Transport, stability, and biological activity of resveratrol

Annals of the New York Academy of Sciences

Volumn 1215, Issue 1, 2011, Pages 48-59

  Delmas, Dominique ^a,b   Aires, Virginie ^a,b   Limagne, Emeric ^a,b   Dutartre, Patrick ^a,b   Mazué, Frédéric ^a,b   Ghiringhelli, François ^a,b   Latruffe, Norbert ^a,b  

^a Chu   (France)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

Biotransformation; Metabolites; Resveratrol; Resveratrol analogues; Stability; Transport

Indexed keywords

FATTY ACID; LIPOPROTEIN; PICEATANNOL; RESVERATROL; RESVERATROL 3 O DEXTRO GLUCURONIDE; RESVERATROL 3 O SULFATE; RESVERATROL 4' O DEXTRO GLUCURONIDE; RESVERATROL 4' O SULFATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PARAMETERS; CHEMOPROPHYLAXIS; DRUG ABSORPTION; DRUG ACTIVITY; DRUG BINDING; DRUG FORMULATION; DRUG HALF LIFE; DRUG METABOLISM; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG TRANSPORT; HUMAN; ISOMERIZATION; NONHUMAN; OXIDATION REDUCTION REACTION;

EID: 78851469143     PISSN: 00778923     EISSN: 17496632     Source Type: Book Series    
DOI: 10.1111/j.1749-6632.2010.05871.x     Document Type: Article

References (69)

