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Jean-michel Mérillon - One of the best experts on this subject based on the ideXlab platform.
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Diastereomeric Stilbenoid glucoside dimers from the rhizomes of Gnetum africanum
Phytochemistry Letters, 2020Co-Authors: Julien Gabaston, Jonathan Bisson, Jean-michel Mérillon, Thierry Buffeteau, Thierry Brotin, Caroline Rouger, Pierre Waffo-téguoAbstract:Abstract In a continuing search for neuroprotective Stilbenoids, two uncommon diastereomeric Stilbenoid glucosides, africanoside A (1) and B (2) as well as fifteen known stilbenes, E-resveratrol, E-gnetifolin E, E-piceid, E-resveratroloside, E-gnetifolin K, E-gnetol, E-isorhapontigenin, E-isorhapontin, E-isorhapontigenin-4′-O-glucopyranoside, E-gnetin C, E-bisisorhapontigenin B, E-gnemonoside A, E-gnemonoside C, E-gnemonoside D, and E-gnetin E, were isolated from rhizomes of Gnetum africanum, using a combination of centrifugal partition chromatography and preparative HPLC. The structure of these two Stilbenoids was investigated by NMR, vibrational circular dichroism (VCD), and electronic circular dichroism (ECD) experiments. The absolute configurations of 1, and 2 were established by VCD as (7aS,8aS) and (7aR,8aR), respectively. Compound 1 significantly chelated Fe(II) at 100, 250 and 500 μM. The ability of Stilbenoids to chelate ferrous ions which are implicated in physiopathological hallmark of Alzheimer’s disease provides useful data for potential treatment.
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New E-miyabenol isomer isolated from grapevine cane using centrifugal partition chromatography guided by mass spectrometry
Tetrahedron, 2015Co-Authors: Yorgos Papastamoulis, Tristan Richard, Jonathan Bisson, Jean-michel Mérillon, Hamza Temsamani, Axel Marchal, Pierre Waffo-téguoAbstract:Stilbenoids have received increasing attention over the last two decades since the discovery of resveratrol in wine. With an ever-growing rhythm, a multitude of biological activities of naturally occurring stilbenes are being reported. In this work, we investigated minor Stilbenoid compounds from Vitis vinifera stalks. The compounds were purified by means of centrifugal partition chromatography (CPC), a countercurrent-separation technique. Electrospray ionization–ion trap mass spectrometry (ESI–IT-MS) after optimization proved to be extremely efficient for the detection of these new molecules, providing both structural information for structure elucidation and a means to achieve identification even with minute amounts. Here a new stereoisomer of E-miyabenol C, E-cis-cis-miyabenol C (2), along with the already reported E-trans-cis-miyabenol C (1) and E-cis-trans-miyabenol C (3), was purified from a complex Vitis vinifera cane extract, using adapted solvent systems K and L from the ‘Arizona’ solvent system range, without the need for any solid support. Moreover, compounds 1–3 showed an inhibitory activity on α-synuclein filament formation.
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Stilbenoid Profiles of Canes from Vitis and Muscadinia Species
Journal of agricultural and food chemistry, 2013Co-Authors: Alison D. Pawlus, Tristan Richard, Jonathan Bisson, Pierre Waffo-téguo, Céline Rivière, Louis Bordenave, Jean-claude Delaunay, Ramla Sahli, Eric Gomès, Jean-michel MérillonAbstract:We present Stilbenoid profiles of canes from 16 grapevines. Fifteen Stilbenoids were obtained through isolation and structure identification using MS, NMR, and [α](D) or as commercial standards. An HPLC-UV method for the simultaneous quantification of nine of these Stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis × champini, Vitis × doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V. vinifera × M. rotundifolia hybrid. In these species, E-ampelopsin E, E-amurensin B, E-piceid, E-piceatannol, E-resveratrol, E-resveratroloside, E-e-viniferin, E-ω-viniferin, and E-vitisin B were quantified, when found in sufficient amounts. Total concentrations ranged from ~2.2 to 19.5 g/kg of dry weight. Additional Stilbenoids, E-3,5,4'-trihydroxystilbene 2-C-glucoside, Z-ampelopsin E, Z-trans-miyabenol C, E-trans-miyabenol C, scirpusin A, and Z-vitisin B, were identified but not quantified. Our results indicate that canes, particularly those of non-vinifera species, have substantial quantities of valuable, health-promoting Stilbenoids.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography–nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Abstract Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC–MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD–MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC–NMR. 1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC–NMR in conjunction with LC–MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC-MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD-MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC-NMR.1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC-NMR in conjunction with LC-MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry. © 2013 Elsevier B.V.
