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Jean-michel Mérillon - One of the best experts on this subject based on the ideXlab platform.
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characterization of Stilbene composition in grape berries from wild vitis species in year to year harvest
Journal of Agricultural and Food Chemistry, 2020Co-Authors: Julien Gabaston, Tristan Richard, Josep Valls Fonayet, Celine Franc, Pierre Waffoteguo, Gilles De Revel, Ghislaine Hilbert, Eric Gomes, Jean-michel MérillonAbstract:Asian and American Vitis species possess a strong potential for crossbreeding programs, owing to their several resistance properties. Stilbenes are phenolic compounds present in grape berries and are well-known for their main role as phytoalexins and resistance to biotic stresses in plants. However, their identification and quantification in grape berries from wild Vitis remains unexplored. A mass spectrometry multiple reaction monitoring method combined with the analysis of pure standards allowed for the unambiguous characterization of 20 Stilbenes in the grape berry skin extracts of nine native Vitis species and one cultivated Vitis vinifera species (cv. Cabernet Sauvignon). A main occurrence of monomeric (Z-piceid, E-piceid, E-isorhapontin, and E-astringin), dimeric (E-e-viniferin, Z-e-viniferin, and pallidol), and oligomeric (isohopeaphenol and r-viniferin) Stilbenes was highlighted. Some Stilbenes were clearly characterized for the first time in grape berries, such as the dimers ampelopsin A, E-vitisinol C, and parthenocissin A as well as the tetramers r2-viniferin and r-viniferin. Stilbene composition and content varied widely among several Vitis species and vintage years.
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Unusual Stilbene glucosides from Vitis vinifera roots
OENO One, 2019Co-Authors: Iris Aja, Jean-michel Mérillon, Grégory Da Costa, Eric Pedrot, Marie-laure Iglesias, Antonio Palos Pinto, Josep Valls, Nassima Chaher, M. Begoña Ruiz-larrea, Djebbar AtmaniAbstract:Aim: Stilbenes are well-known phytoalexins present in vine and wine. Stilbene glucosides have been identified in wine; however, other than piceid, these compounds have never been reported to be present in the woody parts of grapevine. The aims of this study were to investigate the presence of Stilbene glucosides in the woody parts of the vine and to evaluate their cytotoxic activity, in comparison with that of resveratrol, in human hepatoma HepG2 cells. Methods and results: Stilbene glucosides were isolated from a Vitis vinifera root extract. The extract was partitioned with ethyl acetate and fractionated by polyamide gel column chromatography. Pure compounds were obtained by semipreparative high-performance liquid chromatography. These were then identified by mass spectrometry and nuclear magnetic resonance (NMR) analyses, including analysis of two-dimensional NMR spectra. In addition to resveratrol, five Stilbene glucosides were found: resveratroloside, resveratrol rutinoside, trans-epsilon-viniferin diglucoside, cis-epsilon-viniferin diglucoside and piceid. Of these, the first four showed cytotoxic effects against HepG2 cells when the crystal violet assay was used to determine cell viability. Conclusion: In addition to resveratrol and piceid, this is the first report of the presence of four glucosylated derivatives of resveratrol (resveratroloside, resveratrol rutinoside, and trans- and cis-epsilon-viniferin diglucosides) in the woody parts of vine. These compounds showed significant cytotoxicity against HepG2 cells. Significance and impact of the study: Stilbenes are well-known biological compounds. Grapevine is one of the main sources of this family of polyphenols. Other than piceid, Stilbene glucosides have been identified in wine but never in the woody parts of vine. This is the first study in which five glucosylated derivatives of resveratrol were isolated from woody parts of vine. They were also shown to exert antiproliferative effects in human hepatoma HepG2 cells.
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Stilbenes from Vitis vinifera L. Waste: A Sustainable Tool for Controlling Plasmopara Viticola.
Journal of agricultural and food chemistry, 2017Co-Authors: Julien Gabaston, Emma Cantos-villar, Benoit Biais, Pierre Waffo-teguo, Elodie Renouf, Marie-france Corio-costet, Tristan Richard, Jean-michel MérillonAbstract:Stilbene-enriched extracts from Vitis vinifera waste (cane, wood, and root) were characterized by UHPLC-MS. Eleven Stilbenes were identified and quantified as follows: ampelopsin A, (E)-piceatannol, pallidol, (E)-resveratrol, hopeaphenol, isohopeaphenol, (E)-e-viniferin, (E)-miyabenol C, (E)-ω-viniferin, r2-viniferin, and r-viniferin. The fungicide concentration inhibiting 50% of growth of Plasmopara viticola sporulation (IC50) was determined for the extracts and also for the main compounds isolated. r-Viniferin followed by hopeaphenol and r2-viniferin showed low IC50 and thus high efficacy against Plasmopara viticola. Regarding Stilbene extracts, wood extract followed by root extract showed the highest antifungal activities. These data suggest that Stilbene complex mixtures from Vitis vinifera waste could be used as a cheap source of bioactive Stilbenes for the development of natural fungicides.