1. Langcake, P. & R. Pryce 1977. A new class of phytoalexins from grapevines. Experentia. 33: 1151-1152.
2. Romero-Perez, A.I. et al 1999. Piceid, the major resveratrol derivative in grape juices. J. Agric. Food Chem. 47: 1533-1536.
3. Kris-Etherton, P.M. & C.L. Keen 2002. Evidence that the antioxidant flavonoids in tea and cocoa are beneficial for cardiovascular health. Curr. Opin. Lipidol. 13: 41-49.
4. Delmas, D., B. Jannin & N. Latruffe 2005. Resveratrol: preventing properties against vascular alterations and ageing. Mol. Nutr. Food Res. 49: 377-395.
5. Delmas, D. et al 2006. Resveratrol as a chemopreventive agent: a promising molecule for fighting cancer. Curr. Drug Targets. 7: 423-442.
6. Walle, T. et al 2004. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos. 32: 1377-1382.
7. Belguendouz, L., L. Fremont & A. Linard 1997. Resveratrol inhibits metal ion-dependent and independent peroxidation of porcine low-density lipoproteins. Biochem. Pharmacol. 53: 1347-1355.
8. Delmas, D. et al 2000. Inhibitory effect of resveratrol on the proliferation of human and rat hepatic derived cell lines. Oncol. Rep. 7: 847-852.
9. Laza-Knoerr, A.L., R. Gref & P. Couvreur 2010. Cyclodextrins for drug delivery. J. Drug Target 18: 645-656.
10. Lopez-Nicolas, J.M. et al 2006. Determination of stoichiometric coefficients and apparent formation constants for beta-cyclodextrin complexes of trans-resveratrol using reversed-phase liquid chromatography. J. Chromatogr A. 1135: 158-165.
11. Riva, S. et al 1998. Enzymatic modification of natural compounds with pharmacological properties. Ann. N.Y. Acad. Sci. 864: 70-80.
12. Colin, D. et al 2009. Effects of resveratrol analogs on cell cycle progression, cell cycle associated proteins and 5fluoro-uracil sensitivity in human derived colon cancer cells. Int. J. Cancer 124: 2780-2788.
13. Marel, A.K. et al 2008. Inhibitory effects of trans-resveratrol analogs molecules on the proliferation and the cell cycle progression of human colon tumoral cells. Mol. Nutr. Food Res. 52: 538-548.
14. Jiang, Y.L. 2008. Design, synthesis and spectroscopic studies of resveratrol aliphatic acid ligands of human serum albumin. Bioorg. Med. Chem. 16: 6406-6414.
15. Lu, Z. et al 2007. Transport of a cancer chemopreventive polyphenol, resveratrol: interaction with serum albumin and hemoglobin. J. Fluoresc. 17: 580-587.
16. Chen, X. et al 2007. Stereospecific determination of cis- and trans-resveratrol in rat plasma by HPLC: application to pharmacokinetic studies. Biomed. Chromatogr. 21: 257-265.
17. Camont, L. et al 2009. Simple spectrophotometric assessment of the trans-/cis-resveratrol ratio in aqueous solutions. Anal. Chim. Acta. 634: 121-128.
18. Blache, D. et al 1997. Gas chromatographic analysis of resveratrol in plasma, lipoproteins and cells after in vitro incubations. J. Chromatogr. B Biomed. Sci. Appl. 702: 103-110.
19. Basly, J.P. et al 2000. Estrogenic/antiestrogenic and scavenging properties of (E)- and (Z)-resveratrol. Life Sci. 66: 769-777.
20. Urpi-Sarda, M. et al 2007. HPLC-tandem mass spectrometric method to characterize resveratrol metabolism in humans. Clin Chem. 53: 292-299.
21. Zamora-Ros, R. et al 2006. Diagnostic performance of urinary resveratrol metabolites as a biomarker of moderate wine consumption. Clin Chem. 52: 1373-1380.
22. Orallo, F. 2006. Comparative studies of the antioxidant effects of cis- and trans-resveratrol. Curr Med Chem. 13: 87-98.
23. Campos-Toimil, M. et al 2007. Effects of trans- and cis-resveratrol on Ca2+ handling in A7r5 vascular myocytes. Eur. J. Pharmacol. 577: 91-99.
24. Yanez, M. et al 2006. Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity. Biochem. Biophys. Res. Commun. 344: 688-695.
25. Mazue, F. et al. 2010. Structural determinants of resveratrol for cell proliferation inhibition potency: experimental and docking studies of new analogs. Eur. J. Med. Chem. 45: 2972-2980.
26. Sang, S. et al 2007. Autoxidative quinone formation in vitro and metabolite formation in vivo from tea polyphenol (-)-epigallocatechin-3-gallate: studied by real-time mass spectrometry combined with tandem mass ion mapping. Free Radic. Biol. Med. 43: 362-371.
27. Yang, N.C., C.H. Lee & T.Y. Song 2010. Evaluation of resveratrol oxidation in vitro and the crucial role of bicarbonate ions. Biosci. Biotechnol. Biochem. 74: 63-68.
28. Long, L.H., A. Hoi & B. Halliwell 2010. Instability of, and generation of hydrogen peroxide by, phenolic compounds in cell culture media. Arch. Biochem. Biophys. 501: 162-169.
29. Jensen, J.S., C.F. Wertz & V.A. O'Neill 2010. Preformulation Stability of trans-Resveratrol and trans-Resveratrol Glucoside (Piceid). J. Agric. Food Chem. 58: 1685-1690.
30. Hadi, S.M. et al 2010. Resveratrol Mobilizes Endogenous Copper in Human Peripheral Lymphocytes Leading to Oxidative DNA Breakage: a Putative Mechanism for Chemoprevention of Cancer. Pharm. Res. 27: 979-988.
31. Colin, D. et al 2008. Antiproliferative activities of resveratrol and related compounds in human hepatocyte derived HepG2 cells are associated with biochemical cell disturbance revealed by fluorescence analyses. Biochimie. 90: 1674-1684.
32. Lancon, A. et al 2004. Human hepatic cell uptake of resveratrol: involvement of both passive diffusion and carrier-mediated process. Biochem. Biophys. Res. Commun. 316: 1132-1137.
33. Guy, R. et al 1996. Fluorescent taxoids. Chem. Biol. 3: 1021-1031.
34. Bertelli, A. et al 1998. Plasma and tissue resveratrol concentrations and pharmacological activity. Drugs Exp. Clin. Res. 24: 133-138.
