Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a

stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are prod ...

, a type of

natural phenol In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to eco ...

, and a

phytoalexin Phytoalexins are antimicrobial substances, some of which are antioxidative as well. They are defined, not by their having any particular chemical structure or character, but by the fact that they are defensively synthesized ''de novo'' by plants t ...

produced by several plants in response to injury or when the plant is under attack by

pathogen In biology, a pathogen ( el, πάθος, "suffering", "passion" and , "producer of") in the oldest and broadest sense, is any organism or agent that can produce disease. A pathogen may also be referred to as an infectious agent, or simply a germ ...

s, such as

bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...

fungi A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from ...

. Sources of resveratrol in food include the skin of

grape A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began perhaps 8,000 years ago, ...

blueberries Blueberries are a widely distributed and widespread group of perennial flowering plants with blue or purple berries. They are classified in the section ''Cyanococcus'' within the genus ''Vaccinium''. ''Vaccinium'' also includes cranberries, bi ...

raspberries The raspberry is the edible fruit of a multitude of plant species in the genus ''Rubus'' of the rose family, most of which are in the subgenus '' Idaeobatus''. The name also applies to these plants themselves. Raspberries are perennial with w ...

mulberries ''Morus'', a genus of flowering plants in the family Moraceae, consists of diverse species of deciduous trees commonly known as mulberries, growing wild and under cultivation in many temperate world regions. Generally, the genus has 64 identif ...

, and

peanut The peanut (''Arachis hypogaea''), also known as the groundnut, goober (US), pindar (US) or monkey nut (UK), is a legume crop grown mainly for its edible Seed, seeds. It is widely grown in the tropics and subtropics, important to both small ...

s. Although commonly used as a

dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...

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, 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 Cardiovascular disease (CVD) is a class of diseases that involve the heart or blood vessels. CVD includes coronary artery diseases (CAD) such as angina and myocardial infarction (commonly known as a heart attack). Other CVDs include stroke, hea ...

. A 2018

meta-analysis A meta-analysis is a statistical analysis that combines the results of multiple scientific studies. Meta-analyses can be performed when there are multiple scientific studies addressing the same question, with each individual study reporting me ...

found no effect on

systolic Systole ( ) is the part of the cardiac cycle during which some chambers of the heart contract after refilling with blood. The term originates, via New Latin, from Ancient Greek (''sustolē''), from (''sustéllein'' 'to contract'; from ''sun ...

diastolic blood pressure Blood pressure (BP) is the pressure of circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term "blood pressure" r ...

; 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. 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 Blood pressure (BP) is the pressure of circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term "blood pressure" r ...

from resveratrol doses of 150 mg per day.

Cancer

, there is no evidence of an effect of resveratrol on cancer in humans.

Metabolic syndrome

There is no conclusive evidence for an effect of resveratrol on human

metabolic syndrome Metabolic syndrome is a clustering of at least three of the following five medical conditions: abdominal obesity, high blood pressure, high blood sugar, high serum triglycerides, and low serum high-density lipoprotein (HDL). Metabolic syndrome ...

. One 2015 review found little evidence for use of resveratrol to treat

diabetes Diabetes, also known as diabetes mellitus, is a group of metabolic disorders characterized by a high blood sugar level ( hyperglycemia) over a prolonged period of time. Symptoms often include frequent urination, increased thirst and increased ap ...

. A 2015 meta-analysis found little evidence for an effect of resveratrol on diabetes

biomarker In biomedical contexts, a biomarker, or biological marker, is a measurable indicator of some biological state or condition. Biomarkers are often measured and evaluated using blood, urine, or soft tissues to examine normal biological processes, ...

s. One review found limited evidence that resveratrol lowered

fasting plasma glucose Many types of glucose tests exist and they can be used to estimate blood sugar levels at a given time or, over a longer period of time, to obtain average levels or to see how fast body is able to normalize changed glucose levels. Eating food for e ...

in people with diabetes. Two reviews indicated that resveratrol supplementation may reduce

body weight Human body weight is a person's mass or weight. Strictly speaking, body weight is the measurement of weight without items located on the person. Practically though, body weight may be measured with clothes on, but without shoes or heavy accessor ...

and

body mass index Body mass index (BMI) is a value derived from the mass (weight) and height of a person. The BMI is defined as the body mass divided by the square of the body height, and is expressed in units of kg/m2, resulting from mass in kilograms and he ...