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Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae
Natural product reports, 2012Co-Authors: Céline Rivière, Alison D. Pawlus, Jean-michel MérillonAbstract:Covering: up to the end of March 2012 Stilbenoids, a family of polyphenols known for the complexity of their structure and for their diverse biological activities, occur with a limited but heterogeneous distribution in the plant kingdom. The most prominent Stilbene containing plant family, the Vitaceae, represented by the famous wine producing grape vines Vitis vinifera L., is one of the richest sources of novel Stilbenes currently known, together with other families, such as Dipterocarpaceae, Gnetaceae and Fabaceae. This review focuses on the distribution of Stilbenes and 2-arylbenzofuran derivatives in the plant kingdom, the chemical structure of Stilbenes in the Vitaceae family and their taxonomic implication.
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determination of Stilbenes delta viniferin trans astringin trans piceid cis and trans resveratrol epsilon viniferin in brazilian wines
Journal of Agricultural and Food Chemistry, 2005Co-Authors: Xavier Vitrac, Tristan Richard, Jean-michel Mérillon, Josep Valls, Aurelie Bornet, Regina Vanderlinde, Jeanclaude Delaunay, Pierrelouis TeissedreAbstract:Phenolics from grapes and wines can play a role against oxidation and development of atherosclerosis. Stilbenes have been shown to protect lipoproteins from oxidative damage and to have cancer chemopreventive activity. We describe a method for the direct determination of Stilbenes in several red wines using high-performance liquid chromatography with UV detection. In a survey of 12 commercial wines from the south of Brazil (Rio Grande del Sul), levels of delta-viniferin are reported for the first time in different varieties of red wines. Brazilian red wine contains trans-astringin, trans-piceid, trans-resveratrol, cis-resveratrol (in high quantity: 5 times more than the trans form), epsilon-viniferin, and a compound isolated for the first time in wine, trans-delta-viniferin. Isolation and identification of delta-viniferin was achieved by NMR after extraction and fractionation of red wine phenolics. delta-Viniferin contributes, as well as cis-resveratrol and trans-piceid, to a significant proportion of Stilbenes in wine dietary intake, particularly with Merlot varieties containing an average level of 10 mg/L for delta-viniferin, 15 mg/L for cis-resveratrol, and 13 mg/L for trans-piceid. The total Stilbene intake from wine origin was estimated for the Brazilian population as 5.3 mg/day per person (on the basis of a regular wine consumption of 160 mL/day). delta-Viniferin can contribute to around 20% of total Stilbenes in wine (average of 6.4 mg/L in red Brazilian wines). It would be important in the future to investigate the origins of the differences in wine Stilbene levels in relation to the vine varieties, and the bioavailability of the newly extracted Stilbene delta-viniferin in plasma after consumption of different types of wines.
K V Kiselev - One of the best experts on this subject based on the ideXlab platform.
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effect of spruce pjsts1a pjsts2 or pjsts3 gene overexpression on Stilbene biosynthesis in callus cultures of vitis amurensis rupr
Biotechnology and Applied Biochemistry, 2020Co-Authors: K V Kiselev, A S Dubrovina, Andrey R Suprun, Zlata V OgnevaAbstract:Stilbenes are natural compounds protecting plants against microbial pathogens and known to possess valuable biologically active properties. In the present study, we established transgenic grapevine callus cell cultures overexpressing three Stilbene synthase (STS) genes of spruce Picea jezoensis PjSTS1a, PjSTS2, and PjSTS3. Transformation of Vitis amurensis calli with the PjSTS1a, PjSTS2, and PjSTS3 genes significantly increased total content of Stilbenes in 3.6-6, 2.5-2.9, and 4.1-16.1 times, respectively, in comparison with the control calli. The most pronounced positive effect on the accumulation of Stilbenes was observed for the PjSTS3-overexpressing calli where the total content of Stilbenes was increased up to 3.1 mg/g DW, and the Stilbene production reached 25.4 mg/L. These values were higher than those achieved for the grapevine callus cell cultures overexpressing three STS genes from V. amurensis. Thus, transformation of grapevine cell cultures with spruce STS genes with a relatively low degree of homology to the endogenous VaSTSs is a more effective strategy for induction of plant secondary metabolite biosynthesis than using the grapevine genes for the overexpression experiments.
