Analysis of resveratrol in Burgundy wines

Recent studies have shown that resveratrol (3,5,4'‐trihydroxystilbene), a phytoalexin related to grape disease resistance, could occur in American and Bordeaux wines. It was also suggested that resveratrol might have cardioprotective activities in humans, as a result of drinking wine. We report here the presence of this compound in Burgundy wines. Analysis of resveratrol in wine was carried out using gas chromatography and gas chromatography—mass spectrometry.

Effects of resveratrol on the ultrastructure of Botrytis cinerea conidia and biological significance in plant/pathogen interactions

International audience; Many roles have been ascribed to stilbenes, namely as antimicrobial, deterrent or repellent compounds in plants, protecting them from attacks by fungi, bacteria, nematodes or herbivores, acting both as constitutive and active defense (phytoalexin) compounds. More recently, stilbenes (especially resveratrol and its derivatives) were acclaimed for their wondrous effects and wide range of purported healing and preventive powers as cardioprotective, antitumor, neuroprotective and antioxidant agents. Although there is a huge number of works concerning the role of resveratrol in human health, reports on the antifungal activity of this compound are still scarce. This study …

Anti-Cancer Activity of Resveratrol and Derivatives Produced by Grapevine Cell Suspensions in a 14 L Stirred Bioreactor

International audience; In the present study, resveratrol and various oligomeric derivatives were obtained from a 14 L bioreactor culture of elicited grapevine cell suspensions (Vitis labrusca L.). The crude ethyl acetate stilbene extract obtained from the culture medium was fractionated by centrifugal partition chromatography (CPC) using a gradient elution method and the major stilbenes contained in the fractions were subsequently identified by using a (13)C-NMR-based dereplication procedure and further 2D NMR analyses including HSQC, HMBC, and COSY. Beside δ-viniferin (2), leachianol F (4) and G (4'), four stilbenes (resveratrol (1), ε-viniferin (5), pallidol (3) and a newly characterized…

The climate in relation to the quality/typicity of the wines of Burgundy: the 1995 vintage

(1996). The climate in relation to the quality/typicity of the wines of Burgundy: the 1995 vintage. Journal of Wine Research: Vol. 7, No. 2, pp. 125-129.

Changes in the Phytoalexin Content of Various Vitis Spp. in Response to Ultraviolet C Elicitation

The phytoalexin production potential of three American Vitis species and that of three cultivars of Vitis vinifera were evaluated in response to UV-C irradiation. Time course changes in resveratrol, piceid, epsilon-viniferin, and pterostilbene contents were studied within 3 days after a short UV-C irradiation. Results show that the two major stilbenes accumulated as a response to UV-C elicitation are resveratrol and epsilon-viniferin, a resveratrol dehydrodimer, the concentration of both compounds usually reaching quantities >100 microgram/g of fresh weight. In contrast, piceid and pterostilbene were constantly produced in low quantities. Owing to the results obtained, the role of stilbene …

Development of methods using phytoalexin (resveratrol) assessment as a selection criterion to screen grapevine in vitro cultures for resistance to grey mould (Botrytis cinerea)

The purpose of this research was, firstly to determine the ability of grapevine in vitro cultures to synthesize resveratrol, a stilbene-type phytoalexin that is considered to be a good marker for resistance of grapevines to Botrytis cinerea, the causal organism for grey mould. Secondly, this study sought to establish the relationship between phytoalexin production potential and resistance to Botrytis cinerea in grapevines. In this aim, resveratrol production was assessed in 13 Vitis species or cultivars. A good correlation appeared between resveratrol production by grapevine in vitro cultures and grey mould resistance except for two Vitis spp. for which no correlation was observed, thus sug…

Biological activity of resveratrol, a stilbenic compound from grapevines, against Botrytis cinerea, the causal agent for gray mold

The biological activity of resveratrol, a stilbenic compound synthesized by grapevines in response to various stresses, was reevaluated against Botrytis cinerea using a novel in vitro system that enabled direct observation of the fungus with an inverted microscope. We determined that 90 μg resveratrol/ml reduced germination of B. cinerea conidia by ca. 50%. Moreover, resveratrol was shown to significantly reduce mycelial growth of B. cinerea at concentrations ranging from 60 to 140 μg/ml. Exposure to resveratrol at concentrations ranging from 60 to 140 μg/ml resulted in cytological changes in B. cinerea, such as production of secondary or tertiary germ tubes by conidia, cytoplasmic granulat…

Chemical messages in 170-year-old champagne bottles from the Baltic Sea: Revealing tastes from the past

International audience; Archaeochemistry as the application of the most recent analytical techniques to ancient samples now provides an unprecedented understanding of human culture throughout history. In this paper, we report on a multiplatform analytical investigation of 170-y-old champagne bottles found in a shipwreck at the bottom of the Baltic Sea, which provides insight into winemaking practices used at the time. Organic spectroscopy-based nontargeted metabolomics and metallomics give access to the detailed composition of these wines, revealing, for instance, unexpected chemical characteristics in terms of small ion, sugar, and acid contents as well as markers of barrel aging and Maill…

The production of resveratrol (3,5,4'‐trihydroxystilbene) by grapevinein vitrocultures, and its application to screening for grey mould resistance

The ability of grapevine in vitro cultures to synthesise the phytoalexin precursor resveratrol in response to ultraviolet light irradiations is investigated in order to develop methods for screening for resistance to grey mould (Botrytis cinerea Pers.) in grapevines produced as a result of somatic embryogenesis. It is demonstrated that resveratrol formation can be reproducibly induced in leaves of in vitro plantlets. Differences in the production of resveratrol among the three varieties of Vitis vinifera tested (Pinot Noir, Chardonnay and Cabernet Sauvignon) were consistent with observations regarding their field susceptibility to grey mould. The use of phytoalexin induction and of in vitro…

Metabolism of stilbene phytoalexins by Botrytis cinerea: 1. Characterization of a resveratrol dehydrodimer

Abstract Resveratrol, a grapevine phytoalexin, is metabolized by a laccase-like stilbene-oxidase of Botrytis cinerea, the causal organism for grey mould. Characterization of one major metabolite formed during this degradation process as a resveratrol dehydrodimer allowed us to precize the reaction mechanism of this enzyme on stilbenes.

