Resveratrol | Youth Resvpro

<div id="globalWrapper"> <div id="column-content"> <div id="content"> <a name="top" id="top"></a> <div id="siteNotice"><script type="text/javascript" language="JavaScript"> /* <![CDATA[ */ document.writeln("\x3cp\x3e\x3c/p\x3e\n"); /* ]]> */ </script></div> <h1 id="firstHeading" class="firstHeading">Resveratrol : Resveratrol</h1> <div id="bodyContent"> <h3 id="siteSub">From Wikipedia, the free encyclopedia</h3> <div id="contentSub"></div> <div id="jump-to-nav">Jump to: <a href="#column-one">navigation</a>, <a href="#searchInput">search</a></div>  <table class="toccolours" border="1" width="250px" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"> <tr> <th style="width: 30%; background: #F8EABA; text-align: center;" colspan="2">Resveratrol</th> </tr> <tr> <td align="center" colspan="2" bgcolor="#FFFFFF"><a href="/wiki/File:Resveratrol.svg" class="image" title="Chemical structure of trans-resveratrol"><img alt="Chemical structure of trans-resveratrol" src="http://upload.wikimedia.org/wikipedia/commons/thumb/1/17/Resveratrol.svg/250px-Resveratrol.svg.png" width="250" height="144" /></a></td> </tr> <tr> <td align="center" colspan="2" bgcolor="#FFFFFF"><a href="/wiki/File:Resveratrol3d.png" class="image" title="Chemical structure of trans-resveratrol"><img alt="Chemical structure of trans-resveratrol" src="http://upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Resveratrol3d.png/180px-Resveratrol3d.png" width="180" height="131" /></a></td> </tr> <tr> <td>Other names</td> <td><i>trans</i>-3,5,4'-Trihydroxystilbene;<br /> 3,4',5-Stilbenetriol;<br /> <i>trans</i>-Resveratrol;<br /> (<i>E</i>)-5-(<i>p</i>-Hydroxystyryl)resorcinol (<i>E</i>)-5-(4-hydroxystyryl)benzene-1,3-diol</td> </tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2">Identifiers</th> </tr> <tr> <td bgcolor=""><a href="/wiki/CAS_registry_number" title="CAS registry number">CAS number</a></td> <td bgcolor="">[<span class="reflink plainlinksneverexpand"><a href="http://www.commonchemistry.org/ChemicalDetail.aspx?ref=501-36-0" class="external text" title="http://www.commonchemistry.org/ChemicalDetail.aspx?ref=501-36-0" rel="nofollow">501-36-0</a></span>]</td> </tr> <tr> <td><a href="/wiki/Simplified_molecular_input_line_entry_specification" title="Simplified molecular input line entry specification">SMILES</a></td> <td> <div class="NavFrame collapsed" style="border:none; padding:0;"> <div class="NavHead" style="width:100%; background:transparent;" align="left"><small><tt> </tt></small></div> <div class="NavContent" style="text-align:left;display:none;"><small><tt>Oc2ccc(C=Cc1cc(O)cc(O)c1)cc2</tt></small></div> </div> </td> </tr> <tr> <td><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></td> <td> <div class="NavFrame collapsed" style="border:none; padding:0;"> <div class="NavHead" style="width:100%; background:transparent;" align="left"><small> </small></div> <div class="NavContent" style="text-align:left;display:none;"><small>1/C14H12O3/c15-<br /> 12-5-3-10(4-6-12)<br /> 1-2-11-7-13(16)9-<br /> 14(17)8-11/h1-9,15-<br /> 17H/b2-1+</small></div> </div> </td> </tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> ID</td> <td><span class="reflink plainlinksneverexpand"><a href="http://www.chemspider.com/392875" class="external text" title="http://www.chemspider.com/392875" rel="nofollow">392875</a></span></td> </tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2">Properties</th> </tr> <tr> <td><a href="/wiki/Chemical_formula" title="Chemical formula">Molecular formula</a></td> <td>C<sub>14</sub>H<sub>12</sub>O<sub>3</sub></td> </tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></td> <td>228.25</td> </tr> <tr> <td>Appearance</td> <td>white powder with<br /> slight yellow cast</td> </tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Water" title="Water">water</a></td> <td>0.03 g/L</td> </tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">DMSO</a></td> <td>16 g/L</td> </tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a></td> <td>50 g/L</td> </tr> <tr> <td style="width: 30%; background: #F8EABA; text-align: center;" colspan="2"><small>Except where noted otherwise, data are given for<br /> materials in their <a href="/wiki/Standard_state" title="Standard state">standard state<br /> (at 25 °C, 100 kPa)</a><br /> <a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></small></td> </tr> </table> <p><b>Resveratrol</b> (<i>trans</i>-resveratrol) is a <a href="/wiki/Phytoalexin" title="Phytoalexin">phytoalexin</a> produced naturally by several plants when under attack by <a href="/wiki/Pathogen" title="Pathogen">pathogens</a> such as <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> or <a href="/wiki/Fungi" title="Fungi" class="mw-redirect">fungi</a>. Resveratrol has also been produced by chemical synthesis<sup id="cite_ref-pmid16401555_0-0" class="reference"><a href="#cite_note-pmid16401555-0"><span>[</span>1<span>]</span></a></sup> and is sold as a <a href="/wiki/Nutritional_supplement" title="Nutritional supplement" class="mw-redirect">nutritional supplement</a> derived primarily from <a href="/wiki/Japanese_knotweed" title="Japanese knotweed">Japanese knotweed</a>. In mouse and rat experiments, anti-cancer, <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">anti-inflammatory</a>, blood-sugar-lowering and other beneficial cardiovascular effects of resveratrol have been reported. Most of these results have yet to be replicated in humans. In the only positive human trial, extremely high doses (3–5 g) of resveratrol in a proprietary formulation have been necessary to significantly lower blood sugar.<sup id="cite_ref-PMID_18393104_1-0" class="reference"><a href="#cite_note-PMID_18393104-1"><span>[</span>2<span>]</span></a></sup> Resveratrol is found in the skin of red grapes and is a constituent of red wine, but apparently not in sufficient amounts to explain the <a href="/wiki/French_paradox" title="French paradox">French paradox</a>. Experiments have shown that resveratrol treatment extended the life of fruit flies, nematode worms and short living fish but it did not increase the life span of mice.</p> <table id="toc" class="toc" summary="Contents"> <tr> <td> <div id="toctitle"> <h2>Contents</h2> </div> <ul> <li class="toclevel-1"><a href="#Life_extension"><span class="tocnumber">1</span> <span class="toctext">Life extension</span></a></li> <li class="toclevel-1"><a href="#Cancer_prevention"><span class="tocnumber">2</span> <span class="toctext">Cancer prevention</span></a></li> <li class="toclevel-1"><a href="#Resveratrol_and_experimental_diabetes"><span class="tocnumber">3</span> <span class="toctext">Resveratrol and experimental diabetes</span></a></li> <li class="toclevel-1"><a href="#Other_applications"><span class="tocnumber">4</span> <span class="toctext">Other applications</span></a></li> <li class="toclevel-1"><a href="#Pharmacokinetics"><span class="tocnumber">5</span> <span class="toctext">Pharmacokinetics</span></a> <ul> <li class="toclevel-2"><a href="#Adverse_effects_and_unknowns"><span class="tocnumber">5.1</span> <span class="toctext">Adverse effects and unknowns</span></a></li> </ul> </li> <li class="toclevel-1"><a href="#Mechanisms_of_action"><span class="tocnumber">6</span> <span class="toctext">Mechanisms of action</span></a></li> <li class="toclevel-1"><a href="#Chemical_and_physical_properties"><span class="tocnumber">7</span> <span class="toctext">Chemical and physical properties</span></a></li> <li class="toclevel-1"><a href="#Plants_and_foods"><span class="tocnumber">8</span> <span class="toctext">Plants and foods</span></a> <ul> <li class="toclevel-2"><a href="#Content_in_wines_and_grape_juice"><span class="tocnumber">8.1</span> <span class="toctext">Content in wines and grape juice</span></a></li> <li class="toclevel-2"><a href="#Content_in_selected_foods"><span class="tocnumber">8.2</span> <span class="toctext">Content in selected foods</span></a></li> </ul> </li> <li class="toclevel-1"><a href="#Supplementation"><span class="tocnumber">9</span> <span class="toctext">Supplementation</span></a></li> <li class="toclevel-1"><a href="#See_also"><span class="tocnumber">10</span> <span class="toctext">See also</span></a> <ul> <li class="toclevel-2"><a href="#Other_articles"><span class="tocnumber">10.1</span> <span class="toctext">Other articles</span></a></li> </ul> </li> <li class="toclevel-1"><a href="#References"><span class="tocnumber">11</span> <span class="toctext">References</span></a></li> <li class="toclevel-1"><a href="#Further_reading"><span class="tocnumber">12</span> <span class="toctext">Further reading</span></a></li> <li class="toclevel-1"><a href="#External_links"><span class="tocnumber">13</span> <span class="toctext">External links</span></a></li> </ul> </td> </tr> </table> <script type="text/javascript"> //<![CDATA[ if (window.showTocToggle) { var tocShowText = "show"; var tocHideText = "hide"; showTocToggle(); } //]]> </script> <p><a name="Life_extension" id="Life_extension"></a></p> <h3><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=1" title="Edit section: Life extension">edit</a>]</span> <span class="mw-headline">Life extension</span></h3> <p>The groups of Howitz and Sinclair reported in 2003 in the journal <i><a href="/wiki/Nature_(journal)" title="Nature (journal)">Nature</a></i> that resveratrol significantly extends the lifespan of the <a href="/wiki/Yeast" title="Yeast">yeast</a> <i><a href="/wiki/Saccharomyces_cerevisiae" title="Saccharomyces cerevisiae">Saccharomyces cerevisiae</a></i>.<sup id="cite_ref-Howitz2003_2-0" class="reference"><a href="#cite_note-Howitz2003-2"><span>[</span>3<span>]</span></a></sup> Later studies conducted by Sinclair showed that resveratrol also prolongs the lifespan of the worm <i><a href="/wiki/Caenorhabditis_elegans" title="Caenorhabditis elegans">Caenorhabditis elegans</a></i> and the fruit fly <i><a href="/wiki/Drosophila_melanogaster" title="Drosophila melanogaster">Drosophila melanogaster</a></i>.<sup id="cite_ref-Wood2004_3-0" class="reference"><a href="#cite_note-Wood2004-3"><span>[</span>4<span>]</span></a></sup> In 2007, a different group of researchers was able to reproduce Sinclair's results with <i>C. elegans</i>,<sup id="cite_ref-Gruber2007_4-0" class="reference"><a href="#cite_note-Gruber2007-4"><span>[</span>5<span>]</span></a></sup> but a third group could not achieve consistent increases in lifespan of <i>D. melanogaster</i> or <i>C. elegans</i>.<sup id="cite_ref-Bass2007_5-0" class="reference"><a href="#cite_note-Bass2007-5"><span>[</span>6<span>]</span></a></sup></p> <p>In 2006, Italian scientists obtained the first positive result of resveratrol supplementation in a <a href="/wiki/Vertebrate" title="Vertebrate">vertebrate</a>. Using a short-lived fish, <i><a href="/wiki/Nothobranchius_furzeri" title="Nothobranchius furzeri">Nothobranchius furzeri</a></i>, 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's 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.<sup id="cite_ref-Valenzano2006_6-0" class="reference"><a href="#cite_note-Valenzano2006-6"><span>[</span>7<span>]</span></a></sup></p> <p>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 <a href="/wiki/Coconut_oil" title="Coconut oil">coconut oil</a> to the standard diet; it provided 60% of energy from fat, and the mice on it consumed about 30% more calories than 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. <a href="/wiki/Gene_expression" title="Gene expression">Gene expression</a> analysis indicated the addition of resveratrol opposed the alteration of 144 out of 155 gene pathways changed by the high-fat diet. <a href="/wiki/Insulin" title="Insulin">Insulin</a> and <a href="/wiki/Glucose" title="Glucose">glucose</a> levels in mice on the high-fat+resveratrol diet were closer to the mice on standard diet than 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.<sup id="cite_ref-Baur2006_7-0" class="reference"><a href="#cite_note-Baur2006-7"><span>[</span>8<span>]</span></a></sup> A further study by a group of scientists, which included Sinclair, indicated that resveratrol treatment had a range of beneficial effects in elderly mice but did not increase the longevity of <a href="/wiki/Ad_libitum" title="Ad libitum">ad libitum</a>-fed mice when started midlife.