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action of ultraviolet c radiation and p coumaric acid on Stilbene accumulation and expression of Stilbene biosynthesis related genes in the grapevine vitis amurensis rupr
Acta Physiologiae Plantarum, 2019Co-Authors: K V Kiselev, V P Grigorchuk, Andrey R Suprun, Zlata V Ogneva, A S DubrovinaAbstract:This paper investigated the effects of p-coumaric acid (CA) on Stilbene biosynthesis in healthy cuttings of grapevine Vitis amurensis Rupr. under control conditions and after ultraviolet (UV-C) irradiation. It has been shown that the content of the detected six Stilbenes (cis-piceid, t-piceid, t-e-viniferin, cis-e-viniferin, t-resveratrol, and t-δ-viniferin) increased after feeding with CA up to 0.5 mg g−1 of the dry weight (DW), which is 2.4 times higher than that under control conditions. Feeding with CA and UV-C irradiation exerted a combined positive effect on the content of Stilbenes increasing it to 0.7 mg g−1 DW. In addition, the CA treatment improved viability of the cuttings after the UV-C treatment. The elevation in Stilbene content induced by CA and UV-C correlated with induction of Stilbene biosynthetic genes encoding Stilbene synthases, resveratrol O-glucosyltransferase, polyphenol oxidase, and cationic peroxidase. The data indicate that feeding with the precursors of phenolic compounds could be an effective strategy for activation of Stilbene production.
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Stilbene content and expression of Stilbene synthase genes in cell cultures of vitis amurensis treated with cinnamic and caffeic acids
Biotechnology and Applied Biochemistry, 2018Co-Authors: A P Tyunin, K V Kiselev, V P Grigorchuk, Nikolay N. NityagovskyAbstract:It has previously been shown that exogenous application of p-coumaric acid (CA), a precursor of phenolic compounds, improved Stilbene production in cell cultures of Vitis amurensis. This study examines the effect of cinnamic (Cin) and caffeic (Caf) acids, which are also phenolic precursors, on Stilbene biosynthesis in the cell cultures. Five Stilbenes, t-resveratrol diglucoside, t-piceid (t-resveratrol glucoside), t-resveratrol, t-e-viniferin, and t-δ-viniferin, were found in the treated and untreated cells. Cin acid increased the total Stilbene production in the grape cell cultures 2.3-3.5 times in comparison with that in the untreated cells. Caf acid increased the total Stilbene production by 1.8- to 1.9-fold, but this increase was not considerably different from Stilbene production in the untreated cells. Cin acid affected the total Stilbene production via a marked increase in the content of t-resveratrol diglucoside (up to 2.2 times), t-piceid (up to three times), t-resveratrol (up to 5.1 times), t-e-viniferin (up to eight times), and t-δ-viniferin (up to 9.2 times). Transcription levels of VaSTS5, 6, 7, 8, and 10 genes considerably increased under 0.1, 0.25, and 0.5 mM Cin acid. These results indicate that Cin acid increased Stilbene production in V. amurensis calli via a selective enhancement of STS gene expression.
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activation of Stilbene synthesis in cell cultures of vitis amurensis by calcium dependent protein kinases vacpk1 and vacpk26
Plant Cell Tissue and Organ Culture, 2017Co-Authors: Olga A Aleynova, K V Kiselev, A S DubrovinaAbstract:Stilbenes, including trans-resveratrol (3,4′,5-trihydroxy-trans-Stilbene), are known to exert beneficial health effects and contribute to plant biotic stress resistance. Much remains to be discovered about the cell signaling pathways regulating Stilbene biosynthesis. It has recently been shown that overexpression of the calcium-dependent protein kinase VaCPK20 gene considerably increased t-resveratrol accumulation in cell cultures of Vitis amurensis. In this study, we analyzed the involvement of other CDPK family members, VaCPK1 and VaCPK26, on Stilbene synthesis and biomass production by cell cultures of V. amurensis. We showed that overexpression of the VaCPK1 and 26 genes induced production of Stilbenes by 1.7–4.6-fold (for VaCPK1) and by 2.5–6.2-fold (for VaCPK26) in several independently established cell lines compared to the empty vector-transformed control. Using HPLC-UV-MS, we detected five Stilbenes in the grape cells: t-resveratrol diglucoside, t-piceid, t-resveratrol, e- and δ-viniferin. The VaCPK1- and VaCPK26-transformed calli were capable of producing 1.4–3.1 and 1.8–4.9 mg/l of t-resveratrol, respectively (up to 0.4 for and 0.6 mg/g of dry weight for VaCPK26 and VaCPK1, respectively), while the control line synthesized only 0.5 mg/l of t-resveratrol (0.07 mg/g DW). The up-regulation of t-resveratrol production in the VaCPK1- and VaCPK26-overexpressing grape calli correlated with a significant up-regulation of Stilbene synthase (STS) gene expression, especially VaSTS7. The data indicate that VaCPK1 and 26 genes, which are close homologues of VaCPK20, are positive regulators of Stilbene biosynthesis in grapevine.
