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Fengping Miao - One of the best experts on this subject based on the ideXlab platform.
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trichocarotins a h and trichocadinin a nine Sesquiterpenes from the marine alga epiphytic fungus trichoderma virens
Bioorganic Chemistry, 2018Co-Authors: Zhenzhen Shi, Fengping Miao, Shengtao Fang, Xiuli YinAbstract:Abstract In addition to CAF-603, 14-hydroxy CAF-603 (trichocarane B), 7-β-hydroxy CAF-603, and trichocarane A, eight new carotane Sesquiterpenes, trichocarotins A–H, and one new cadinane sesquiterpene, trichocadinin A, were isolated from the culture of Trichoderma virens Y13-3, obtained from the surface of a marine red alga. Their structures and relative configurations were unambiguously assigned by interpretation of 1D/2D NMR and MS data, and their absolute configurations were established by X-ray diffraction or ECD spectra aided by quantum chemical calculations. These compounds represent two rarely occurring sesquiterpene types from filamentous fungi, and six of them feature potent inhibition against some marine plankton species.
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Sesquiterpenes and acetogenins from the marine red alga laurencia okamurai
Fitoterapia, 2012Co-Authors: Fengping MiaoAbstract:Three new halogenated Sesquiterpenes, 10-bromo-7 alpha,8 alpha-expoxychamigr-1-en-3-ol (1), 10-bromo-beta-chamigren-8-ol (2), and 10-bromo-3-chlorocupar-5-en-2-ol (3), one new C-12-acetogenin, desepilaurallene (7), one new naturally occurring sesquiterpene, 7-hydroxylaurene acetate (4), two known Sesquiterpenes, allolaurinterol acetate (5) and laurene (6), and one known C-15-acetogenin, epilaurallene (8), were isolated from the marine red alga Laurencia okamurai collected from the coast of Rongcheng, China. The structures of these compounds were unambiguously established by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 4,5 exhibited potent antibacterial activity, and 1, 4, 5 were toxic to brine shrimp.
Mary Dawn Celiz - One of the best experts on this subject based on the ideXlab platform.
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functional identification of valerena 1 10 diene synthase a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active Sesquiterpenes in valeriana officinalis
Journal of Biological Chemistry, 2013Co-Authors: Eric S Nybo, Amar G Chittiboyina, Aruna D Weerasooriya, Y H Wang, Elsa Gongoracastillo, Brieanne Vaillancourt, Robin C Buell, Dean Dellapenna, Mary Dawn Celiz, Daniel A JonesAbstract:Valerian is an herbal preparation from the roots of Valeriana officinalis used as an anxiolytic and sedative and in the treatment of insomnia. The biological activities of valerian are attributed to valerenic acid and its putative biosynthetic precursor valerenadiene, Sesquiterpenes, found in V. officinalis roots. These Sesquiterpenes retain an isobutenyl side chain whose origin has been long recognized as enigmatic because a chemical rationalization for their biosynthesis has not been obvious. Using recently developed metabolomic and transcriptomic resources, we identified seven V. officinalis terpene synthase genes (VoTPSs), two that were functionally characterized as monoterpene synthases and three that preferred farnesyl diphosphate, the substrate for sesquiterpene synthases. The reaction products for two of the sesquiterpene synthases exhibiting root-specific expression were characterized by a combination of GC-MS and NMR in comparison to the terpenes accumulating in planta. VoTPS7 encodes for a synthase that biosynthesizes predominately germacrene C, whereas VoTPS1 catalyzes the conversion of farnesyl diphosphate to valerena-1,10-diene. Using a yeast expression system, specific labeled [13C]acetate, and NMR, we investigated the catalytic mechanism for VoTPS1 and provide evidence for the involvement of a caryophyllenyl carbocation, a cyclobutyl intermediate, in the biosynthesis of valerena-1,10-diene. We suggest a similar mechanism for the biosynthesis of several other biologically related isobutenyl-containing Sesquiterpenes.
