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Encyclopedia > Resveratrol
Resveratrol
Chemical structure of trans-resveratrol
Chemical structure of trans-resveratrol
Other names trans-3,5,4'-Trihydroxystilbene;
3,4',5-Stilbenetriol;
trans-Resveratrol;
(E)-5-(p-Hydroxystyryl)resorcinol
Identifiers
CAS number [501-36-0]
SMILES Oc2ccc(C=Cc1cc(O)cc(O)c1)cc2
InChI 1/C14H12O3/c15-
12-5-3-10(4-6-12)
1-2-11-7-13(16)9-
14(17)8-11/h1-9,15-
17H/b2-1+
Properties
Molecular formula C14H12O3
Molar mass 228.25
Appearance white powder with
slight yellow cast
Solubility in water 0.03 g/L
Solubility in DMSO 16 g/L
Solubility in ethanol 50 g/L
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
The cis-isomer of resveratrol
The cis-isomer of resveratrol

Resveratrol is a phytoalexin produced naturally by several plants when under attack by bacteria or fungi. Phytoalexins are antibacterial and anti-fungal chemicals produced by plants as a defense against infection by pathogens. Resveratrol has also been produced by chemical synthesis,[1] and is sold as a nutritional supplement derived primarily from Japanese knotweed. A number of beneficial health effects, such as anti-cancer, antiviral, neuroprotective, anti-aging, and anti-inflammatory effects have been reported, but all of these studies are "in-vitro" (test tube) or in yeast, worms, fruit flies, fish, mice, and rats. Resveratrol is found in the skin of red grapes and is a constituent of red wine but, based on extrapolation from animal trials, apparently not in sufficient amounts to explain the "French paradox" that the incidence of coronary heart disease is relatively low in southern France despite high dietary intake of saturated fats.[2] Image File history File links No higher resolution available. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The IUPAC International Chemical Identifier (InChI), developed by IUPAC and NIST, is a digital equivalent of the IUPAC name for any particular covalent compound. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Dimethyl sulfoxide (DMSO) is the chemical compound with the formula (CH3)2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Grain alcohol redirects here. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Phytoalexins are antibiotics produced by plants that are under attack. ... For other uses, see Plant (disambiguation). ... Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ... Divisions Chytridiomycota Zygomycota Ascomycota Basidiomycota The Fungi (singular: fungus) are a large group of organisms ranked as a kingdom within the Domain Eukaryota. ... A pathogen (from Greek pathos, suffering/emotion, and gene, to give birth to), infectious agent, or more commonly germ, is a biological agent that causes disease or illness to its host. ... In the United States, a dietary supplement is defined under the Dietary Supplement Health and Education Act of 1994 as a product taken by the mouth that contains a dietary ingredient that is intended as a supplement to the diet. ... Binomial name Houtt. ... Antiviral drugs are a class of medication used specifically for treating viral infections. ... Anti-aging addresses how to prevent, slow, or reverse the effects of aging and help people live longer, healthier, happier lives. ... Anti-inflammatory refers to the property of a substance or treatment that reduces inflammation. ... This article is about the fruits of the genus Vitis. ... This article is about the beverage. ... This article or section does not cite any references or sources. ... Coronary heart disease (CHD), also called coronary artery disease (CAD), ischaemic heart disease, atherosclerotic heart disease, is the end result of the accumulation of atheromatous plaques within the walls of the arteries that supply the myocardium (the muscle of the heart) with oxygen and nutrients. ... Saturated fat is fat that consists of triglycerides containing only saturated fatty acids. ...


The four stilbenes cis- and trans-resveratrol, and their glucosides cis- and trans-piceid are sometimes analyzed together as a group.[3] For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids. ... A glucoside is a glycoside that is derived from glucose. ... Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. ...

Contents

Chemical and physical properties

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. Polyphenols are a group of chemical substances found in plants, characterized by the presence of more than one phenol unit or building block per molecule. ... Phytoalexins are antibiotics produced by plants that are under attack. ... Stilbenoids are secondary products of heartwood formation in trees that can act as phytoalexins. ... For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids. ...


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.[4] 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.[5] Resveratrol content also stayed stable in the skins of grapes and pomace taken after fermentation and stored for a long period.[6] Cis-2-butene Trans-2-butene In chemistry, geometric isomerism or cis-trans isomerism is a form of stereoisomerism and describes the orientation of functional groups at the ends of a bond around which no rotation is possible. ... For other uses, see Ultraviolet (disambiguation). ... Pomace is a substance prepared by pressing or grinding various fruits, for example in the manufacture of olive oil (from olives), wine (from grapes), or cider (from apples). ...


Plants and foods

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 the wider attention only in 1992, when its presence in wine was used as the explanation for cardioprotective effects of wine.[7] Binomial name Houtt. ...


In grapes, resveratrol is found primarily in the skin,[8] and in muscadine grapes—also in the seeds.[9] 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.[8]


The amount of resveratrol in food varies greatly. Red wine contains between 0.2 and 5.8 mg/L,[10] depending on the grape variety, while white wine has much less — the reason being that red wine is fermented with the skins, allowing the wine to absorb the resveratrol, whereas white wine is fermented after the skin has been removed.[8] Wines produced from muscadine grapes, however, both red and white, may contain more than 40 mg/L.[11][3] Fermenting must. ... This article is about the beverage. ... Categories: Stub | Fruit | Grape varieties ...