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Stilbene accumulation and expression of Stilbene biosynthesis pathway genes in wild grapevine vitis amurensis rupr
Planta, 2017Co-Authors: K V Kiselev, Olga A Aleynova, V P Grigorchuk, A S DubrovinaAbstract:Main conclusion We detected and quantified six Stilbenes (cis-piceid,t-piceid,t-e-viniferin,cis-e-viniferin,t-resveratrol, andt-δ-viniferin) in the leaves, petioles, berry skins, and seeds of wild-growingVitis amurensis. The highest content of Stilbenes and expression of Stilbene biosynthesis genes were in the probes collected in the autumn and after ultraviolet elicitation. Stilbenes, including the best-studied Stilbene resveratrol, are known to display valuable bioactivities and protect plants against various pathogens. There is a lack of studies on Stilbene quantities and spectrum combined with an analysis of the Stilbene biosynthesis pathway gene expression in Vitaceae species, despite grapevine is an important source of Stilbenes. This study presents an analysis of Stilbene spectrum, Stilbene content, and expression of Stilbene biosynthesis genes both in natural conditions and after ultraviolet (UV-C) elicitation in the leaves, petioles, berry skins, and seeds of wild-growing Vitis amurensis, a highly stress-tolerant plant species. Using HPLC analysis, we detected six main Stilbenes: cis-piceid (up to 0.257 mg/g of dry weight (DW) of plant material), t-piceid (up to 0.055 mg/g DW), t-e-viniferin (up to 0.122 mg/g DW), cis-e-viniferin (up to 0.031 mg/g DW), t-resveratrol (from 0.004 to 0.121 mg/g DW), and t-δ-viniferin (up to 0.019 mg/g DW). The Stilbenes were actively synthesized in the leaves (total Stilbenes 0.39 mg/g DW) and berry skins (total Stilbenes 0.249 mg/g DW) of V. amurensis collected in the autumn. qRT-PCR revealed that the Stilbene synthase (STS), resveratrol O-glucosyltransferase (Glu1), and polyphenol oxidase (PPO1) genes were actively expressed in the analyzed tissues. The resveratrol methyltransferase (Romt1) gene, which is known to catalyze biosynthesis of pteroStilbene, was also expressed, but no pteroStilbene has been detected in V. amurensis. The content of all detected Stilbenes and expression of Stilbene biosynthesis genes increased after UV-C treatment, except for Romt1. The data are important for understanding the Stilbene biosynthesis in grapevine.
Tristan Richard - One of the best experts on this subject based on the ideXlab platform.
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characterization of Stilbene composition in grape berries from wild vitis species in year to year harvest
Journal of Agricultural and Food Chemistry, 2020Co-Authors: Julien Gabaston, Tristan Richard, Josep Valls Fonayet, Celine Franc, Pierre Waffoteguo, Gilles De Revel, Ghislaine Hilbert, Eric Gomes, Jean-michel MérillonAbstract:Asian and American Vitis species possess a strong potential for crossbreeding programs, owing to their several resistance properties. Stilbenes are phenolic compounds present in grape berries and are well-known for their main role as phytoalexins and resistance to biotic stresses in plants. However, their identification and quantification in grape berries from wild Vitis remains unexplored. A mass spectrometry multiple reaction monitoring method combined with the analysis of pure standards allowed for the unambiguous characterization of 20 Stilbenes in the grape berry skin extracts of nine native Vitis species and one cultivated Vitis vinifera species (cv. Cabernet Sauvignon). A main occurrence of monomeric (Z-piceid, E-piceid, E-isorhapontin, and E-astringin), dimeric (E-e-viniferin, Z-e-viniferin, and pallidol), and oligomeric (isohopeaphenol and r-viniferin) Stilbenes was highlighted. Some Stilbenes were clearly characterized for the first time in grape berries, such as the dimers ampelopsin A, E-vitisinol C, and parthenocissin A as well as the tetramers r2-viniferin and r-viniferin. Stilbene composition and content varied widely among several Vitis species and vintage years.
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Stilbenes from Vitis vinifera L. Waste: A Sustainable Tool for Controlling Plasmopara Viticola.
