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Chemical Compound Review

Resvida     5-[(E)-2-(4-hydroxyphenyl) ethenyl]benzene...

Synonyms: resveratrol, Prestwick_619, CHEMBL165, CPD-83, SRT-501, ...
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Disease relevance of Resvida


Psychiatry related information on Resvida


High impact information on Resvida


Chemical compound and disease context of Resvida


Biological context of Resvida

  • The structure of CHS complexed with resveratrol also suggests how stilbene synthase, a related enzyme, uses the same substrates and an alternate cyclization pathway to form resveratrol [24].
  • Chemopreventive agent resveratrol, a natural product derived from grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells [25].
  • Resveratrol inhibited proliferation of both cell lines in a dose-dependent fashion (5-75 microM) by arresting the cells at S phase, thus preventing their progression through the cell cycle; IL-1beta partially reversed this inhibitory effect [3].
  • Finally, resveratrol suppressed colony-forming cell proliferation of fresh AML marrow cells from 5 patients with newly diagnosed AML in a dose-dependent fashion [3].
  • Indeed, incubation of OCIM2 cells with resveratrol resulted in apoptotic cell death [3].

Anatomical context of Resvida


Associations of Resvida with other chemical compounds


Gene context of Resvida

  • Resveratrol inhibits transcription of CYP1A1 in vitro by preventing activation of the aryl hydrocarbon receptor [32].
  • Resveratrol showed no discernable activity with ER-alpha, but with ER-beta, E(2) was displaced with an IC(50) of 125 microM [33].
  • In addition, resveratrol mediated suppression of a functional activity of PR as demonstrated by down-regulation of alpha(1)-integrin expression induced by E(2) plus progesterone [33].
  • These data suggest that ER may play a role in the rapid effects of resveratrol in EC and that some of the atheroprotective effects of resveratrol may be mediated through rapid activation of ER signaling in EC [34].
  • Transient transfection of either a dominant-negative mutant of FADD, E8, or MC159 viral proteins that interfere with the DISC function, decreases the apoptotic response of SW480 cells to resveratrol and partially prevents resveratrol-induced Bax and Bak conformational changes [35].
  • Yeast cells expressing 4CL and STS produce resveratrol when fed with 4-coumaric acid, the substrate of 4CL [36].
  • Our data also indicate that these effects of resveratrol are mediated via AMPK activation and Akt inhibition, and in the case of AMPK, is dependent on the presence of the AMPK kinase, LKB1 [37].