<sup id="cite_ref-Pearson2008_8-0" class="reference"><a href="#cite_note-Pearson2008-8"><span>[</span>9<span>]</span></a></sup></p> <p><a name="Cancer_prevention" id="Cancer_prevention"></a></p> <h3><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=2" title="Edit section: Cancer prevention">edit</a>]</span> <span class="mw-headline">Cancer prevention</span></h3> <p>In 1997, Jang reported that topical resveratrol applications prevented the skin cancer development in mice treated with a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>.<sup id="cite_ref-pmid8985016_9-0" class="reference"><a href="#cite_note-pmid8985016-9"><span>[</span>10<span>]</span></a></sup> There have since been dozens of studies of the anti-cancer activity of resveratrol in animal models.<sup id="cite_ref-pmid16732220_10-0" class="reference"><a href="#cite_note-pmid16732220-10"><span>[</span>11<span>]</span></a></sup> No results of human clinical trials for cancer have been reported.<sup id="cite_ref-pmid17306316_11-0" class="reference"><a href="#cite_note-pmid17306316-11"><span>[</span>12<span>]</span></a></sup> However, clinical trials to investigate the effects on colon cancer and <a href="/wiki/Melanoma" title="Melanoma">melanoma</a> (skin cancer) are currently recruiting patients.<sup id="cite_ref-clinicaltrials_12-0" class="reference"><a href="#cite_note-clinicaltrials-12"><span>[</span>13<span>]</span></a></sup></p> <p><a href="/wiki/In_vitro" title="In vitro">In vitro</a> resveratrol interacts with multiple molecular targets (see <a href="/wiki/Resveratrol#mechanisms_of_action" title="Resveratrol">the mechanisms of action</a>), and has positive effects on the cells of breast, skin, gastric, colon, esophageal, prostate, and pancreatic cancer, and <a href="/wiki/Leukemia" title="Leukemia">leukemia</a>.<sup id="cite_ref-pmid16732220_10-1" class="reference"><a href="#cite_note-pmid16732220-10"><span>[</span>11<span>]</span></a></sup> However, the study of pharmacokinetics of resveratrol in humans concluded that even high doses of resveratrol might be insufficient to achieve resveratrol concentrations required for the systemic prevention of cancer.<sup id="cite_ref-pmid17548692_13-0" class="reference"><a href="#cite_note-pmid17548692-13"><span>[</span>14<span>]</span></a></sup> This is consistent with the results from the animal cancer models, which indicate that the <a href="/wiki/In_vivo" title="In vivo">in vivo</a> effectiveness of resveratrol is limited by its poor systemic bioavailability.<sup id="cite_ref-pmid17306316_11-1" class="reference"><a href="#cite_note-pmid17306316-11"><span>[</span>12<span>]</span></a></sup><sup id="cite_ref-pmid16988123_14-0" class="reference"><a href="#cite_note-pmid16988123-14"><span>[</span>15<span>]</span></a></sup> <sup id="cite_ref-pmid15779067_15-0" class="reference"><a href="#cite_note-pmid15779067-15"><span>[</span>16<span>]</span></a></sup> The strongest evidence of anti-cancer action of resveratrol exists for tumors it can come into direct contact with, such as skin and <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a> tumors. For other cancers, the evidence is equivocal, even if massive doses of resveratrol are used.<sup id="cite_ref-pmid17306316_11-2" class="reference"><a href="#cite_note-pmid17306316-11"><span>[</span>12<span>]</span></a></sup></p> <p>Thus, <a href="/wiki/Topical_application" title="Topical application" class="mw-redirect">topical application</a> of resveratrol in mice, both before and after the <a href="/wiki/UVB" title="UVB" class="mw-redirect">UVB</a> exposure, inhibited the skin damage and decreased skin cancer incidence. However, oral resveratrol was ineffective in treating mice <a href="/wiki/Innoculation" title="Innoculation" class="mw-redirect">inoculated</a> with melanoma cells. Resveratrol given orally also had no effect on leukemia and lung cancer;<sup id="cite_ref-pmid17306316_11-3" class="reference"><a href="#cite_note-pmid17306316-11"><span>[</span>12<span>]</span></a></sup><sup id="cite_ref-pmid12097696_16-0" class="reference"><a href="#cite_note-pmid12097696-16"><span>[</span>17<span>]</span></a></sup> however, injected <a href="/wiki/Intraperitoneal_injection" title="Intraperitoneal injection">intraperitoneally</a>, 2.5 or 10 mg/kg of resveratrol slowed the growth of metastatic <a href="/w/index.php?title=Lewis_lung_carcinoma&action=edit&redlink=1" class="new" title="Lewis lung carcinoma (page does not exist)">Lewis lung carcinomas</a> in mice.<sup id="cite_ref-pmid17306316_11-4" class="reference"><a href="#cite_note-pmid17306316-11"><span>[</span>12<span>]</span></a></sup><sup id="cite_ref-pmid11385077_17-0" class="reference"><a href="#cite_note-pmid11385077-17"><span>[</span>18<span>]</span></a></sup> Resveratrol (1 mg/kg orally) reduced the number and size of the esophageal tumors in rats treated with a carcinogen.<sup id="cite_ref-pmid12189197_18-0" class="reference"><a href="#cite_note-pmid12189197-18"><span>[</span>19<span>]</span></a></sup> In several studies, small doses (0.02–8 mg/kg) of resveratrol, given <a href="/wiki/Prophylactic" title="Prophylactic" class="mw-redirect">prophylactically</a>, reduced or prevented the development of intestinal and colon tumors in rats given different carcinogens.<sup id="cite_ref-pmid17306316_11-5" class="reference"><a href="#cite_note-pmid17306316-11"><span>[</span>12<span>]</span></a></sup></p> <p>Resveratrol treatment appeared to prevent the development of mammary tumors in animal models; however, it had no effect on the growth of existing tumors. Paradoxically, treatment of pre-pubertal mice with high doses of resveratrol enhanced formation of tumors. Injected in high doses into mice, resveratrol slowed the growth of <a href="/wiki/Neuroblastoma" title="Neuroblastoma">neuroblastomas</a>.<sup id="cite_ref-pmid17306316_11-6" class="reference"><a href="#cite_note-pmid17306316-11"><span>[</span>12<span>]</span></a></sup></p> <p><a name="Resveratrol_and_experimental_diabetes" id="Resveratrol_and_experimental_diabetes"></a></p> <h3><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=3" title="Edit section: Resveratrol and experimental diabetes">edit</a>]</span> <span class="mw-headline">Resveratrol and experimental diabetes</span></h3> <p>Palsamy and Subramanian have recently published articles on the antihyperglycemic potential of resveratrol in experimental diabetic rats. In their study, the oral administration of resveratrol (5mg/kg b.w) to streptozotocin-nicotinamide-induced experimental diabetic rats for 30 days significantly normalizes the levels of blood glucose, plasma insulin, glycosylated hemoglobin, AST, ALP, ALT,<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span>[</span>20<span>]</span></a></sup> and modulates the altered activities of carbohydrate metabolizing enzymes in the liver and kidney tissus of diabetic rats. The results thus obtained showed the antidiabetic property of resveratrol in experimental diabetes.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span>[</span>21<span>]</span></a></sup> Resveratol activates <a href="/wiki/AMPK" title="AMPK" class="mw-redirect">AMPK</a>.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span>[</span>22<span>]</span></a></sup></p> <p><a name="Other_applications" id="Other_applications"></a></p> <h3><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=4" title="Edit section: Other applications">edit</a>]</span> <span class="mw-headline">Other applications</span></h3> <p>Johan Auwerx (at the Institute of Genetics and Molecular and Cell Biology in Illkirch, France) and coauthors published an online article in the journal <i><a href="/wiki/Cell_(journal)" title="Cell (journal)">Cell</a></i> in November, 2006. Mice fed resveratrol for fifteen 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 the <a href="/wiki/Sirtuin_1" title="Sirtuin 1">Sirtuin 1</a> gene.</p> <p>Nicholas Wade's interview-article with Dr. Auwerx<sup id="cite_ref-Red_Wine_Ingredient_Increases_Endurance.2C_Study_Shows_22-0" class="reference"><a href="#cite_note-Red_Wine_Ingredient_Increases_Endurance.2C_Study_Shows-22"><span>[</span>23<span>]</span></a></sup> 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 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). Long-term safety has not been evaluated in humans.</p> <p>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.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span>[</span>24<span>]</span></a></sup></p> <p>In November 2008, researchers at the Weill Medical College of Cornell University reported that dietary supplementation with resveratrol significantly reduced plaque formation in animal brains, a component of <a href="/wiki/Alzheimer" title="Alzheimer" class="mw-redirect">Alzheimer</a> and other Neurodegenerative diseases.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span>[</span>25<span>]</span></a></sup> In mice, oral resveratrol produced large reductions in brain plaque in the hypothalamus (-90%), striatum (-89%), and medial cortex (-48%) sections of the brain. In humans it is theorized that oral doses of resveratrol may reduce beta amyloid plaque associated with aging changes in the brain. Researchers theorize that one mechanism for plaque eradication is the ability of resveratrol to chelate (remove) copper.</p> <p><a name="Pharmacokinetics" id="Pharmacokinetics"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=5" title="Edit section: Pharmacokinetics">edit</a>]</span> <span class="mw-headline">Pharmacokinetics</span></h2> <p>The most efficient way of administering resveratrol in humans appears to be <a href="/wiki/Buccal_mucosa" title="Buccal mucosa">buccal</a> delivery, that is without swallowing, by direct absorption through the inside of the mouth. When one mg of resveratrol in 50 mL solution was retained in the mouth for one min before swallowing, 37 ng/ml of free resveratrol were measured in plasma two minutes later. This level of unchanged resveratrol in blood can only be achieved with 250 mg of resveratrol taken in a pill form.<sup id="cite_ref-pmid12126761_25-0" class="reference"><a href="#cite_note-pmid12126761-25"><span>[</span>26<span>]</span></a></sup></p> <p>About 70% of the resveratrol dose given orally as a pill is absorbed; nevertheless, oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of resveratrol is low because it is rapidly metabolized in intestines and liver into <a href="/wiki/Conjugate" title="Conjugate" class="mw-redirect">conjugated</a> forms: <a href="/wiki/Glucuronate" title="Glucuronate" class="mw-redirect">glucuronate</a> and <a href="/wiki/Sulfonate" title="Sulfonate">sulfonate</a>.<sup id="cite_ref-Walle_26-0" class="reference"><a href="#cite_note-Walle-26"><span>[</span>27<span>]</span></a></sup> Only trace amounts (below 5 ng/mL) of unchanged resveratrol could be detected in the blood after 25 mg oral dose.<sup id="cite_ref-Walle_26-1" class="reference"><a href="#cite_note-Walle-26"><span>[</span>27<span>]</span></a></sup> Even when a very large dose of resveratrol (2.5 and 5 g) was given as an uncoated pill, the concentration of resveratrol in blood failed to reach the level necessary for the systemic cancer prevention.<sup id="cite_ref-Boocock_27-0" class="reference"><a href="#cite_note-Boocock-27"><span>[</span>28<span>]</span></a></sup> However, resveratrol given in a proprietary formulation SRT-501 (3 or 5 g), developed by Sirtris Pharmaceuticals, reached 5–8 times higher blood levels. These levels did approach the concentration necessary to exert the effects shown in animal models and in vitro experiments.<sup id="cite_ref-PMID_18393104_1-1" class="reference"><a href="#cite_note-PMID_18393104-1"><span>[</span>2<span>]</span></a></sup></p> <p>In humans<sup id="cite_ref-Walle_26-2" class="reference"><a href="#cite_note-Walle-26"><span>[</span>27<span>]</span></a></sup><sup id="cite_ref-Boocock_27-1" class="reference"><a href="#cite_note-Boocock-27"><span>[</span>28<span>]</span></a></sup> and rats,<sup id="cite_ref-pmid12065739_28-0" class="reference"><a href="#cite_note-pmid12065739-28"><span>[</span>29<span>]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span>[</span>30<span>]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span>[</span>31<span>]</span></a></sup> less than 5% of the oral dose is being observed as free resveratrol in blood plasma. The most abundant resveratrol metabolites in humans, rats, and mice are trans-resveratrol-3-O-glucuronide and trans-resveratrol-3-sulfate.