Journal of agricultural and food chemistry, 2017Co-Authors: Julien Gabaston, Emma Cantos-villar, Benoit Biais, Pierre Waffo-teguo, Elodie Renouf, Marie-france Corio-costet, Tristan Richard, Jean-michel MérillonAbstract:Stilbene-enriched extracts from Vitis vinifera waste (cane, wood, and root) were characterized by UHPLC-MS. Eleven Stilbenes were identified and quantified as follows: ampelopsin A, (E)-piceatannol, pallidol, (E)-resveratrol, hopeaphenol, isohopeaphenol, (E)-e-viniferin, (E)-miyabenol C, (E)-ω-viniferin, r2-viniferin, and r-viniferin. The fungicide concentration inhibiting 50% of growth of Plasmopara viticola sporulation (IC50) was determined for the extracts and also for the main compounds isolated. r-Viniferin followed by hopeaphenol and r2-viniferin showed low IC50 and thus high efficacy against Plasmopara viticola. Regarding Stilbene extracts, wood extract followed by root extract showed the highest antifungal activities. These data suggest that Stilbene complex mixtures from Vitis vinifera waste could be used as a cheap source of bioactive Stilbenes for the development of natural fungicides.
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isorhapontigenin a novel bioactive Stilbene from wine grapes
Food Chemistry, 2012Co-Authors: Maria Isabel Fernandezmarin, Tristan Richard, Raul F Guerrero, M C Garciaparrilla, Belen Puertas, Miriam Rodriguezwerner, Peter Winterhalter, Jeanpierre Monti, Emma CantosvillarAbstract:Abstract Stilbenes are a family of bioactive compounds found in plants. However, only a few Stilbenes are present in the human diet. Grape and wine are the main dietary source of Stilbenes, resveratrol and piceid being the most common ones. Ultraviolet C light (UVC) postharvest treatment was used to obtain significantly increased Stilbene concentration in grapes. A new, previously undescribed-in-grapes Stilbene was found after UVC treatment. The process followed to isolate and identify this unknown Stilbene is described in the present work. This isolation involved several fractionation steps including counter current chromatography and semi-preparative HPLC due to its low concentration and the presence of structurally related compounds. The structure of the compound was unequivocally identified by NMR spectroscopy analyses including 1 H-NMR; COSY; ROESY; HSQC and HMBC. The compound was identified as isorhapontigenin (ISOR), a Stilbene found in traditional Asian medicinal plants. To the best of our knowledge this is the first report of its occurrence in grapes.
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determination of Stilbenes delta viniferin trans astringin trans piceid cis and trans resveratrol epsilon viniferin in brazilian wines
Journal of Agricultural and Food Chemistry, 2005Co-Authors: Xavier Vitrac, Tristan Richard, Jean-michel Mérillon, Josep Valls, Aurelie Bornet, Regina Vanderlinde, Jeanclaude Delaunay, Pierrelouis TeissedreAbstract:Phenolics from grapes and wines can play a role against oxidation and development of atherosclerosis. Stilbenes have been shown to protect lipoproteins from oxidative damage and to have cancer chemopreventive activity. We describe a method for the direct determination of Stilbenes in several red wines using high-performance liquid chromatography with UV detection. In a survey of 12 commercial wines from the south of Brazil (Rio Grande del Sul), levels of delta-viniferin are reported for the first time in different varieties of red wines. Brazilian red wine contains trans-astringin, trans-piceid, trans-resveratrol, cis-resveratrol (in high quantity: 5 times more than the trans form), epsilon-viniferin, and a compound isolated for the first time in wine, trans-delta-viniferin. Isolation and identification of delta-viniferin was achieved by NMR after extraction and fractionation of red wine phenolics. delta-Viniferin contributes, as well as cis-resveratrol and trans-piceid, to a significant proportion of Stilbenes in wine dietary intake, particularly with Merlot varieties containing an average level of 10 mg/L for delta-viniferin, 15 mg/L for cis-resveratrol, and 13 mg/L for trans-piceid. The total Stilbene intake from wine origin was estimated for the Brazilian population as 5.3 mg/day per person (on the basis of a regular wine consumption of 160 mL/day). delta-Viniferin can contribute to around 20% of total Stilbenes in wine (average of 6.4 mg/L in red Brazilian wines). It would be important in the future to investigate the origins of the differences in wine Stilbene levels in relation to the vine varieties, and the bioavailability of the newly extracted Stilbene delta-viniferin in plasma after consumption of different types of wines.
A S Dubrovina - One of the best experts on this subject based on the ideXlab platform.