35. Lu, J. et al 2001. Resveratrol analog, 3, 4, 5, 4'-tetrahydroxystilbene, differentially induces pro-apoptotic p53/Bax gene expression and inhibits the growth of transformed cells but not their normal counterparts. Carcinogenesis 22: 321-328.
36. Gao, X. et al 2002. Disparate in vitro and in vivo antileukemic effects of resveratrol, a natural polyphenolic compound found in grapes. J. Nutr. 132: 2076-2081.
37. Khan, M.A., S. Muzammil & J. Musarrat 2002. Differential binding of tetracyclines with serum albumin and induced structural alterations in drug-bound protein. Int. J. Biol. Macromol. 30: 243-249.
38. Jannin, B. et al 2004. Transport of resveratrol, a cancer chemopreventive agent, to cellular targets: plasmatic protein binding and cell uptake. Biochem. Pharmacol. 68: 1113-1118.
39. Bourassa, P. et al 2010. Resveratrol, genistein, and curcumin bind bovine serum albumin. J. Phys. Chem. B. 114: 3348-3354.
40. Yang, F. et al 2007. Effect of human serum albumin on drug metabolism: structural evidence of esterase activity of human serum albumin. J. Struct. Biol. 157: 348-355.
41. Belguendouz, L., L. Fremont & M.T. Gozzelino 1998. Interaction of transresveratrol with plasma lipoproteins. Biochem. Pharmacol. 55: 811-816.
42. Burkon, A. & V. Somoza 2008. Quantification of free and protein-bound trans-resveratrol metabolites and identification of trans-resveratrol-C/O-conjugated diglucuronides - two novel resveratrol metabolites in human plasma. Mol. Nutr. Food Res. 52: 549-557.
43. Witztum, J.L. 1994. The oxidation hypothesis of atherosclerosis. Lancet 344: 793-795.
44. Lin, H.Y. et al 2006. Integrin alphaVbeta3 contains a receptor site for resveratrol. Faseb. J. 20: 1742-1744.
45. Lin, H.Y. et al 2008. Resveratrol is pro-apoptotic and thyroid hormone is anti-apoptotic in glioma cells: both actions are integrin and ERK mediated. Carcinogenesis. 29: 62-69.
46. Belleri, M. et al 2008. alphavbeta3 Integrin-dependent antiangiogenic activity of resveratrol stereoisomers. Mol Cancer Ther. 7: 3761-3770.
47. Casper, R.F. et al 1999. Resveratrol has antagonist activity on the aryl hydrocarbon receptor: implications for prevention of dioxin toxicity. Mol Pharmacol. 56: 784-790.
48. Bowers, J.L. et al 2000. Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta. Endocrinology 141: 3657-3667.
49. Abou-Zeid, L.A. & A.M. El-Mowafy 2004. Differential recognition of resveratrol isomers by the human estrogen receptor-alpha: molecular dynamics evidence for stereoselective ligand binding. Chirality 16: 190-195.
50. Cottart, C.H. et al 2010. Resveratrol bioavailability and toxicity in humans. Mol. Nutr. Food Res. 54: 7-16.
51. Boocock, D.J. et al 2007. Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol. Biomarkers Prev. 16: 1246-1252.
52. Crozier, A., I.B. Jaganath & M.N. Clifford 2009. Dietary phenolics: chemistry, bioavailability and effects on health. Nat Prod Rep. 26: 1001-1043.
53. Lancon, A. et al 2007. Resveratrol in human hepatoma HepG2 cells: metabolism and inducibility of detoxifying enzymes. Drug Metab. Dispos. 35: 699-703.
54. Wenzel, E. & V. Somoza 2005. Metabolism and bioavailability of trans-resveratrol. Mol. Nutr. Food Res. 49: 472-481.
55. Vitrac, X. et al 2003. Distribution of [14C]-trans-resveratrol, a cancer chemopreventive polyphenol, in mouse tissues after oral administration. Life Sci. 72: 2219-2233.
56. Marier, J.F. et al 2002. Metabolism and disposition of resveratrol in rats: extent of absorption, glucuronidation, and enterohepatic recirculation evidenced by a linked-rat model. J. Pharmacol. Exp. Ther. 302: 369-373.
57. Rimando, A.M. et al 2004. Resveratrol, pterostilbene, and piceatannol in vaccinium berries. J. Agric. Food Chem. 52: 4713-4719.
58. Roupe, K. et al 2004. Determination of piceatannol in rat serum and liver microsomes: pharmacokinetics and phase I and II biotransformation. Biomed. Chromatogr. 18: 486-491.
59. Potter, G.A. et al 2002. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br. J. Cancer. 86: 774-778.
60. Piver, B. et al 2004. Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem Pharmacol 68: 773-782.
61. Camont, L. et al 2010. Liquid chromatographic/electrospray ionization mass spectrometric identification of the oxidation end-products of trans-resveratrol in aqueous solutions. Rapid Commun Mass Spectrom. 24: 634-642.
62. Kimura, Y. & H. Okuda 2000. Effects of naturally occurring stilbene glucosides from medicinal plants and wine, on tumour growth and lung metastasis in Lewis lung carcinoma-bearing mice. J. Pharm. Pharmacol. 52: 1287-1295.
63. Wieder, T. et al 2001. 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. Leukemia 15: 1735-1742.
64. Wolter, F. et al 2002. Piceatannol, a natural analog of resveratrol, inhibits progression through the S phase of the cell cycle in colorectal cancer cell lines. J. Nutr. 132: 298-302.
65. Liu, W.H. & L.S. Chang 2010. Piceatannol induces Fas and FasL up-regulation in human leukemia U937 cells via Ca2+/p38alpha MAPK-mediated activation of c-Jun and ATF-2 pathways. Int J Biochem Cell Biol. 42: 1498-1506.
66. Wang, L.X. et al 2004. Resveratrol glucuronides as the metabolites of resveratrol in humans: characterization, synthesis, and anti-HIV activity. J. Pharm. Sci. 93: 2448-2457.
67. Hoshino, J. et al 2010. Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites. J. Med. Chem. 53: 5033-5043.
68. Calamini, B. et al 2010. Pleiotropic mechanisms facilitated by resveratrol and its metabolites. Biochem J. 429: 273-282.
69. Soleas, G.J., E.P. Diamandis & D.M. Goldberg 1997. Resveratrol: a molecule whose time has come? And gone? Clin Biochem. 30: 91-113.