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span>[</span>32<span>]</span></a></sup> Walle suggests sulfate conjugates are the primary source of activity,<sup id="cite_ref-Walle_26-3" class="reference"><a href="#cite_note-Walle-26"><span>[</span>27<span>]</span></a></sup> Wang et al. suggests the glucuronides,<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span>[</span>33<span>]</span></a></sup> and Boocock et al. also emphasized the need for further study of the effects of the <a href="/wiki/Metabolite" title="Metabolite">metabolites</a>, including the possibility of deconjugation to free resveratrol inside cells. Goldberd, who studied the <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of resveratrol, <a href="/wiki/Catechin" title="Catechin">catechin</a> and <a href="/wiki/Quercetin" title="Quercetin">quercetin</a> in humans, concluded "it seems that the potential health benefits of these compounds based upon the in vitro activities of the unconjugated compounds are unrealistic and have been greatly exaggerated. Indeed, the profusion of papers describing such activities can legitimately be described as irrelevant and misleading. Henceforth, investigations of this nature should focus upon the potential health benefits of their <a href="/wiki/Glucuronide" title="Glucuronide">glucuronide</a> and <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> conjugates."<sup id="cite_ref-pmid12554065_33-0" class="reference"><a href="#cite_note-pmid12554065-33"><span>[</span>34<span>]</span></a></sup></p> <p>The hypothesis that resveratrol from wine could have higher <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> than resveratrol from a pill,<sup id="cite_ref-pmid16732220_10-2" class="reference"><a href="#cite_note-pmid16732220-10"><span>[</span>11<span>]</span></a></sup><sup id="cite_ref-pmid15779070_34-0" class="reference"><a href="#cite_note-pmid15779070-34"><span>[</span>35<span>]</span></a></sup> has been disproved by experimental data.<sup id="cite_ref-pmid12554065_33-1" class="reference"><a href="#cite_note-pmid12554065-33"><span>[</span>34<span>]</span></a></sup><sup id="cite_ref-pmid15830336_35-0" class="reference"><a href="#cite_note-pmid15830336-35"><span>[</span>36<span>]</span></a></sup> For example, after five men took 600 mL of red wine with the resveratrol content of 3.2 mg/L (total dose about 2 mg) before breakfast, unchanged resveratrol was detected in the blood of only two of them, and only in trace amounts (below 2.5 ng/mL). Resveratrol levels appeared to be slightly higher if red wine (600 mL of red wine containing 0.6 mg/mL resveratrol; total dose about 0.5 mg) was taken with meal: trace amounts (1–6 ng/mL) were found in four out of ten subjects.<sup id="cite_ref-pmid15830336_35-1" class="reference"><a href="#cite_note-pmid15830336-35"><span>[</span>36<span>]</span></a></sup> In another study, the pharmacokinetics of resveratrol (25 mg) did not change whether it was taken with vegetable juice, white wine or white grape juice. The highest level of unchanged resveratrol in the <a href="/wiki/Serum" title="Serum">serum</a> (7–9 ng/mL) was achieved after thirty minutes, and it completely disappeared from blood after four hours.<sup id="cite_ref-pmid12554065_33-2" class="reference"><a href="#cite_note-pmid12554065-33"><span>[</span>34<span>]</span></a></sup> The authors of both studies concluded that the trace amounts of resveratrol reached in the blood are insufficient to explain the French paradox. It appears that the beneficial effects of wine could be explained by the effects of alcohol<sup id="cite_ref-pmid12554065_33-3" class="reference"><a href="#cite_note-pmid12554065-33"><span>[</span>34<span>]</span></a></sup> or the whole complex of substances wine contains;<sup id="cite_ref-pmid15830336_35-2" class="reference"><a href="#cite_note-pmid15830336-35"><span>[</span>36<span>]</span></a></sup> for example, the cardiovascular benefits of wine appear to correlate with the content of <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">procyanidins</a>.<sup id="cite_ref-pmid17136085_36-0" class="reference"><a href="#cite_note-pmid17136085-36"><span>[</span>37<span>]</span></a></sup></p> <p><a name="Adverse_effects_and_unknowns" id="Adverse_effects_and_unknowns"></a></p> <h3><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=6" title="Edit section: Adverse effects and unknowns">edit</a>]</span> <span class="mw-headline">Adverse effects and unknowns</span></h3> <p>While the health benefits of resveratrol seem promising, one study has theorized that it may stimulate the growth of human <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> cells, possibly because of resveratrol's chemical structure, which is similar to a <a href="/wiki/Phytoestrogen" title="Phytoestrogen" class="mw-redirect">phytoestrogen</a>.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span>[</span>38<span>]</span></a></sup><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span>[</span>39<span>]</span></a></sup> However, other studies have found that resveratrol actually fights breast cancer.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span>[</span>40<span>]</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span>[</span>41<span>]</span></a></sup> Some studies suggest that resveratrol slows the development of blood vessels, which suppresses tumors, but also slows healing.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span>[</span>42<span>]</span></a></sup> Citing the evidence that resveratrol is <a href="http://en.wiktionary.org/wiki/estrogenic" class="extiw" title="wikt:estrogenic">estrogenic</a>, some retailers of resveratrol advise that the compound may interfere with oral contraceptives and that women who are pregnant or intending to become pregnant should not use the product, while others advise that resveratrol should not be taken by children or young adults under eighteen, as no studies have shown how it affects their natural development.<sup id="cite_ref-revgenetics_42-0" class="reference"><a href="#cite_note-revgenetics-42"><span>[</span>43<span>]</span></a></sup> A small study found that a single dose of up to 5 g of <i>trans</i>-resveratrol caused no serious adverse effects in healthy volunteers.<sup id="cite_ref-pmid17548692_13-1" class="reference"><a href="#cite_note-pmid17548692-13"><span>[</span>14<span>]</span></a></sup></p> <p><a name="Mechanisms_of_action" id="Mechanisms_of_action"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=7" title="Edit section: Mechanisms of action">edit</a>]</span> <span class="mw-headline">Mechanisms of action</span></h2> <p>The mechanisms of resveratrol's apparent effects on <a href="/wiki/Life_extension" title="Life extension">life extension</a> are not fully understood, but they appear to mimic several of the <a href="/wiki/Biochemical" title="Biochemical" class="mw-redirect">biochemical</a> effects of <a href="/wiki/Calorie_restriction" title="Calorie restriction">calorie restriction</a>. A new report indicates that resveratrol activates <a href="/wiki/Sirtuin_1" title="Sirtuin 1">Sirtuin 1</a> (SIRT1) and PGC-1α and improve functioning of the <a href="/wiki/Mitochondria" title="Mitochondria" class="mw-redirect">mitochondria</a>.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span>[</span>44<span>]</span></a></sup> Other research calls into question the theory connecting resveratrol, SIRT1, and calorie restriction.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span>[</span>45<span>]</span></a></sup><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span>[</span>46<span>]</span></a></sup></p> <dl> <dd><i>For the debate about Resveratrol effects on longevity, see <a href="/wiki/Calorie_restriction#Sir2.2FSIRT1_and_resveratrol" title="Calorie restriction">Calorie restriction#Sir2.2FSIRT1 and resveratrol</a>.</i></dd> </dl> <p>A paper by Robb <i>et al.</i> discusses resveratrol action in cells. It reports a fourteen-fold increase in the action of MnSOD (<a href="/wiki/SOD2" title="SOD2">SOD2</a>).<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span>[</span>47<span>]</span></a></sup> MnSOD reduces superoxide to <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> (H<sub>2</sub>O<sub>2</sub>), but H<sub>2</sub>O<sub>2</sub> is not increased due to other cellular activity. Superoxide O<sub>2</sub><sup>-</sup> is a byproduct of respiration in complex 1 and 3 of the <a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a>. It is "not highly toxic, [but] can extract an electron from biological membrane and other cell components, causing free radical chain reactions. Therefore it is essential for the cell to keep superoxide anions in check."<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span>[</span>48<span>]</span></a></sup> MnSOD reduces superoxide and thereby confers resistance to <a href="/wiki/Mitochondrial_disease" title="Mitochondrial disease">mitochondrial dysfunction</a>, permeability transition, and <a href="/wiki/Apoptosis" title="Apoptosis">apoptotic</a> death in various diseases.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span>[</span>49<span>]</span></a></sup> It has been implicated in lifespan extension, inhibits cancer, (e.g. pancreatic cancer<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span>[</span>50<span>]</span></a></sup><sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span>[</span>51<span>]</span></a></sup>) and provides resistance to reperfusion injury and irradiation damage.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span>[</span>52<span>]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span>[</span>53<span>]</span></a></sup><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span>[</span>54<span>]</span></a></sup> These effects have also been observed with resveratrol. Robb 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<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span>[</span>55<span>]</span></a></sup> which stimulates FOXO3a transcriptional activity<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span>[</span>56<span>]</span></a></sup> and it has been shown to enhance the sirtuin-catalyzed deacetylation (activity) of <a href="/wiki/FOXO3A" title="FOXO3A" class="mw-redirect">FOXO3a</a>. MnSOD is known to be a target of FOXO3a, and MnSOD expression is strongly induced in cells overexpressing FOXO3a.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span>[</span>57<span>]</span></a></sup></p> <p>Resveratrol interferes with all three stages of <a href="/wiki/Carcinogenesis" title="Carcinogenesis">carcinogenesis</a> — initiation, promotion and progression. Experiments in <a href="/wiki/Cell_cultures" title="Cell cultures" class="mw-redirect">cell cultures</a> of varied types and isolated subcellular systems <a href="/wiki/In_vitro" title="In vitro">in vitro</a> imply many mechanisms in the <a href="/wiki/Pharmacological" title="Pharmacological" class="mw-redirect">pharmacological</a> activity of resveratrol. These mechanisms include modulation of the <a href="/wiki/Transcription_factor" title="Transcription factor">transcription factor</a> <a href="/wiki/NF-kB" title="NF-kB" class="mw-redirect">NF-kB</a>,<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span>[</span>58<span>]</span></a></sup> inhibition of the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> isoenzyme <a href="/wiki/CYP1A1" title="CYP1A1" class="mw-redirect">CYP1A1</a><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span>[</span>59<span>]</span></a></sup> (although this may not be relevant to the CYP1A1-mediated bioactivation of the procarcinogen <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">benzo(a)pyrene</a><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span>[</span>60<span>]</span></a></sup>), alterations in <a href="/wiki/Androgenic" title="Androgenic" class="mw-redirect">androgenic</a><sup id="cite_ref-Benitez_2006_60-0" class="reference"><a href="#cite_note-Benitez_2006-60"><span>[</span>61<span>]</span></a></sup> actions and expression and activity of <a href="/wiki/Cyclooxygenase" title="Cyclooxygenase">cyclooxygenase</a> (COX) enzymes. In vitro, resveratrol "inhibited the proliferation of human pancreatic cancer cell lines." In some lineages of cancer <a href="/wiki/Cell_culture" title="Cell culture">cell culture</a>, resveratrol has been shown to induce <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>, which means it kills cells and may kill cancer cells.