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Resveratrol

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Resveratrol
Image:Resveratrol.png
General
Systematic name 5-[(E)-2-(4-hydroxyphenyl)-
ethenyl]benzene-1,3-diol
Other names trans-3,5,4'-trihydroxystilbene
3,4',5-stilbenetriol
trans-resveratrol
(E)-5-(p-hydroxystyryl)resorcinol
Molecular formula C14H12O3
SMILES C1=CC(=CC=C1C=CC2=
CC(=CC(=C2)O)O)O
Molar mass 228.25 g/mol
Appearance white powder with
slight yellow cast
CAS number [501-36-0]
Properties
Solubility in ethanol 50 mg/mL
Solubility in DMSO ~16 mg/mL
Solubility in water ~0.03 mg/mL
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Resveratrol is a phytoalexin produced by several plants that is sold as a nutritional supplement. A number of beneficial health effects, such as anti-cancer, antiviral, neuroprotective, anti-aging, anti-inflammatory and life-prolonging effects have been reported. Resveratrol is found in the skin of red grapes and as a constituent of red wine but apparently not in sufficient amounts to explain the “French paradox” that the incidence of coronary heart disease is relatively low in southern France despite high dietary intake of saturated fats.

The four stilbenes cis and trans resveratrol, and cis and trans piceid are similar and related, and sometimes analyzed together as a group. [1]

Contents

[edit] Plants and foods

Resveratrol is produced by several plants, apparently for its antifungal properties. It is found in widely varying amounts in grapes (primarily the skins), raspberries, mulberries, in peanuts, berries of Vaccinium species, including blueberries, bilberries, and cranberries, some pines, such as Scots pine and eastern white pine, and the roots and stalks of giant knotweed and Japanese knotweed, called hu zhang in China. Resveratrol was first isolated from an extract of the Peruvian legume Cassia quinquangulata in 1974.

The amount of resveratrol in food substances varies greatly. Ordinary non-muscadine Red wine contains between 0.2 and 5.8 mg/L <ref> Gu X, Creasy L, Kester A, et al., Capillary electrophoretic determination of resveratrol in wines. J Agric Food Chem 47:3323-3277, 1999</ref>, depending on the grape variety, whilst white wine has much less - the reason being that red wine is fermented with the skins, allowing the wine to absorb the resveratrol, whereas white wine is fermented after the skin has been removed. Wines produced from muscadine grapes, however, both red and white, may contain more than 40 mg/L.<ref> Ector BJ, Magee JB, Hegwood CP, Coign MJ. Resveratrol Concentration in Muscadine Berries, Juice, Pomace, Purees, Seeds, and Wines. http://www.ajevonline.org/cgi/content/abstract/47/1/57</ref>. [2]

Fresh grape skin contains about 50 to 100 micrograms of resveratrol per gram.[3]

In grapes, resveratrol is found primarily in the skin and seeds. This is particularly true for muscadine grapes, whose skin and seeds have about one hundred times the concentration as the pulp.[4] 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.[5]

[edit] Total resveratrol content of wines and grape juice

Beverage Total resveratrol (mg/L) Total resveratrol in a 5 ounce glass (mg)
White Wines (Spanish) 0.05-1.80 0.01-0.27
Pinot Noir 0.4-2.0 0.06-0.30
Rose Wines (Spanish) 0.43-3.52 0.06-.53
Red Wines (Spanish) 1.92-12.59 .29-1.89
Red Wines (Global) 1.98-7.13 0.30-1.07
Red grape juice (Spanish) 1.14-8.69 0.17-1.30

Sources: http://www.pbrc.edu/Division_of_Education/pdf/PNS_resveratrol.pdf http://etd.lsu.edu/docs/available/etd-01202006-082858/unrestricted/LeBlanc_dis.pdf

The trans-resveratrol concentration in 40 Tuscan wines ranged from 0.3 to 2.1 mg/L in the 32 red wines and had a maximum of 0.1 mg/L in the 8 white wines tested. Both the cis- and trans- isomers of resveratrol were detected in all tested samples. Cis-resveratrol levels were comparable to those of the trans-isomer. They ranged from 0.5 mg/L to 1.9 mg/L in red wines and had a maximum of 0.2 mg/L in white wines.[6]

