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*’resveratrol’ (3,5,4′-trihydroxy-trans-stilbene) is a*
‘stilbenoid’,
a type of natural phenol,
and a phytoalexin
.
produced 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 peanuts
Although commonly used as a dietary supplement and studied in laboratory models of human diseases, there is no high-quality evidence that resveratrol improves lifespan or has a substantial effect on any human disease
.
Research
Resveratrol has been studied for its potential therapeutic use,[13] with little evidence of anti-disease effects or health benefits in humans
.
Cardiovascular disease
There is no evidence of benefit from resveratrol in people who already have heart disease.[9][14] A 2018 meta-analysis found no effect on systolic or diastolic blood pressure; a sub-analysis revealed a 2 mmHg decrease in systolic pressure only from resveratrol doses of 300 mg per day, and only in diabetic people.[15] A 2014 Chinese meta-analysis found no effect on systolic or diastolic blood pressure; a sub-analysis found an 11.90 mmHg reduction in systolic blood pressure from resveratrol doses of 150 mg per day.[16]
Cancer[edit]
As of 2020, there is no evidence of an effect of resveratrol on cancer in humans.[9][17]
Metabolic syndrome[edit]
There is no conclusive evidence for an effect of resveratrol on human metabolic syndrome.[9][18][19] One 2015 review found little evidence for use of resveratrol to treat diabetes.[20] A 2015 meta-analysis found little evidence for an effect of resveratrol on diabetes biomarkers.[21]
One review found limited evidence that resveratrol lowered fasting plasma glucose in people with diabetes.[22] Two reviews indicated that resveratrol supplementation may reduce body weight and body mass index, but not fat mass or total blood cholesterol.[23][24] A 2018 review found that resveratrol supplementation may reduce biomarkers of inflammation, TNF-α and C-reactive protein.[25]
Lifespan[edit]
There is insufficient evidence to indicate that consuming resveratrol has an effect on human lifespan.[10]
Cognition[edit]
Resveratrol has been assessed for a possible effect on cognition, but with mixed evidence for an effect. One review concluded that resveratrol had no effect on neurological function, but reported that supplementation improved recognition and mood, although there were inconsistencies in study designs and results.[26]
Other[edit]
There is no significant evidence that resveratrol affects vascular endothelial function, neuroinflammation, Alzheimer’s disease, skin infections or aging skin.[5][9]
A review of basic research on animals reported that resveratrol decreased bone loss in periodontal disease.[27]
A 2019 review of human studies found mixed effects of resveratrol on certain bone biomarkers, such as increases in blood and bone alkaline phosphatase, while reporting no effect on other biomarkers, such as calcium and collagen.[28]
Pharmacology[edit]
Pharmacodynamics[edit]
Resveratrol has been identified as a pan-assay interference compound, which produces positive results in many different laboratory assays.[29] Its ability for varied interactions may be due to direct effects on cell membranes.[30]
As of 2015, many specific biological targets for resveratrol had been identified, including NQO2 (alone and in interaction with AKT1), GSTP1, estrogen receptor beta, CBR1, and integrin αVβ. It was unclear at that time if any or all of these were responsible for the observed effects in cells and model organisms.[31]
In vitro studies indicate resveratrol activates sirtuin 1,[32] although this may be a downstream effect from its immediate biological target(s).[33][34][35] It appears to signal through PGC-1α, thereby affecting mitochondria.[36] In cells treated with resveratrol, an increase is observed in the action of MnSOD (SOD2)[37] and in GPER activity.[38] In vitro, resveratrol was shown to act as an agonist of Peroxisome proliferator-activated receptor gamma, a nuclear receptor under pharmacological research as a potential treatment for type 2 diabetes.[39]
Pharmacokinetics[edit]
One way of administering resveratrol in humans may be buccal delivery by direct absorption through the saliva. However, the viability of a buccal delivery method is unlikely due to the low aqueous solubility of the molecule.[40][41] The bioavailability of resveratrol is about 0.5% due to extensive hepatic glucuronidation and sulfation.[42] Due to rapid metabolism, the half-life of resveratrol is short (about 8–14 minutes), but the half-life of the sulphate and glucoronide metabolites is above 9 hours.[43]
Metabolism[edit]
Resveratrol is extensively metabolized in the body,[5] with the liver and intestines as the major sites of its metabolism.[44][43] Liver metabolites are products of phase II (conjugation) enzymes,[45] which are themselves induced by resveratrol in vitro.[46]
Chemistry[edit]
Resveratrol (3,5,4′-trihydroxystilbene) is a stilbenoid, a derivative of stilbene.[5] It exists as two geometric isomers: cis- (Z) and trans- (E), with the trans-isomer shown in the top image. Resveratrol exists conjugated to glucose.[47]
The trans- form can undergo photoisomerization to the cis- form when exposed to ultraviolet irradiation.[48][49]
Resveratrol photoisomerization
UV irradiation to cis-resveratrol induces further photochemical reaction, producing a fluorescent molecule named “Resveratrone”.[50]
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.[51] The trans isomer is also stabilized by the presence of transport proteins.[52] Resveratrol content also was stable in the skins of grapes and pomace taken after fermentation and stored for a long period.[53] lH- and 13C-NMR data for the four most common forms of resveratrols are reported in literature.[47]
Biosynthesis[edit]
Resveratrol is produced in plants via the enzyme, resveratrol synthase (stilbene synthase).[54][55] Its immediate precursor is a tetraketide derived from malonyl CoA and 4-coumaroyl CoA.[54][55] The latter is derived from phenylalanine
.