<sup id="cite_ref-Benitez_2006_60-1" class="reference"><a href="#cite_note-Benitez_2006-60"><span>[</span>61<span>]</span></a></sup><sup id="cite_ref-Faber_2006_61-0" class="reference"><a href="#cite_note-Faber_2006-61"><span>[</span>62<span>]</span></a></sup><sup id="cite_ref-Riles_2006_62-0" class="reference"><a href="#cite_note-Riles_2006-62"><span>[</span>63<span>]</span></a></sup><sup id="cite_ref-Sareen_2006_63-0" class="reference"><a href="#cite_note-Sareen_2006-63"><span>[</span>64<span>]</span></a></sup><sup id="cite_ref-Tang_2006_64-0" class="reference"><a href="#cite_note-Tang_2006-64"><span>[</span>65<span>]</span></a></sup><sup id="cite_ref-aziz_2006_65-0" class="reference"><a href="#cite_note-aziz_2006-65"><span>[</span>66<span>]</span></a></sup> Resveratrol has been shown to induce Fas/Fas <a href="/wiki/Ligand" title="Ligand">ligand</a> mediated <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>, <a href="/wiki/P53" title="P53">p53</a> and <a href="/wiki/Cyclin" title="Cyclin">cyclins</a> A, B1 and <a href="/wiki/Cyclin-dependent_kinase" title="Cyclin-dependent kinase">cyclin-dependent kinases</a> cdk 1 and 2. Resveratrol also possesses <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> and anti-<a href="/wiki/Angiogenic" title="Angiogenic" class="mw-redirect">angiogenic</a> properties.<sup id="cite_ref-pmid15621628_66-0" class="reference"><a href="#cite_note-pmid15621628-66"><span>[</span>67<span>]</span></a></sup><sup id="cite_ref-pmid10963727_67-0" class="reference"><a href="#cite_note-pmid10963727-67"><span>[</span>68<span>]</span></a></sup></p> <p>Resveratrol was reported effective against <a href="/wiki/Neuron" title="Neuron">neuronal</a> cell dysfunction and cell death, and in theory could help against diseases such as <a href="/wiki/Huntington%27s_disease" title="Huntington's disease">Huntington's disease</a> and <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span>[</span>69<span>]</span></a></sup><sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span>[</span>70<span>]</span></a></sup> Again, this has not yet been tested in humans for any disease.</p> <p>Research at the <a href="/wiki/Northeastern_Ohio_Universities_College_of_Medicine" title="Northeastern Ohio Universities College of Medicine" class="mw-redirect">Northeastern Ohio Universities College of Medicine</a> and <a href="/wiki/Ohio_State_University" title="Ohio State University">Ohio State University</a> indicates that resveratrol has direct inhibitory action on cardiac fibroblasts, and may inhibit the progression of <a href="/wiki/Heart" title="Heart">cardiac</a> <a href="/wiki/Fibrosis" title="Fibrosis">fibrosis</a>.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span>[</span>71<span>]</span></a></sup></p> <p>According to <a href="/wiki/Patrick_Arnold" title="Patrick Arnold">Patrick Arnold</a>, it also <a href="http://anabolicminds.com/forum/809122-post19.html" class="external text" title="http://anabolicminds.com/forum/809122-post19.html" rel="nofollow">significantly</a> increases natural <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> production from being both a <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a><sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span>[</span>72<span>]</span></a></sup><sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span>[</span>73<span>]</span></a></sup> and an <a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">aromatase inhibitor</a>.<sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span>[</span>74<span>]</span></a></sup><sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span>[</span>75<span>]</span></a></sup></p> <p>In December 2007, work from Irfan Rahman's laboratory at the <a href="/wiki/University_of_Rochester" title="University of Rochester">University of Rochester</a> demonstrated that resveratrol increased intracellular glutathione levels via Nrf2-dependent upregulation of <a href="/wiki/Gamma-Glutamylcysteine" title="Gamma-Glutamylcysteine">gamma-glutamylcysteine</a> ligase in lung epithelial cells, which protected them against cigarette smoke extract induced oxidative stress.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span>[</span>76<span>]</span></a></sup></p> <p><a name="Chemical_and_physical_properties" id="Chemical_and_physical_properties"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=8" title="Edit section: Chemical and physical properties">edit</a>]</span> <span class="mw-headline">Chemical and physical properties</span></h2> <p>Resveratrol (3,5,4'-trihydroxystilbene) is a <a href="/wiki/Polyphenol" title="Polyphenol">polyphenolic</a> <a href="/wiki/Phytoalexin" title="Phytoalexin">phytoalexin</a>. It is a <a href="/wiki/Stilbenoid" title="Stilbenoid">stilbenoid</a>, a derivate of <a href="/wiki/Stilbene" title="Stilbene">stilbene</a>, and is produced in plants with the help of the enzyme stilbene synthase.</p> <p>It exists as two <a href="/wiki/Cis-trans_isomerism" title="Cis-trans isomerism">geometric isomers</a>: <i>cis-</i> (<i>Z</i>) and <i>trans-</i> (<i>E</i>), with the <i>trans</i>-isomer shown in the top image. The <i>trans-</i> form can undergo isomerisation to the <i>cis-</i> form when exposed to <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> irradiation.<sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span>[</span>77<span>]</span></a></sup> <i>Trans</i>-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.<sup id="cite_ref-pmid16579722_77-0" class="reference"><a href="#cite_note-pmid16579722-77"><span>[</span>78<span>]</span></a></sup> Resveratrol content also stayed stable in the skins of grapes and <a href="/wiki/Pomace" title="Pomace">pomace</a> taken after fermentation and stored for a long period.<sup id="cite_ref-pmid10051967_78-0" class="reference"><a href="#cite_note-pmid10051967-78"><span>[</span>79<span>]</span></a></sup></p> <p><a name="Plants_and_foods" id="Plants_and_foods"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=9" title="Edit section: Plants and foods">edit</a>]</span> <span class="mw-headline">Plants and foods</span></h2> <p>Resveratrol was originally isolated by Takaoka from the roots of <a href="/wiki/White_hellebore" title="White hellebore" class="mw-redirect">white hellebore</a> in 1940, and later, in 1963, from the roots of <a href="/wiki/Japanese_knotweed" title="Japanese knotweed">Japanese knotweed</a>. However, it attracted wider attention only in 1992, when its presence in wine was suggested as the explanation for cardioprotective effects of wine.<sup id="cite_ref-pmid16732220_10-3" class="reference"><a href="#cite_note-pmid16732220-10"><span>[</span>11<span>]</span></a></sup></p> <p>In grapes, resveratrol is found primarily in the skin,<sup id="cite_ref-PNS_79-0" class="reference"><a href="#cite_note-PNS-79"><span>[</span>80<span>]</span></a></sup> and — in muscadine grapes — also in the seeds.<sup id="cite_ref-LeBlanc_80-0" class="reference"><a href="#cite_note-LeBlanc-80"><span>[</span>81<span>]</span></a></sup> 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.<sup id="cite_ref-PNS_79-1" class="reference"><a href="#cite_note-PNS-79"><span>[</span>80<span>]</span></a></sup></p> <p>The levels of resveratrol found in food varies greatly. Red wine contains between 0.2 and 5.8 mg/L,<sup id="cite_ref-Gu_81-0" class="reference"><a href="#cite_note-Gu-81"><span>[</span>82<span>]</span></a></sup> depending on the grape variety, while white wine has much less — the reason being that red wine is <a href="/wiki/Fermentation_(wine)" title="Fermentation (wine)">fermented</a> with the skins, allowing the wine to absorb the resveratrol, whereas <a href="/wiki/White_wine" title="White wine" class="mw-redirect">white wine</a> is fermented after the skin has been removed.<sup id="cite_ref-PNS_79-2" class="reference"><a href="#cite_note-PNS-79"><span>[</span>80<span>]</span></a></sup> A number of reports have indicated that <a href="/wiki/Muscadine" title="Muscadine">muscadine</a> grapes may contain high concentrations of resveratrol and that wines produced from these grapes, both red and white, may contain more than 40 mg/L.<sup id="cite_ref-LeBlanc_80-1" class="reference"><a href="#cite_note-LeBlanc-80"><span>[</span>81<span>]</span></a></sup><sup id="cite_ref-Ector_82-0" class="reference"><a href="#cite_note-Ector-82"><span>[</span>83<span>]</span></a></sup> However, subsequent studies have found little or no resveratrol in different varieties of muscadine grapes.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span>[</span>84<span>]</span></a></sup><sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span>[</span>85<span>]</span></a></sup></p> <p>The fruit of the <a href="/wiki/Mulberry" title="Mulberry" class="mw-redirect">mulberry</a> (esp. the skin<sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span>[</span>86<span>]</span></a></sup>) is a source, and sold as a nutritional supplement.</p> <p><a name="Content_in_wines_and_grape_juice" id="Content_in_wines_and_grape_juice"></a></p> <h3><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=10" title="Edit section: Content in wines and grape juice">edit</a>]</span> <span class="mw-headline">Content in wines and grape juice</span></h3> <table class="wikitable"> <tr> <th>Beverage</th> <th>Total resveratrol (mg/L)<sup id="cite_ref-PNS_79-3" class="reference"><a href="#cite_note-PNS-79"><span>[</span>80<span>]</span></a></sup><sup id="cite_ref-LeBlanc_80-2" class="reference"><a href="#cite_note-LeBlanc-80"><span>[</span>81<span>]</span></a></sup></th> <th>Total resveratrol in 150 mL wine (mg)<sup id="cite_ref-PNS_79-4" class="reference"><a href="#cite_note-PNS-79"><span>[</span>80<span>]</span></a></sup><sup id="cite_ref-LeBlanc_80-3" class="reference"><a href="#cite_note-LeBlanc-80"><span>[</span>81<span>]</span></a></sup></th> </tr> <tr> <td>Red Wines (Global)</td> <td>1.98 - 7.13</td> <td>0.30 - 1.07</td> </tr> <tr> <td>Red Wines (Spanish)</td> <td>1.92 - 12.59</td> <td>0.29 - 1.89</td> </tr> <tr> <td>Red grape juice (Spanish)</td> <td>1.14 - 8.69</td> <td>0.17 - 1.30</td> </tr> <tr> <td>Rose Wines (Spanish)</td> <td>0.43 - 3.52</td> <td>0.06 - 0.53</td> </tr> <tr> <td>Pinot Noir</td> <td>0.40 - 2.0</td> <td>0.06 - 0.30</td> </tr> <tr> <td>White Wines (Spanish)</td> <td>0.05 - 1.80</td> <td>0.01 - 0.27</td> </tr> </table> <p>The <i>trans</i>-resveratrol concentration in forty Tuscan wines ranged from 0.3 to 2.1 mg/L in the 32 red wines tested and had a maximum of 0.1 mg/L in the 8 white wines in the test. Both the <i>cis</i>- and <i>trans</i>-isomers of resveratrol were detected in all tested samples. <i>cis</i>-Resveratrol levels were comparable to those of the <i>trans</i>-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.<sup id="cite_ref-Ref24_86-0" class="reference"><a href="#cite_note-Ref24-86"><span>[</span>87<span>]</span></a></sup></p> <p>In a review of published resveratrol concentrations, the average resveratrol concentration in red wines is 1.9 ± 1.7 mg trans-resveratrol/l (8.2 ± 7.5 μM), ranging from non-detectable levels to 14.3 mg/l (62.7 μM) trans-resveratrol. Levels of cis-resveratrol follow the same trend as trans-resveratrol.<sup id="cite_ref-Stervbo2007_87-0" class="reference"><a href="#cite_note-Stervbo2007-87"><span>[</span>88<span>]</span></a></sup></p> <p>Reports suggest that some aspect of the wine making process converts <a href="/wiki/Piceid" title="Piceid">piceid</a> to resveratrol in wine, as wine seems to have twice the average resveratrol concentration of the equivalent commercial juices.<sup id="cite_ref-LeBlanc_80-4" class="reference"><a href="#cite_note-LeBlanc-80"><span>[</span>81<span>]</span></a></sup></p> <p>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 resveratrol concentrations than any other wine or region.<sup id="cite_ref-Stervbo2007_87-1" class="reference"><a href="#cite_note-Stervbo2007-87"><span>[</span>88<span>]</span></a></sup></p> <p><a name="Content_in_selected_foods" id="Content_in_selected_foods"></a></p> <h3><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=11" title="Edit section: Content in selected foods">edit</a>]</span> <span class="mw-headline">Content in selected foods</span></h3> <table class="wikitable"> <tr> <th>Food</th> <th>Serving</th> <th>Total resveratrol (mg)<sup id="cite_ref-Ref5_88-0" class="reference"><a href="#cite_note-Ref5-88"><span>[</span>89<span>]</span></a></sup></th> </tr> <tr> <td>Peanuts (raw)</td> <td>1 c (146 g)</td> <td>0.01 - 0.26</td> </tr> <tr> <td>Peanuts (boiled)</td> <td>1 c (180 g)</td> <td>0.32 - 1.28</td> </tr> <tr> <td>Peanut butter</td> <td>1 c (258 g)</td> <td>0.04 - 0.13</td> </tr> <tr> <td>Red grapes</td> <td>1 c (160 g)</td> <td>0.24 - 1.25</td> </tr> </table> <p>Ounce for ounce, peanuts have about half the amount of resveratrol as that found in red wine. The average amount of resveratrol in one ounce of peanuts in the marketplace (about 15 whole) is 79.4 µg/ounce.