, but not

fat mass Adipose tissue, body fat, or simply fat is a loose connective tissue composed mostly of adipocytes. In addition to adipocytes, adipose tissue contains the stromal vascular fraction (SVF) of cells including preadipocytes, fibroblasts, vascular e ...

or total

blood cholesterol Blood lipids (or blood fats) are lipids in the blood, either free or bound to other molecules. They are mostly transported in a protein capsule, and the density of the lipids and type of protein determines the fate of the particle and its influence ...

. A 2018 review found that resveratrol supplementation may reduce

s of

inflammation Inflammation (from la, wikt:en:inflammatio#Latin, inflammatio) is part of the complex biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or Irritation, irritants, and is a protective response involving im ...

TNF-α Tumor necrosis factor (TNF, cachexin, or cachectin; formerly known as tumor necrosis factor alpha or TNF-α) is an adipokine and a cytokine. TNF is a member of the TNF superfamily, which consists of various transmembrane proteins with a homolog ...

and

C-reactive protein C-reactive protein (CRP) is an annular (ring-shaped) pentameric protein found in blood plasma, whose circulating concentrations rise in response to inflammation. It is an acute-phase protein of hepatic origin that increases following interleukin-6 ...

Lifespan

There is insufficient evidence to indicate that consuming resveratrol has an effect on human lifespan.

Cognition

Resveratrol has been assessed for a possible effect on

cognition Cognition refers to "the mental action or process of acquiring knowledge and understanding through thought, experience, and the senses". It encompasses all aspects of intellectual functions and processes such as: perception, attention, thought, ...

, 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.

Diabetes

Although animal experiments have found some evidence that resveratrol may help improve

insulin sensitivity Insulin resistance (IR) is a pathological condition in which cells fail to respond normally to the hormone insulin. Insulin is a hormone that facilitates the transport of glucose from blood into cells, thereby reducing blood glucose (blood suga ...

and so potentially help manage diabetes, subsequent research on people is limited and does not support the use of resveratrol for this purpose.

Other

There is no significant evidence that resveratrol affects vascular endothelial function,

neuroinflammation Neuroinflammation is inflammation of the nervous tissue. It may be initiated in response to a variety of cues, including infection, traumatic brain injury,Ebert SE, Jensen P, Ozenne B, Armand S, Svarer C, Stenbaek DS ''et al.'' Molecular imaging of ...

Alzheimer's disease Alzheimer's disease (AD) is a neurodegeneration, neurodegenerative disease that usually starts slowly and progressively worsens. It is the cause of 60–70% of cases of dementia. The most common early symptom is difficulty in short-term me ...

skin infection A skin infection is an infection of the skin in humans and other animals, that can also affect the associated soft tissues such as loose connective tissue and mucous membranes. They comprise a category of infections termed skin and skin structure ...

s or

aging Ageing ( BE) or aging ( AE) is the process of becoming older. The term refers mainly to humans, many other animals, and fungi, whereas for example, bacteria, perennial plants and some simple animals are potentially biologically immortal. In ...

skin. A 2019 review of human studies found mixed effects of resveratrol on certain bone

s, such as increases in blood and bone

alkaline phosphatase The enzyme alkaline phosphatase (EC 3.1.3.1, alkaline phosphomonoesterase; phosphomonoesterase; glycerophosphatase; alkaline phosphohydrolase; alkaline phenyl phosphatase; orthophosphoric-monoester phosphohydrolase (alkaline optimum), systematic ...

, while reporting no effect on other biomarkers, such as

calcium Calcium is a chemical element with the symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar to ...

and

collagen Collagen () is the main structural protein in the extracellular matrix found in the body's various connective tissues. As the main component of connective tissue, it is the most abundant protein in mammals, making up from 25% to 35% of the whole ...

Pharmacology

Pharmacodynamics

Resveratrol has been identified as a pan-assay interference compound, which produces positive results in many different laboratory assays. Its ability for varied interactions may be due to direct effects on

cell membrane The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of all cells from the outside environment ( ...

s. As of 2015, many specific

biological target A biological target is anything within a living organism to which some other entity (like an endogenous ligand or a drug) is directed and/or binds, resulting in a change in its behavior or function. Examples of common classes of biological targets ...

s for resveratrol had been identified, including NQO2 (alone and in interaction with

AKT1 RAC(Rho family)-alpha serine/threonine-protein kinase is an enzyme that in humans is encoded by the ''AKT1'' gene. This enzyme belongs to the AKT subfamily of serine/threonine kinases that contain SH2 (Src homology 2-like) protein domains. It i ...