Content in wines and grape juice

Beverage Total resveratrol (mg/L)[8][3] Total resveratrol in a 5 ounce glass (mg)[8][3]
Muscadine Wines 14.1 - 40 2.12 - 6
Red Wines (Global) 1.98 - 7.13 0.30 - 1.07
Red Wines (Spanish) 1.92 - 12.59 0.29 - 1.89
Red grape juice (Spanish) 1.14 - 8.69 0.17 - 1.30
Rose Wines (Spanish) 0.43 - 3.52 0.06 - 0.53
Pinot Noir 0.40 - 2.0 0.06 - 0.30
White Wines (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 and had a maximum of 0.1 mg/L in the 8 white wines tested. 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.[12]


Reports suggest that some aspect 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.[3] Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. ...


"All of the muscadine table wines sampled had greater trans and cis resveratrol concentrations than any other wines sampled. The muscadine table wines varied between 9.2 and 31.9 mg/L cis-resveratrol and between 4.9 and 13.4 mg/L trans-resveratrol."[3]


Content in selected foods

Food Serving Total resveratrol (mg)[13]
Peanuts (raw) 1 c (146 g) 0.01 - 0.26
Peanuts (boiled) 1 c (180 g) 0.32 - 1.28
Peanut butter 1 c (258 g) 0.04 - 0.13
Red grapes 1 c (160 g) 0.24 - 1.25

Ounce for ounce, peanuts have more than half the amount of resveratrol in red wine. The average amount of resveratrol in one ounce of peanuts in the marketplace (about 15 whole) is 79.4 µg/ounce.


In comparison, some red wines contain approximately 160 µg/fluid ounce.[14] 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 micromol/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.[15]


Blueberries have about twice as much resveratrol as bilberries, but there is great regional variation. These fruits have less than ten percent 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. [16] For other uses, see Blueberry (disambiguation). ... Binomial name Vaccinium myrtillus L. Bilberry is a name given to several species of low-growing shrubs in the genus Vaccinium (family Ericaceae) that bear tasty fruits. ...


Supplementation

Resveratrol nutritional supplements, first sourced from ground dried grape skins and seeds (sometimes from residual byproducts of winemaking),[citation needed] are now primarily derived from the cheaper, more concentrated Japanese knotweed which contains up to 187 mg/kg in the dried root.[citation needed] In the United States, a dietary supplement is defined under the Dietary Supplement Health and Education Act of 1994 as a product taken by the mouth that contains a dietary ingredient that is intended as a supplement to the diet. ... Binomial name Houtt. ...


As a result of extensive news coverage,[17][18] sales of supplements greatly increased in 2006,[19][20] despite cautions that benefits to humans are unproven.[21][20]


Physiological effects

Life extension

The groups of Howitz and Sinclair reported in 2003 in the journal Nature that resveratrol significantly extends the lifespan of the yeast Saccharomyces cerevisiae.[22] Later studies conducted by Sinclair showed that resveratrol also prolongs the lifespan of the worm Caenorhabditis elegans and the fruit fly Drosophila melanogaster.[23] In 2007 a different group of researchers was able to reproduce the Sinclair's results with C. elegans[24] but a third group could not achieve consistent increases in lifespan of Drosophila or C. elegans.[25] Nature is a prominent scientific journal, first published on 4 November 1869. ... Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic microorganisms classified in the kingdom Fungi, with approximately 1,500 species described. ... Binomial name Meyen ex E.C. Hansen Saccharomyces cerevisiae is a species of budding yeast. ... Binomial name Maupas, 1900 Caenorhabditis elegans (IPA: ) is a free-living nematode (roundworm), about 1 mm in length, which lives in temperate soil environments. ... Binomial name Meigen, 1830[1] Drosophila melanogaster (from the Greek for black-bellied dew-lover) is a two-winged insect that belongs to the Diptera, the order of the flies. ...


In 2006, Italian scientists obtained the first positive result of resveratrol supplementation in a vertebrate. Using a short-lived fish, Nothobranchius furzeri, with a median life span of nine weeks, they found that a maximal dose of resveratrol increased the median lifespan by 56%. Compared with the control fish at nine weeks, that is by the end of the latter life, the fish supplemented with resveratrol showed significantly higher general swimming activity and better learning to avoid an unpleasant stimulus. The authors noted a slight increase of mortality in young fish caused by resveratrol and hypothesized that it is its weak toxic action that stimulated the defense mechanisms and resulted in the life span extension.[26] Later the same year, Sinclair reported that resveratrol counteracted the detrimental effects of a high-fat diet in mice. The high fat diet was compounded by adding hydrogenated coconut oil to the standard diet; it provided 60% of energy from fat, and the mice on it consumed about 30% more calories then the mice on standard diet. Both the mice fed the standard diet and the high-fat diet plus 22 mg/kg resveratrol had a 30% lower risk of death than the mice on the high-fat diet. Gene expression analysis indicated the addition of resveratrol opposed the alteration of 144 out of 155 gene pathways changed by the high-fat diet. Insulin and glucose levels in mice on the high-fat+resveratrol diet were closer to the mice on standard diet then to the mice on the high-fat diet. However, addition of resveratrol to the high-fat diet did not change the levels of free fatty acids and cholesterol, which were much higher than in the mice on standard diet. [27]


Cancer prevention

In 1997 Jang reported that topical resveratrol applications prevented the skin cancer development in mice treated with a carcinogen.[28] There have since been dozens of studies of the anti-cancer activity of resveratrol in animal models.[7][29] The effectiveness of resveratrol in animal cancer models is limited by its poor bioavailability. The strongest evidence of anti-cancer action of resveratrol exists for the tumors it can come into direct contact with, such as skin and gastrointestinal tract tumors. For other cancers, the evidence is equivocal, even if massive dose of resveratrol are used.[29] Look up carcinogen in Wiktionary, the free dictionary. ...