Tristan Richard - One of the best experts on this subject based on the ideXlab platform.
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Daily Preharvest UV-C Light Maintains the High Stilbenoid Concentration in Grapes
Journal of agricultural and food chemistry, 2016Co-Authors: Raúl F. Guerrero, Emma Cantos-villar, Belén Puertas, Tristan RichardAbstract:The fact that it is possible to induce Stilbenoid synthesis in grapevine (Vitis vinifera) by UV-C light allows the possibility of stimulating grapevine phytoalexin production to increase disease resistance and immunity, and subsequently to limit the use of pesticides in vineyards. UV-C light was applied daily during three days before the harvesting of table grape variety Crimson seedless to study the accumulation of Stilbenoid compounds during ripeness. The E-resveratrol concentration was monitored during daily preharvest UV-C light application and compared with that after a single application. Daily periodic preharvest UV-C light treatment showed a cumulative effect on grape Stilbenoids. An 86-fold Stilbenoid level increase (sum of E-resveratrol, E-piceatannol, e-viniferin, E-piceid, isorhapontigenin, ω-viniferin, and Z-piceid) in grapes was achieved. The effects of UV-C light on Stilbenoid in grape cane was also addressed for the first time. Stilbenoid oligomers such as hopeaphenol, ampelopsin A, and r-...
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Daily preharvest UV-C light maintains the high Stilbenoid concentration in grapes
Journal of Agricultural and Food Chemistry, 2016Co-Authors: Raúl F. Guerrero, Emma Cantos-villar, Belén Puertas, Tristan RichardAbstract:The fact that it is possible to induce Stilbenoid synthesis in grapevine (Vitis vinifera) by UV-C light allows the possibility of stimulating grapevine phytoalexin production to increase disease resistance and immunity, and subsequently to limit the use of pesticides in vineyards. UV-C light was applied daily during three days before the harvesting of table grape variety Crimson seedless to study the accumulation of Stilbenoid compounds during ripeness. The E-resveratrol concentration was monitored during daily preharvest UV-C light application and compared with that after a single application. Daily periodic preharvest UV-C light treatment showed a cumulative effect on grape Stilbenoids. An 86-fold Stilbenoid level increase (sum of E-resveratrol, E-piceatannol, ε-viniferin, E-piceid, isorhapontigenin, ω-viniferin, and Z-piceid) in grapes was achieved. The effects of UV-C light on Stilbenoid in grape cane was also addressed for the first time. Stilbenoid oligomers such as hopeaphenol, ampelopsin A, and r-viniferin were quantified in cane samples. Quality grape parameters indicated an acceleration of ripening in UV-C samples.
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New E-miyabenol isomer isolated from grapevine cane using centrifugal partition chromatography guided by mass spectrometry
Tetrahedron, 2015Co-Authors: Yorgos Papastamoulis, Tristan Richard, Jonathan Bisson, Jean-michel Mérillon, Hamza Temsamani, Axel Marchal, Pierre Waffo-téguoAbstract:Stilbenoids have received increasing attention over the last two decades since the discovery of resveratrol in wine. With an ever-growing rhythm, a multitude of biological activities of naturally occurring stilbenes are being reported. In this work, we investigated minor Stilbenoid compounds from Vitis vinifera stalks. The compounds were purified by means of centrifugal partition chromatography (CPC), a countercurrent-separation technique. Electrospray ionization–ion trap mass spectrometry (ESI–IT-MS) after optimization proved to be extremely efficient for the detection of these new molecules, providing both structural information for structure elucidation and a means to achieve identification even with minute amounts. Here a new stereoisomer of E-miyabenol C, E-cis-cis-miyabenol C (2), along with the already reported E-trans-cis-miyabenol C (1) and E-cis-trans-miyabenol C (3), was purified from a complex Vitis vinifera cane extract, using adapted solvent systems K and L from the ‘Arizona’ solvent system range, without the need for any solid support. Moreover, compounds 1–3 showed an inhibitory activity on α-synuclein filament formation.