Reports suggest that some aspect of the wine making process converts piceid to resveratrol in wine, as wine seems to have twice the average resveratrol concentration of the equivalent commercial juices.[7]

"All of the muscadine table wines sampled had greater trans and cis resveratrol concentrations than any other wines sampled. The muscadine table wines varied between 9.2 and 31.9 mg/L cis resveratrol and between 4.9 and 13.4 mg/L trans resveratrol." [8]

[edit] Total resveratrol content of selected foods

Food Serving Total resveratrol (mg)
Peanuts (raw) 1 c (146 g) .01-0.26
Peanuts (boiled) 1 c (180 g) .32-1.28
Peanut butter 1 c (258 g) .04-0.13
Red grapes 1 c (160 g) .24-1.25
Source: http://lpi.oregonstate.edu/infocenter/phytochemicals/resveratrol/index.html#sources

Ounce for ounce, peanuts have more than half the amount of resveratrol in red wine. The average amount of resveratrol in one ounce of peanuts in the marketplace (about 15 whole) is 79.4 ug/ounce. In comparison, some red wines contains approximately 160 ug/fluid ounce.[9]

"The concentrations of resveratrol were silmilar in cranberry and grape juice".[10]

Blueberries have about twice as much resveratrol as bilberries, but there is great regional variation. These fruits have less than ten percent as much as grapes. Cooking or heat processing of these berries will contribute to the degradation of resveratrol, reducing it by up to half.[11] Resveratrol in raw and baked blueberries and bilberries. J Agric Food Chem. 2003 Sep 24;51(20):5867-70. Lyons MM, Yu C, Toma RB, Cho SY, Reiboldt W, Lee J, van Breemen RB. Food and Nutritional Science Division, California State University-Long Beach, CA 90840

When humans ingest resveratrol orally, most of it seems to be rapidly metabolized and excreted.[12] [13]

[edit] Chemical and physical properties

Resveratrol (3,5,4'-trihydroxystilbene) is a polyphenolic phytoalexin. It is a stilbenoid, a derivate of stilbene, and is produced in plants with the help of the enzyme stilbene synthase.

It exists as two structural isomers: cis- (Z) and trans- (E), with the trans-isomer shown in the image. Trans-resveratrol can undergo isomerisation to the cis- form when heated or exposed to ultraviolet irradiation.[citation needed]

[edit] Supplement

Resveratrol is available as a nutritional supplement but not as a therapeutic agent (although it has been registered as an investigational drug in some jurisdictions). Supplements, first sourced from ground dried red grape skins and grape seeds (sometimes from residual byproducts of winemaking[14]), are now primarily derived from the cheaper, more concentrated Japanese knotweed. Capsules are sold containing from 1 mg to over 40 mg of Resveratrol, at a cost of USD $.10 to over $1.00 each. A less common form is packets of powder, which might be more convenient for frequent ingestion as suggested by the rapid metabolism in the body.[15]

Some supplement makers claim that only the trans- form matters, and that the cis- form is not useful or perhaps even a bad thing. Other makers simply report total resveratrol content -- or in some cases, just the quantity of an "extract" source, which only contains some percentage of resveratrol.

The following is an excerpt from a FDA New Dietary Ingredient Notification:

"First, trans-Resveratrol is excluded from the definition of a “dietary supplement” under 21 U.S.C. 321 (ff) (3) (B), because it is an article authorized for investigation as a new drug for which substantial clinical investigations have been instituted and made public in the U. S."
"FDA authorized trans-Resveratrol, which is also known as “resveratrol” or 3,5,4’-trihydroxystilbene, to be an Investigational New Drug on January 30, 2001. The Dietary Supplement Health and Education Act (DSHEA) of 1994 defined a “new dietary ingredient” as one that was marketed in the U.S. on or after October 15, 1994. This office does not have any information that indicates that trans-Resveratrol was legally marketed as a dietary ingredient in the U.S. before October 15, 1994."