Thus, topical application of resveratrol in mice, both before and after the UVB exposure, inhibited the skin damage and decreased skin cancer incidence. However, oral resveratrol was ineffective in treating mice inoculated with melanoma cells.[29] Resveratrol (1 mg/kg orally) reduced the number and size of the esophageal tumors in rats treated with a carcinogen.[30] In several studies, small doses (0.02-8 mg/kg) of resveratrol, given prophylactically, reduced or prevented the development of intesinal and colon tumors in rats given different carcinogens.[29]


Resveratrol is under extensive investigation as a cancer chemopreventive agent.[31][32] Studies show that small doses of dietary resveratrol can reduce colon carcinogenesis in rats and mice.[33] One German study has already been shown to that under special conditions, resveratrol induces apoptosis in human fat cells. In addition, it inhibits production of cytokines which are involved in the development of obesity-related disorders.[34] Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ...


Athletic performance

Johan Auwerx (at the Institute of Genetics and Molecular and Cell Biology in Illkirch, France) and coauthors published an online article in the journal CELL in November 2006. Mice fed resveratrol for 15 weeks had better treadmill endurance than controls. The study supported Sinclair's hypothesis that the effects of resveratrol are indeed due to the activation of SIRT1.


Nicholas Wade's interview-article with Dr. Auwerx[35] states that the dose was 400 mg/kg of body weight (much higher than the 22 mg/kg of the Sinclair study). For an 80 kg (176 lb) person, the 400 mg/kg of body weight amount used in Dr. Auwerx's mouse study would come to 32,000 mg/day. Compensating for the fact that humans have slower metabolic rates than mice would change the equivalent human dose to roughly 4571 mg/day. Again, there is no published evidence anywhere in the scientific literature of any clinical trial for efficacy in humans. There is limited human safety data (see above). It is premature to take resveratrol and expect any particular results. Long-term safety has not been evaluated in humans.


In a study of 123 Finnish adults, those born with certain increased variations of the SIRT1 gene had faster metabolisms, helping them to burn energy more efficiently—indicating that the same pathway shown in the lab mice works in humans too.[36]


Antiviral effects

Resveratrol seems to increase the potency of some antiretroviral drugs against HIV in vitro.[37] HAART redirects here. ... Species Human immunodeficiency virus 1 Human immunodeficiency virus 2 Human immunodeficiency virus (HIV) is a retrovirus that causes acquired immunodeficiency syndrome (AIDS, a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections). ... In vitro (Latin: within the glass) refers to the technique of performing a given experiment in a test tube, or, generally, in a controlled environment outside a living organism. ...


Infection by herpes simplex virus ordinarily activates the cell protein Nuclear Factor κB (NF-κB). A Northeastern Ohio Universities College of Medicine study undertaken in Vero cells found that resveratrol suppresses the activation of this transcription- and apoptosis-related protein. The study further found that multiple viral protein products were reduced or completely blocked, as well as a reduction in viral DNA production.[38] This article is about the disease. ... NF-κB, or Nuclear Factor kappa B, is a nuclear transcription factor found in all cell types and is involved in cellular responses to stimuli such as stress, cytokines, free radicals, ultraviolet irradiation, and bacterial or viral antigens. ... Vero cells are used in cell cultures. ... A micrograph of ongoing gene transcription of ribosomal RNA illustrating the growing primary transcripts. ... A section of mouse liver showing an apoptotic cell indicated by an arrow Apoptosis (pronounced apo tō sis) is a process of suicide by a cell in a multicellular organism. ...


A cell culture study found that resveratrol blocks the influenza virus from transporting viral proteins to the viral assembly site, hence restricting its ability to replicate. The effect was 90% when resveratrol was added six hours after infection and continued for 24 hours thereafter.[39] Epithelial cells in culture, stained for keratin (red) and DNA (green) Cell culture is the process by which either prokaryotic or eukaryotic cells are grown under controlled conditions. ... Negatively stained flu virions. ...


Adverse effects and unknowns

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.[40][41] However, other studies have found that resveratrol actually fights breast cancer.[42][43] 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 18, as no studies have shown how it affects their natural development.[44] A small study found that a single dose of up to 5 g of trans-resveratrol caused no serious adverse effects in healthy volunteers.[45] Phytoestrogens are plant compounds with effects similar to those of estrogen, although somewhat weaker. ...


