Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes

Piver, Bertrand; Fer, Maude; Vitrac, Xavier; Mérillon, Jean‐Michel; Dréano, Yvonne; Berthou, F.; Lucas, Danièle

doi:10.1016/j.bcp.2004.05.008

Cited by 128 publications

(85 citation statements)

References 24 publications

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“…PIC is a metabolite of RES (Fig. 1), and differs from its parent compound due to the extra hydroxyl group on the 3'-position of phenyl ring B [38][39][40]. In the present analysis, RAW 264.7 macrophages demonstrated greatest sensitivity to PIC.…”

Section: Discussionmentioning

confidence: 60%

In Vitro evaluation of the cytotoxic and anti-proliferative properties of resveratrol and several of its analogs

Billack¹,

Radkar²,

Adiabouah³

2008

Cellular and Molecular Biology Letters

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Resveratrol (RES), a component of red wine, possesses antiinflammatory properties. The studies described in the present work were aimed at evaluating the potential for RES and related stilbene analogs (piceatannol, PIC; pterostilbene, TPS; trans-stilbene, TS; and trans-stilbene oxide, TSO) to exhibit toxicity towards RAW 264.7 mouse macrophages. The effect of TS, TSO, RES and TPS on RAW 264.7 macrophage viability was determined by two standard methods: (a) the MTT assay and (b) the trypan blue dye exclusion test. Whereas macrophages were more sensitive to PIC (LC 50 trypan ~ 1.3 μM) and to TPS (LC 50 trypan ~ 4.0 μM and LC 50 MTT ~ 8.3 μM) than to RES (LC 50 trypan ~ 8.9 μM and LC 50 MTT ~ 29.0 μM), they were relatively resistant to TSO (LC 50 trypan ~ 61.0 μM and LC 50 MTT > 100 μM) and to TS (LC 50 trypan ≥ 5.0 μM and LC 50 MTT ≥ 5.0 μM). The ability of selected stilbenes (RES, TPS and PIC) to exhibit growth inhibitory effects was also examined. Although RES and TPS were observed to inhibit cell proliferation in macrophages (IC 50 ≤ 25 µM), these cells were resistant to growth inhibition by PIC (IC 50 ≥ 50 µM). The data obtained in the present analysis demonstrate that substituted stilbene compounds such as RES have the capacity to exhibit cytotoxic and anti-proliferative activities in macrophages.

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Section: Discussionmentioning

confidence: 60%

In Vitro evaluation of the cytotoxic and anti-proliferative properties of resveratrol and several of its analogs

Billack¹,

Radkar²,

Adiabouah³

2008

Cellular and Molecular Biology Letters

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“…Several studies have shown, using human liver microsomes or monitoring metabolites in vivo in pharmacokinetic studies, that hydroxylation can occur at various positions on lignans, isoflavones, and other flavonoids, producing an array of novel secondary oxidation products [18][19][20][21][22]. However, oxidation products appear to be minor metabolites of most polyphenols, probably due to rapid conjugation of the would-be Phase I substrates in the intestinal epithelium and the liver.…”

Section: Sources Of Variation In Phytochemical Metabolism and Disposimentioning

confidence: 99%

Interindividual differences in phytochemical metabolism and disposition

Lampe

Chang

2007

Seminars in Cancer Biology

109

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Many phytochemicals, the bioactive nonnutrient compounds found in plant foods, possess biologic effects associated with reduced risk of various diseases such as cancer. Genetic variation in pathways affecting absorption, metabolism, and distribution of phytochemicals is likely to influence exposure at the tissue level, thus modifying disease risk in individuals. Few studies have examined these genephytochemical interactions in humans. In this review, we discuss the sources of variation in metabolism and disposition of phytochemicals, and focus on two aspects of phytochemical handling that have received some attention: the impact of intestinal bacteria and genetically polymorphic phase II, conjugating enzymes.

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“…It was found that resveratrol is metabolized to piceatannol in the reaction of hydroxylation catalyzed by CYP1A2 (Piver et al 2004) and CYP1B1 (Potter et al 2002). Poor bioavailability of resveratrol caused by its fast metabolism to glucuronides and sulphates limits the use of this stilbene as a potent chemopreventive / chemotherapeutic agent (Walle et al, 2004).…”

Section: Trans-resveratrolmentioning

confidence: 99%

“…The major metabolite M2 has been identified as piceatannol (3,4,3',5'-tetrahydroxystilbene), while 3,4,5,4'-tetrahydroxystilbene was proposed as the M1 product. More recent work (Piver et al, 2004) provided evidence that CYP1A2 is also engaged in the metabolism of transresveratrol to piceatannol and tetrahydroxystilbene M1. Our studies confirmed the possibility of two pathways of metabolism on the grounds of molecular docking analysis.…”

mentioning

confidence: 99%

The Inhibitory Effect of Natural Stilbenes and Their Analogues on Catalytic Activity of Cytochromes P450 Family 1 in Comparison with Other Phenols - Structure and Activity Relationship

Mikstacka¹,

Dutkiewicz²,

Sobiak³

et al. 2012

Phytochemicals - A Global Perspective of Their Role in Nutrition and Health

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Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes

Cited by 128 publications

References 24 publications

In Vitro evaluation of the cytotoxic and anti-proliferative properties of resveratrol and several of its analogs

In Vitro evaluation of the cytotoxic and anti-proliferative properties of resveratrol and several of its analogs

Interindividual differences in phytochemical metabolism and disposition

The Inhibitory Effect of Natural Stilbenes and Their Analogues on Catalytic Activity of Cytochromes P450 Family 1 in Comparison with Other Phenols - Structure and Activity Relationship

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