GSTP1 Glutathione S-transferase P is an enzyme that in humans is encoded by the ''GSTP1'' gene. Function Glutathione S-transferases (GSTs) are a family of enzymes that play an important role in detoxification by catalyzing the conjugation of many hydr ...

estrogen receptor beta Estrogen receptor beta (ERβ) also known as NR3A2 (nuclear receptor subfamily 3, group A, member 2) is one of two main types of estrogen receptor—a nuclear receptor which is activated by the sex hormone estrogen. In humans ERβ is encoded by ...

CBR1 Carbonyl reductase 1, also known as CBR1, is an enzyme which in humans is encoded by the ''CBR1'' gene. The protein encoded by this gene belongs to the short-chain dehydrogenases/reductases (SDR) family, which function as NADPH-dependent oxidore ...

, 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.

Pharmacokinetics

The viability of an oral delivery method is unlikely due to the low aqueous solubility of the molecule. The

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...

of resveratrol is about 0.5% due to extensive

hepatic The liver is a major organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the synthesis of proteins and biochemicals necessary for digestion and growth. In humans, it i ...

glucuronidation Glucuronidation is often involved in drug metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosid ...

and

sulfation Sulfation is the chemical reaction that entails the addition of SO3 group. In principle, many sulfations would involve reactions of sulfur trioxide (SO3). In practice, most sulfations are effected less directly. Regardless of the mechanism, the ...

. Glucuronidation occurs in the intestine as well as in the liver, whereas sulfonation not only occurs in the liver but in the intestine and by microbial gut activity. Due to rapid metabolism, the

half-life Half-life (symbol ) is the time required for a quantity (of substance) to reduce to half of its initial value. The term is commonly used in nuclear physics to describe how quickly unstable atoms undergo radioactive decay or how long stable ato ...

of resveratrol is short (about 8–14 minutes), but the half-life of the sulphate and glucoronide metabolites is above 9 hours.

Metabolism

Resveratrol is extensively metabolized in the body, with the liver and intestines as the major sites of its metabolism. Liver metabolites are products of phase II (conjugation) enzymes, which are themselves induced by resveratrol in vitro.

Chemistry

Resveratrol (3,5,4'-trihydroxystilbene) is a stilbenoid, a derivative of

stilbene Stilbene may refer to one of the two stereoisomers of 1,2-diphenylethene: * (''E'')-Stilbene (''trans'' isomer) * (''Z'')-Stilbene (''cis'' isomer) See also * Stilbenoids, a class of molecules found in plants * 1,1-Diphenylethylene 1,1-Diphenyl ...

. It exists as two

geometric isomers Geometry (; ) is, with arithmetic, one of the oldest branches of mathematics. It is concerned with properties of space such as the distance, shape, size, and relative position of figures. A mathematician who works in the field of geometry is ...

: ''cis-'' (''Z'') and ''trans-'' (''E''), with the ''trans''-isomer shown in the top image. Resveratrol exists conjugated to glucose. The ''trans-'' form can undergo

photoisomerization In chemistry, photoisomerization is a form of isomerization induced by photoexcitation. Both reversible and irreversible photoisomerizations are known for photoswitchable compounds. The term "photoisomerization" usually, however, refers to a re ...

to the ''cis-'' form when exposed to

ultraviolet Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than ...

irradiation. Rasveratrol isomerization

UV irradiation to cis-resveratrol induces further photochemical reaction, producing a fluorescent molecule named "Resveratrone". ''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 Pomace ( ), or marc (; from French ''marc'' ), is the solid remains of grapes, olives, or other fruit after pressing for juice or oil. It contains the skins, pulp, seeds, and stems of the fruit. Grape pomace has traditionally been used to prod ...

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.

Biosynthesis

Resveratrol is produced in plants via the enzyme resveratrol synthase ( stilbene synthase). Its immediate precursor is a tetraketide derived from

malonyl CoA Malonyl-CoA is a coenzyme A derivative of malonic acid. Functions It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis. Fatty acid biosynthesis Malonyl-CoA provides 2-carbon units to fatty acids and commi ...

and 4-coumaroyl CoA. The latter is derived from

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino a ...