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The Bark of the Spruce Picea jezoensis Is a Rich Source of Stilbenes
'MDPI AG', 2021Co-Authors: Andrey R Suprun, Olga A Aleynova, A S Dubrovina, Konstantin V. KiselevAbstract:Stilbenes are plant phenolic secondary metabolites that show beneficial effects on human health and possess high antifungal activity against plant pathogens. Currently, a search for plant sources with high Stilbene levels is relevant, since Stilbene content in various plant species can vary substantially and is often at a low level. In this paper, the bark and wood of Picea jezoensis were analyzed for the content and composition of Stilbenes and compared with other known Stilbene sources. The HPLC-MS analysis of P. jezoensis bark and wood extracted with different solvents and at different temperatures revealed the presence of 11 and 5 Stilbenes, respectively. The highest number of Stilbenes of 171 and 229 mg per g of the dry weight (mg/g DW) was extracted from the bark of P. jezoensis using methanol or ethanol at 60 °C for 2 h. Trans-astringin, trans-piceid, and trans-isorhapontin prevailed over other stilbenoids (99% of all detected Stilbenes). The most abundant Stilbene was trans-isorhapontin, reaching 217 mg/g DW or 87% of all Stilbenes. An increase in the extraction time from 2 to 6 h did not considerably increase the detected level of Stilbenes, while lower extraction temperatures (20 and 40 °C) significantly lowered Stilbene yield. The content of Stilbenes in the P. jezoensis bark considerably exceeded Stilbene levels in other Stilbene-producing plant species. The present data revealed that the bark of P. jezoensis is a rich source of Stilbenes (primarily trans-isorhapontin) and provided effective Stilbene extraction procedures
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The Influence of the Grapevine Bacterial and Fungal Endophytes on Biomass Accumulation and Stilbene Production by the In Vitro Cultivated Cells of Vitis amurensis Rupr.
'MDPI AG', 2021Co-Authors: Olga A Aleynova, A S Dubrovina, Andrey R Suprun, Nikolay N. Nityagovsky, Konstantin V. KiselevAbstract:Plant endophytes are known to alter the profile of secondary metabolites in plant hosts. In this study, we identified the main bacterial and fungal representatives of the wild grape Vitis amurensis Rupr. microbiome and investigated a cocultivation effect of the 14 endophytes and the V. amurensis cell suspension on biomass accumulation and Stilbene biosynthesis. The cocultivation of the V. amurensis cell culture with the bacteria Agrobacterium sp., Bacillus sp., and Curtobacterium sp. for 2 weeks did not significantly affect the accumulation of cell culture fresh biomass. However, it was significantly inhibited by the bacteria Erwinia sp., Pantoea sp., Pseudomonas sp., and Xanthomonas sp. and fungi Alternaria sp., Biscogniauxia sp., Cladosporium sp., Didymella sp. 2, and Fusarium sp. Cocultivation of the grapevine cell suspension with the fungi Didymella sp. 1 and Trichoderma sp. resulted in cell death. The addition of endophytic bacteria increased the total Stilbene content by 2.2–5.3 times, while the addition of endophytic fungi was more effective in inducing Stilbene accumulation by 2.6–16.3 times. The highest content of Stilbenes in the grapevine cells cocultured with endophytic fungi was 13.63 and 13.76 mg/g of the cell dry weight (DW) after cultivation with Biscogniauxia sp. and Didymella sp. 2, respectively. The highest content of Stilbenes in the grapevine cells cocultured with endophytic bacteria was 4.49 mg/g DW after cultivation with Xanthomonas sp. The increase in Stilbene production was due to a significant activation of phenylalanine ammonia lyase (PAL) and Stilbene synthase (STS) gene expression. We also analyzed the sensitivity of the selected endophytes to eight antibiotics, fluconazole, and trans-resveratrol. The endophytic bacteria were sensitive to gentamicin and kanamycin, while all selected fungal strains were resistant to fluconazole with the exception of Cladosporium sp. All endophytes were tolerant of trans-resveratrol. This study showed that grape endophytes stimulate the production of Stilbenes in grape cell suspension, which could further contribute to the generation of a new stimulator of Stilbene biosynthesis in grapevine or grape cell cultures
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Exogenous Stilbenes Improved Tolerance of Arabidopsis thaliana to a Shock of Ultraviolet B Radiation