There is some evidence that resveratrol might exacerbate West Nile virus, since West Nile is p53 mediated and worsened by increased rates of apoptosis of infected cells. [7]


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. A new report indicates that resveratrol activates SIRT1 and PGC-1α and improve functioning of the mitochondria.[46] Other research calls into question the theory connecting resveratrol, SIRT1, and calorie restriction.[47][48] Life extension refers to an increase in maximum or average lifespan, especially in humans, by slowing down or reversing the processes of aging. ... Biochemistry is the chemistry of life. ... See also Negative calorie diet, very low calorie diet CRON redirects here. ... Sir2 is a family of closely related enzymes. ... In cell biology, a mitochondrion is an organelle found in the cells of most eukaryotes. ... Sir2 is a family of closely related enzymes. ... See also Negative calorie diet, very low calorie diet CRON redirects here. ...


An article in press as of January 2008 discusses resveratrol action in cells. It reports a 14-fold increase in the action of MnSOD.[49] MnSOD reduces superoxide to H2O2, but H2O2 is not increased due to other cellular activity. Superoxide O2- is a byproduct of respiration in complex 1 and 3 of the electron transport chain. It is "not highly toxic, [but] can extract an electron from biological membrane and other cell components, causing free radical chain reactions. Therefore is it essential for the cell to keep superoxide anions in check."[50] MnSOD reduces superoxide and thereby confers resistance to mitochondrial dysfunction, permeability transition, and apoptotic death in various diseases.[51] It has been implicated in lifespan extension, inhibits cancer (e.g. pancreatic cancer [52][53]), and provides resistance to reperfusion injury and irradiation damage [54] [55] [56]. These effects have also been observed with resveratrol. Ellen et al propose MnSOD is increased by the pathway RESV --> SIRT1 / NAD+ --> FOXO3a --> MnSOD. Resveratrol has been shown to cause SIRT1 to cause migration of FOXO transcription factors to the nucleus [57] which stimulates FOXO3a transcriptional activity [58] and it has been shown to enhance the sirtuin-catalyzed deacetylation (activity) of FOXO3a. MnSOD is known to be a target of FOXO3a, and MnSOD expression is strongly induced in cells overexpressing FOXO3a [59].


Resveratrol interferes with all three stages of carcinogenesis - initiation, promotion and progression. Experiments in cell cultures of varied types and isolated subcellular systems in vitro imply many mechanisms in the pharmacological activity of resveratrol. These mechanisms include modulation of the transcription factor NF-kB,[60] inhibition of the cytochrome P450 isoenzyme CYP1A1[61] (although this may not be relevant to the CYP1A1-mediated bioactivation of the procarcinogen benzo(a)pyrene[62]), alterations in androgenic[63] actions and expression and activity of cyclooxygenase (COX) enzymes. In some lineages of cancer cell culture, resveratrol has been shown to induce apoptosis, which means it kills cells and may kill cancer cells.[63][64][65][66][67][68] Resveratrol has been shown to induce Fas/Fas ligand mediated apoptosis, p53 and cyclins A, B1 and cyclin-dependent kinases cdk 1 and 2. Resveratrol also possesses antioxidant and anti-angiogenic properties.[69][70] Cancers are caused by a series of mutations. ... Epithelial cells in culture, stained for keratin (red) and DNA (green) Cell culture is the term applied when growing cells in a synthetic environment. ... In vitro (Latin: within the glass) refers to the technique of performing a given experiment in a test tube, or, generally, in a controlled environment outside a living organism. ... Pharmacology (in Greek: pharmacon is drug, and logos is science) is the study of how chemical substances interfere with living systems. ... In molecular biology, a transcription factor is a protein that binds DNA at a specific promoter or enhancer region or site, where it regulates transcription. ... NF-κB, or Nuclear Factor kappa B, is a nuclear transcription factor found in all cell types and is involved in cellular responses to stimuli such as stress, cytokines, free radicals, ultraviolet irradiation, and bacterial or viral antigens. ... Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ... CYP1A1 is a gene that encodes a member of the cytochrome P450 oxidase superfamily of enzymes. ... Chemical structure of benzo-[a]-pyrene Benzopyrene is a five-ring polycyclic aromatic hydrocarbon that is crystalline and yellow color as part of its physical properties. ... Androgen is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of masculine characteristics in vertebrates. ... Cyclooxygenase (COX) is an enzyme (EC 1. ... Epithelial cells in culture, stained for keratin (red) and DNA (green) Cell culture is the process by which either prokaryotic or eukaryotic cells are grown under controlled conditions. ... A section of mouse liver showing an apoptotic cell indicated by an arrow Apoptosis (pronounced apo tō sis) is a process of suicide by a cell in a multicellular organism. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a... A section of mouse liver showing an apoptotic cell indicated by an arrow Apoptosis (pronounced apo tō sis) is a process of suicide by a cell in a multicellular organism. ... TP53 bound to a short DNA fragment. ... Cyclins are a family of proteins involved in the progression of cells through the cell cycle. ... Cyclin-dependent kinases (CDK) belong to a group of protein kinases originally discovered as being involved in the regulation of the cell cycle. ... Space-filling model of the antioxidant metabolite glutathione. ... Angiogenesis is the physiological process involving the growth of new blood vessels from pre-existing vessels. ...


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.[71][72] Again, this has not yet been tested in humans for any disease. This article is about cells in the nervous system. ...