Biotransformation

The grapevine fungal

Botrytis cinerea ''Botrytis cinerea'' is a necrotrophic fungus that affects many plant species, although its most notable hosts may be wine grapes. In viticulture, it is commonly known as "botrytis bunch rot"; in horticulture, it is usually called "grey mould" or ...

'' 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 Pallidol is a resveratrol dimer. It can be found in ''red wine Red wine is a type of wine made from dark-colored grape varieties. The color of the wine can range from intense violet, typical of young wines, through to brick red for mature wine ...

. The soil bacterium ''

Bacillus cereus ''Bacillus cereus'' is a Gram-positive rod-shaped bacterium commonly found in soil, food, and marine sponges. The specific name, ''cereus'', meaning "waxy" in Latin, refers to the appearance of colonies grown on blood agar. Some strains are ha ...

'' can be used to transform resveratrol into

piceid Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can be found in the bark of ''Picea sitchensis''. It can also be isolated from ''Reynoutria japonica'' ( syn. ''Fallopia japonica''), the Japanese knotweed ...

(resveratrol 3-O-beta-D-

glucoside A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. The name was o ...

Adverse effects

Only a few human studies have been done to determine the

adverse effect An adverse effect is an undesired harmful effect resulting from a medication or other intervention, such as surgery. An adverse effect may be termed a "side effect", when judged to be secondary to a main or therapeutic effect. The term complica ...

s 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 Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...

stomach pain Abdominal pain, also known as a stomach ache, is a symptom associated with both non-serious and serious medical issues. Common causes of pain in the abdomen include gastroenteritis and irritable bowel syndrome. About 15% of people have a m ...

flatulence Flatulence, in humans, is the expulsion of gas from the intestines via the anus, commonly referred to as farting. "Flatus" is the medical word for gas generated in the stomach or bowels. A proportion of intestinal gas may be swallowed environm ...

, and

diarrhea Diarrhea, also spelled diarrhoea, is the condition of having at least three loose, liquid, or watery bowel movements each day. It often lasts for a few days and can result in dehydration due to fluid loss. Signs of dehydration often begin wi ...

. 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. In a year-long preliminary

clinical trial Clinical trials are prospective biomedical or behavioral research studies on human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, dietar ...

in people with

, the most frequent adverse effects were nausea and weight loss. A 2018 review of resveratrol effects on blood pressure found that some people had increased frequency of

bowel movement Defecation (or defaecation) follows digestion, and is a necessary process by which organisms eliminate a solid, semisolid, or liquid waste material known as feces from the digestive tract via the anus. The act has a variety of names ranging fro ...

s and loose stools.

Occurrences

Plants

Resveratrol is a

, a class of compounds produced by many plants when they are infected by pathogens or physically harmed by cutting, crushing, or ultraviolet radiation. Plants that synthesize resveratrol include knotweeds,

pine A pine is any conifer tree or shrub in the genus ''Pinus'' () of the family Pinaceae. ''Pinus'' is the sole genus in the subfamily Pinoideae. The World Flora Online created by the Royal Botanic Gardens, Kew and Missouri Botanical Garden accep ...

trees including

Scots pine ''Pinus sylvestris'', the Scots pine (UK), Scotch pine (US) or Baltic pine, is a species of tree in the pine family Pinaceae that is native to Eurasia. It can readily be identified by its combination of fairly short, blue-green leaves and orang ...

and

Eastern white pine ''Pinus strobus'', commonly called the eastern white pine, northern white pine, white pine, Weymouth pine (British), and soft pine is a large pine native to eastern North America. It occurs from Newfoundland, Canada west through the Great Lakes ...

, grape vines, raspberries, mulberries, peanut plants, cocoa bushes, and ''

Vaccinium ''Vaccinium'' is a common and widespread genus of shrubs or dwarf shrubs in the heath family (Ericaceae). The fruits of many species are eaten by humans and some are of commercial importance, including the cranberry, blueberry, bilberry (whort ...

'' shrubs that produce berries, including blueberries, cranberries, and bilberries.

Foods

The levels of resveratrol found in food varies considerably, even in the same food from season to season and batch to batch.

Wine and grape juice

Resveratrol concentrations in red wines average trans-resveratrol/L (), 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. In general, wines made from grapes of the

Pinot noir Pinot Noir () is a red-wine grape variety of the species ''Vitis vinifera''. The name may also refer to wines created predominantly from pinot noir grapes. The name is derived from the French language, French words for ''pine'' and ''black.' ...