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functional identification of valerena 1 10 diene synthase a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active Sesquiterpenes in valeriana officinalis
Journal of Biological Chemistry, 2013Co-Authors: Yun Soo Yeo, Eric S Nybo, Amar G Chittiboyina, Y H Wang, Elsa Gongoracastillo, Brieanne Vaillancourt, Robin C Buell, Dean Dellapenna, Aruna Weerasooriya, Mary Dawn CelizAbstract:Valerian is an herbal preparation from the roots of Valeriana officinalis used as an anxiolytic and sedative and in the treatment of insomnia. The biological activities of valerian are attributed to valerenic acid and its putative biosynthetic precursor valerenadiene, Sesquiterpenes, found in V. officinalis roots. These Sesquiterpenes retain an isobutenyl side chain whose origin has been long recognized as enigmatic because a chemical rationalization for their biosynthesis has not been obvious. Using recently developed metabolomic and transcriptomic resources, we identified seven V. officinalis terpene synthase genes (VoTPSs), two that were functionally characterized as monoterpene synthases and three that preferred farnesyl diphosphate, the substrate for sesquiterpene synthases. The reaction products for two of the sesquiterpene synthases exhibiting root-specific expression were characterized by a combination of GC-MS and NMR in comparison to the terpenes accumulating in planta. VoTPS7 encodes for a synthase that biosynthesizes predominately germacrene C, whereas VoTPS1 catalyzes the conversion of farnesyl diphosphate to valerena-1,10-diene. Using a yeast expression system, specific labeled [13C]acetate, and NMR, we investigated the catalytic mechanism for VoTPS1 and provide evidence for the involvement of a caryophyllenyl carbocation, a cyclobutyl intermediate, in the biosynthesis of valerena-1,10-diene. We suggest a similar mechanism for the biosynthesis of several other biologically related isobutenyl-containing Sesquiterpenes. Background: Therapeutic values of Valeriana officinalis have been associated with Sesquiterpenes whose biosynthetic origins have remained enigmatic. Results: A cyclobutenyl intermediate in the catalytic cascade of valerena-1,10-diene synthase is reported. Conclusion: A new class of sesquiterpene synthases for the biosynthesis of Sesquiterpenes harboring isobutenyl functional groups is proposed. Significance: Similar catalytic mechanisms from evolutionarily diverse organisms are proposed and portend sources for sesquiterpene diversity.
Xiuli Yin - One of the best experts on this subject based on the ideXlab platform.
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trichocarotins a h and trichocadinin a nine Sesquiterpenes from the marine alga epiphytic fungus trichoderma virens
Bioorganic Chemistry, 2018Co-Authors: Zhenzhen Shi, Fengping Miao, Shengtao Fang, Xiuli YinAbstract:Abstract In addition to CAF-603, 14-hydroxy CAF-603 (trichocarane B), 7-β-hydroxy CAF-603, and trichocarane A, eight new carotane Sesquiterpenes, trichocarotins A–H, and one new cadinane sesquiterpene, trichocadinin A, were isolated from the culture of Trichoderma virens Y13-3, obtained from the surface of a marine red alga. Their structures and relative configurations were unambiguously assigned by interpretation of 1D/2D NMR and MS data, and their absolute configurations were established by X-ray diffraction or ECD spectra aided by quantum chemical calculations. These compounds represent two rarely occurring sesquiterpene types from filamentous fungi, and six of them feature potent inhibition against some marine plankton species.
Eric S Nybo - One of the best experts on this subject based on the ideXlab platform.
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functional identification of valerena 1 10 diene synthase a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active Sesquiterpenes in valeriana officinalis
Journal of Biological Chemistry, 2013Co-Authors: Eric S Nybo, Amar G Chittiboyina, Aruna D Weerasooriya, Y H Wang, Elsa Gongoracastillo, Brieanne Vaillancourt, Robin C Buell, Dean Dellapenna, Mary Dawn Celiz, Daniel A JonesAbstract:Valerian is an herbal preparation from the roots of Valeriana officinalis used as an anxiolytic and sedative and in the treatment of insomnia. The biological activities of valerian are attributed to valerenic acid and its putative biosynthetic precursor valerenadiene, Sesquiterpenes, found in V. officinalis roots. These Sesquiterpenes retain an isobutenyl side chain whose origin has been long recognized as enigmatic because a chemical rationalization for their biosynthesis has not been obvious. Using recently developed metabolomic and transcriptomic resources, we identified seven V. officinalis terpene synthase genes (VoTPSs), two that were functionally characterized as monoterpene synthases and three that preferred farnesyl diphosphate, the substrate for sesquiterpene synthases. The reaction products for two of the sesquiterpene synthases exhibiting root-specific expression were characterized by a combination of GC-MS and NMR in comparison to the terpenes accumulating in planta. VoTPS7 encodes for a synthase that biosynthesizes predominately germacrene C, whereas VoTPS1 catalyzes the conversion of farnesyl diphosphate to valerena-1,10-diene. Using a yeast expression system, specific labeled [13C]acetate, and NMR, we investigated the catalytic mechanism for VoTPS1 and provide evidence for the involvement of a caryophyllenyl carbocation, a cyclobutyl intermediate, in the biosynthesis of valerena-1,10-diene. We suggest a similar mechanism for the biosynthesis of several other biologically related isobutenyl-containing Sesquiterpenes.