</p> <p>In comparison, some red wines contain approximately 160 µg/fluid ounce.<sup id="cite_ref-Ref6_89-0" class="reference"><a href="#cite_note-Ref6-89"><span>[</span>90<span>]</span></a></sup> 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.<sup id="cite_ref-Ref7_90-0" class="reference"><a href="#cite_note-Ref7-90"><span>[</span>91<span>]</span></a></sup></p> <p><a href="/wiki/Blueberries" title="Blueberries" class="mw-redirect">Blueberries</a> have about twice as much resveratrol as <a href="/wiki/Bilberries" title="Bilberries" class="mw-redirect">bilberries</a>, 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. <sup id="cite_ref-Lyons_91-0" class="reference"><a href="#cite_note-Lyons-91"><span>[</span>92<span>]</span></a></sup></p> <p><a name="Supplementation" id="Supplementation"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=12" title="Edit section: Supplementation">edit</a>]</span> <span class="mw-headline">Supplementation</span></h2> <p>Resveratrol <a href="/wiki/Nutritional_supplements" title="Nutritional supplements" class="mw-redirect">nutritional supplements</a>, first sourced from ground dried grape skins and seeds, are now primarily derived from the less expensive, more concentrated <a href="/wiki/Japanese_knotweed" title="Japanese knotweed">Japanese knotweed</a>, which contains up to 187 mg/kg in the dried root and can be concentrated in an extract up to 50%.<sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span>[</span>93<span>]</span></a></sup></p> <p>As a result of extensive news coverage,<sup id="cite_ref-93" class="reference"><a href="#cite_note-93"><span>[</span>94<span>]</span></a></sup><sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span>[</span>95<span>]</span></a></sup> sales of supplements greatly increased in 2006,<sup id="cite_ref-wsj_95-0" class="reference"><a href="#cite_note-wsj-95"><span>[</span>96<span>]</span></a></sup> despite cautions that benefits to humans are unproven.<sup id="cite_ref-wsj_95-1" class="reference"><a href="#cite_note-wsj-95"><span>[</span>96<span>]</span></a></sup><sup id="cite_ref-96" class="reference"><a href="#cite_note-96"><span>[</span>97<span>]</span></a></sup><sup id="cite_ref-97" class="reference"><a href="#cite_note-97"><span>[</span>98<span>]</span></a></sup></p> <p><a name="See_also" id="See_also"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=13" title="Edit section: See also">edit</a>]</span> <span class="mw-headline">See also</span></h2> <div class="noprint tright portal" style="border:solid #aaa 1px;margin:0.5em 0 0.5em 0.5em;"> <table style="background:#f9f9f9; font-size:85%; line-height:110%;"> <tr> <td><a href="/wiki/File:Tabletten.JPG" class="image" title="Tabletten.JPG"><img alt="" src="http://upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Tabletten.JPG/32px-Tabletten.JPG" width="32" height="26" /></a></td> <td style="padding:0 0.2em;"><i><b><a href="/wiki/Portal:Pharmacy_and_Pharmacology" title="Portal:Pharmacy and Pharmacology">Pharmacy and Pharmacology portal</a></b></i></td> </tr> </table> </div> <p><a name="Other_articles" id="Other_articles"></a></p> <h3><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=14" title="Edit section: Other articles">edit</a>]</span> <span class="mw-headline">Other articles</span></h3> <div> <table width="100%" border="0" cellspacing="0" cellpadding="0" style="background-color:transparent;table-layout:fixed;"> <tr valign="top"> <td> <div style="margin-right:20px;"> <ul> <li><a href="/wiki/Codex_Alimentarius" title="Codex Alimentarius">Codex Alimentarius</a></li> <li><a href="/wiki/Japanese_knotweed" title="Japanese knotweed">Japanese knotweed</a></li> <li><a href="/wiki/List_of_grape_varieties" title="List of grape varieties">List of grape varieties</a></li> <li><a href="/wiki/Mulberry" title="Mulberry" class="mw-redirect">Mulberry</a></li> </ul> </div> </td> <td> <div style="margin-right: 20px;"> <ul> <li><a href="/wiki/Muscadine" title="Muscadine">Muscadine</a></li> <li><a href="/wiki/Piceatannol" title="Piceatannol">Piceatannol</a>, an active <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of resveratrol.</li> <li><a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">Proanthocyanidin</a></li> <li><a href="/wiki/Polyphenol_antioxidant" title="Polyphenol antioxidant">Polyphenol antioxidant</a></li> </ul> </div> </td> </tr> </table> </div> <p><a name="References" id="References"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=15" title="Edit section: References">edit</a>]</span> <span class="mw-headline">References</span></h2> <div class="references-small references-column-count references-column-count-2" style="-moz-column-count:2; column-count:2;"> <ol class="references"> <li id="cite_note-pmid16401555-0"><b><a href="#cite_ref-pmid16401555_0-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFFarina_A.2C_Ferranti_C.2C_Marra_C2006">Farina A, Ferranti C, Marra C (2006). "An improved synthesis of resveratrol". <i>Nat. Prod. Res.</i> <b>20</b> (3): 247–52. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1080%2F14786410500059532" class="external text" title="http://dx.doi.org/10.1080%2F14786410500059532" rel="nofollow">10.1080/14786410500059532</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/16401555" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/16401555">PMID 16401555</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=An+ improved+synthesis+of+resveratrol&rft.jtitle=Nat.+Prod.+Res.&rft.aulast=Farina+A%2C+Ferranti+C%2C+Marra+C&rft. au=Farina+A%2C+Ferranti+C%2C+Marra+C&rft.date=2006&rft.volume=20&rft.issue=3&rft.pages=247%E2%80%9352& rft_id=info:doi/10.1080%2F14786410500059532&rft_id=info:pmid/16401555&rfr_id=info:sid/en.wikipedia.org:Resveratrol "><span style="display: none;"> </span></span></li> <li id="cite_note-PMID_18393104-1">^ <a href="#cite_ref-PMID_18393104_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PMID_18393104_1-1"><sup><i><b>b</b></i></sup></a> <cite style="font-style:normal" class="" id="CITEREFElliott_PJ.2C_Jirousek.2C_M.2008">Elliott PJ, Jirousek, M. (2008). "Sirtuins: Novel targets for metabolic disease". <i>Current Opinion in Investigational Drugs</i> <b>9</b> (4): 1472–4472. <a href="http://www.ncbi.nlm.nih.gov/pubmed/18393104" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/18393104">PMID 18393104</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Sir tuins%3A+Novel+targets+for+metabolic+disease&rft.jtitle=Current+Opinion+in+Investigational+Drugs&rft.aulast=Elliot t+PJ%2C+Jirousek%2C+M.&rft.au=Elliott+PJ%2C+Jirousek%2C+M.&rft.date=2008&rft.volume=9&rft.issue=4&rft. pages=1472%E2%80%934472&rft_id=info:pmid/18393104&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Howitz2003-2"><b><a href="#cite_ref-Howitz2003_2-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFHowitz_KT.2C_Bitterman_KJ.2C_Cohen_HY.2C_Lamming_DW.2C_Lavu_S.2C_Wood_JG.2C_Zipkin_RE.2C_Chung_P.2C_Kisielewski _A.2C_Zhang_LL.2C_Scherer_B.2C_Sinclair_DA2003">Howitz KT, Bitterman KJ, Cohen HY, Lamming DW, Lavu S, Wood JG, Zipkin RE, Chung P, Kisielewski A, Zhang LL, Scherer B, Sinclair DA (2003). "<a href="http://www.fiestaterrace.com/dlamming/nature2003.pdf" class="external text" title="http://www.fiestaterrace.com/dlamming/nature2003.pdf" rel="nofollow">Small molecule activators of sirtuins extend <i>Saccharomyces cerevisiae</i> lifespan</a>" (PDF). <i>Nature</i> <b>425</b> (6954): 191–196. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1038%2Fnature01960" class="external text" title="http://dx.doi.org/10.1038%2Fnature01960" rel="nofollow">10.1038/nature01960</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/12939617" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/12939617">PMID 12939617</a><span class="printonly">. <a href="http://www.fiestaterrace.com/dlamming/nature2003.pdf" class="external free" title="http://www.fiestaterrace.com/dlamming/nature2003.pdf" rel="nofollow">http://www.fiestaterrace.com/dlamming/nature2003.pdf</a></span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Sma ll+molecule+activators+of+sirtuins+extend+%27%27Saccharomyces+cerevisiae%27%27+lifespan&rft.jtitle=Nature&rft.aula st=Howitz+KT%2C+Bitterman+KJ%2C+Cohen+HY%2C+Lamming+DW%2C+Lavu+S%2C+Wood+JG%2C+Zipkin+RE%2C+Chung+P%2C+Kisielewski+A%2C+Zh ang+LL%2C+Scherer+B%2C+Sinclair+DA&rft.au=Howitz+KT%2C+Bitterman+KJ%2C+Cohen+HY%2C+Lamming+DW%2C+Lavu+S%2C+Wood+JG%2C+ Zipkin+RE%2C+Chung+P%2C+Kisielewski+A%2C+Zhang+LL%2C+Scherer+B%2C+Sinclair+DA&rft.date=2003&rft.volume=425&rft .issue=6954&rft.pages=191%E2%80%93196&rft_id=info:doi/10.1038%2Fnature01960&rft_id=info:pmid/12939617&rft_ id=http%3A%2F%2Fwww.fiestaterrace.com%2Fdlamming%2Fnature2003.pdf&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Wood2004-3"><b><a href="#cite_ref-Wood2004_3-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFWood_JG.2C_Rogina_B.2C_Lavu1_S.2C_Howitz_K.2C_Helfand_SL.2C_Tatar_M.2C_Sinclair_D2004">Wood JG, Rogina B, Lavu1 S, Howitz K, Helfand SL, Tatar M, Sinclair D (2004). "<a href="http://sinclairfs.med.harvard.edu/pdfs/nature2004.pdf" class="external text" title="http://sinclairfs.med.harvard.edu/pdfs/nature2004.pdf" rel="nofollow">Sirtuin activators mimic caloric restriction and delay aging in metazoans</a>" (PDF). <i>Nature</i> <b>430</b> (7000): 686–9. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1038%2Fnature02789" class="external text" title="http://dx.doi.org/10.1038%2Fnature02789" rel="nofollow">10.1038/nature02789</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/15254550" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/15254550">PMID 15254550</a><span class="printonly">. <a href="http://sinclairfs.med.harvard.edu/pdfs/nature2004.pdf" class="external free" title="http://sinclairfs.med.harvard.edu/pdfs/nature2004.pdf" rel="nofollow">http://sinclairfs.med.harvard.edu/pdfs/nature2004.pdf</a></span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Sir tuin+activators+mimic+caloric+restriction+and+delay+aging+in+metazoans&rft.jtitle=Nature&rft.aulast=Wood+JG%2C+Rog ina+B%2C+Lavu1+S%2C+Howitz+K%2C+Helfand+SL%2C+Tatar+M%2C+Sinclair+D&rft.au=Wood+JG%2C+Rogina+B%2C+Lavu1+S%2C+Howitz+K% 2C+Helfand+SL%2C+Tatar+M%2C+Sinclair+D&rft.date=2004&rft.volume=430&rft.issue=7000&rft.pages=686%E2%80%939 &rft_id=info:doi/10.1038%2Fnature02789&rft_id=info:pmid/15254550&rft_id=http%3A%2F%2Fsinclairfs.med.harvard.ed u%2Fpdfs%2Fnature2004.pdf&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Gruber2007-4"><b><a href="#cite_ref-Gruber2007_4-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFGruber_J.2C_Tang_SY.2C_Halliwell_B2007">Gruber J, Tang SY, Halliwell B (April 2007). 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"Cancer chemopreventive activity of resveratrol, a natural product derived from grapes". <i>Science</i> <b>275</b> (5297): 218–20. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1126%2Fscience.275.5297.218" class="external text" title="http://dx.doi.org/10.1126%2Fscience.275.5297.218" rel="nofollow">10.1126/science.275.5297.218</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/8985016" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/8985016">PMID 8985016</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Can cer+chemopreventive+activity+of+resveratrol%2C+a+natural+product+derived+from+grapes&rft.jtitle=Science&rft.aulast =Jang+M%2C+Cai+L%2C+Udeani+GO%2C+Slowing+KV%2C+Thomas+CF%2C+Beecher+CW%2C+Fong+HH%2C+Farnsworth+NR%2C+Kinghorn+AD%2C+Mehta +RG%2C+Moon+RC%2C+Pezzuto+JM&rft.au=Jang+M%2C+Cai+L%2C+Udeani+GO%2C+Slowing+KV%2C+Thomas+CF%2C+Beecher+CW%2C+Fong+HH%2 C+Farnsworth+NR%2C+Kinghorn+AD%2C+Mehta+RG%2C+Moon+RC%2C+Pezzuto+JM&rft.date=1997&rft.volume=275&rft.issue=529 7&rft.pages=218%E2%80%9320&rft_id=info:doi/10.1126%2Fscience.275.5297.218&rft_id=info:pmid/8985016&rfr_id= info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-pmid16732220-10">^ <a href="#cite_ref-pmid16732220_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid16732220_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid16732220_10-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pmid16732220_10-3"><sup><i><b>d</b></i></sup></a> See review:<cite style="font-style:normal" class="" id="CITEREFBaur_JA.2C_Sinclair_DA2006">Baur JA, Sinclair DA (2006). "Therapeutic potential of resveratrol: the in vivo evidence". <i>Nat Rev Drug Discov</i> <b>5</b> (6): 493–506. