Transport, stability, and biological activity of resveratrol

被引:205
作者
Delmas, Dominique [1 ,2 ]
Aires, Virginie [2 ]
Limagne, Emeric [2 ]
Dutartre, Patrick [2 ,3 ]
Mazue, Frederic [2 ]
Ghiringhelli, Francois [4 ]
Latruffe, Norbert [2 ]
机构
[1] INSERM, Fac Sci Vie, Lipids Nutr Canc UMR866, U866, F-21000 Dijon, France
[2] Univ Bourgogne, Fac Sci Gabriel, Ctr Rech Biochim Metab & Nutr, Dijon, France
[3] COHIRO, Fac Med, Dijon, France
[4] Univ Bourgogne, Fac Med, Ctr Rech Immunotherapie & Chimiotherapie Canc, Dijon, France
来源
RESVERATROL AND HEALTH | 2011年 / 1215卷
关键词
resveratrol; transport; stability; resveratrol analogues; metabolites; biotransformation; CANCER CHEMOPREVENTIVE POLYPHENOL; CELL-CYCLE PROGRESSION; CIS-RESVERATROL; IN-VITRO; SERUM-ALBUMIN; AGENT RESVERATROL; HEPG2; CELLS; PHASE-I; PICEATANNOL; METABOLISM;
D O I
10.1111/j.1749-6632.2010.05871.x
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Numerous studies have reported interesting properties of trans-resveratrol, a phytoalexin, as a preventive agent of several important pathologies: vascular diseases, cancers, viral infections, and neurodegenerative processes. These beneficial effects of resveratrol have been supported by observations at the cellular and molecular levels in both cellular and in vivo models, but the cellular fate of resveratrol remains unclear. We suggest here that resveratrol uptake, metabolism, and stability of the parent molecule could influence the biological effects of resveratrol. It appears that resveratrol stability involves redox reactions and biotransformation that influence its antioxidant properties. Resveratrol's pharmacokinetics and metabolism represent other important issues, notably, the putative effects of its metabolites on pathology models. For example, some metabolites, mainly sulfate-conjugated resveratrol, show biological effects in cellular models. The modifications of resveratrol stability, chemical structure, and metabolism could change its cellular and molecular targets and could be crucial for improving or decreasing its chemopreventive properties.
引用
收藏
页码:48 / 59
页数:12
相关论文
共 69 条
[51]   The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYPIBI [J].
Potter, GA ;
Patterson, LH ;
Wanogho, E ;
Perry, PJ ;
Butler, PC ;
Ijaz, T ;
Ruparelia, KC ;
Lamb, JH ;
Farmer, PB ;
Stanley, LA ;
Burke, MD .
BRITISH JOURNAL OF CANCER, 2002, 86 (05) :774-778
[52]   Resveratrol, pterostilbene, and piceatannol in Vaccinium berries [J].
Rimando, AM ;
Kalt, W ;
Magee, JB ;
Dewey, J ;
Ballington, JR .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (15) :4713-4719
[53]   Enzymatic modification of natural compounds with pharmacological properties [J].
Riva, S ;
Monti, D ;
Luisetti, M ;
Danieli, B .
ENZYME ENGINEERING XIV, 1998, 864 :70-80
[54]   Piceid, the major resveratrol derivative in grape juices [J].
Romero-Pérez, AI ;
Ibern-Gómez, M ;
Lamuela-Raventós, RM ;
de la Torre-Boronat, MC .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1999, 47 (04) :1533-1536
[55]   Determination of piceatannol in rat serum and liver microsomes: pharmacokinetics and phase I and II biotransformation [J].
Roupe, K ;
Teng, XW ;
Fu, X ;
Meadows, GG ;
Davies, NM .
BIOMEDICAL CHROMATOGRAPHY, 2004, 18 (08) :486-491
[56]   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 [J].
Sang, Shengmin ;
Yang, Ill ;
Buckley, Brian ;
Ho, Chi-Tang ;
Yang, Chung S. .
FREE RADICAL BIOLOGY AND MEDICINE, 2007, 43 (03) :362-371
[57]   Resveratrol: A molecule whose time has come? And gone? [J].
Soleas, GJ ;
Diamandis, EP ;
Goldberg, DM .
CLINICAL BIOCHEMISTRY, 1997, 30 (02) :91-113
[58]   HPLC-tandem mass spectrometric method to characterize resveratrol metabolism in humans [J].
Urpi-Sarda, Mireia ;
Zamora-Ros, Raul ;
Lamuela-Raventos, Rosa ;
Cherubini, Antonio ;
Jauregui, Olga ;
De la Torre, Rafael ;
Isabel Covas, Maria ;
Estruch, Ramon ;
Jaeger, Walter ;
Andres-Lacueva, Cristina .
CLINICAL CHEMISTRY, 2007, 53 (02) :292-299
[59]   Distribution of [14C]-trans-resveratrol, a cancer chemopreventive polyphenol, in mouse tissues after oral administration [J].
Vitrac, X ;
Desmoulière, A ;
Brouillaud, B ;
Krisa, S ;
Deffieux, G ;
Barthe, N ;
Rosenbaum, J ;
Mérillon, JM .
LIFE SCIENCES, 2003, 72 (20) :2219-2233
[60]   High absorption but very low bioavailability of oral resveratrol in humans [J].
Walle, T ;
Hsieh, F ;
DeLegge, MH ;
Oatis, JE ;
Walle, UK .
DRUG METABOLISM AND DISPOSITION, 2004, 32 (12) :1377-1382