.
Resveratrol (3,5,4'-trihydroxystilbene) is a stilbenoid, a derivative of stilbene.
Trans-resveratrol in the powder form was found to be stable under "accelerated stability" conditions of 75% humidity and 40 °C in the presence of air. The trans isomer is also stabilized by the presence of transport proteins. Resveratrol content also was stable in the skins of grapes and pomace taken after fermentation and stored for a long period. lH- and 13C-NMR data for the four most common forms of resveratrols are reported in literature.
The grapevine fungal pathogen Botrytis cinerea is able to oxidise resveratrol into metabolites showing attenuated antifungal activities. Those include the resveratrol dimers restrytisol A, B, and C, resveratrol trans-dehydrodimer, leachinol F, and pallidol. The soil bacterium Bacillus cereus can be used to transform resveratrol into piceid (resveratrol 3-O-beta-D-glucoside).
In grapes, trans-resveratrol is a phytoalexin produced against the growth of fungal pathogens such as Botrytis cinerea. Its presence in Vitis vinifera grapes can also be constitutive, with accumulation in ripe berries of different levels of bound and free resveratrols, according to the genotype. In grapes, resveratrol is found primarily in the skin, and, in muscadine grapes, also in the seeds. The amount found in grape skins also varies with the grape cultivar, its geographic origin, and exposure to fungal infection. The amount of fermentation time a wine spends in contact with grape skins is an important determinant of its resveratrol content.
It is also found in Pinus strobus, the eastern white pine.
The levels of resveratrol found in food varies considerably. Red wine contains between 0.2 and 5.8 mg/l, depending on the grape variety. White wine has much less because red wine is fermented with the skins, allowing the wine to extract the resveratrol, whereas white wine is fermented after the skin has been removed. The composition of wine is different from that of grapes since the extraction of resveratrol from grapes depends on the duration of the skin contact, and the resveratrol 3-glucosides are in part hydrolysed, yielding both trans- and cis-resveratrol.
Muscadine grapes may contain concentrations of resveratrol possibly as high as 40 mg/l, but subsequent studies have found little or no resveratrol in different varieties of muscadine grapes.
Peanuts, especially sprouted peanuts, have a content similar to grapes in a range of 2.3 to 4.5 μg/g before sprouting, and after sprouting, in a range of 11.7 to 25.7 μg/g, depending upon peanut cultivar.
Wine and grape juice
|Beverage||Total resveratrol (mg/l)||Total resveratrol (mg/150 ml)|
|Red wine (global)||1.98 – 7.13||0.30 – 1.07|
|Red wine (Spanish)||1.92 – 12.59||0.29 – 1.89|
|Red grape juice (Spanish)||1.14 – 8.69||0.17 – 1.30|
|Rose wine (Spanish)||0.43 – 3.52||0.06 – 0.53|
|Pinot noir||0.40 – 2.0||0.06 – 0.30|
|White wine (Spanish)||0.05 – 1.80||0.01 – 0.27|
The trans-resveratrol concentration in 40 Tuscan wines ranged from 0.3 to 2.1 mg/l in the 32 red wines tested and had a maximum of 0.1 mg/l in the 8 white wines in the test. Both the cis- and trans-isomers of resveratrol were detected in all tested samples. cis-resveratrol levels were comparable to those of the trans-isomer. They ranged from 0.5 mg/l to 1.9 mg/l in red wines and had a maximum of 0.2 mg/l in white wines.
In a review of published resveratrol concentrations, the average in red wines is ±1.7 mg trans-resveratrol/L ( 1.9±7.5 µM, ranging from nondetectable levels to 14.3 mg/l (62.7 μM) trans-resveratrol. Levels of cis-resveratrol follow the same trend as trans-resveratrol. 8.2
Reports suggest some aspect[which?] of the wine making process converts piceid to resveratrol in wine, as wine seems to have twice the average resveratrol concentration of the equivalent commercial juices.
In general, wines made from grapes of the Pinot Noir and St. Laurent varieties showed the highest level of trans-resveratrol, though no wine or region can yet be said to produce wines with significantly higher concentrations than any other wine or region. Champagne and vinegar also contain appreciable levels of resveratrol.
|Food||Serving||Total resveratrol (mg)|
|Peanuts (raw)||1 cup (146 grams)||0.01 – 0.26|
|Peanuts (boiled)||1 cup (180 grams)||0.32 – 1.28|
|Peanut butter||1 cup (258 grams)||0.04 – 0.13|
|Red grapes||1 cup (160 grams)||0.24 – 1.25|
|Cocoa powder||1 cup (200 grams)||0.28 – 0.46|
In comparison, some red wines contain approximately 2 mg per litre or 0.3 mg per 5 ounce glass. Resveratrol was detected in grape, cranberry, and wine samples. Concentrations ranged from 1.56 to 1042 nmol/g in Concord grape products, and from 8.63 to 24.84 µmol/L in Italian red wine. The concentrations of resveratrol were similar in cranberry and grape juice at 1.07 and 1.56 nmol/g, respectively.