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Stilbenoid Profiles of Canes from Vitis and Muscadinia Species
Journal of agricultural and food chemistry, 2013Co-Authors: Alison D. Pawlus, Tristan Richard, Jonathan Bisson, Pierre Waffo-téguo, Céline Rivière, Louis Bordenave, Jean-claude Delaunay, Ramla Sahli, Eric Gomès, Jean-michel MérillonAbstract:We present Stilbenoid profiles of canes from 16 grapevines. Fifteen Stilbenoids were obtained through isolation and structure identification using MS, NMR, and [α](D) or as commercial standards. An HPLC-UV method for the simultaneous quantification of nine of these Stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis × champini, Vitis × doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V. vinifera × M. rotundifolia hybrid. In these species, E-ampelopsin E, E-amurensin B, E-piceid, E-piceatannol, E-resveratrol, E-resveratroloside, E-e-viniferin, E-ω-viniferin, and E-vitisin B were quantified, when found in sufficient amounts. Total concentrations ranged from ~2.2 to 19.5 g/kg of dry weight. Additional Stilbenoids, E-3,5,4'-trihydroxystilbene 2-C-glucoside, Z-ampelopsin E, Z-trans-miyabenol C, E-trans-miyabenol C, scirpusin A, and Z-vitisin B, were identified but not quantified. Our results indicate that canes, particularly those of non-vinifera species, have substantial quantities of valuable, health-promoting Stilbenoids.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography–nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Abstract Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC–MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD–MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC–NMR. 1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC–NMR in conjunction with LC–MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry.
Alison D. Pawlus - One of the best experts on this subject based on the ideXlab platform.
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Stilbenoid Profiles of Canes from Vitis and Muscadinia Species
Journal of agricultural and food chemistry, 2013Co-Authors: Alison D. Pawlus, Tristan Richard, Jonathan Bisson, Pierre Waffo-téguo, Céline Rivière, Louis Bordenave, Jean-claude Delaunay, Ramla Sahli, Eric Gomès, Jean-michel MérillonAbstract:We present Stilbenoid profiles of canes from 16 grapevines. Fifteen Stilbenoids were obtained through isolation and structure identification using MS, NMR, and [α](D) or as commercial standards. An HPLC-UV method for the simultaneous quantification of nine of these Stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis × champini, Vitis × doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V. vinifera × M. rotundifolia hybrid. In these species, E-ampelopsin E, E-amurensin B, E-piceid, E-piceatannol, E-resveratrol, E-resveratroloside, E-e-viniferin, E-ω-viniferin, and E-vitisin B were quantified, when found in sufficient amounts. Total concentrations ranged from ~2.2 to 19.5 g/kg of dry weight. Additional Stilbenoids, E-3,5,4'-trihydroxystilbene 2-C-glucoside, Z-ampelopsin E, Z-trans-miyabenol C, E-trans-miyabenol C, scirpusin A, and Z-vitisin B, were identified but not quantified. Our results indicate that canes, particularly those of non-vinifera species, have substantial quantities of valuable, health-promoting Stilbenoids.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography–nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Abstract Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC–MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD–MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC–NMR. 1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC–NMR in conjunction with LC–MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC-MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD-MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC-NMR.1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC-NMR in conjunction with LC-MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry. © 2013 Elsevier B.V.