bio-transformation
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.[57] The soil bacterium Bacillus cereus can be used to transform resveratrol into piceid (resveratrol 3-O-beta-D-glucoside).[58]
Adverse effects[edit]
Only a few human studies have been done to determine the adverse effects of resveratrol, all of them preliminary with small participant numbers. Adverse effects resulted mainly from long-term use (weeks or longer) and daily doses of 1000 mg or higher, causing nausea, stomach pain, flatulence, and diarrhea.[5] A review of 136 patients in seven studies who were given more than 500 mg for a month showed 25 cases of diarrhea, 8 cases of abdominal pain, 7 cases of nausea, and 5 cases of flatulence.[59] In a year-long preliminary clinical trial in people with Alzheimer’s disease, the most frequent adverse effects were nausea and weight loss.[60] A 2018 review of resveratrol effects on blood pressure found that some people had increased frequency of bowel movements and loose stools.[15]
Occurrences[edit]
Plants[edit]
Resveratrol is a phytoalexin, a class of compounds produced by many plants when they are infected by pathogens or physically harmed by cutting, crushing, or ultraviolet radiation.[61]
Plants that synthesize resveratrol include knotweeds, pine trees including Scots pine and Eastern white pine, grape vines, peanut plants, cocoa bushes, and Vaccinium shrubs that produce berries, including blueberries, raspberries, mulberries, cranberries, and bilberries.[5][7][61]
Foods[edit]
The levels of resveratrol found in food varies considerably, even in the same food from season to season and batch to batch.[5]
Wine and grape juice[edit]
Beverage Resveratrol (mg/100 ml)[8]
mean range
Red wine 0.27 0 — 2.78
Rosé wine 0.12 5.00×10−03 — 0.29
White wine 0.04 0.00 — 0.17
Sparkling wine 0.009 8.00×10−03 — 1.00×10−02
Green grape juice 0.00508 0.00 — 1.00×10−02
Resveratrol concentrations in red wines average 1.9±1.7 mg trans-resveratrol/L (8.2±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.[62]
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.[62] Champagne and vinegar also contain appreciable levels of resveratrol.[8]
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.[5] 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.[5][63]
Selected foods[edit]
Food Serving Total resveratrol (mg)[5]
Peanuts (raw) 1 cup (146 grams) 0.01 – 0.26
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
Ounce for ounce, peanuts have about 25% as much resveratrol as red wine.[5] 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 on peanut cultivar.[8][61]
Mulberries (especially the skin) are a source of as much as 50 micrograms of resveratrol per gram dry weight.[64]
History[edit]
The first mention of resveratrol was in a Japanese article in 1939 by Michio Takaoka, who isolated it from Veratrum album, variety grandiflorum, and later, in 1963, from the roots of Japanese knotweed.[61][65][66][67] Harvard University professor David Sinclair co-founded Sirtris Pharmaceuticals, the initial product of which was a resveratrol formulation.[68][69][70]
[edit]
Dihydro-resveratrol
Epsilon-viniferin, Pallidol and Quadrangularin A three different resveratrol dimers
Elafibranor, a structurally related compound that acts as a dual PPARα/δ agonist
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[71]
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[72]
Rhaponticin a glucoside of the stilbenoid rhapontigenin, found in rhubarb rhizomes
See also[edit]
Phenolic compounds in wine
Polyphenol antioxidant
Wine and health
List of phytochemicals in food
Nutrition
Phytochemistry
Secondary metabolites
References[edit]
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^ Prokop J, Abrman P, Seligson AL, Sovak M; Abrman; Seligson; Sovak (2006). “Resveratrol and its glycon piceid are stable polyphenols”. J Med Food. 9 (1): 11–4. doi:10.1089/jmf.2006.9.11. PMID 16579722.CS1 maint: multiple names: authors list (link)
^ Pantusa M, Bartucci R, Rizzuti B; Bartucci; Rizzuti (2014). “Stability of trans-resveratrol associated with transport proteins”. J Agric Food Chem. 62 (19): 4384–91. doi:10.1021/jf405584a. PMID 24773207.CS1 maint: multiple names: authors list (link)
^ Bertelli AA, Gozzini A, Stradi R, Stella S, Bertelli A; Gozzini; Stradi; Stella; Bertelli (1998). “Stability of resveratrol over time and in the various stages of grape transformation”. Drugs Exp Clin Res. 24 (4): 207–11. PMID 10051967.CS1 maint: multiple names: authors list (link)
^ Jump up to: a b Valletta, Alessio; Iozia, Lorenzo Maria; Leonelli, Francesca (January 2021). “Impact of Environmental Factors on Stilbene Biosynthesis”. Plants. 10 (1): 90. doi:10.3390/plants10010090.