Resveratrol is often called a nutraceutical, like other bioactive plant compounds studied for potential clinical applications: curcumin, EGCG, silibinin, etc.

In a 2004 issue of Science, Dr. Sinclair of Harvard University said resveratrol is not an easy molecule to protect from oxidation. It has been claimed that it is readily degraded by exposure to light, heat, and oxygen.[16] Other researchers indicate that resveratrol retains its health effects rather well. Most commonly-available supplements tested have no ability to stimulate the Sirtuin 1 enzymes.[citation needed]

The pharmacokinetics of resveratrol metabolism have not been investigated in humans. Rat studies, however, suggest a half life as high as 1.6 hours. In a 2002 issue of J Pharm Exper Therapeutics[17], Dr. Marier reported that rats given a single oral dose of 50 mg/kg body weight initially experienced a rapid drop in serum resveratrol levels: the half life, or T1/2, of the drug was found to be 8 minutes, meaning that blood levels had dropped to half of peak by that time. However, detectable levels of the drug remained for 12 hours, probably due to enterohepatic recirculation--that it, a release of stored resveratrol from liver tissue, yielding an overall half life of between 1.3 and 1.6 hours [Marier JF et al. J Pharm Exper Theraputics 2002;302(1):369-373]. It is expected that chemically modified resveratrol-like molecules (drugs) will have a longer half-life and thus more potency.

[edit] Physiological effects

[edit] Activities and mechanisms of action

Resveratrol interferes with all three stages of carcinogenesis - initiation, promotion and progression Experiments in cell cultures of varied types and isolated subcellular systems in vitro imply many mechanisms in the pharmacological activity of resveratrol. These mechanisms include inhibition of the transcription factor NF-kB, cytochrome P450 isoenzyme CYP1A1, androgenic.<ref name="Benitez_2006">Benitez DA, Pozo-Guisado E, Alvarez-Barrientos A, Fernandez-Salguero PM, Castellon EA (Oct 18 2006). "Mechanisms involved in resveratrol-induced apoptosis and cell cycle arrest in prostate cancer-derived cell lines". Journal of Andrology. PMID 17050787.</ref> actions and expression and activity of cyclooxygenase (COX) enzymes.

In some lineages of cancer cell culture, resveratrol has been shown to induce apoptosis.<ref name="Benitez_2006"/><ref name="Faber 2006">Faber AC, Chiles TC (Dec 2006). "Resveratrol induces apoptosis in transformed follicular lymphoma OCI-LY8 cells: Evidence for a novel mechanism involving inhibition of BCL6 signaling". International Journal of Oncology 29 (6). PMID 17088997.</ref><ref name="Riles_2006">Riles WL, Erickson J, Nayyar S, Atten MJ, Attar BM, Holian O (21 Sep 2006). "Resveratrol engages selective apoptotic signals in gastric adenocarcinoma cells". World Journal of Gastroenterology 12 (35). PMID 17007014.</ref><ref name="Sareen 2006">Sareen D, van Ginkel PR, Takach JC, Mohiuddin A, Darjatmoko SR, Albert DM, Polans AS (Sep 2006). "Mitochondria as the primary target of resveratrol-induced apoptosis in human retinoblastoma cells". Investigative Ophthamology & Visual Science 47 (9). PMID 16936077.</ref><ref name="Tang 2006">Tang HY, Shih A, Cao HJ, Davis FB, Davis PJ, Lin HY (Aug 2006). "Resveratrol-induced cyclooxygenase-2 facilitates p53-dependent apoptosis in human breast cancer cells" 5 (8). PMID 16928824.</ref><ref name="aziz 2006">Aziz MH, Nihal M, Fu VX, Jarrard DF, Ahmad N (May 2006). "Resveratrol-caused apoptosis of human prostate carcinoma LNCaP cells is mediated via modulation of phosphatidylinositol 3'-kinase/Akt pathway and Bcl-2 family proteins". Molecular Cancer Therapeutics 5 (5). PMID 16731767.</ref>