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Stilbenoid profiles of canes from Vitis and Muscadinia species
Journal of Agricultural and Food Chemistry, 2013Co-Authors: Alison D. Pawlus, Tristan Richard, Jonathan Bisson, Pierre Waffo-téguo, Céline Rivière, Louis Bordenave, Jean-claude Delaunay, Eric Gomès, Ramla Salhi, Jean-michel MérillonAbstract:We present Stilbenoid profiles of canes from 16 grapevines. Fifteen Stilbenoids were obtained through isolation and structure identification using MS, NMR, and [alpha](D) or as commercial standards. An HPLC-UV method for the simultaneous quantification of nine of these Stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis x champini, Vitis x doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V. vinifera x M. rotundifolia hybrid. In these species, E-ampelopsin E, E-amurensin B, E-piceid, E-piceatannol, E-resveratrol, E-resveratroloside, E-omega-viniferin, E-omega-viniferin, and E-vitisin B were quantified, when found in sufficient amounts. Total concentrations ranged from similar to 2.2 to 19.5 g/kg of dry weight. Additional Stilbenoids, E-3,5,4'-trihydroxystilbene 2-C-glucoside, Z-ampelopsin E, Z-trans-miyabenol C, E-trans-miyabenol C, scirpusin A, and Z-vitisin B, were identified but not quantified. Our results indicate that canes, particularly those of non-vinifera species, have substantial quantities of valuable, health-promoting Stilbenoids.
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Stilbenoid chemistry from wine and the genus "Vitis", a review
OENO One, 2012Co-Authors: Alison D. Pawlus, Pierre Waffo-téguo, Jonah Shaver, Jean-michel MérillonAbstract:Stilbenoids are of great interest on account of their many promising biological activities, especially in regards to prevention and potential treatment of many chronic diseases associated with aging. The simple Stilbenoid monomer, E-resveratrol, has received the most attention due to early in vitro and in vivo biological activities in anti-aging assays. Since Vitis vinifera, primarily in the form of wine, is a major dietary source of these compounds, there is a tremendous amount of research on resveratrol in wine and grapes. Relatively few biological studies have been performed on other Stilbenoids from Vitis, primarily due to the lack of commercial sources of many of these compounds. The diverse Stilbenoids from this economically important genus are an untapped source of health promoting compounds and because of this, numerous efforts for isolation, identification and quantification of additional Stilbenoids have been ongoing. Additionally, due to their role as phytoalexins, Stilbenoids play an important role in the defense against pathogens. Therefore, the compounds produced by highly resistant strains are of great interest for the development of resistant crops, natural spray reagents, and as new dietary supplements or pharmaceuticals. Since closely related species are likely to have similar metabolic pathways, a more thorough understanding of the chemical diversity of Stilbenoids within Vitis is useful in this endeavor. In this review, we focus on Stilbenoids found in the Vitis genus with the aim of aiding future Stilbenoid chemistry, particularly in V. vinifera and wine. Additionally, we discuss the efforts to quantify Stilbenoids in Vitis, with a focus on non-resveratrol Stilbenoid compounds.
Pierre Waffo-téguo - One of the best experts on this subject based on the ideXlab platform.
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Diastereomeric Stilbenoid glucoside dimers from the rhizomes of Gnetum africanum
Phytochemistry Letters, 2020Co-Authors: Julien Gabaston, Jonathan Bisson, Jean-michel Mérillon, Thierry Buffeteau, Thierry Brotin, Caroline Rouger, Pierre Waffo-téguoAbstract:Abstract In a continuing search for neuroprotective Stilbenoids, two uncommon diastereomeric Stilbenoid glucosides, africanoside A (1) and B (2) as well as fifteen known stilbenes, E-resveratrol, E-gnetifolin E, E-piceid, E-resveratroloside, E-gnetifolin K, E-gnetol, E-isorhapontigenin, E-isorhapontin, E-isorhapontigenin-4′-O-glucopyranoside, E-gnetin C, E-bisisorhapontigenin B, E-gnemonoside A, E-gnemonoside C, E-gnemonoside D, and E-gnetin E, were isolated from rhizomes of Gnetum africanum, using a combination of centrifugal partition chromatography and preparative HPLC. The structure of these two Stilbenoids was investigated by NMR, vibrational circular dichroism (VCD), and electronic circular dichroism (ECD) experiments. The absolute configurations of 1, and 2 were established by VCD as (7aS,8aS) and (7aR,8aR), respectively. Compound 1 significantly chelated Fe(II) at 100, 250 and 500 μM. The ability of Stilbenoids to chelate ferrous ions which are implicated in physiopathological hallmark of Alzheimer’s disease provides useful data for potential treatment.