Blueberries have about twice as much resveratrol as bilberries, but there is great regional variation. These fruits have less than 10% of the resveratrol of grapes. Cooking or heat processing of these berries will contribute to the degradation of resveratrol, reducing it by up to half.
Supplements vary in purity and can contain anywhere from 50 percent to 99 percent resveratrol. Many brands consist of an unpurified extract of Japanese knotweed (Polygonum cuspidatum), an introduced species in many countries. These contain about 50 percent resveratrol by weight, as well as emodin, which, while considered safe in moderate quantities, can have a laxative effect in high amounts. Resveratrol can be produced from its glucoside piceid from Japanese knotweed fermented by Aspergillus oryzae.
Harvard University scientist and professor David Sinclair was often quoted in online ads for resveratrol supplements, many of which implied endorsement of the advertised product; however, Sinclair, a pioneer in resveratrol research, went on record to say he never uttered many of the statements attributed to him on these sites.
The first mention of resveratrol was in a Japanese article in 1939 by Michio Takaoka, who isolated it from Veratrum album, variety grandiflorum. The name presumably derives from the resorcinol derivative of a Veratrum species. In 2003, David Sinclair from Harvard Medical School reported that resveratrol activated sirtuins in yeast cells. The finding eventually led to the launch of Sirtris Pharmaceuticals, an early-stage biotechnology company.
A 2011 systematic review of existing resveratrol research demonstrated there was not enough evidence to demonstrate its effect on longevity or human diseases, nor could there be recommendations for intake beyond the amount normally obtained through dietary sources. Much of the research showing positive effects has been done on animals, with insufficient clinical research on humans.
As of 2014[update], the results of limited human clinical trials with small samples sizes of the effects of resveratrol on cancer are inconsistent. Testing of resveratrol in animal models of cancer have also shown mixed results. The strongest evidence of anticancer action of resveratrol exists for tumors it can contact directly, such as skin and gastrointestinal tract tumors. For other cancers, the evidence is uncertain, even if massive doses of resveratrol are used. Resveratrol treatment appeared to prevent the development of mammary tumors in animal models; however, it had no effect on the growth of existing tumors. Paradoxically, treatment of prepubertal mice with high doses of resveratrol enhanced formation of tumors. Injected in high doses into mice, resveratrol slowed the growth of neuroblastomas.
A preliminary, one-year clinical trial of subjects with Alzheimer's disease showed that consuming 2 grams of resveratrol daily was well-tolerated and reduced some disease biomarkers in cerebrospinal fluid and blood, although other biomarkers and progressive dementia were unaffected. Other preliminary human studies indicated that short-term ingestion of resveratrol increased cerebral blood flow in normal subjects and in those with diabetes.
Studies suggest resveratrol in red wine may play an important role in this phenomenon. It appears to stimulate endothelial nitric oxide synthase (eNOS) activity and inhibit platelet aggregation.
Animal studies have demonstrated an antidiabetic effects of resveratrol. This compound was shown to act as agonist of PPARgamma, nuclear receptor that is current pharmacological target for the treatment of type 2 diabetes. A systematic review and meta-analysis noted that resveratrol is a "leading candidate" compound for serving as an adjunct pharmacotherapy for type 2 diabetes.
|This section needs to be updated. (October 2016)|
Despite considerable in vitro and animal research, there is no evidence that resveratrol taken orally or topically has any effect on human skin. Preliminary studies support human research on resveratrol to understand its potential as a therapy for melanoma.
- Epsilon-viniferin, Pallidol and Quadrangularin A three different resveratrol dimers
- Trans-diptoindonesin B, a resveratrol trimer
- Hopeaphenol, a resveratrol tetramer
- Oxyresveratrol, the aglycone of mulberroside A, a compound found in Morus alba, the white mulberry
- Piceatannol, an active metabolite of resveratrol found in red wine
- Piceid, a resveratrol glucoside
- Pterostilbene, a doubly methylated resveratrol
- 4'-Methoxy-(E)-resveratrol 3-O-rutinoside, a compound found in the stem bark of Boswellia dalzielii
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