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1038%2Fnrd2060" class="external text" title="http://dx.doi.org/10.1038%2Fnrd2060" rel="nofollow">10.1038/nrd2060</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/16732220" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/16732220">PMID 16732220</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=The rapeutic+potential+of+resveratrol%3A+the+in+vivo+evidence&rft.jtitle=Nat+Rev+Drug+Discov&rft.aulast=Baur+JA%2C+Sin clair+DA&rft.au=Baur+JA%2C+Sinclair+DA&rft.date=2006&rft.volume=5&rft.issue=6&rft.pages=493%E2%80%9350 6&rft_id=info:doi/10.1038%2Fnrd2060&rft_id=info:pmid/16732220&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><s pan style="display: none;"> </span></span></li> <li id="cite_note-pmid17306316-11">^ <a href="#cite_ref-pmid17306316_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid17306316_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid17306316_11-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pmid17306316_11-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pmid17306316_11-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pmid17306316_11-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-pmid17306316_11-6"><sup><i><b>g</b></i></sup></a> See review:<cite style="font-style:normal" class="" id="CITEREFAthar_M.2C_Back_JH.2C_Tang_X.2C_.27.27et_al..27.272007">Athar M, Back JH, Tang X, <i>et al.</i> (November 2007). "<a href="http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2083123" class="external text" title="http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2083123" rel="nofollow">Resveratrol: a review of preclinical studies for human cancer prevention</a>". <i>Toxicol. Appl. Pharmacol.</i> <b>224</b> (3): 274–83. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1016%2Fj.taap.2006.12.025" class="external text" title="http://dx.doi.org/10.1016%2Fj.taap.2006.12.025" rel="nofollow">10.1016/j.taap.2006.12.025</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/17306316" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/17306316">PMID 17306316</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Res veratrol%3A+a+review+of+preclinical+studies+for+human+cancer+prevention&rft.jtitle=Toxicol.+Appl.+Pharmacol.&rft.a ulast=Athar+M%2C+Back+JH%2C+Tang+X%2C+%27%27et+al.%27%27&rft.au=Athar+M%2C+Back+JH%2C+Tang+X%2C+%27%27et+al.%27%27&amp ;rft.date=November+2007&rft.volume=224&rft.issue=3&rft.pages=274%E2%80%9383&rft_id=info:doi/10.1016%2Fj.ta ap.2006.12.025&rft_id=info:pmid/17306316&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-clinicaltrials-12"><b><a href="#cite_ref-clinicaltrials_12-0">^</a></b> <a href="http://clinicaltrials.gov/ct2/results?term=resveratrol" class="external text" title="http://clinicaltrials.gov/ct2/results?term=resveratrol" rel="nofollow">Resveratrol</a>. From <a href="/wiki/Clinicaltrials.gov" title="Clinicaltrials.gov" class="mw-redirect">Clinicaltrials.gov</a>. Retrieved August 15, 2008..</li> <li id="cite_note-pmid17548692-13">^ <a href="#cite_ref-pmid17548692_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid17548692_13-1"><sup><i><b>b</b></i></sup></a> <cite style="font-style:normal" class="" id="CITEREFBoocock_DJ.2C_Faust_GE.2C_Patel_KR.2C_.27.27et_al..27.272007">Boocock DJ, Faust GE, Patel KR, <i>et al.</i> (June 2007). "Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent". <i>Cancer Epidemiol. 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"Resveratrol induces glutathione synthesis by activation of Nrf2 and protects against cigarette smoke-mediated oxidative stress in human lung epithelial cells". <i>Am J Physiol Lung Cell Mol Physiol.</i> <b>294</b> (3): L478–88. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1152%2Fajplung.00361.2007" class="external text" title="http://dx.doi.org/10.1152%2Fajplung.00361.2007" rel="nofollow">10.1152/ajplung.00361.2007</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/18162601" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/18162601">PMID 18162601</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Res veratrol+induces+glutathione+synthesis+by+activation+of+Nrf2+and+protects+against+cigarette+smoke-mediated+oxidative+stres s+in+human+lung+epithelial+cells&rft.jtitle=Am+J+Physiol+Lung+Cell+Mol+Physiol.&rft.aulast=Kode+A%2C+Rajendrasozha n+S%2C+Caito+S%2C+Yang+SR%2C+Megson+IL%2C+Rahman+I&rft.au=Kode+A%2C+Rajendrasozhan+S%2C+Caito+S%2C+Yang+SR%2C+Megson+I L%2C+Rahman+I&rft.date=March+2008&rft.volume=294&rft.issue=3&rft.pages=L478%E2%80%9388&rft_id=info:doi /10.1152%2Fajplung.00361.2007&rft_id=info:pmid/18162601&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-76"><b><a href="#cite_ref-76">^</a></b> <cite style="font-style:normal" class="" id="CITEREFLamuela-Raventos1995">Lamuela-Raventos, RM (1995). "<a href="http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/1995/43/i02/f-pdf/f_jf00050a003.pdf?sessid=6006l3" class="external text" title="http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/1995/43/i02/f-pdf/f_jf00050a003.pdf?sessid=6006l3" rel="nofollow">Direct HPLC Analysis of cis- and trans-Resveratrol and Piceid Isomers in Spanish Red Vitis vinifera Wines</a>" (<sup class="noprint Inline-Template"><span title=" since December 2008" style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Dead_external_links" title="Wikipedia:Dead external links">dead link</a></i>]</span></sup> – <sup><a href="http://scholar.google.co.uk/scholar?hl=en&lr=&q=author%3ALamuela-Raventos+intitle%3ADirect+HPLC+Analysis+of+ cis-+and+trans-Resveratrol+and+Piceid+Isomers+in+Spanish+Red+Vitis+vinifera+Wines&as_publication=J.+Agric.+Food+Chem.& amp;as_ylo=1995&as_yhi=1995&btnG=Search" class="external text" title="http://scholar.google.co.uk/scholar?hl=en&lr=&q=author%3ALamuela-Raventos+intitle%3ADirect+HPLC+Analysis+of +cis-+and+trans-Resveratrol+and+Piceid+Isomers+in+Spanish+Red+Vitis+vinifera+Wines&as_publication=J.+Agric.+Food+Chem. &as_ylo=1995&as_yhi=1995&btnG=Search" rel="nofollow">Scholar search</a></sup>). <i>J. Agric. Food Chem.</i> (pubs.acs.org) <b>43</b> (43): 281–283. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1021%2Fjf00050a003" class="external text" title="http://dx.doi.org/10.1021%2Fjf00050a003" rel="nofollow">10.1021/jf00050a003</a></span><span class="printonly">. <a href="http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/1995/43/i02/f-pdf/f_jf00050a003.pdf?sessid=6006l3" class="external free" title="http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/1995/43/i02/f-pdf/f_jf00050a003.pdf?sessid=6006l3" rel="nofollow">http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/1995/43/i02/f-pdf/f_jf00050a003.pdf?sessid=6006l3</a></span >.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Dir ect+HPLC+Analysis+of+cis-+and+trans-Resveratrol+and+Piceid+Isomers+in+Spanish+Red+Vitis+vinifera+Wines&rft.jtitle=J.+A gric.+Food+Chem.&rft.aulast=Lamuela-Raventos&rft.aufirst=RM&rft.au=Lamuela-Raventos%2C+RM&rft.date=1995&am p;rft.volume=43&rft.issue=43&rft.pages=281%E2%80%93283&rft.pub=pubs.acs.org&rft_id=info:doi/10.1021%2Fjf00 050a003&rft_id=http%3A%2F%2Fpubs.acs.org%2Fcgi-bin%2Fabstract.cgi%2Fjafcau%2F1995%2F43%2Fi02%2Ff-pdf%2Ff_jf00050a003.p df%3Fsessid%3D6006l3&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-pmid16579722-77"><b><a href="#cite_ref-pmid16579722_77-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFProkop_J.2C_Abrman_P.2C_Seligson_AL.2C_Sovak_M2006">Prokop J, Abrman P, Seligson AL, Sovak M (2006). "Resveratrol and its glycon piceid are stable polyphenols". <i>J Med Food</i> <b>9</b> (1): 11–4. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1089%2Fjmf.2006.9.11" class="external text" title="http://dx.doi.org/10.1089%2Fjmf.2006.9.11" rel="nofollow">10.1089/jmf.2006.9.11</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/16579722" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/16579722">PMID 16579722</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Res veratrol+and+its+glycon+piceid+are+stable+polyphenols&rft.jtitle=J+Med+Food&rft.aulast=Prokop+J%2C+Abrman+P%2C+Sel igson+AL%2C+Sovak+M&rft.au=Prokop+J%2C+Abrman+P%2C+Seligson+AL%2C+Sovak+M&rft.date=2006&rft.volume=9&rft.i ssue=1&rft.pages=11%E2%80%934&rft_id=info:doi/10.1089%2Fjmf.2006.9.11&rft_id=info:pmid/16579722&rfr_id=inf o:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-pmid10051967-78"><b><a href="#cite_ref-pmid10051967_78-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFBertelli_AA.2C_Gozzini_A.2C_Stradi_R.2C_Stella_S.2C_Bertelli_A1998">Bertelli AA, Gozzini A, Stradi R, Stella S, Bertelli A (1998). "Stability of resveratrol over time and in the various stages of grape transformation". <i>Drugs Exp Clin Res</i> <b>24</b> (4): 207–11. <a href="http://www.ncbi.nlm.nih.gov/pubmed/10051967" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/10051967">PMID 10051967</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Sta bility+of+resveratrol+over+time+and+in+the+various+stages+of+grape+transformation&rft.jtitle=Drugs+Exp+Clin+Res&rf t.aulast=Bertelli+AA%2C+Gozzini+A%2C+Stradi+R%2C+Stella+S%2C+Bertelli+A&rft.au=Bertelli+AA%2C+Gozzini+A%2C+Stradi+R%2C +Stella+S%2C+Bertelli+A&rft.date=1998&rft.volume=24&rft.issue=4&rft.pages=207%E2%80%9311&rft_id=info:p mid/10051967&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-PNS-79">^ <a href="#cite_ref-PNS_79-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PNS_79-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PNS_79-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PNS_79-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-PNS_79-4"><sup><i><b>e</b></i></sup></a> Roy, H., Lundy, S., <a href="http://www.pbrc.edu/Division_of_Education/pdf/PNS_resveratrol.pdf" class="external text" title="http://www.pbrc.edu/Division_of_Education/pdf/PNS_resveratrol.pdf" rel="nofollow">Resveratrol</a>, Pennington Nutrition Series, 2005 No. 7</li> <li id="cite_note-LeBlanc-80">^ <a href="#cite_ref-LeBlanc_80-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-LeBlanc_80-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-LeBlanc_80-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-LeBlanc_80-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-LeBlanc_80-4"><sup><i><b>e</b></i></sup></a> <cite style="font-style:normal" class="web" id="CITEREFLeBlanc2005">LeBlanc, Mark Rene (2005-12-13). "<a href="http://etd.lsu.edu/docs/available/etd-01202006-082858/" class="external text" title="http://etd.lsu.edu/docs/available/etd-01202006-082858/" rel="nofollow">Cultivar, Juice Extraction, Ultra Violet Irradiation and Storage Influence the Stilbene Content of Muscadine Grapes (Vitis Rotundifolia Michx.)</a>"<span class="printonly">. <a href="http://etd.lsu.edu/docs/available/etd-01202006-082858/" class="external free" title="http://etd.lsu.edu/docs/available/etd-01202006-082858/" rel="nofollow">http://etd.lsu.edu/docs/available/etd-01202006-082858/</a></span><span class="reference-accessdate">. Retrieved on 2007-08-15</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.btitle=Culti var%2C+Juice+Extraction%2C+Ultra+Violet+Irradiation+and+Storage+Influence+the+Stilbene+Content+of+Muscadine+Grapes+%28Viti s+Rotundifolia+Michx.%29&rft.atitle=&rft.aulast=LeBlanc&rft.aufirst=Mark+Rene&rft.au=LeBlanc%2C+Mark+Rene& amp;rft.date=2005-12-13&rft_id=http%3A%2F%2Fetd.lsu.edu%2Fdocs%2Favailable%2Fetd-01202006-082858%2F&rfr_id=info:si d/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Gu-81"><b><a href="#cite_ref-Gu_81-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFGu_X.2C_Creasy_L.2C_Kester_A.2C_Zeece_M1999">Gu X, Creasy L, Kester A, Zeece M (August 1999). "Capillary electrophoretic determination of resveratrol in wines". <i>J Agric Food Chem.</i> <b>47</b> (8): 3223–7. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1021%2Fjf981211e" class="external text" title="http://dx.doi.org/10.1021%2Fjf981211e" rel="nofollow">10.1021/jf981211e</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/10552635" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/10552635">PMID 10552635</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Cap illary+electrophoretic+determination+of+resveratrol+in+wines&rft.jtitle=J+Agric+Food+Chem.