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.[73] Northeastern Ohio Universities College Of Medicine (NEOUCOM) is a community-based, state medical school that offers a combined B.S./M.D. program that allows students to graduate with their B.S./M.D. in as few as six years. ... The Ohio State University (OSU) is a coeducational public research university in the state of Ohio. ... The heart and lungs, from an older edition of Grays Anatomy. ... Fibrosis is the formation or development of excess fibrous connective tissue in an organ or tissue as a reparative or reactive process, as opposed to a formation of fibrous tissue as a normal constituent of an organ or tissue. ...


According to Patrick Arnold it also significantly increases natural testosterone production from being both a selective estrogen receptor modulator[74][75] and an aromatase inhibitor.[76][77] Patrick Doctor Evil Arnold is an American organic chemist responsible for creating the designer steroid tetrahydrogestrinone, also known as THG.[1] THG, along with two other anabolic steroids that Patrick Arnold manufactured (norbolethone and desoxymethyltestosterone (DMT)), were drugs at the heart of the BALCO scandal[2]. At the time of... Selective estrogen receptor modulators (SERMs) is a class of medication that acts on the estrogen receptor. ... Aromatase inhibitors (AI) are a class of drugs used in the treatment of breast cancer in post- menopausal women. ...


In December, 2007, work from Irfan Rahman's laboratory at the University of Rochester demonstrated that resveratrol increased intracellular glutathionelevels via Nrf2-dependent upregulation of gamma-glutamylcysteine ligase in lung epithelial cells, which protected them against cigarette smoke extract induced oxidative stress. [78]


Pharmacokinetics

Resveratrol bioavailability depends on its conjugate forms: glucuronate and sulfonate, but most in vitro studies use the aglycone form of resveratrol ('aglycone' means without a sugar molecule attached, as in the figure in this article). In humans[79] [80] and rats,[81] [82] [83] resveratrol rapidly undergoes conjugation resulting in less than 5% of the oral dose being observed as free resveratrol in blood plasma. The effect of conjugation on efficacy is debated.[84][85] The studies[80] [81] show rats have 72% more free resveratrol and 6 times more of a glucuronide form as humans for a dose of about 60 mg/kg. The most abundant conjugates in humans, rats, and mice are trans-resveratrol-3-O-glucuronide and trans-resveratrol-3-sulfate.[86] Walle suggests sulfate conjugates are the primary source of activity[79], Wang et al suggests the glucuronides,[87] and Boocock et al also emphasized the need for further study of the effects of the metabolites including the possibility of deconjugation to free reservatrol inside cells. In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Conjugate can be: in mathematics in terms of complex numbers, the complex conjugate; more generally see conjugate element (field theory). ... Glucuronic acid (from Greek γλυκερός - sweet) is a carboxylic acid. ... The structure of a typical sulfonate group. ... In chemistry, glycosides are certain molecules in which a sugar part is bound to some other part. ...


In humans, Walle et al reported at least 70% absorbed and 99% is quickly metabolized to conjugates using 25mg doses. Half life of resveratrol and its metabolites was 9 hours. 73% was excreted in urine and feces after 12 hours. [79] Boocock et al reported 3% of the total metabolites in the blood plasma of humans was free resveratrol, measured as area under the concentration curve. Half life was 4 to 11 hours for the various metabolites. [80] This article is about the computer game. ...


A study on rats given an oral dose of 50 mg/kg showed resveratrol and its metabolites have an initial apparent half life of 8 minutes but a "terminal" half life of 1.5 hours in blood plasma. The free resveratrol was 46 times less than the glucuronide form (measured as area under the concentration curve).[81]


When trying to calculate an equivalent dose for humans, it is not accurate to use the mg dose per body weight method as was commonly reported in the media when the life-extension resveratrol studies came out.[88] This method leads to much larger quantities than is accurate because larger animals have a slower metabolic rate for their weight. The comparative dosage should be based on mg per Calories consumed per day. If the Calories consumed per day are not known, it is estimated from the body weight.[89] This results in the formula: (human dose/kg) = (animal dose mg/kg) x (animal kg/human kg)^(1-P) where P=2/3 is used by convention to give a larger margin of safety for FDA pharmaceutical and EPA toxicology uses, but P=3/4 is more accurate.[90] [91] The absorption, metabolism, and excretion is very different in different species so that even adjusting for metabolic rate is not very accurate. For example, as mentioned in the absorption section, rats have much more free resveratrol and glucuronide forms in their blood than humans for a given dose, eventhough the metabolic rate adjustment implies they should have much less.


Related compounds

Scientists are also studying three other synthetic compounds based on resveratrol which more effectively activate the same biological mechanism.[92]


The compound called SRT 1720 seems to be 1000 times more effective than resveratrol, although it only increases SIRT1 activation by 6 times. No data has been publicly produced by Sirtris regarding this difference in SIRT1 efficiency for the new compound.[93]


A study by Professor Roger Corder has identified a particular group of polyphenols, known as oligomeric procyanidins, which they believe offer the greatest degree of protection to human blood-vessel cells. These are found in greatest concentration in European red wines from certain areas, which correlates with longevity in those regions. This new data may impact the supplement market.[94] Because they are present in red wine in more significant quantities, they could offer an alternate explanation of the French paradox. Polyphenols are a group of vegetable chemical substances, characterized by the presence of more than one phenolic group. ... Proanthocyanidin (also known as OPC, pycno-genol, leukocyanidin and leucoanthocyanin) is a a class of bioflavonoids. ... This article or section does not cite any references or sources. ...


