Two new complex triterpenoid saponins from Gledistsia dolavayi Franch
Two new triterpenoid saponins, gledistside A (1) and gledistside B (2), isolated from the fruits of Gledistsia dolavayi Franch., were characterized as the 3,28‐O‐bisdesmoside of echinocystic acid acylated with monoterpene carboxylic acids. On the basis of spectroscopic and chemical evidence, their s...
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description | Two new triterpenoid saponins, gledistside A (1) and gledistside B (2), isolated from the fruits of Gledistsia dolavayi Franch., were characterized as the 3,28‐O‐bisdesmoside of echinocystic acid acylated with monoterpene carboxylic acids. On the basis of spectroscopic and chemical evidence, their structures were elucidated as 3‐O‐β‐D‐xylopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐28‐O‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐[β‐D‐galactopyranosyl‐(1→2)]‐α‐L‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2,6‐dimethyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D‐glucopyranosylechinocystic acid (1) and 3‐O‐β‐D‐xylopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐28‐O‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐[β‐D‐galactopyranosyl‐(1→2)]‐α‐L‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2‐hydroxymethyl‐6‐methyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D‐glucopyranosylechinocystic acid (2). The complete 1H and 13C assignments of saponins 1 and 2 were achieved on the basis of 2D NMR spectra including HMQC‐TOCSY, TOCSY, 1H–1H COSY, HMBC, ROESY and HMQC spectra. Copyright © 2002 John Wiley & Sons, Ltd. |
doi_str_mv | 10.1002/mrc.1061 |
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On the basis of spectroscopic and chemical evidence, their structures were elucidated as 3‐O‐β‐D‐xylopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐28‐O‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐[β‐D‐galactopyranosyl‐(1→2)]‐α‐L‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2,6‐dimethyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D‐glucopyranosylechinocystic acid (1) and 3‐O‐β‐D‐xylopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐28‐O‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐[β‐D‐galactopyranosyl‐(1→2)]‐α‐L‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2‐hydroxymethyl‐6‐methyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D‐glucopyranosylechinocystic acid (2). The complete 1H and 13C assignments of saponins 1 and 2 were achieved on the basis of 2D NMR spectra including HMQC‐TOCSY, TOCSY, 1H–1H COSY, HMBC, ROESY and HMQC spectra. Copyright © 2002 John Wiley & Sons, Ltd.</description><identifier>ISSN: 0749-1581</identifier><identifier>EISSN: 1097-458X</identifier><identifier>DOI: 10.1002/mrc.1061</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>13C NMR ; 1H NMR ; 2D NMR ; Gledistsia dolavayi Franch ; gledistside A ; gledistside B ; Leguminosae ; NMR ; NMR complete assignments ; triterpenoid saponin</subject><ispartof>Magnetic resonance in chemistry, 2002-09, Vol.40 (9), p.609-613</ispartof><rights>Copyright © 2002 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3671-76de2e28784711b6dbfddc7ca7d89e6d2b0096c6e44e97a5bed80948f9ab598d3</citedby><cites>FETCH-LOGICAL-c3671-76de2e28784711b6dbfddc7ca7d89e6d2b0096c6e44e97a5bed80948f9ab598d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fmrc.1061$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fmrc.1061$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Teng, Rong Wei</creatorcontrib><creatorcontrib>Ni, Wei</creatorcontrib><creatorcontrib>Wang, De Zu</creatorcontrib><creatorcontrib>Ding, Jing Kai</creatorcontrib><creatorcontrib>Chen, Chang Xiang</creatorcontrib><title>Two new complex triterpenoid saponins from Gledistsia dolavayi Franch</title><title>Magnetic resonance in chemistry</title><addtitle>Magn. Reson. Chem</addtitle><description>Two new triterpenoid saponins, gledistside A (1) and gledistside B (2), isolated from the fruits of Gledistsia dolavayi Franch., were characterized as the 3,28‐O‐bisdesmoside of echinocystic acid acylated with monoterpene carboxylic acids. On the basis of spectroscopic and chemical