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functional identification of valerena 1 10 diene synthase a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active Sesquiterpenes in valeriana officinalis
Journal of Biological Chemistry, 2013Co-Authors: Yun Soo Yeo, Eric S Nybo, Amar G Chittiboyina, Y H Wang, Elsa Gongoracastillo, Brieanne Vaillancourt, Robin C Buell, Dean Dellapenna, Aruna Weerasooriya, Mary Dawn CelizAbstract:Valerian is an herbal preparation from the roots of Valeriana officinalis used as an anxiolytic and sedative and in the treatment of insomnia. The biological activities of valerian are attributed to valerenic acid and its putative biosynthetic precursor valerenadiene, Sesquiterpenes, found in V. officinalis roots. These Sesquiterpenes retain an isobutenyl side chain whose origin has been long recognized as enigmatic because a chemical rationalization for their biosynthesis has not been obvious. Using recently developed metabolomic and transcriptomic resources, we identified seven V. officinalis terpene synthase genes (VoTPSs), two that were functionally characterized as monoterpene synthases and three that preferred farnesyl diphosphate, the substrate for sesquiterpene synthases. The reaction products for two of the sesquiterpene synthases exhibiting root-specific expression were characterized by a combination of GC-MS and NMR in comparison to the terpenes accumulating in planta. VoTPS7 encodes for a synthase that biosynthesizes predominately germacrene C, whereas VoTPS1 catalyzes the conversion of farnesyl diphosphate to valerena-1,10-diene. Using a yeast expression system, specific labeled [13C]acetate, and NMR, we investigated the catalytic mechanism for VoTPS1 and provide evidence for the involvement of a caryophyllenyl carbocation, a cyclobutyl intermediate, in the biosynthesis of valerena-1,10-diene. We suggest a similar mechanism for the biosynthesis of several other biologically related isobutenyl-containing Sesquiterpenes. Background: Therapeutic values of Valeriana officinalis have been associated with Sesquiterpenes whose biosynthetic origins have remained enigmatic. Results: A cyclobutenyl intermediate in the catalytic cascade of valerena-1,10-diene synthase is reported. Conclusion: A new class of sesquiterpene synthases for the biosynthesis of Sesquiterpenes harboring isobutenyl functional groups is proposed. Significance: Similar catalytic mechanisms from evolutionarily diverse organisms are proposed and portend sources for sesquiterpene diversity.
Daniel A Jones - One of the best experts on this subject based on the ideXlab platform.
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functional identification of valerena 1 10 diene synthase a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active Sesquiterpenes in valeriana officinalis
Journal of Biological Chemistry, 2013Co-Authors: Eric S Nybo, Amar G Chittiboyina, Aruna D Weerasooriya, Y H Wang, Elsa Gongoracastillo, Brieanne Vaillancourt, Robin C Buell, Dean Dellapenna, Mary Dawn Celiz, Daniel A JonesAbstract:Valerian is an herbal preparation from the roots of Valeriana officinalis used as an anxiolytic and sedative and in the treatment of insomnia. The biological activities of valerian are attributed to valerenic acid and its putative biosynthetic precursor valerenadiene, Sesquiterpenes, found in V. officinalis roots. These Sesquiterpenes retain an isobutenyl side chain whose origin has been long recognized as enigmatic because a chemical rationalization for their biosynthesis has not been obvious. Using recently developed metabolomic and transcriptomic resources, we identified seven V. officinalis terpene synthase genes (VoTPSs), two that were functionally characterized as monoterpene synthases and three that preferred farnesyl diphosphate, the substrate for sesquiterpene synthases. The reaction products for two of the sesquiterpene synthases exhibiting root-specific expression were characterized by a combination of GC-MS and NMR in comparison to the terpenes accumulating in planta. VoTPS7 encodes for a synthase that biosynthesizes predominately germacrene C, whereas VoTPS1 catalyzes the conversion of farnesyl diphosphate to valerena-1,10-diene. Using a yeast expression system, specific labeled [13C]acetate, and NMR, we investigated the catalytic mechanism for VoTPS1 and provide evidence for the involvement of a caryophyllenyl carbocation, a cyclobutyl intermediate, in the biosynthesis of valerena-1,10-diene. We suggest a similar mechanism for the biosynthesis of several other biologically related isobutenyl-containing Sesquiterpenes.