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Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 172nd day of the year (173rd in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... March 26 is the 85th day of the year (86th in leap years) in the Gregorian calendar. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... March 26 is the 85th day of the year (86th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... is the 14th day of the year in the Gregorian calendar. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 169th day of the year (170th in leap years) in the Gregorian calendar. ...

Further reading

  • Gescher AJ, Steward WP. Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: a conundrum., Cancer Epidemiol Biomarkers Prev. 2003;12(10):953–957.
  • Sinclair, David A., et al. "Calorie Restriction Promotes Mammalian Cell Survival by Inducing the SIRT1 Deacetylase." Science 305 (July 16 2004): 309–392.
  • Wolf, George. "Calorie Restriction Increases Life Span: A Molecular Mechanism." Nutrition Reviews 64.2 (Feb. 2006): 89–92

See also

This article or section does not cite any references or sources. ... Binomial name Houtt. ... For other uses, see Mulberry (disambiguation). ... Categories: Stub | Fruit | Grape varieties ... A metabolite is the product of metabolism. ...

External links

  • PDRHealth Resveratrol
  • Resveratrol in Human Health and Disease: Books and Discussion
  • Sirtris Pharmaceuticals
v • d • e
Types of Phenylpropanoids
Phenylpropanoids Cinnamic acids • Cinnamaldehydes • Monolignols • Coumarins • Flavonoids • Stilbenoids • Furanocoumarin • Lignans • Lignins • Suberins
v • d • e
Stilbenoids
Stilbenoids Resveratrol • Pterostilbene • Piceatannol • Pinosylvin
v • d • e
Dietary supplements
Types Amino acids • Bodybuilding supplement • Energy drink • Energy bar • Fatty acids • Herbal Supplements • Minerals • Prebiotics • Probiotics (Lactobacillus, Bifidobacterium)• Vitamins • Whole food supplements
Vitamins and minerals Retinol (Vitamin A) • B vitamins: Thiamine (B1) • Riboflavin (B2)• Niacin (B3)• Pantothenic acid (B5)• Pyridoxine (B6)• Biotin (B7)• Folic acid (B9) • Cyanocobalamin (B12) • Ascorbic acid (Vitamin C) • Ergocalciferol and Cholecalciferol (Vitamin D) • Tocopherol (Vitamin E) • Naphthoquinone (Vitamin K) • Calcium • Choline • Chlorine • Chromium • Cobalt • Copper • Fluorine • Iodine • Iron • Magnesium • Manganese • Molybdenum • Phosphorus • Potassium • Selenium • Sodium • Sulfur • Zinc
Other common ingredients Carnitine • Chondroitin sulfate • Cod liver oil • Copper gluconate • Creatine/Creatine supplements • Dietary fiber • Elemental calcium • Ephedra • Fish oil • Folic acid • Ginseng • Glucosamine • Glutamine • Iron supplements • Japanese Honeysuckle • Krill oil • Lingzhi • Linseed oil • Melatonin • Red yeast rice • Royal jelly • Saw palmetto • Spirulina • Taurine • Wheatgrass • Wolfberry • Yohimbine • Zinc gluconate
Related articles Codex Alimentarius • Enzyte • Metabolife • Hadacol • Nutraceutical • Multivitamin • Nutrition
Phenylpropanoids are a class of plant-derived organic compounds that are biosynthesized from the amino acid phenylalanine. ... Phenylpropanoids are a class of plant-derived organic compounds that are biosynthesized from the amino acid phenylalanine. ... Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. ... Cinnamic aldehyde or cinnamaldehyde (more precisely trans-cinnamaldehyde, the only naturally-occurring form) is the chemical compound that gives cinnamon its spice. ... Structures of the three commonly occurring monolignols Monolignols are phytochemicals acting as source materials for biosynthesis of lignin. ... Coumarin is a chemical compound; a toxin found in many plants, notably in high concentration in the tonka bean, woodruff, and bison grass. ... Flavonoids are a group of chemical compounds naturally found in certain fruits, vegetables, teas, wines, nuts, seeds, and roots. ... Resveratrol is a biologically important stilbenoid. ... Furanocoumarins, or furocoumarins, are a class of organic chemical compounds produced by a variety of plants. ... A lignan is a chemical compound found in plants. ... Lignin (sometimes lignen) is a chemical compound (complex, highly cross-linked aromatic polymer) that is most commonly derived from wood and is an integral part of the cell walls of plants, especially in tracheids, xylem fibres and sclereids. ... Suberin is a waxy substance found in higher plants. ... Resveratrol is a biologically important stilbenoid. ... Resveratrol is a biologically important stilbenoid. ... Pterostilbene is thought to be the key compound found predominantly in blueberries (as well as grapes) that exhibit anti-cancer, anti-hypercholesterolemia, anti-hypertriglyceridemia properties, as well as fight off and reverse cognitive decline. ... Pinosylvin is a pre-infectious stilbenoid toxin (i. ... A dietary supplement is intended to supply nutrients, (vitamins, minerals, fatty acids or amino acids) that are missing or not consumed in sufficient quantity in a persons diet. ... An essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo by the organism (usually referring to humans), and therefore must be supplied in the diet. ... Many supplements come in capsule form. ... A variety of energy drinks are available; the skinny bullet can shape is popular. ... An energy bar is a dietary supplement often consumed by athletes or other physically active people to maintain their caloric needs in light of their strenuous physical activity. ... Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components (generally all references are to humans) by any known chemical pathways; and therefore must be obtained from the diet. ... Herbalism is a traditional medicinal or folk medicine practice based on the use of plants and plant extracts. ... mccall is cooool Dietary minerals are the chemical elements required by living organisms, other than the four elements carbon, hydrogen, nitrogen, and oxygen which are present in common organic molecules. ... The word prebiotic has two separate and disparate meanings: Before Life From the roots pre (meaning before) and biotic (referring to life), the word prebiotic can refer to the time before life appeared on the earth or any other planet with the capacity to harbor it. ... Probiotics are dietary supplements containing potentially beneficial bacteria or yeasts. ... Species L. acidophilus L. brevis L. delbrueckii subsp. ... Bifidobacteria (genus Bifidobacterium) are a group of anaerobic bacteria and a form of probiotic that is thought to have health-promoting properties for humans. ... Retinol (one vitamer of Vitamin A) A vitamin is an organic compound required as a nutrient in tiny amounts by an organism. ... Whole food supplements comprise a unique class within the food supplement industry. ... Retinol (one vitamer of Vitamin A) A vitamin is an organic compound required as a nutrient in tiny amounts by an organism. ... mccall is cooool Dietary minerals are the chemical elements required by living organisms, other than the four elements carbon, hydrogen, nitrogen, and oxygen which are present in common organic molecules. ... The structure of retinol, the most common dietary form of vitamin A Vitamin A is an essential human nutrient. ... The B vitamins are eight water-soluble vitamins that play important roles in cell metabolism. ... For the similarly spelled nucleic acid, see Thymine Thiamine or