Resveratrol has been shown to induce Fas/Fas ligand mediated apoptosis, p53 and cyclins A, B1 and cyclin-dependent kinases cdk 1 and 2. Resveratrol is also reported to possess antioxidant and anti-angiogenic properties.[citation needed] Resveratrol is under extensive investigation as a cancer chemopreventive agent.<ref name="Saiko 2006">Saiko P, Horvath Z, Murias M, Handler N, Jaeger W, Erker T, Fritzer-Szekeres M, Szekeres T. "Antitumor Effects of 3,3',4,4',5,5'-Hexahydroxystilbene in hl-60 Human Promyelocytic Leukemia Cells". Nucleosides Nucleotides Nucleic Acids 25 (9). PMID 17065056.</ref>

Resveratrol was reported effective against neuronal cell dysfunction and cell death, and help against diseases such as Huntington's disease <ref>Parker JA, Arango M, Abderrahmane S, Lambert E, Tourette C, Catoire H, Néri C. Resveratrol rescues mutant polyglutamine cytotoxicity in C. elegans and mammalian neurons. Nature Genetics 2005 ; 4 : 349-50. PMID 15793589</ref> and Alzheimer's disease.<ref>Philippe Marambaud, Study of Alzheimers Disease and Memory Disorders. Journal of Biological Chemistry 2005 ; November 11</ref>

Research at the Northeastern Ohio Universities College of Medicine and Ohio State University indicate that resveratrol has direct inhibitory action on cardiac fibroblasts and may inhibit the progression of cardiac fibrosis.<ref>Olson ER, Naugle JE, Zhang X, Bomser JA, Meszaros JG. Inhibition of cardiac fibroblast proliferation and myofibroblast differentiation by resveratrol. Am J Physiol Heart Circ Physiol 2005 Mar;288(3):H1131-8. PMID 15498824</ref>

Note that resveratrol bioavailability depends on its conjugate forms: glucuronate and sulfonate, despite that most in-vitro studies use the aglycone form of resveratrol ('aglycone' means without a sugar molecule attached, as in the figure in this article).

[edit] Life extension and anti-aging

Experiments from the Harvard laboratory of David Sinclair (Biologist) published in 2003 the journal Nature demonstrated that resveratrol significantly extends the lifespan of the yeast Saccharomyces cerevisiae. <ref>Howitz KT, Bitterman KJ, Cohen HY, Lamming DW, Lavu S, Wood JG, Zipkin RE, Chung P, Kisielewski A, Zhang LL, Scherer B, Sinclair DA. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan. Nature. 2003 Sep 11;425(6954):191-6. Epub 2003 Aug 24. PMID 12939617</ref> Dr. Sinclair then founded Sirtris Pharmaceuticals to commercialize resveratrol or related compounds as an anti-aging drug.

Later studies showed that resveratrol prolongs the lifespan of the worm Caenorhabditis elegans and the fruit fly Drosophila melanogaster.[citation needed] In 2006, it also extended the maximum lifespan of a short-lived fish, Nothobranchius furzeri, by 59%, and extended its median lifespan by 56%. Also noted were an increase in swimming performance, an increase in cognitive performance (learning tasks), and a lack of neurofibrillary degeneration (found in a control group). The authors observed that "[resveratrol's] supplementation with food extends vertebrate lifespan and delays motor and cognitive age-related decline could be of high relevance for the prevention of aging-related diseases in the human population."<ref>Valenzano DR, Terzibasi E, Genade T, Cattaneo A, Domenici L, Cellerino A "Resveratrol Prolongs Lifespan and Retards the Onset of Age-Related Markers in a Short-Lived Vertebrate." Current Biology 2006 Feb 7;16 (3):296-300 PMID 16461283</ref> Later in 2006, a report in the journal Nature by Sinclair's laboratory showed that the compound improves health and survival of mice on a high-calorie diet<ref>Baur JA, Pearson KJ, Price NL, Jamieson HA, Lerin C, Kalra A, Prabhu VV, Allard JS, Lopez-Lluch G, Lewis K, Pistell PJ, Poosala S, Becker KG, Boss O, Gwinn D, Wang M, Ramaswamy S, Fishbein KW, Spencer RG, Lakatta EG, Le Couteur D, Shaw RJ, Navas P, Puigserver P, Ingram DK, de Cabo R, Sinclair DA. "Resveratrol improves health and survival of mice on a high-calorie diet" Nature 2006 advanced publication</ref>.

