δ-Viniferin, a Resveratrol Dehydrodimer: One of the Major Stilbenes Synthesized by Stressed Grapevine Leaves

Pezet, R.; Perret, Camille; Jean-Denis, Julien Bernard; Tabacchi, Raffaele; Gindro, Katia; Viret, Olivier

doi:10.1021/jf030227o

Cited by 249 publications

(233 citation statements)

References 23 publications

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“…8A) showed a resveratrol oxidation product with a mass of 454 ([M Ϫ H] Ϫ ϭ 453). This mass is consistent with the formation of a resveratrol dihydrodimer (28,29), which can only occur through a radical mechanism (the complete characterization of this product will be the subject of another article).…”

Section: Mechanism-based Inactivation Of Cox-1 By Resveratrol-supporting

confidence: 76%

Resveratrol is a Peroxidase-mediated Inactivator of COX-1 but Not COX-2

Szewczuk

Forti

Stivala

et al. 2004

Journal of Biological Chemistry

212

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Resveratrol (3,4 ,5-trihydroxy-trans-stilbene) is a phytoalexin found in grapes that has anti-inflammatory, cardiovascular protective, and cancer chemopreventive properties. It has been shown to target prostaglandin H 2 synthase (COX)-1 and COX-2, which catalyze the first committed step in the synthesis of prostaglandins via sequential cyclooxygenase and peroxidase reactions. Resveratrol discriminates between both COX isoforms. It is a potent inhibitor of both catalytic activities of COX-1, the desired drug target for the prevention of cardiovascular disease, but only a weak inhibitor of the peroxidase activity of COX-2, the isoform target for nonsteroidal anti-inflammatory drugs. We have investigated the unique inhibitory properties of resveratrol. We find that it is a potent peroxidase-mediated mechanism-based inactivator of COX-1 only (k inact ‫؍‬ 0.069 ؎ 0.004 s ؊1 , K i(inact) ‫؍‬ 1.52 ؎ 0.15 M), with a calculated partition ratio of 22. Inactivation of COX-1 was time-and concentration-dependent, it had an absolute requirement for a peroxide substrate, and it was accompanied by a concomitant oxidation of resveratrol. Resveratrolinactivated COX-1 was devoid of both the cyclooxygenase and peroxidase activities, neither of which could be restored upon gel-filtration chromatography. Inactivation of COX-1 by [ 3 H]resveratrol was not accompanied by stable covalent modification as evident by both SDS-PAGE and reverse phase-high performance liquid chromatography analysis. Structure activity relationships on methoxy-resveratrol analogs showed that the m-hydroquinone moiety was essential for irreversible inactivation of COX-1. We propose that resveratrol inactivates COX-1 by a "hit-and-run" mechanism, and offers a basis for the design of selective COX-1 inactivators that work through a mechanism-based event at the peroxidase active site.

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Section: Mechanism-based Inactivation Of Cox-1 By Resveratrol-supporting

confidence: 76%

Resveratrol is a Peroxidase-mediated Inactivator of COX-1 but Not COX-2

Szewczuk

Forti

Stivala

et al. 2004

Journal of Biological Chemistry

212

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“…ε-viniferin, Fig. 7) were also identified in grapevine leaves and wine by-products (Jiang et al, 2010;Lima et al, 1999;Moreno-Labanda et al, 2004;Pezet et al, 2003;Püssa et al, 2006;Vitrac et al, 2005).…”

Section: Stilbenesmentioning

confidence: 96%

Wine and grape polyphenols—A chemical perspective

Garrido

Borges

2011

Food Research International

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a b s t r a c tPhenolic compounds constitute a diverse group of secondary metabolites which are present in both grapes and wine. The phenolic content and composition of grape processed products (wine) are greatly influenced by the technological practice to which grapes are exposed. During the handling and maturation of the grapes several chemical changes may occur with the appearance of new compounds and/or disappearance of others, and consequent modification of the characteristic ratios of the total phenolic content as well as of their qualitative and quantitative profile. The non-volatile phenolic qualitative composition of grapes and wines, the biosynthetic relationships between these compounds, and the most relevant chemical changes occurring during processing and storage will be highlighted in this review.

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“…For example, the -viniferin has been identified as the main dimer of trans-resveratrol synthesized in Vitis vinifera leaves infected by Plasmopara viticola [25]. These stilbene phytoalexins were found to be more or less toxic against fungi according to their chemical structure.…”

Section: Introductionmentioning

confidence: 99%

MALDI Mass Spectrometry Imaging for the Simultaneous Location of Resveratrol, Pterostilbene and Viniferins on Grapevine Leaves

et al. 2014

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Abstract:To investigate the in-situ response to a stress, grapevine leaves have been subjected to mass spectrometry imaging (MSI) experiments. The Matrix Assisted Laser Desorption/Ionisation (MALDI) approach using different matrices has been evaluated. Among all the tested matrices, the 2,5-dihydroxybenzoic acid (DHB) was found to be the most efficient matrix allowing a broader range of detected stilbene phytoalexins. Resveratrol, but also more toxic compounds against fungi such as pterostilbene and viniferins, were identified and mapped. Their spatial distributions on grapevine leaves irradiated by UV show their specific colocation around the veins. Moreover, MALDI MSI reveals that resveratrol (and piceids) and viniferins are not specifically located on the same area when leaves are infected by Plasmopara viticola. Results obtained by MALDI mass spectrometry imaging demonstrate that this technique would be essential to improve the level of knowledge concerning the role of the stilbene phytoalexins involved in a stress event.

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δ-Viniferin, a Resveratrol Dehydrodimer: One of the Major Stilbenes Synthesized by Stressed Grapevine Leaves

Cited by 249 publications

References 23 publications

Resveratrol is a Peroxidase-mediated Inactivator of COX-1 but Not COX-2

Resveratrol is a Peroxidase-mediated Inactivator of COX-1 but Not COX-2

Wine and grape polyphenols—A chemical perspective

MALDI Mass Spectrometry Imaging for the Simultaneous Location of Resveratrol, Pterostilbene and Viniferins on Grapevine Leaves

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