Analytical, diagnostic and therapeutic context of Resvida


  1. Resveratrol Improves Mitochondrial Function and Protects against Metabolic Disease by Activating SIRT1 and PGC-1alpha. Lagouge, M., Argmann, C., Gerhart-Hines, Z., Meziane, H., Lerin, C., Daussin, F., Messadeq, N., Milne, J., Lambert, P., Elliott, P., Geny, B., Laakso, M., Puigserver, P., Auwerx, J. Cell (2006) [Pubmed]
  2. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Gehm, B.D., McAndrews, J.M., Chien, P.Y., Jameson, J.L. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  3. Resveratrol blocks interleukin-1beta-induced activation of the nuclear transcription factor NF-kappaB, inhibits proliferation, causes S-phase arrest, and induces apoptosis of acute myeloid leukemia cells. Estrov, Z., Shishodia, S., Faderl, S., Harris, D., Van, Q., Kantarjian, H.M., Talpaz, M., Aggarwal, B.B. Blood (2003) [Pubmed]
  4. Resveratrol inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells. Mitchell, S.H., Zhu, W., Young, C.Y. Cancer Res. (1999) [Pubmed]
  5. Peroxisome proliferator-activated receptor gamma as a molecular target of resveratrol-induced modulation of polyamine metabolism. Ulrich, S., Loitsch, S.M., Rau, O., von Knethen, A., Brüne, B., Schubert-Zsilavecz, M., Stein, J.M. Cancer Res. (2006) [Pubmed]
  6. Resveratrol inhibits proliferation, induces apoptosis, and overcomes chemoresistance through down-regulation of STAT3 and nuclear factor-kappaB-regulated antiapoptotic and cell survival gene products in human multiple myeloma cells. Bhardwaj, A., Sethi, G., Vadhan-Raj, S., Bueso-Ramos, C., Takada, Y., Gaur, U., Nair, A.S., Shishodia, S., Aggarwal, B.B. Blood (2007) [Pubmed]
  7. Dietary resveratrol alters lipid metabolism-related gene expression of mice on an atherogenic diet. Ahn, J., Cho, I., Kim, S., Kwon, D., Ha, T. J. Hepatol. (2008) [Pubmed]
  8. Role of non-canonical Beclin 1-independent autophagy in cell death induced by resveratrol in human breast cancer cells. Scarlatti, F., Maffei, R., Beau, I., Codogno, P., Ghidoni, R. Cell Death Differ. (2008) [Pubmed]
  9. Resveratrol Selectively Induces DNA Damage, Independent of Smad4 Expression, in Its Efficacy against Human Head and Neck Squamous Cell Carcinoma. Tyagi, A., Gu, M., Takahata, T., Frederick, B., Agarwal, C., Siriwardana, S., Agarwal, R., Sclafani, R.A. Clin. Cancer Res. (2011) [Pubmed]
  10. Suppression of 7,12-dimethylbenz(a)anthracene-induced mammary carcinogenesis in rats by resveratrol: role of nuclear factor-kappaB, cyclooxygenase 2, and matrix metalloprotease 9. Banerjee, S., Bueso-Ramos, C., Aggarwal, B.B. Cancer Res. (2002) [Pubmed]
  11. Resveratrol promotes clearance of Alzheimer's disease amyloid-beta peptides. Marambaud, P., Zhao, H., Davies, P. J. Biol. Chem. (2005) [Pubmed]
  12. Resveratrol--a boon for treating Alzheimer's disease? Anekonda, T.S. Brain Res. Brain Res. Rev. (2006) [Pubmed]
  13. Resveratrol prolongs lifespan and retards the onset of age-related markers in a short-lived vertebrate. Valenzano, D.R., Terzibasi, E., Genade, T., Cattaneo, A., Domenici, L., Cellerino, A. Curr. Biol. (2006) [Pubmed]
  14. Resveratrol inhibits vascular smooth muscle cell proliferation and induces apoptosis. Poussier, B., Cordova, A.C., Becquemin, J.P., Sumpio, B.E. J. Vasc. Surg. (2005) [Pubmed]
  15. In vino veritas: a tale of two sirt1s? Koo, S.H., Montminy, M. Cell (2006) [Pubmed]
  16. Resveratrol rescues mutant polyglutamine cytotoxicity in nematode and mammalian neurons. Parker, J.A., Arango, M., Abderrahmane, S., Lambert, E., Tourette, C., Catoire, H., Néri, C. Nat. Genet. (2005) [Pubmed]
  17. Modulation of NF-kappaB-dependent transcription and cell survival by the SIRT1 deacetylase. Yeung, F., Hoberg, J.E., Ramsey, C.S., Keller, M.D., Jones, D.R., Frye, R.A., Mayo, M.W. EMBO J. (2004) [Pubmed]
  18. Protein kinase CK2 and protein kinase D are associated with the COP9 signalosome. Uhle, S., Medalia, O., Waldron, R., Dumdey, R., Henklein, P., Bech-Otschir, D., Huang, X., Berse, M., Sperling, J., Schade, R., Dubiel, W. EMBO J. (2003) [Pubmed]
  19. Differential effects on growth, cell cycle arrest, and induction of apoptosis by resveratrol in human prostate cancer cell lines. Hsieh, T.C., Wu, J.M. Exp. Cell Res. (1999) [Pubmed]