&rft.aulast=Gu+X%2C+Crea sy+L%2C+Kester+A%2C+Zeece+M&rft.au=Gu+X%2C+Creasy+L%2C+Kester+A%2C+Zeece+M&rft.date=August+1999&rft.volume=47& amp;rft.issue=8&rft.pages=3223%E2%80%937&rft_id=info:doi/10.1021%2Fjf981211e&rft_id=info:pmid/10552635&rfr _id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Ector-82"><b><a href="#cite_ref-Ector_82-0">^</a></b> Ector BJ, Magee JB, Hegwood CP, Coign MJ., <a href="http://www.ajevonline.org/cgi/content/abstract/47/1/57" class="external text" title="http://www.ajevonline.org/cgi/content/abstract/47/1/57" rel="nofollow">Resveratrol Concentration in Muscadine Berries, Juice, Pomace, Purees, Seeds, and Wines.</a></li> <li id="cite_note-83"><b><a href="#cite_ref-83">^</a></b> <cite style="font-style:normal" class="" id="CITEREFPastrana-Bonilla_E.2C_Akoh_CC.2C_Sellappan_S.2C_Krewer_G2003">Pastrana-Bonilla E, Akoh CC, Sellappan S, Krewer G (August 2003). "Phenolic content and antioxidant capacity of muscadine grapes". <i>J. Agric. Food Chem.</i> <b>51</b> (18): 5497–503. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1021%2Fjf030113c" class="external text" title="http://dx.doi.org/10.1021%2Fjf030113c" rel="nofollow">10.1021/jf030113c</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/12926904" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/12926904">PMID 12926904</a>. "Contrary to previous results, ellagic acid and not resveratrol was the major phenolic in muscadine grapes. The HPLC solvent system used coupled with fluorescence detection allowed separation of ellagic acid from resveratrol and detection of resveratrol." "trans-resveratrol had the lowest concentrations of the detected phenolics, ranging from not detected in two varieties to 0.2 mg/ 100 g of FW (Tables 1 and 2). Our result for resveratrol differed from previous results [Ector et al., 1996] indicating high concentrations. These researchers apparently were not able to separate ellagic acid from resveratrol with UV detection alone.".</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Phe nolic+content+and+antioxidant+capacity+of+muscadine+grapes&rft.jtitle=J.+Agric.+Food+Chem.&rft.aulast=Pastrana-Bon illa+E%2C+Akoh+CC%2C+Sellappan+S%2C+Krewer+G&rft.au=Pastrana-Bonilla+E%2C+Akoh+CC%2C+Sellappan+S%2C+Krewer+G&rft.d ate=August+2003&rft.volume=51&rft.issue=18&rft.pages=5497%E2%80%93503&rft_id=info:doi/10.1021%2Fjf030113c& amp;rft_id=info:pmid/12926904&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-84"><b><a href="#cite_ref-84">^</a></b> <cite style="font-style:normal" class="" id="CITEREFHudson_TS.2C_Hartle_DK.2C_Hursting_SD.2C_.27.27et_al..27.272007">Hudson TS, Hartle DK, Hursting SD, <i>et al.</i> (September 2007). "Inhibition of prostate cancer growth by muscadine grape skin extract and resveratrol through distinct mechanisms". <i>Cancer Res.</i> <b>67</b> (17): 8396–405. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1158%2F0008-5472.CAN-06-4069" class="external text" title="http://dx.doi.org/10.1158%2F0008-5472.CAN-06-4069" rel="nofollow">10.1158/0008-5472.CAN-06-4069</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/17804756" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/17804756">PMID 17804756</a>. "MSKE [muscadine grape skin extract] does not contain significant quantities of resveratrol and differs from MSEE. To determine whether MSKE contains significant levels of resveratrol and to compare the chemical content of MSKE (skin) with MSEE (seed), HPLC analyses were done. As depicted in Supplementary Fig. S1A and B, MSKE does not contain significant amounts of resveratrol (<1 ?g/g by limit of detection).".</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Inh ibition+of+prostate+cancer+growth+by+muscadine+grape+skin+extract+and+resveratrol+through+distinct+mechanisms&rft.jtit le=Cancer+Res.&rft.aulast=Hudson+TS%2C+Hartle+DK%2C+Hursting+SD%2C+%27%27et+al.%27%27&rft.au=Hudson+TS%2C+Hartle+D K%2C+Hursting+SD%2C+%27%27et+al.%27%27&rft.date=September+2007&rft.volume=67&rft.issue=17&rft.pages=8396%E 2%80%93405&rft_id=info:doi/10.1158%2F0008-5472.CAN-06-4069&rft_id=info:pmid/17804756&rfr_id=info:sid/en.wikipe dia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-85"><b><a href="#cite_ref-85">^</a></b> <cite style="font-style:normal" class="" id="CITEREFStewart_JR.2C_Artime_MC.2C_O.27Brian_CA2003">Stewart JR, Artime MC, O'Brian CA (01 July 2003). 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(1996). "<a href="http://cat.inist.fr/?aModele=afficheN&cpsidt=3123149" class="external text" title="http://cat.inist.fr/?aModele=afficheN&cpsidt=3123149" rel="nofollow">Resveratrol content in some Tuscan wines</a>". <i>Ital. J. Food sci.</i> (Chiriotti, Pinerolo, ITALIE) <b>8</b> (2): 145–52<span class="printonly">. <a href="http://cat.inist.fr/?aModele=afficheN&cpsidt=3123149" class="external free" title="http://cat.inist.fr/?aModele=afficheN&cpsidt=3123149" rel="nofollow">http://cat.inist.fr/?aModele=afficheN&cpsidt=3123149</a></span><span class="reference-accessdate">. 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"A review of the content of the putative chemopreventive phytoalexin resveratrol in red wine". <i>Food Chemistry</i> <b>101</b> (2): 449–57. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1016%2Fj.foodchem.2006.01.047" class="external text" title="http://dx.doi.org/10.1016%2Fj.foodchem.2006.01.047" rel="nofollow">10.1016/j.foodchem.2006.01.047</a></span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=A+r eview+of+the+content+of+the+putative+chemopreventive+phytoalexin+resveratrol+in+red+wine&rft.jtitle=Food+Chemistry&amp ;rft.aulast=Stervbo%2C+U.&rft.au=Stervbo%2C+U.&rft.au=Vang%2C+O.%3B+Bonnesen%2C+C.&rft.date=2007&rft.volum e=101&rft.issue=2&rft.pages=449%E2%80%9357&rft_id=info:doi/10.1016%2Fj.foodchem.2006.01.047&rfr_id=info:si d/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Ref5-88"><b><a href="#cite_ref-Ref5_88-0">^</a></b> <cite style="font-style:normal" class="web" id="CITEREFHigdon2005">Higdon, Jane (2005). "<a href="http://lpi.oregonstate.edu/infocenter/phytochemicals/resveratrol/" class="external text" title="http://lpi.oregonstate.edu/infocenter/phytochemicals/resveratrol/" rel="nofollow">Resveratrol</a>". <i><span>Oregon State University</span></i>. The Linus Pauling Institute Micronutrient Information Center<span class="printonly">. <a href="http://lpi.oregonstate.edu/infocenter/phytochemicals/resveratrol/" class="external free" title="http://lpi.oregonstate.edu/infocenter/phytochemicals/resveratrol/" rel="nofollow">http://lpi.oregonstate.edu/infocenter/phytochemicals/resveratrol/</a></span><span class="reference-accessdate">. Retrieved on 2007-06-18</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.btitle=Resve ratrol&rft.atitle=Oregon+State+University&rft.aulast=Higdon&rft.aufirst=Jane&rft.au=Higdon%2C+Jane&rft .date=2005&rft.pub=The+Linus+Pauling+Institute+Micronutrient+Information+Center&rft_id=http%3A%2F%2Flpi.oregonstat e.edu%2Finfocenter%2Fphytochemicals%2Fresveratrol%2F&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Ref6-89"><b><a href="#cite_ref-Ref6_89-0">^</a></b> <cite style="font-style:normal" class="web">"<a href="http://www.peanut-institute.org/kidsFFT.html" class="external text" title="http://www.peanut-institute.org/kidsFFT.html" rel="nofollow">Resveratrol</a>". The Peanut Institute. 1999<span class="printonly">. <a href="http://www.peanut-institute.org/kidsFFT.html" class="external free" title="http://www.peanut-institute.org/kidsFFT.html" rel="nofollow">http://www.peanut-institute.org/kidsFFT.html</a></span><span class="reference-accessdate">. Retrieved on 2008-01-28</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.btitle=Resve ratrol&rft.atitle=&rft.date=1999&rft.pub=The+Peanut+Institute&rft_id=http%3A%2F%2Fwww.peanut-institute.org %2FkidsFFT.html&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Ref7-90"><b><a href="#cite_ref-Ref7_90-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFWang_Y.2C_Catana_F.2C_Yang_Y.2C_Roderick_R.2C_van_Breemen_RB2002">Wang Y, Catana F, Yang Y, Roderick R, van Breemen RB (2002). 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Food Chem.</i> <b>50</b> (3): 431–5. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1021%2Fjf010812u" class="external text" title="http://dx.doi.org/10.1021%2Fjf010812u" rel="nofollow">10.1021/jf010812u</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/11804508" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/11804508">PMID 11804508</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=An+ LC-MS+method+for+analyzing+total+resveratrol+in+grape+juice%2C+cranberry+juice%2C+and+in+wine&rft.jtitle=J.+Agric.+Foo d+Chem.&rft.aulast=Wang+Y%2C+Catana+F%2C+Yang+Y%2C+Roderick+R%2C+van+Breemen+RB&rft.au=Wang+Y%2C+Catana+F%2C+Yang+ Y%2C+Roderick+R%2C+van+Breemen+RB&rft.date=2002&rft.volume=50&rft.issue=3&rft.pages=431%E2%80%935&rft_ id=info:doi/10.1021%2Fjf010812u&rft_id=info:pmid/11804508&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-Lyons-91"><b><a href="#cite_ref-Lyons_91-0">^</a></b> <cite style="font-style:normal" class="" id="CITEREFLyons_MM.2C_Yu_C.2C_Toma_RB.2C_.27.27et_al..27.272003">Lyons MM, Yu C, Toma RB, <i>et al.</i> (2003). 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Food Chem.</i> <b>51</b> (20): 5867–70. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">doi</a>:<span class="neverexpand"><a href="http://dx.doi.org/10.1021%2Fjf034150f" class="external text" title="http://dx.doi.org/10.1021%2Fjf034150f" rel="nofollow">10.1021/jf034150f</a></span>. <a href="http://www.ncbi.nlm.nih.gov/pubmed/13129286" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/13129286">PMID 13129286</a>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Res veratrol+in+raw+and+baked+blueberries+and+bilberries&rft.jtitle=J.+Agric.+Food+Chem.&rft.aulast=Lyons+MM%2C+Yu+C%2 C+Toma+RB%2C+%27%27et+al.%27%27&rft.au=Lyons+MM%2C+Yu+C%2C+Toma+RB%2C+%27%27et+al.%27%27&rft.date=2003&rft.vol ume=51&rft.issue=20&rft.pages=5867%E2%80%9370&rft_id=info:doi/10.1021%2Fjf034150f&rft_id=info:pmid/1312928 6&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-92"><b><a href="#cite_ref-92">^</a></b> <a href="http://www.wholehealth.com/index.cfm?fuseaction=product.display&Product_ID=214" class="external text" title="http://www.wholehealth.com/index.cfm?fuseaction=product.display&Product_ID=214" rel="nofollow">Resveratrol Information</a></li> <li id="cite_note-93"><b><a href="#cite_ref-93">^</a></b> <cite style="font-style:normal" class="news" id="CITEREFRimas">Rimas, Andrew (<span class="mw-formatted-date" title="2006-12-11"><a href="/wiki/2006" title="2006">2006</a>-<a href="/wiki/December_11" title="December 11">12-11</a></span>). "<a href="http://www.boston.com/news/globe/health_science/articles/2006/12/11/his_research_targets_the_aging_process/" class="external text" title="http://www.boston.com/news/globe/health_science/articles/2006/12/11/his_research_targets_the_aging_process/" rel="nofollow">MOLECULAR BIOLOGIST DAVID SINCLAIR, MEETING THE MINDS</a>". <i>Boston Globe</i> (boston.com)<span class="printonly">. <a href="http://www.boston.com/news/globe/health_science/articles/2006/12/11/his_research_targets_the_aging_process/" class="external free" title="http://www.boston.com/news/globe/health_science/articles/2006/12/11/his_research_targets_the_aging_process/" rel="nofollow">http://www.boston.com/news/globe/health_science/articles/2006/12/11/his_research_targets_the_aging_process/ </a></span><span class="reference-accessdate">. Retrieved on 2007-06-22</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=MOL ECULAR+BIOLOGIST+DAVID+SINCLAIR%2C+MEETING+THE+MINDS&rft.jtitle=Boston+Globe&rft.aulast=Rimas&rft.aufirst=Andr ew&rft.au=Rimas%2C+Andrew&rft.date=%5B%5B2006-12-11%5D%5D&rft.pub=boston.com&rft_id=http%3A%2F%2Fwww.bosto n.com%2Fnews%2Fglobe%2Fhealth_science%2Farticles%2F2006%2F12%2F11%2Fhis_research_targets_the_aging_process%2F&rfr_id=i nfo:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-94"><b><a href="#cite_ref-94">^</a></b> <cite style="font-style:normal" class="news" id="CITEREFStipp">Stipp, David (<span class="mw-formatted-date" title="2007-01-19"><a href="/wiki/2007" title="2007">2007</a>-<a href="/wiki/January_19" title="January 19">01-19</a></span>). "<a href="http://money.cnn.com/2007/01/18/magazines/fortune/Live_forever.fortune/index.htm?postversion=2007011912" class="external text" title="http://money.cnn.com/2007/01/18/magazines/fortune/Live_forever.fortune/index.htm?postversion=2007011912" rel="nofollow">Can red wine help you live forever?