'MDPI AG', 2021Co-Authors: Zlata V Ogneva, Olga A Aleynova, A S Dubrovina, Andrey R Suprun, Vlada V. Volkonskaia, Konstantin V. KiselevAbstract:Excessive ultraviolet B (UV-B) irradiation is one of the most serious threats leading to severe crop production losses. It is known that secondary metabolite biosynthesis plays an important role in plant defense and forms a protective shield against excessive UV-B irradiation. The contents of Stilbenes and other plant phenolics are known to sharply increase after UV-B irradiation, but there is little direct evidence for the involvement of Stilbenes and other plant phenolics in plant UV-B protection. This study showed that foliar application of trans-resveratrol (1 and 5 mM) and trans-piceid (5 mM) considerably increased tolerance to a shock of UV-B (10 min at 1800 µW cm−2 of irradiation intensity) of four-week-old Arabidopsis thaliana plants that are naturally incapable of Stilbene production. Application of trans-resveratrol and trans-piceid increased the leaf survival rates by 1–2%. This Stilbene-induced improvement in UV-B tolerance was higher than after foliar application of the Stilbene precursors, p-coumaric and trans-cinnamic acids (only 1–3%), but less than that after treatment with octocrylene (19–24%), a widely used UV-B absorber. Plant treatment with trans-resveratrol increased expression of antioxidant and stress-inducible genes in A.thaliana plants and decreased expression of DNA repair genes. This study directly demonstrates an important positive role of Stilbenes in plant tolerance to excessive UV-B irradiation, and offers a new approach for plant UV-B protection
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effect of spruce pjsts1a pjsts2 or pjsts3 gene overexpression on Stilbene biosynthesis in callus cultures of vitis amurensis rupr
Biotechnology and Applied Biochemistry, 2020Co-Authors: K V Kiselev, A S Dubrovina, Andrey R Suprun, Zlata V OgnevaAbstract:Stilbenes are natural compounds protecting plants against microbial pathogens and known to possess valuable biologically active properties. In the present study, we established transgenic grapevine callus cell cultures overexpressing three Stilbene synthase (STS) genes of spruce Picea jezoensis PjSTS1a, PjSTS2, and PjSTS3. Transformation of Vitis amurensis calli with the PjSTS1a, PjSTS2, and PjSTS3 genes significantly increased total content of Stilbenes in 3.6-6, 2.5-2.9, and 4.1-16.1 times, respectively, in comparison with the control calli. The most pronounced positive effect on the accumulation of Stilbenes was observed for the PjSTS3-overexpressing calli where the total content of Stilbenes was increased up to 3.1 mg/g DW, and the Stilbene production reached 25.4 mg/L. These values were higher than those achieved for the grapevine callus cell cultures overexpressing three STS genes from V. amurensis. Thus, transformation of grapevine cell cultures with spruce STS genes with a relatively low degree of homology to the endogenous VaSTSs is a more effective strategy for induction of plant secondary metabolite biosynthesis than using the grapevine genes for the overexpression experiments.
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action of ultraviolet c radiation and p coumaric acid on Stilbene accumulation and expression of Stilbene biosynthesis related genes in the grapevine vitis amurensis rupr
Acta Physiologiae Plantarum, 2019Co-Authors: K V Kiselev, V P Grigorchuk, Andrey R Suprun, Zlata V Ogneva, A S DubrovinaAbstract:This paper investigated the effects of p-coumaric acid (CA) on Stilbene biosynthesis in healthy cuttings of grapevine Vitis amurensis Rupr. under control conditions and after ultraviolet (UV-C) irradiation. It has been shown that the content of the detected six Stilbenes (cis-piceid, t-piceid, t-e-viniferin, cis-e-viniferin, t-resveratrol, and t-δ-viniferin) increased after feeding with CA up to 0.5 mg g−1 of the dry weight (DW), which is 2.4 times higher than that under control conditions. Feeding with CA and UV-C irradiation exerted a combined positive effect on the content of Stilbenes increasing it to 0.7 mg g−1 DW. In addition, the CA treatment improved viability of the cuttings after the UV-C treatment. The elevation in Stilbene content induced by CA and UV-C correlated with induction of Stilbene biosynthetic genes encoding Stilbene synthases, resveratrol O-glucosyltransferase, polyphenol oxidase, and cationic peroxidase. The data indicate that feeding with the precursors of phenolic compounds could be an effective strategy for activation of Stilbene production.