  20. Resveratrol has antagonist activity on the aryl hydrocarbon receptor: implications for prevention of dioxin toxicity. Casper, R.F., Quesne, M., Rogers, I.M., Shirota, T., Jolivet, A., Milgrom, E., Savouret, J.F. Mol. Pharmacol. (1999) [Pubmed]
  21. Isorhapontigenin, a new resveratrol analog, attenuates cardiac hypertrophy via blocking signaling transduction pathways. Li, H.L., Wang, A.B., Huang, Y., Liu, D.P., Wei, C., Williams, G.M., Zhang, C.N., Liu, G., Liu, Y.Q., Hao, D.L., Hui, R.T., Lin, M., Liang, C.C. Free Radic. Biol. Med. (2005) [Pubmed]
  22. Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts. Wieder, T., Prokop, A., Bagci, B., Essmann, F., Bernicke, D., Schulze-Osthoff, K., Dörken, B., Schmalz, H.G., Daniel, P.T., Henze, G. Leukemia (2001) [Pubmed]
  23. Is resveratrol an estrogen agonist in growing rats? Turner, R.T., Evans, G.L., Zhang, M., Maran, A., Sibonga, J.D. Endocrinology (1999) [Pubmed]
  24. Structure of chalcone synthase and the molecular basis of plant polyketide biosynthesis. Ferrer, J.L., Jez, J.M., Bowman, M.E., Dixon, R.A., Noel, J.P. Nat. Struct. Biol. (1999) [Pubmed]
  25. Chemopreventive agent resveratrol, a natural product derived from grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells. Clément, M.V., Hirpara, J.L., Chawdhury, S.H., Pervaiz, S. Blood (1998) [Pubmed]
  26. Resveratrol increases nitric oxide synthase, induces accumulation of p53 and p21(WAF1/CIP1), and suppresses cultured bovine pulmonary artery endothelial cell proliferation by perturbing progression through S and G2. Hsieh, T.C., Juan, G., Darzynkiewicz, Z., Wu, J.M. Cancer Res. (1999) [Pubmed]
  27. Resveratrol induces extensive apoptosis by depolarizing mitochondrial membranes and activating caspase-9 in acute lymphoblastic leukemia cells. Dörrie, J., Gerauer, H., Wachter, Y., Zunino, S.J. Cancer Res. (2001) [Pubmed]
  28. Effect of antioxidants, resveratrol, quercetin, and N-acetylcysteine, on the functions of cultured rat hepatic stellate cells and Kupffer cells. Kawada, N., Seki, S., Inoue, M., Kuroki, T. Hepatology (1998) [Pubmed]
  29. Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models. Bhat, K.P., Lantvit, D., Christov, K., Mehta, R.G., Moon, R.C., Pezzuto, J.M. Cancer Res. (2001) [Pubmed]
  30. Analgesic resveratrol? Bertelli, A., Falchi, M., Dib, B., Pini, E., Mukherjee, S., Das, D.K. Antioxid. Redox Signal. (2008) [Pubmed]
  31. Resveratrol exerts antiproliferative activity and induces apoptosis in Waldenström's macroglobulinemia. Roccaro, A.M., Leleu, X., Sacco, A., Moreau, A.S., Hatjiharissi, E., Jia, X., Xu, L., Ciccarelli, B., Patterson, C.J., Ngo, H.T., Russo, D., Vacca, A., Dammacco, F., Anderson, K.C., Ghobrial, I.M., Treon, S.P. Clin. Cancer Res. (2008) [Pubmed]
  32. Resveratrol inhibits transcription of CYP1A1 in vitro by preventing activation of the aryl hydrocarbon receptor. Ciolino, H.P., Daschner, P.J., Yeh, G.C. Cancer Res. (1998) [Pubmed]
  33. Resveratrol exhibits cytostatic and antiestrogenic properties with human endometrial adenocarcinoma (Ishikawa) cells. Bhat, K.P., Pezzuto, J.M. Cancer Res. (2001) [Pubmed]
  34. Resveratrol and estradiol rapidly activate MAPK signaling through estrogen receptors alpha and beta in endothelial cells. Klinge, C.M., Blankenship, K.A., Risinger, K.E., Bhatnagar, S., Noisin, E.L., Sumanasekera, W.K., Zhao, L., Brey, D.M., Keynton, R.S. J. Biol. Chem. (2005) [Pubmed]
  35. Resveratrol-induced apoptosis is associated with Fas redistribution in the rafts and the formation of a death-inducing signaling complex in colon cancer cells. Delmas, D., Rébé, C., Lacour, S., Filomenko, R., Athias, A., Gambert, P., Cherkaoui-Malki, M., Jannin, B., Dubrez-Daloz, L., Latruffe, N., Solary, E. J. Biol. Chem. (2003) [Pubmed]
  36. Using unnatural protein fusions to engineer resveratrol biosynthesis in yeast and Mammalian cells. Zhang, Y., Li, S.Z., Li, J., Pan, X., Cahoon, R.E., Jaworski, J.G., Wang, X., Jez, J.M., Chen, F., Yu, O. J. Am. Chem. Soc. (2006) [Pubmed]
  37. Resveratrol inhibits cardiac hypertrophy via AMP-activated protein kinase and Akt. Chan, A.Y., Dolinsky, V.W., Soltys, C.L., Viollet, B., Baksh, S., Light, P.E., Dyck, J.R. J. Biol. Chem. (2008) [Pubmed]
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