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 Champagne (, ) is a sparkling wine originated and produced in the Champagne wine region of France under the rules of the appellation, that demand specific vineyard practices, sourcing of grapes exclusively from designated places within it, spe ...

and

vinegar Vinegar is an aqueous solution of acetic acid and trace compounds that may include flavorings. Vinegar typically contains 5–8% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting simple sugars to et ...

also contain appreciable levels of resveratrol.

Red wine Red wine is a type of wine made from dark-colored grape varieties. The color of the wine can range from intense violet, typical of young wines, through to brick red for mature wines and brown for older red wines. The juice from most purple grap ...

contains between 0.2 and 5.8 mg/L, depending on the grape variety. White wine has much less because red wine is

fermented Fermentation is a metabolic process that produces chemical changes in organic substrates through the action of enzymes. In biochemistry, it is narrowly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food ...

with the skins, allowing the wine to extract the resveratrol, whereas

white wine White wine is a wine that is Fermentation in winemaking, fermented without skin contact. The wine color, colour can be straw-yellow, yellow-green, or yellow-gold. It is produced by the alcoholic fermentation of the non-coloured Juice vesicles, ...

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.

Selected foods

Ounce for ounce, peanuts have about 25% as much resveratrol as red wine.

Peanut The peanut (''Arachis hypogaea''), also known as the groundnut, goober (US), pindar (US) or monkey nut (UK), is a legume crop grown mainly for its edible Seed, seeds. It is widely grown in the tropics and subtropics, important to both small ...

s, 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 A cultivar is a type of cultivated plant that people have selected for desired traits and when propagated retain those traits. Methods used to propagate cultivars include: division, root and stem cuttings, offsets, grafting, tissue culture, ...

Mulberries ''Morus'', a genus of flowering plants in the family Moraceae, consists of diverse species of deciduous trees commonly known as mulberries, growing wild and under cultivation in many temperate world regions. Generally, the genus has 64 identif ...

(especially the skin) are a source of as much as 50 micrograms of resveratrol per gram dry weight.

History

The first mention of resveratrol was in a

Japanese Japanese may refer to: * Something from or related to Japan, an island country in East Asia * Japanese language, spoken mainly in Japan * Japanese people, the ethnic group that identifies with Japan through ancestry or culture ** Japanese diaspor ...

article in 1939 by Michio Takaoka, who isolated it from ''

Veratrum album ''Veratrum album'', the false helleborine, white hellebore, European white hellebore, or white veratrum ( syn. ''Veratrum lobelianum'' Bernh.) is a poisonous plant in the family Melanthiaceae. It is native to Europe and parts of western Asia (west ...

'', variety ''grandiflorum'', and later, in 1963, from the roots of

Japanese knotweed ''Reynoutria japonica'', synonyms ''Fallopia japonica'' and ''Polygonum cuspidatum'', is a species of herbaceous perennial plant in the knotweed and buckwheat family Polygonaceae. Common names include Japanese knotweed and Asian knotweed. It is ...

. In 2004,

Harvard University Harvard University is a private Ivy League research university in Cambridge, Massachusetts. Founded in 1636 as Harvard College and named for its first benefactor, the Puritan clergyman John Harvard, it is the oldest institution of higher le ...

professor David Sinclair co-founded

Sirtris Pharmaceuticals Sirtris Pharmaceuticals, Inc. was a biotechnology company based in Cambridge, MA that developed therapies for type 2 diabetes, cancer, and other diseases. Conceived in 2004 by Harvard University biologist David Sinclair and serial entrepreneur An ...

, the initial product of which was a resveratrol formulation.

Related compounds

Dihydro-resveratrol Dihydro-resveratrol is a dihydrostilbenoid found in wine. It is also a metabolite of trans-resveratrol formed in the intestine by the hydrogenation of the double bond by microflora. It is also a non-cannabinoid estrogenic compound found in cannabi ...