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Stilbene biosynthesis and gene expression in response to methyl jasmonate and continuous light treatment in vitis vinifera cv malvasia del lazio and vitis rupestris du lot cell cultures
Physiologia Plantarum, 2019Co-Authors: Livia Donati, Alessio Valletta, Luca Ferretti, Jacopo Frallicciardi, Roberta Rosciani, Gabriella PasquaAbstract:Vitis rupestris is used as rootstock or to obtain hybrids with Vitis vinifera, due to its resistance to certain pathogens. Its resistance mechanisms are poorly understood, while it is known that Stilbene neo-synthesis is a central defense strategy in V. vinifera. In the present study, the response to methyl jasmonate (MeJa) and light treatment in terms of Stilbene biosynthesis and the expression of genes involved in polyphenol biosynthesis was investigated in V. vinifera and V. rupestris cells. The two species exhibited a similar constitutive Stilbene content [2.50-2.80 mg g-1 dry weight (DW)], which greatly increased in response to elicitation (8.97-11.90 mg g-1 DW). In V. vinifera, continuous light treatment amplified the effect of MeJa, with a Stilbene production that had never previously been obtained (26.49 mg g-1 DW). By contrast, it suppressed the effect of MeJa in V. rupestris. Gene expression was consistent with Stilbene production in V. vinifera, whereas discrepancies were recorded in V. rupestris that could be explained by the synthesis of Stilbenes that had never before been analyzed in this species.
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Stilbene production in response to methyl jasmonate and light in cell cultures of several Vitis species
2016Co-Authors: Livia Donati, Alessio Valletta, Luca Ferretti, Roberta Rosciani, Francesco Fagioli, Gabriella PasquaAbstract:Stilbenes are secondary metabolites produced by grapevine in response to stress, which play the role of phytoalexins in the plant (1). Recently, Stilbenes have received a great deal of attention both for their biological role in the plant and for their well-proven biological activities on human health (1). Plant cell cultures have been investigated for their potential as valuable system for Stilbene production (2). Among different elicitors, methyl jasmonate (MeJa) was shown to be the most effective in stimulating Stilbene biosynthesis in cell suspension cultures of cultivar Italia (2). In the plant, the accumulation of Stilbenes is induced by the presence of phytopathogenic fungi (3) or by abiotic stimuli as UV radiation (4). Different Stilbenes produced by grapevine show a synergistic activity, furthermore the quali-quantitative composition of Stilbene content determines the resistance against specific pathogens. The species Vitis vinifera includes several cultivars quite different from the genetic point of view, since they are exclusively agamic propagated. Consequently, each of these shows different levels of susceptibility to pathogens, such as Botrytis cinerea, Aspergillus spp. and Plasmopara viticola in relation to the different Stilbene profile. Recently, great interest has been also addressed for species of Vitis popularly known as “american grapes”, introduced in Europe as rootstocks due to their resistance against some important pathogens of V. vinifera . At present, resistance mechanisms of the american grapes are still unknown. The few avaiable data has been obtained from samples cultivated in field, where the conditions are not fully under control. Our study is focused on the biosynthesis of Stilbenes, firstly resveratrol (the main exponent) and viniferins (resveratrol oligomers), in response to biotic stress in cell cultures of several Vitis species. Stilbene content was compared in cell extracts obtained from Vitis spp. cell lines subjected to elicitation with MeJa, grown under continuous darkness or 16/8 h (light/dark) photoperiod. The main Stilbenes involved in resistance against phytopathogenic fungi were identified and quantified by means of HPLC. Unexpectedly, the obtained results indicate that cultivars of V. vinifera have a higher Stilbene content than the american grapes. For instance, V. vinifera cv. Malvasia, in response to MeJa, increases the production of total Stilbenes from 2.58 to 15.58 mg/g DW while Vitis rupestris cv. du Lot increases from 2.80 to 8.97 mg/g DW. Moreover, cell lines grown under photoperiod accumulate higher levels of total Stilbenes, both constitutively and in response to elicitation (e.g. Malvasia: from 8.69 to 37.81 mg/g DW)
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effects of elicitors on the production of resveratrol and viniferins in cell cultures of vitis vinifera l cv italia
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Anna Rita Santamaria, Nadia Mulinacci, Alessio Valletta, Marzia Innocenti, Gabriella PasquaAbstract:Methyl jasmonate, jasmonic acid and chitosan were tested as elicitors on cell suspension cultures obtained from Vitis vinifera cv Italia to investigate their effect on Stilbene production. Stilbene accumulation in the callus, grown under nonelicited conditions, was also investigated. Calli and cell suspensions were obtained in a B5 culture medium supplemented with 0.2 mg L–1 NAA and 1 mg L–1 KIN. Stilbene determination was achieved by HPLC/DAD/MS. Whereas callus biosynthesized only piceid, cell suspensions elicited with jasmonates produced several Stilbenes, mainly viniferins. In suspended cells, methyl jasmonate and jasmonic acid were the most effective in stimulating Stilbene biosynthesis, whereas chitosan was less effective; in fact, the amount of Stilbenes obtained with this elicitor was not significantly different from that obtained for the control cells. The maximum production of total Stilbenes was at day 20 of culture with 0.970 and 1.023 mg g–1 DW for MeJA and JA, respectively.