</a>". <i><a href="/wiki/Fortune_magazine" title="Fortune magazine" class="mw-redirect">Fortune magazine</a></i> (<a href="/wiki/CNN" title="CNN">CNN</a>): pp. 3<span class="printonly">. <a href="http://money.cnn.com/2007/01/18/magazines/fortune/Live_forever.fortune/index.htm?postversion=2007011912" class="external free" title="http://money.cnn.com/2007/01/18/magazines/fortune/Live_forever.fortune/index.htm?postversion=2007011912" rel="nofollow">http://money.cnn.com/2007/01/18/magazines/fortune/Live_forever.fortune/index.htm?postversion=2007011912</a> </span><span class="reference-accessdate">. Retrieved on 2007-08-15</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Can +red+wine+help+you+live+forever%3F&rft.jtitle=%5B%5BFortune+magazine%5D%5D&rft.aulast=Stipp&rft.aufirst=David& amp;rft.au=Stipp%2C+David&rft.date=%5B%5B2007-01-19%5D%5D&rft.pages=pp.%26nbsp%3B3&rft.pub=%5B%5BCNN%5D%5D&amp ;rft_id=http%3A%2F%2Fmoney.cnn.com%2F2007%2F01%2F18%2Fmagazines%2Ffortune%2FLive_forever.fortune%2Findex.htm%3Fpostversion %3D2007011912&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-wsj-95">^ <a href="#cite_ref-wsj_95-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-wsj_95-1"><sup><i><b>b</b></i></sup></a> <cite style="font-style:normal" class="web" id="CITEREFZachary_M._Seward2006">Zachary M. Seward (2006-11-30). "<a href="http://www.post-gazette.com/pg/06334/742471-114.stm" class="external text" title="http://www.post-gazette.com/pg/06334/742471-114.stm" rel="nofollow">Quest for youth drives craze for 'wine' pills</a>" (htm). The Wall Street Journal<span class="printonly">. <a href="http://www.post-gazette.com/pg/06334/742471-114.stm" class="external free" title="http://www.post-gazette.com/pg/06334/742471-114.stm" rel="nofollow">http://www.post-gazette.com/pg/06334/742471-114.stm</a></span><span class="reference-accessdate">. Retrieved on 2008-02-02</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.btitle=Quest +for+youth+drives+craze+for+%27wine%27+pills&rft.atitle=&rft.aulast=Zachary+M.+Seward&rft.au=Zachary+M.+Seward &rft.date=2006-11-30&rft.pub=The+Wall+Street+Journal&rft_id=http%3A%2F%2Fwww.post-gazette.com%2Fpg%2F06334%2F7 42471-114.stm&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-96"><b><a href="#cite_ref-96">^</a></b> <cite style="font-style:normal" class="news">"<a href="http://www.upi.com/NewsTrack/Science/2006/11/30/caution_urged_with_resveratrol/9504/" class="external text" title="http://www.upi.com/NewsTrack/Science/2006/11/30/caution_urged_with_resveratrol/9504/" rel="nofollow"><sup class="noprint Inline-Template"><span title=" since January 2009" style="white-space: nowrap;">[</span></sup></a><a href="/wiki/Wikipedia:Dead_external_links" title="Wikipedia:Dead external links">dead link</a></cite>] Caution urged with resveratrol". <i>United Press International</i> (Upi.com). <span class="mw-formatted-date" title="2006-11-30"><a href="/wiki/2006" title="2006">2006</a>-<a href="/wiki/November_30" title="November 30">11-30</a></span><span class="printonly">. <a href="http://www.upi.com/NewsTrack/Science/2006/11/30/caution_urged_with_resveratrol/9504/" class="external free" title="http://www.upi.com/NewsTrack/Science/2006/11/30/caution_urged_with_resveratrol/9504/" rel="nofollow">http://www.upi.com/NewsTrack/Science/2006/11/30/caution_urged_with_resveratrol/9504/</a><sup class="noprint Inline-Template"><span title=" since January 2009" style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Dead_external_links" title="Wikipedia:Dead external links">dead link</a></i>]</span></sup></span><span class="reference-accessdate">. Retrieved on 2007-06-21</span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Cau tion+urged+with+resveratrol&rft.jtitle=United+Press+International&rft.date=%5B%5B2006-11-30%5D%5D&rft.pub=Upi. com&rft_id=http%3A%2F%2Fwww.upi.com%2FNewsTrack%2FScience%2F2006%2F11%2F30%2Fcaution_urged_with_resveratrol%2F9504%2F+ %5B%5BCategory%3AAll+articles+with+dead+external+links%5D%5D%5B%5BCategory%3AArticles+with+dead+external+links+from+Januar y+2009%5D%5D%3Csup+class%3D%22noprint+Inline-Template%22%3E%3Cspan+title%3D%22%26nbsp%3Bsince+January+2009%22+style%3D%22w hite-space%3A+nowrap%3B%22%3E%26%2391%3B%3Ci%3E%5B%5BWP%3ADead+external+links%7Cdead+link%5D%5D%3C%2Fi%3E%26%2393%3B%3C%2F span%3E%3C%2Fsup%3E&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> <li id="cite_note-97"><b><a href="#cite_ref-97">^</a></b> <cite style="font-style:normal" class="news" id="CITEREFAleccia">Aleccia, JoNel (<span class="mw-formatted-date" title="2008-04-22"><a href="/wiki/2008" title="2008">2008</a>-<a href="/wiki/April_22" title="April 22">04-22</a></span>). "<a href="http://www.msnbc.msn.com/id/23359040/" class="external text" title="http://www.msnbc.msn.com/id/23359040/" rel="nofollow">Longevity quest moves slowly from lab to life</a>". <i>MSNBC</i> (msnbc.com)<span class="printonly">. <a href="http://www.msnbc.msn.com/id/23359040/" class="external free" title="http://www.msnbc.msn.com/id/23359040/" rel="nofollow">http://www.msnbc.msn.com/id/23359040/</a></span><span class="reference-accessdate">. Retrieved on 2008-04-22</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Lon gevity+quest+moves+slowly+from+lab+to+life&rft.jtitle=MSNBC&rft.aulast=Aleccia&rft.aufirst=JoNel&rft.au=Al eccia%2C+JoNel&rft.date=%5B%5B2008-04-22%5D%5D&rft.pub=msnbc.com&rft_id=http%3A%2F%2Fwww.msnbc.msn.com%2Fid%2F 23359040%2F&rfr_id=info:sid/en.wikipedia.org:Resveratrol"><span style="display: none;"> </span></span></li> </ol> </div> <p><a name="Further_reading" id="Further_reading"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=16" title="Edit section: Further reading">edit</a>]</span> <span class="mw-headline">Further reading</span></h2> <ul> <li><cite style="font-style:normal" class="" id="CITEREFGescher_AJ.2C_Steward_WP2003">Gescher AJ, Steward WP (01 October 2003). "<a href="http://cebp.aacrjournals.org/cgi/content/full/12/10/953" class="external text" title="http://cebp.aacrjournals.org/cgi/content/full/12/10/953" rel="nofollow">Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: a conundrum</a>". <i>Cancer Epidemiol Biomarkers Prev.</i> <b>12</b> (10): 953–7. <a href="http://www.ncbi.nlm.nih.gov/pubmed/14578128" class="external" title="http://www.ncbi.nlm.nih.gov/pubmed/14578128">PMID 14578128</a><span class="printonly">. <a href="http://cebp.aacrjournals.org/cgi/content/full/12/10/953" class="external free" title="http://cebp.aacrjournals.org/cgi/content/full/12/10/953" rel="nofollow">http://cebp.aacrjournals.org/cgi/content/full/12/10/953</a></span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Rel ationship+between+mechanisms%2C+bioavailibility%2C+and+preclinical+chemopreventive+efficacy+of+resveratrol%3A+a+conundrum& amp;rft.jtitle=Cancer+Epidemiol+Biomarkers+Prev.&rft.aulast=Gescher+AJ%2C+Steward+WP&rft.au=Gescher+AJ%2C+Steward+ WP&rft.date=01+October+2003&rft.volume=12&rft.issue=10&rft.pages=953%E2%80%937&rft_id=info:pmid/145781 28&rft_id=http%3A%2F%2Fcebp.aacrjournals.org%2Fcgi%2Fcontent%2Ffull%2F12%2F10%2F953&rfr_id=info:sid/en.wikipedia.o rg:Resveratrol"><span style="display: none;"> </span></span></li> </ul> <p><a name="External_links" id="External_links"></a></p> <h2><span class="editsection">[<a href="/w/index.php?title=Resveratrol&action=edit&section=17" title="Edit section: External links">edit</a>]</span> <span class="mw-headline">External links</span></h2> <ul> <li><a href="http://ctd.mdibl.org/detail.go?type=chem&acc=C059514&bq=resveratrol" class="external text" title="http://ctd.mdibl.org/detail.go?type=chem&acc=C059514&bq=resveratrol" rel="nofollow">CTD's 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class="mw-redirect">Niacin (B<sub>3</sub>)</a> • <a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid (B<sub>5</sub>)</a> • <a href="/wiki/Vitamin_B6" title="Vitamin B6">Pyridoxine (B<sub>6</sub>)</a> • <a href="/wiki/Biotin" title="Biotin">Biotin (B<sub>7</sub>)</a> • <a href="/wiki/Folic_acid" title="Folic acid">Folic acid (B<sub>9</sub>)</a> • <a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin (B<sub>12</sub>)</a> • <a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid (Vitamin C)</a> • <a href="/wiki/Vitamin_D" title="Vitamin D">Ergocalciferol and Cholecalciferol (Vitamin D)</a> • <a href="/wiki/Vitamin_E" title="Vitamin E">Tocopherol (Vitamin E)</a> • <a href="/wiki/Vitamin_K" title="Vitamin K">Naphthoquinone (Vitamin K)</a> • <a href="/wiki/Calcium" title="Calcium">Calcium</a> • <a href="/wiki/Choline" title="Choline">Choline</a> • <a href="/wiki/Chlorine" title="Chlorine">Chlorine</a> • <a href="/wiki/Chromium" title="Chromium">Chromium</a> • <a href="/wiki/Cobalt" title="Cobalt">Cobalt</a> • <a href="/wiki/Copper" title="Copper">Copper</a> • <a href="/wiki/Fluorine" title="Fluorine">Fluorine</a> • <a href="/wiki/Iodine" title="Iodine">Iodine</a> • <a href="/wiki/Iron" title="Iron">Iron</a> • <a href="/wiki/Magnesium" title="Magnesium">Magnesium</a> • <a href="/wiki/Manganese" title="Manganese">Manganese</a> • <a href="/wiki/Molybdenum" title="Molybdenum">Molybdenum</a> • <a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a> • <a href="/wiki/Potassium" title="Potassium">Potassium</a> • <a href="/wiki/Selenium" title="Selenium">Selenium</a> • <a href="/wiki/Sodium" title="Sodium">Sodium</a> • <a href="/wiki/Sulfur" title="Sulfur">Sulfur</a> • <a href="/wiki/Zinc" title="Zinc">Zinc</a></div> </td> </tr> <tr style="height:2px"> <td></td> </tr> <tr> <td class="navbox-group" style=";;">Other common ingredients</td> <td style="text-align:left;border-left-width:2px;border-left-style:solid;width:100%;padding:0px;;;" class="navbox-list navbox-odd"> <div style="padding:0em 0.25em"><a href="/wiki/AAKG" title="AAKG" class="mw-redirect">AAKG</a> • <a href="/wiki/Carnitine" title="Carnitine">Carnitine</a> • <a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a> • <a href="/wiki/Cod_liver_oil" title="Cod liver oil">Cod liver oil</a> • <a href="/wiki/Copper_gluconate" title="Copper gluconate">Copper gluconate</a> • <a href="/wiki/Creatine" title="Creatine">Creatine</a>/<a href="/wiki/Creatine_supplements" title="Creatine supplements">Creatine supplements</a> • <a href="/wiki/Dietary_fiber" title="Dietary fiber">Dietary fiber</a> • <a href="/wiki/Elemental_calcium" title="Elemental calcium">Elemental calcium</a> • <a href="/wiki/Ephedra" title="Ephedra">Ephedra</a> • <a href="/wiki/Fish_oil" title="Fish oil">Fish oil</a> • <a href="/wiki/Folic_acid" title="Folic acid">Folic acid</a> • <a href="/wiki/Ginseng" title="Ginseng">Ginseng</a> • <a href="/wiki/Glucosamine" title="Glucosamine">Glucosamine</a> • <a href="/wiki/Glutamine" title="Glutamine">Glutamine</a> • <a href="/wiki/Iron_supplements" title="Iron supplements">Iron supplements</a> • <a href="/wiki/Japanese_Honeysuckle" title="Japanese Honeysuckle">Japanese Honeysuckle</a> • <a href="/wiki/Krill_oil" title="Krill oil">Krill oil</a> • <a href="/wiki/Lingzhi" title="Lingzhi">Lingzhi</a> • <a href="/wiki/Linseed_oil" title="Linseed oil">Linseed oil</a> • <a href="/wiki/Melatonin" title="Melatonin">Melatonin</a> • <a href="/wiki/Red_yeast_rice" title="Red yeast rice">Red yeast rice</a> • <a href="/wiki/Royal_jelly" title="Royal jelly">Royal jelly</a> • <a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto</a> • <a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">Spirulina</a> • <a href="/wiki/Taurine" title="Taurine">Taurine</a> • <a href="/wiki/Wheatgrass" title="Wheatgrass">Wheatgrass</a> • <a href="/wiki/Wolfberry" title="Wolfberry">Wolfberry</a> • <a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a> • <a href="/wiki/Zinc_gluconate" title="Zinc gluconate">Zinc gluconate</a></div> </td> </tr> <tr style="height:2px"> <td></td> </tr> <tr> <td class="navbox-group" style=";;">Related articles</td> <td style="text-align:left;border-left-width:2px;border-left-style:solid;width:100%;padding:0px;;;" class="navbox-list navbox-even"> <div style="padding:0em 0.25em"><a href="/wiki/Codex_Alimentarius" title="Codex Alimentarius">Codex Alimentarius</a> • <a href="/wiki/Enzyte" title="Enzyte">Enzyte</a> • <a href="/wiki/Metabolife" title="Metabolife">Metabolife</a> • <a href="/wiki/Hadacol" title="Hadacol">Hadacol</a> • <a href="/wiki/Nutraceutical" title="Nutraceutical">Nutraceutical</a> • <a href="/wiki/Multivitamin" title="Multivitamin">Multivitamin</a> • <a href="/wiki/Nutrition" title="Nutrition">Nutrition</a></div> 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