Induction of Phytoalexin (Resveratrol) Synthesis in Grapevine Leaves Treated with Aluminum Chloride (AlCl3)

Production of the Phytoalexin Resveratrol by Grapes as a Response to Botrytis Attack Under Natural Conditions

Le resveratrol (3,5,4'-trihydroxystilbene) est un des mebolites de stress produit par la vigne en reponse a une infection parasitaire ou une blessure. La distribution de cette molecule dans des lesions limitees causees par Botrytis cinerea sur des grappes de raisins a maturite au vignoble a ete etudiee. Le resveratrol est localise principalement dans les fruits sains entourant les zones infectees. Cette reponse localisee contribue a limiter l'extension du pathogene tant que les conditions climatiques lui sont defavorables. Lorsque les conditions deviennent favorables; c'est-a-dire apres une periode humide et chaude, une expansion rapide des lesions est alors observee sur les fruits en depit…

The Significance of Stilbene-Type Phytoalexin Degradation by Culture Filtrates of Botrytis Cinerea in the Vine-Botrytis Interaction

Phytoalexins, antimicrobial compounds, synthesized by a plant in response to infection or a variety of stresses are known to be the most efficient way by which grapevines withstand an attack by Botrytis cinerea Pers., the causal organism for grey mould. In that plant, such responses include the production of a simple stilbene, resveratrol, and the biosynthetically related compounds, viniferins and pterostilbene. If stilbene-type phytoalexins represent a contributory factor in the resistance of grapevines to B.cinerea, the capacity of the pathogen to metabolize antifungal compounds released by the host could also play a significant role in the outcome of the interaction between grapevines an…

Structural studies of adsorbed protein (betalactoglobulin) on natural clay (montmorillonite)

International audience; In this work, the adsorption of a small globular protein (betalactoglobulin, BLG), on a natural montmorillonite clay (Mt) was investigated in acidic buffer (pH = 3). The combination of different characterization techniques such as zetametry, X-ray diffraction, transmission electronic microscopy, fluorescence and solid state nuclear magnetic resonance spectroscopies shed light on the interaction mechanism between the clay mineral and the proteins. For low BLG concentration, a slight increase of the interlayer spacing of the clay mineral was noticed as well as structural changes of the protein. In contrast, as the concentration of BLG increased, the adsorption led to a…

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Cytotoxicity of Labruscol, a New Resveratrol Dimer Produced by Grapevine Cell Suspensions, on Human Skin Melanoma Cancer Cell Line HT-144

IF 2.861; International audience; A new resveratrol dimer (1) called labruscol, has been purified by centrifugal partition chromatography of a crude ethyl acetate stilbene extract obtained from elicited grapevine cell suspensions of Vitis labrusca L. cultured in a 14-liter stirred bioreactor. One dimensional (1D) and two dimensional (2D) nuclear magnetic resonance (NMR) analyses including ¹H, 13C, heteronuclear single-quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), and correlation spectroscopy (COSY) as well as high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) were used to characterize this compound and to unambiguously identify it as a new st…

Stilbene Content of MatureVitis viniferaBerries in Response to UV-C Elicitation

A method using HPLC analysis has been used to compare the level of resveratrol and its derivatives, piceid, pterostilbene and epsilon-viniferin, in grapevine berries of three Vitis vinifera varieties. The concentration of these compounds has been evaluated in healthy and Botrytis cinerea infected grape clusters, both in natural vineyard conditions and in response to UV elicitation.

Degradation of stilbene-type phytoalexins in relation to the pathogenicity of Botrytis cinerea to grapevines

The ability of eight isolates of Botrytis cinerea to degrade the stilbene phytoalexins, resveratrol and pterostilbene, was compared with their pathogenicity to grapevines. All strains which degraded resveratrol and pterostilbene were highly or moderately pathogenic to in vitro cultures of grapevines (Vitis rupestris) after inoculation with agar disks containing mycelium, while those which were unable to degrade phytoalexins were non-pathogenic. In all cases, the hydroxystilbene-degrading activity was related to the presence of laccase activity in the culture filtrates, as shown by using syringaldazine as substrate. The role of laccase-mediated degradation of phytoalexins in relation to path…

Solid-state NMR investigation on the interactions between a synthetic montmorillonite and two homopolypeptides.

Abstract Interactions of two homopolypeptides (polylysine and polyglutamic acid) with a synthetic montmorillonite were studied by 1H MAS, 1H–27Al HETCOR and 1H–13C CP-MAS NMR experiments. 1H–27Al HETCOR with 1H spin-diffusion NMR appears to be a powerful probe for the identification of the polypeptide fragments, which interact with the montmorillonite interlayer surfaces. In particular, selective interactions were observed between the polypeptide side-chains and the montmorillonite octahedral aluminum atoms. 1H–13C CP-MAS NMR experiments were used to assess the dynamics of the two polypeptides through the measurement of the t1/2 characteristic time of selected carbons. Results indicate that…

CHEMICAL INDUCTION OF PHYTOALEXIN SYNTHESIS IN GRAPEVINES: APPLICATION TO THE CONTROL OF GREY MOULD IN THE VINEYARD