The mechanisms of resveratrol's apparent effects on life extension are not fully understood, but they appear to mimic several of the biochemical effects of calorie restriction. This seems to function by means of lipase inhibition, reducing the absorption of fat through intestinal walls.

Only the "Trans" form of the molecule is capable of activating the mammalian SIRT1 gene in vitro; this is also the form predominantly found in red grape skins and red wine. Red grapes grown in some regions (such as New York state) often have much higher concentrations of resveratrol based on the cooler climate and the resulting increase in fungal attacks that promote resveratrol production.

Recent research by Kaeberlein et al. calls into question this theory connecting resveratrol, Sirt1 and calorie restriction.<ref>Kaeberlein M et al. Sir2-independent life span extension by calorie restriction in yeast. PLoS Biol. 2004 Sep;2(9):E296. PMID 15328540</ref><ref>Kaeberlein et al. Substrate-specific activation of sirtuins by resveratrol. J Biol Chem. 2005 Apr 29; 280(17):17038-45. PMID 15684413.</ref>

Follow up studies by David Sinclair, published in November 2006 by the journal Nature, replicated the life extending benefits of resveratrol in mice, the first such demonstration in a mammal. Preliminary results showed that obese mice provided with resveratrol lived an average of 15% longer than obese mice not provided the supplement.

The amounts used in the mouse study were approximately 22.4 mg/kg body weight per day. Scaling this amount to human body weights would imply an "equivalent human dose" of 1.5 to 2.0 grams/day. Compensating for the fact that humans have slower metabolic rates than mice would change the equivalent human dose to the range of 150 to 200 mg/day, but given that many red wines contain 3-4 milligrams of resveratrol per liter, a comparable intake would require roughly 50 bottles of wine per day. The truth is that many differences exist between mouse and human metabolism, and the effects of any given oral dose in humans remain unknown. As of November 2006 there is only one published human trial in the scientific literature and that was for safety, not efficacy. Single (one day only) oral doses of 1.0, 2.5 and 5.0 grams were given to 29 volunteers. No serious adverse events were noted. <ref>Boocook DJ, et al. Proc Amer Assoc Cancer Res 2006;47:Abstract #5741</ref>. There is no human evidence yet that quantities found in red wine or in standard supplements are sufficient for any health effect.

[edit] Athletic performance

Johan Auwerx (at the Institute of Genetics and Molecular and Cell Biology in Illkirch, France) and coauthors published an online article in the journal CELL in November 2006. Mice fed resveratrol for 15 weeks had better treadmill endurance than controls.

Nicholas Wade's interview-article with Dr. Auwerx<ref name="Red Wine Ingredient Increases Endurance, Study Shows">Wade, Nicholas (Nov 16 2006). "Red Wine Ingredient Increases Endurance, Study Shows". New York Times.</ref> states that the dose was 400 mg/kg of body weight (much higher that the 22 mg/kg of the Sinclair study). The following excerpts are from that article:[18]

“'Resveratrol makes you look like a trained athlete without the training,' Dr. Auwerx said in an interview." ...

"Dr. Auwerx attributes this in large part to the significantly increased number of mitochondria he detected in the muscle cells of treated mice.

"'Mitochondria are the organelles in the body’s cells that generate energy. With extra mitochondria, the treated mice were able to burn more fat and thus avoid weight gain and decreased sensitivity to insulin,' Dr. Auwerx said. He found their muscle fibers had been remodeled by the drug into the type more prevalent in trained human athletes.

"Dr. Ronald M. Evans, an expert on the hormonal control of metabolism at the Salk Institute, said the report by Dr. Auwerx’s team had 'shown very convincingly that resveratrol improves mitochondrial function' and fends off metabolic disease."

"The main theory developed by Dr. Guarente and others is that sirtuins sense the level of energy expenditure in living cells and switch the body’s resources from reproduction to tissue maintenance when food is low."