thiamin, also known as vitamin B1, is one of the B vitamins. ... Riboflavin (E101), also known as vitamin B2, is an easily absorbed micronutrient with a key role in maintaining health in animals. ... Niacin, also known as nicotinic acid or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH play essential roles in energy metabolism in the living cell. ... Pantothenic acid, also called vitamin B5 (a B vitamin), is a water-soluble vitamin required to sustain life (essential nutrient). ... Pyridoxine Pyridoxal phosphate Vitamin B6 is a water-soluble vitamin. ... Vitamin H redirects here. ... Folic acid and folate (the anion form) are forms of the water-soluble Vitamin B9. ... Cyanocobalamin is a compound that is metabolized to a vitamin in the B complex commonly known as vitamin B12 (or B12 for short). ... This article is about the nutrient. ... Vitamin D is a fat soluble vitamin that contributes to the maintenance of normal levels of calcium and phosphorus in the bloodstream. ... Tocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. ... Vitamin K1 (phylloquinone). ... For other uses, see Calcium (disambiguation). ... Choline is an organic compound, classified as an essential nutrient and usually grouped within the Vitamin B complex. ... General Name, symbol, number chlorine, Cl, 17 Chemical series nonmetals Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... REDIRECT [[ Insert text]]EWWWWWWWWWWWWW YO General Name, symbol, number chromium, Cr, 24 Chemical series transition metals Group, period, block 6, 4, d Appearance silvery metallic Standard atomic weight 51. ... For other uses, see Cobalt (disambiguation). ... For other uses, see Copper (disambiguation). ... Distinguished from fluorene and fluorone. ... For other uses, see Iodine (disambiguation). ... General Name, symbol, number iron, Fe, 26 Chemical series transition metals Group, period, block 8, 4, d Appearance lustrous metallic with a grayish tinge Standard atomic weight 55. ... General Name, symbol, number magnesium, Mg, 12 Chemical series alkaline earth metals Group, period, block 2, 3, s Appearance silvery white solid at room temp Standard atomic weight 24. ... General Name, symbol, number manganese, Mn, 25 Chemical series transition metals Group, period, block 7, 4, d Appearance silvery metallic Standard atomic weight 54. ... General Name, Symbol, Number molybdenum, Mo, 42 Chemical series transition metals Group, Period, Block 6, 5, d Appearance gray metallic Standard atomic weight 95. ... General Name, symbol, number phosphorus, P, 15 Chemical series nonmetals Group, period, block 15, 3, p Appearance waxy white/ red/ black/ colorless Standard atomic weight 30. ... General Name, symbol, number potassium, K, 19 Chemical series alkali metals Group, period, block 1, 4, s Appearance silvery white Standard atomic weight 39. ... For other uses, see Selenium (disambiguation). ... For sodium in the diet, see Salt. ... This article is about the chemical element. ... General Name, symbol, number zinc, Zn, 30 Chemical series transition metals Group, period, block 12, 4, d Appearance bluish pale gray Standard atomic weight 65. ... This article or section contains information that has not been verified and thus might not be reliable. ... Chondroitin sulfate (CS) is a glycosaminoglycan (GAG) found in connective tissue and the nervous system, normally attached to a protein core. ... Capsules of Cod Liver Oil Cod liver oil, as its name suggests, is an oil extracted from cod livers. ... Copper gluconate is the copper salt of D-gluconic acid. ... For the use of creatine to enhance athletic performance, please see Creatine supplements. ... For the biochemistry and physiology of creatine, please see Creatine. ... Dietary fibers are the indigestible portion of plant foods that move food through the digestive system, absorbing water and making defecation easier. ... Elemental calcium is a term that is in common use in the context of dietary supplements. ... Ephedra in medicine. ... Fish Oil is oil derived from fishes. ... Folic acid and folate (the anion form) are forms of the water-soluble Vitamin B9. ... Species Subgenus Panax Section Panax Series Notoginseng Panax notoginseng Series Panax Panax bipinnatifidus Panax ginseng Panax japonicus Panax quinquefolius Panax vietnamensis Panax wangianus Panax zingiberensis Section Pseudoginseng Panax pseudoginseng Panax stipuleanatus Subgenus Trifolius Panax trifolius Ginseng field in Wisconsin Ginseng refers to species within Panax, a genus of 11 species... Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. ... Glutamine (abbreviated as Gln or Q; Glx or Z represents either glutamine or glutamic acid) is one of the 20 amino acids encoded by the standard genetic code. ... Iron supplements are supplements that can be prescribed by a doctor for a medical reason. ... Binomial name Thunb. ... Krill oil is made from krill. ... Binomial name (Curtis) P. Karst LíngzhÄ« (traditional Chinese: 靈芝; simplified Chinese: 灵芝; Japanese: reishi; Korean: yeongji, hangul: 영지) is the name for one form of the mushroom Ganoderma lucidum, and its close relative Ganoderma tsugae, which grows in the northern Eastern Hemlock forests. ... Flax oil (in bottles) and coconut oil (in jars in the middle) Linseed oil, also known as flax seed oil, is a yellowish drying oil derived from the dried ripe seeds of the flax plant (Linum usitatissimum, Linaceae). ... Melatonin, 5-methoxy-N-acetyltryptamine, is a hormone found in all living creatures from algae[1] to humans, at levels that vary in a diurnal cycle. ... Dried grain red yeast rice Red yeast rice (Chinese: 紅麴米, 红曲米; pinyin: hóng; lit. ... Royal jelly is a honey bee secretion that is used in the nutrition of the larvae. ... Saw palmetto extract is an extract of the fruit of Serenoa repens. ... Species Spirulina is the common name for human and animal food supplements produced primarily from two species of cyanobacteria: Arthrospira platensis, and Arthrospira maxima. ... Taurine, or 2-aminoethanesulfonic acid, is an organic acid. ... For other uses, see Wheatgrass (disambiguation). ... Species Lycium barbarum L. Lycium chinense Mill. ... Yohimbine, also known under the outdated names quebrachin, aphrodin, corynine, yohimvetol and hydroergotocin, is the principal alkaloid of the bark of the West-African tree Pausinystalia yohimbe Pierre (formerly Corynanthe yohimbe), family Rubiaceae (Madder family). ... Zinc gluconate is the salt of gluconate and zinc II. It is an ionic compound consisting of two moles of gluconate for each mole of zinc. ... The Codex Alimentarius (Latin for food code or food book) is a collection of internationally recognized standards, codes of practice, guidelines and other recommendations relating to foods, food production and food safety under the aegis of consumer protection. ... Enzyte is an herbal nutritional supplement manufactured by Berkeley Premium Nutraceuticals of Cincinnati, Ohio. ... Metabolife is an American corporation which manufactures dietary supplements. ... Hadacol was a patent medicine marketed as a vitamin supplement. ... Nutraceutical is a portmanteau of [Nutrition] and [pharmaceutical] and refers to foods thought to have a beneficial effect on human health. ... A multivitamin is any preparation containing more than a single vitamin. ... The Nutrition Facts table indicates the amounts of nutrients which experts recommend you limit or consume in adequate amounts. ...