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New E-miyabenol isomer isolated from grapevine cane using centrifugal partition chromatography guided by mass spectrometry
Tetrahedron, 2015Co-Authors: Yorgos Papastamoulis, Tristan Richard, Jonathan Bisson, Jean-michel Mérillon, Hamza Temsamani, Axel Marchal, Pierre Waffo-téguoAbstract:Stilbenoids have received increasing attention over the last two decades since the discovery of resveratrol in wine. With an ever-growing rhythm, a multitude of biological activities of naturally occurring stilbenes are being reported. In this work, we investigated minor Stilbenoid compounds from Vitis vinifera stalks. The compounds were purified by means of centrifugal partition chromatography (CPC), a countercurrent-separation technique. Electrospray ionization–ion trap mass spectrometry (ESI–IT-MS) after optimization proved to be extremely efficient for the detection of these new molecules, providing both structural information for structure elucidation and a means to achieve identification even with minute amounts. Here a new stereoisomer of E-miyabenol C, E-cis-cis-miyabenol C (2), along with the already reported E-trans-cis-miyabenol C (1) and E-cis-trans-miyabenol C (3), was purified from a complex Vitis vinifera cane extract, using adapted solvent systems K and L from the ‘Arizona’ solvent system range, without the need for any solid support. Moreover, compounds 1–3 showed an inhibitory activity on α-synuclein filament formation.
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Stilbenoid Profiles of Canes from Vitis and Muscadinia Species
Journal of agricultural and food chemistry, 2013Co-Authors: Alison D. Pawlus, Tristan Richard, Jonathan Bisson, Pierre Waffo-téguo, Céline Rivière, Louis Bordenave, Jean-claude Delaunay, Ramla Sahli, Eric Gomès, Jean-michel MérillonAbstract:We present Stilbenoid profiles of canes from 16 grapevines. Fifteen Stilbenoids were obtained through isolation and structure identification using MS, NMR, and [α](D) or as commercial standards. An HPLC-UV method for the simultaneous quantification of nine of these Stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis × champini, Vitis × doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V. vinifera × M. rotundifolia hybrid. In these species, E-ampelopsin E, E-amurensin B, E-piceid, E-piceatannol, E-resveratrol, E-resveratroloside, E-e-viniferin, E-ω-viniferin, and E-vitisin B were quantified, when found in sufficient amounts. Total concentrations ranged from ~2.2 to 19.5 g/kg of dry weight. Additional Stilbenoids, E-3,5,4'-trihydroxystilbene 2-C-glucoside, Z-ampelopsin E, Z-trans-miyabenol C, E-trans-miyabenol C, scirpusin A, and Z-vitisin B, were identified but not quantified. Our results indicate that canes, particularly those of non-vinifera species, have substantial quantities of valuable, health-promoting Stilbenoids.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography–nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Abstract Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC–MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD–MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC–NMR. 1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC–NMR in conjunction with LC–MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC-MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD-MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC-NMR.1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC-NMR in conjunction with LC-MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry. © 2013 Elsevier B.V.
Jonathan Bisson - One of the best experts on this subject based on the ideXlab platform.
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Diastereomeric Stilbenoid glucoside dimers from the rhizomes of Gnetum africanum
Phytochemistry Letters, 2020Co-Authors: Julien Gabaston, Jonathan Bisson, Jean-michel Mérillon, Thierry Buffeteau, Thierry Brotin, Caroline Rouger, Pierre Waffo-téguoAbstract:Abstract In a continuing search for neuroprotective Stilbenoids, two uncommon diastereomeric Stilbenoid glucosides, africanoside A (1) and B (2) as well as fifteen known stilbenes, E-resveratrol, E-gnetifolin E, E-piceid, E-resveratroloside, E-gnetifolin K, E-gnetol, E-isorhapontigenin, E-isorhapontin, E-isorhapontigenin-4′-O-glucopyranoside, E-gnetin C, E-bisisorhapontigenin B, E-gnemonoside A, E-gnemonoside C, E-gnemonoside D, and E-gnetin E, were isolated from rhizomes of Gnetum africanum, using a combination of centrifugal partition chromatography and preparative HPLC. The structure of these two Stilbenoids was investigated by NMR, vibrational circular dichroism (VCD), and electronic circular dichroism (ECD) experiments. The absolute configurations of 1, and 2 were established by VCD as (7aS,8aS) and (7aR,8aR), respectively. Compound 1 significantly chelated Fe(II) at 100, 250 and 500 μM. The ability of Stilbenoids to chelate ferrous ions which are implicated in physiopathological hallmark of Alzheimer’s disease provides useful data for potential treatment.