According to the article, Dr. Auwerx himself takes 40 mg per day. At this time, 40 mg per capsule is the highest commonly available dosage of resveratrol. For an 80 kg (176 lb) person, the 400 mg/kg of body weight amount used in Dr. Auwerx's mouse study would come to 32,000 mg/day. Compensating for the fact that humans have slower metabolic rates than mice would change the equivalent human dose to roughly 3,200 mg/day. Again, there is no published evidence anywhere in the scientific literature of any clinical trial for efficacy in humans. There is limited human safety data (see above). It is premature to take resveratrol and expect any particular results. Long-term safety has not been evaluated in humans.

In a study of 123 Finnish adults, those born with certain increased variations of the SIRT1 gene had faster metabolisms, helping them to burn energy more efficiently -- indicating that the same pathway shown in the lab mice works in humans too. [19]

Resveratrol Improves Mitochondrial Function and Protects against Metabolic Disease by Activating SIRT1 and PGC-1a; Marie Lagouge, Carmen Argmann, Zachary Gerhart-Hines, Hamid Meziane, Carles Lerin, Frederic Daussin, Nadia Messadeq, Jill Milne, Philip Lambert, Peter Elliott, Bernard Geny, Markku Laakso, Pere Puigserver, and Johan Auwerx; 10.1016/j.cell.2006.11.013 [20]

[edit] Antiviral effects

Resveratrol seems to increase the potency of some antiretroviral drugs against HIV in vitro.<ref>Heredia A, Davis C, Redfield R. Synergistic inhibition of HIV-1 in activated and resting peripheral blood mononuclear cells, monocyte-derived macrophages, and selected drug-resistant isolates with nucleoside analogues combined with a natural product, resveratrol. J Acquir Immune Defic Syndr. 2000 Nov 1;25(3):246-55. PMID 11115955</ref>

Infection by herpes simplex virus ordinarily activates the cell protein Nuclear Factor κB (NF-κB). A Northeastern Ohio Universities College of Medicine study undertaken in Vero cells found that resveratrol suppresses the activation of this transcription- and apoptosis-related protein. The study further found that multiple viral protein products were reduced or completely blocked, as well as a reduction in viral DNA production.<ref>Faith SA, Sweet TJ, Bailey E, Booth T, Docherty JJ. Resveratrol suppresses nuclear factor-kappaB in herpes simplex virus infected cells. Antiviral research 2006 Jul 14 PMID 16876885</ref>

A cell culture study found that resveratrol blocks the influenza virus from transporting viral proteins to the viral assembly site, hence restricting its ability to replicate. The effect was 90% when resveratrol was added six hours after infection and continued for 24 hours thereafter.<ref>Palamara AT, Nencioini L, Aquilano K, et al. Inhibition of influenza A virus replication by resveratrol. Journal of Infectious Diseases May 2005 15;191(10):1719-29. PMID 15838800</ref>

[edit] Metabolism of resveratrol

In humans resveratrol rapidly undergoes phase II conjugation, both glucuronidation and sulphation at multiple sites on the molecule. The effect of conjugation on efficacy is debated ([21] and [22]).

[edit] Adverse effects and unknowns

While the health benefits of resveratrol seem promising, one study has found that it stimulates the growth of human breast cancer cells, possibly because of resveratrol's chemical structure, which is similar to a phytoestrogen.<ref>Gehm BD, McAndrews JM, Chien P, Jameson JL. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc. National. Academy of Sciences 1997 Dec 9;94(25):14138-43. PMID 9391166</ref> <ref>Bowers JL, Tyulmenkov VV, Jernigan SC, Klinge CM. Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta. Endocrinology 2000 Oct;141(10):3657-67. PMID 11014220</ref>

An organization called "Quackwatch" has posted their own analysis and comments on the matter [23], including this: "increased consumption of red wine to boost resveratrol intake could certainly do more harm than good... red wine and other alcoholic beverages pose health risks..."

"Reasons why recommending a population-wide increase would be premature: Little is known about the absorption and clearance of resveratrol, the identities of its metabolic products, or its effects on the liver. The research on resveratrol has focused on its short-term effects and has been mainly done on non-human models."[24]

[edit] References

<references/>

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

[edit] See also

[edit] External links

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