* Epsilon-viniferin,

Pallidol Pallidol is a resveratrol dimer. It can be found in ''red wine Red wine is a type of wine made from dark-colored grape varieties. The color of the wine can range from intense violet, typical of young wines, through to brick red for mature wine ...

and

Quadrangularin A Quadrangularin A is an oligostilbene found in ''Cissus quadrangularis'' and in '' Parthenocissus laetevirens''.Characterization of polyphenol compounds from the roots and stems of Parthenocissus laetevirens by high-performance liquid chromatograph ...

three different resveratrol dimers *

Elafibranor Elafibranor (INN, code name GFT505) is an experimental medication that is being studied and developed by Genfit for the treatment of cardiometabolic diseases including diabetes, insulin resistance, dyslipidemia, and non-alcoholic fatty liver dis ...

, a structurally related compound that acts as a dual PPARα/δ agonist * THSG, a glycoside compound found in He Shou Wu which is very similar to resveratrol. *

Trans-diptoindonesin B ''trans''-Diptoindonesin B is an oligomeric stilbenoid. It is a resveratrol trimer. It can be isolated from ''Dryobalanops oblongifolia ''Dryobalanops oblongifolia'' is a species of plant in the family Dipterocarpaceae, native to regions of ...

, a resveratrol trimer *

Hopeaphenol Hopeaphenol is a stilbenoid. It is a resveratrol tetramer. It has been first isolated from Dipterocarpaceae like '' Shorea ovalis''. It has also been isolated from wines from North Africa. It shows an opposite effect to vitisin A on apoptosis of ...

, a resveratrol tetramer *

Oxyresveratrol Oxyresveratrol is a stilbenoid. It is found in the heartwood of ''Artocarpus lakoocha'' and in the traditional drug 'Puag-Haad' made from it. It is also the aglycone of mulberroside A, a compound found in ''Morus alba ''Morus alba'', known as w ...

, the aglycone of mulberroside A, a compound found in ''

Morus alba ''Morus alba'', known as white mulberry, common mulberry and silkworm mulberry, is a fast-growing, small to medium-sized mulberry tree which grows to tall. It is generally a short-lived tree with a lifespan comparable to that of humans, although ...

'', the white mulberry *

Piceatannol Piceatannol is the organic compound with the formula . Classified as a stilbenoid and a phenol, it is a white solid, although samples often are yellow owing to impurities. Natural occurrences Piceatannol and its glucoside, astringin, are found i ...

, an active metabolite of resveratrol found in red wine *

Piceid Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can be found in the bark of ''Picea sitchensis''. It can also be isolated from ''Reynoutria japonica'' ( syn. ''Fallopia japonica''), the Japanese knotweed ...

, a resveratrol glucoside *

Pterostilbene Pterostilbene () (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role. Natural occurrence Pterostilbene is found in almonds, various ''Vaccinium'' berries ( ...

, a doubly methylated resveratrol * 4'-Methoxy-(E)-resveratrol 3-O-rutinoside, a compound found in the stem bark of ''

Boswellia dalzielii ''Boswellia dalzielii'' is a tree species in the genus ''Boswellia'' found in Africa. The bark of this plant is used in traditional medicines. Gallic and protocatechuic acids were isolated as the main antibacterial and antioxidant principles of ...

''Alemika Taiwo E, Onawunmi Grace O and Olugbade Tiwalade O
Antibacterial phenolics from Boswellia dalzielii.
''Nigerian Journal of Natural Products and Medicines'', 2006 *

Rhaponticin Rhaponticin is a stilbenoid glucoside compound. Its aglycone is called rhapontigenin. It can be found in rhubarb rhizomes. It has beneficial effects on diabetic mice, and ''in vitro'' results suggest it may be relevant to Alzheimer's disease with ...

a glucoside of the stilbenoid

rhapontigenin Rhapontigenin is a stilbenoid. It can be isolated from ''Vitis coignetiae'' or from '' Gnetum cleistostachyum''. It shows an action on prostate cancer cells. It has been shown to inhibit the human cytochrome P450 1A1, an enzyme implicated in the ...

, found in

rhubarb Rhubarb is the fleshy, edible stalks ( petioles) of species and hybrids (culinary rhubarb) of ''Rheum'' in the family Polygonaceae, which are cooked and used for food. The whole plant – a herbaceous perennial growing from short, thick rhizo ...

rhizome In botany and dendrology, a rhizome (; , ) is a modified subterranean plant stem that sends out roots and shoots from its nodes. Rhizomes are also called creeping rootstalks or just rootstalks. Rhizomes develop from axillary buds and grow hori ...

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* {{Stilbenes Aromatase inhibitors GPER agonists Phytoalexins Phytoestrogens Stilbenoids