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New E-miyabenol isomer isolated from grapevine cane using centrifugal partition chromatography guided by mass spectrometry
Tetrahedron, 2015Co-Authors: Yorgos Papastamoulis, Tristan Richard, Jonathan Bisson, Jean-michel Mérillon, Hamza Temsamani, Axel Marchal, Pierre Waffo-téguoAbstract:Stilbenoids have received increasing attention over the last two decades since the discovery of resveratrol in wine. With an ever-growing rhythm, a multitude of biological activities of naturally occurring stilbenes are being reported. In this work, we investigated minor Stilbenoid compounds from Vitis vinifera stalks. The compounds were purified by means of centrifugal partition chromatography (CPC), a countercurrent-separation technique. Electrospray ionization–ion trap mass spectrometry (ESI–IT-MS) after optimization proved to be extremely efficient for the detection of these new molecules, providing both structural information for structure elucidation and a means to achieve identification even with minute amounts. Here a new stereoisomer of E-miyabenol C, E-cis-cis-miyabenol C (2), along with the already reported E-trans-cis-miyabenol C (1) and E-cis-trans-miyabenol C (3), was purified from a complex Vitis vinifera cane extract, using adapted solvent systems K and L from the ‘Arizona’ solvent system range, without the need for any solid support. Moreover, compounds 1–3 showed an inhibitory activity on α-synuclein filament formation.
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Stilbenoid Profiles of Canes from Vitis and Muscadinia Species
Journal of agricultural and food chemistry, 2013Co-Authors: Alison D. Pawlus, Tristan Richard, Jonathan Bisson, Pierre Waffo-téguo, Céline Rivière, Louis Bordenave, Jean-claude Delaunay, Ramla Sahli, Eric Gomès, Jean-michel MérillonAbstract:We present Stilbenoid profiles of canes from 16 grapevines. Fifteen Stilbenoids were obtained through isolation and structure identification using MS, NMR, and [α](D) or as commercial standards. An HPLC-UV method for the simultaneous quantification of nine of these Stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis × champini, Vitis × doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V. vinifera × M. rotundifolia hybrid. In these species, E-ampelopsin E, E-amurensin B, E-piceid, E-piceatannol, E-resveratrol, E-resveratroloside, E-e-viniferin, E-ω-viniferin, and E-vitisin B were quantified, when found in sufficient amounts. Total concentrations ranged from ~2.2 to 19.5 g/kg of dry weight. Additional Stilbenoids, E-3,5,4'-trihydroxystilbene 2-C-glucoside, Z-ampelopsin E, Z-trans-miyabenol C, E-trans-miyabenol C, scirpusin A, and Z-vitisin B, were identified but not quantified. Our results indicate that canes, particularly those of non-vinifera species, have substantial quantities of valuable, health-promoting Stilbenoids.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography–nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Abstract Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC–MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD–MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC–NMR. 1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC–NMR in conjunction with LC–MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry.
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Chemical dereplication of wine Stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy
Journal of Chromatography A, 2013Co-Authors: Alison D. Pawlus, Pierre-louis Teissedre, Emma Cantos-villar, Tristan Richard, Jonathan Bisson, Pascal Poupard, Yorgos Papastamoulis, Jean Pierre Monti, Pierre Waffo-téguo, Jean-michel MérillonAbstract:Wine is a major dietary source of numerous potentially health promoting Stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC-MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic Stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD-MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in Stilbenoids for analysis in stopped-flow LC-NMR.1H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified Stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC-NMR in conjunction with LC-MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry. © 2013 Elsevier B.V.