  Results from FactBites:
 
resveratrol: Definition and Much More from Answers.com (1641 words)
Resveratrol is found in the skin of red grapes and as a constituent of red wine may explain the “French paradox” that the incidence of coronary heart disease is relatively low in southern France despite high dietary intake of saturated fats.
Resveratrol is often referred to as a nutraceutical, along with other bioactive plant compounds that are being studied for potential clinical applications such as curcumin, EGCG and silibinin, among others.
Resveratrol has recently been reported to be effective against neuronal cell dysfunction and cell death, and may be of use for diseases such as Huntington's disease and Alzheimer's disease.
Resveratrol : by Ray Sahelian, M.D., Resveratrol Benefits, Anti-Aging potential (4066 words)
Resveratrol is a potent chemical and studies show it has anti-inflammatory, antioxidant, anti-infective properties, and it activates the longevity gene in fruit flies and worms.
Resveratrol 's anti-influenza activity seems to center on its ability to interfere with key "host-cell functions" that are essential for virus replication, the authors explain in The Journal of Infectious Diseases, May 15, 2005.
After resveratrol treatment, the apoptosis rate of the neuroblastoma cells significantly increased, a significant accumulation of cells occurred at the S phase of the cell cycle, p21 was downregulated, and cyclin E was upregulated.
  More results at FactBites »


 

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