^ Jump up to: a b Dubrovina, A. S.; Kiselev, K. V. (October 2017). “Regulation of stilbene biosynthesis in plants”. Planta. 246 (4): 597–623. doi:10.1007/s00425-017-2730-8. ISSN 0032-0935.
^ Wang, Chuanhong; Zhi, Shuang; Liu, Changying; Xu, Fengxiang; Zhao, Aichun; Wang, Xiling; Ren, Yanhong; Li, Zhengang; Yu, Maode (2017). “Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli”. Journal of Agricultural and Food Chemistry. 65 (8): 1659–1668. doi:10.1021/acs.jafc.6b05212. PMID 28168876.
^ Cichewicz RH, Kouzi SA, Hamann MT; Kouzi; Hamann (January 2000). “Dimerization of resveratrol by the grapevine pathogen Botrytis cinerea”. J. Nat. Prod. 63 (1): 29–33. doi:10.1021/np990266n. PMID 10650073.CS1 maint: multiple names: authors list (link)
^ Cichewicz RH, Kouzi SA; Kouzi (October 1998). “Biotransformation of resveratrol to piceid by Bacillus cereus”. J. Nat. Prod. 61 (10): 1313–4. doi:10.1021/np980139b. PMID 9784180.
^ Cottart C, Nivet-Antoine V, Beaudeux J (2014). “Review of recent data on the metabolism, biological effects, and toxicity of resveratrol in humans”. Molecular Nutrition & Food Research. 58 (1): 7–21. doi:10.1002/mnfr.201200589. PMID 23740855.
^ Ahmed, T; Javed, S; Javed, S; Tariq, A; Šamec, D; Tejada, S; Nabavi, SF; Braidy, N; Nabavi, SM (May 2017). “Resveratrol and Alzheimer’s Disease: Mechanistic Insights”. Molecular Neurobiology. 54 (4): 2622–2635. doi:10.1007/s12035-016-9839-9. PMID 26993301. S2CID 22451655.
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External links[edit]
Media related to Resveratrol at Wikimedia Commons
(stilbenoid)
(limited evidence of health effects in humans)
(allegedly lowers blood sugar?)
en.wikipedia.org /wiki/Resveratrol
Resveratrol
Contributors to Wikimedia projects
30-38 minutes
Resveratrol
Chemical 9–69 structure of trans-resveratrol
Chemical structure of trans-resveratrol
Chemical structures of cis- and trans-resveratrols
Chemical structures of cis- ((Z)-resveratrol, left) and trans-resveratrol ((E)-resveratrol, right)[1]
Names
Other names
trans-3,5,4′-Trihydroxystilbene;
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 check
3D model (JSmol)
Interactive image
ChEBI
CHEBI:45713 check
ChEMBL
ChEMBL165 check
ChemSpider
392875 check
DrugBank
DB02709 check
ECHA InfoCard 100.121.386 Edit this at Wikidata
KEGG
C03582 check
PubChem CID
445154
RTECS number
CZ8987000
UNII
Q369O8926L check
CompTox Dashboard (EPA)
DTXSID4031980 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula
C14H12O3
Molar mass 228.247 g·mol−1
Appearance white powder with
slight yellow cast
Melting point 261 to 263 °C (502 to 505 °F; 534 to 536 K)[2]
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)[1]
Hazards
Safety data sheet Fisher Scientific[2]
Sigma Aldrich[3]
R-phrases (outdated) R36 (irritating to eyes)[3]
S-phrases (outdated) S26 (in case of contact with eyes, rinse immediately with plenty of water and seek medical advice)[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
23.2 μM (5.29 g)[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
check verify (what is check☒ ?)
Infobox references
UV visible spectrum of ‘trans-resveratrol’
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