evidence, their structures were elucidated as 3‐O‐β‐D‐xylopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐28‐O‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐[β‐D‐galactopyranosyl‐(1→2)]‐α‐L‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2,6‐dimethyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D‐glucopyranosylechinocystic acid (1) and 3‐O‐β‐D‐xylopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐28‐O‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐[β‐D‐galactopyranosyl‐(1→2)]‐α‐L‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2‐hydroxymethyl‐6‐methyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D‐glucopyranosylechinocystic acid (2). The complete 1H and 13C assignments of saponins 1 and 2 were achieved on the basis of 2D NMR spectra including HMQC‐TOCSY, TOCSY, 1H–1H COSY, HMBC, ROESY and HMQC spectra. Copyright © 2002 John Wiley & Sons, Ltd.</description><subject>13C NMR</subject><subject>1H NMR</subject><subject>2D NMR</subject><subject>Gledistsia dolavayi Franch</subject><subject>gledistside A</subject><subject>gledistside B</subject><subject>Leguminosae</subject><subject>NMR</subject><subject>NMR complete assignments</subject><subject>triterpenoid saponin</subject><issn>0749-1581</issn><issn>1097-458X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNp1z01LAzEQgOEgCtYq-BNy9LKa7Ec-jlK7VWgVakVvIZvMYnR3syTFtv_eLRXBg6eZw8MwL0KXlFxTQtKbNphhYfQIjSiRPMkL8XaMRoTnMqGFoKfoLMYPQoiUPBuh6WrjcQcbbHzbN7DF6-DWEHrovLM46t53rou4Dr7Fswasi-voNLa-0V9653AZdGfez9FJrZsIFz9zjF7K6Wpyn8yfZg-T23liMsZpwpmFFFLBRc4prZitamsNN5pbIYHZtBreYoZBnoPkuqjACiJzUUtdFVLYbIyuDndN8DEGqFUfXKvDTlGi9vlqyFf7_IEmB7pxDez-dWqxnPz1QyFsf70On4rxjBfq9XGmntMlW5TFnSqzb6mjbA4</recordid><startdate>200209</startdate><enddate>200209</enddate><creator>Teng, Rong Wei</creator><creator>Ni, Wei</creator><creator>Wang, De Zu</creator><creator>Ding, Jing Kai</creator><creator>Chen, Chang Xiang</creator><general>John Wiley & Sons, Ltd</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200209</creationdate><title>Two new complex triterpenoid saponins from Gledistsia dolavayi Franch</title><author>Teng, Rong Wei ; Ni, Wei ; Wang, De Zu ; Ding, Jing Kai ; Chen, Chang Xiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3671-76de2e28784711b6dbfddc7ca7d89e6d2b0096c6e44e97a5bed80948f9ab598d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>13C NMR</topic><topic>1H NMR</topic><topic>2D NMR</topic><topic>Gledistsia dolavayi Franch</topic><topic>gledistside A</topic><topic>gledistside B</topic><topic>Leguminosae</topic><topic>NMR</topic><topic>NMR complete assignments</topic><topic>triterpenoid saponin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Teng, Rong Wei</creatorcontrib><creatorcontrib>Ni, Wei</creatorcontrib><creatorcontrib>Wang, De Zu</creatorcontrib><creatorcontrib>Ding, Jing Kai</creatorcontrib><creatorcontrib>Chen, Chang Xiang</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Magnetic resonance in chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Teng, Rong Wei</au><au>Ni, Wei</au><au>Wang, De Zu</au><au>Ding, Jing Kai</au><au>Chen, Chang Xiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two new complex triterpenoid saponins from Gledistsia dolavayi Franch</atitle><jtitle>Magnetic resonance in chemistry</jtitle><addtitle>Magn. Reson. Chem</addtitle><date>2002-09</date><risdate>2002</risdate><volume>40</volume><issue>9</issue><spage>609</spage><epage>613</epage><pages>609-613</pages><issn>0749-1581</issn><eissn>1097-458X</eissn><abstract>Two new triterpenoid saponins, gledistside A (1) and gledistside B (2), isolated from the fruits of Gledistsia dolavayi Franch., were characterized as the 3,28‐O‐bisdesmoside of echinocystic acid acylated with monoterpene carboxylic acids. On the basis of spectroscopic and chemical evidence, their structures were elucidated as 3‐O‐β‐D‐xylopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐28‐O‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐[β‐D‐galactopyranosyl‐(1→2)]‐α‐L‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2,6‐dimethyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D‐glucopyranosylechinocystic acid (1) and 3‐O‐β‐D‐xylopyranosyl‐(1→2)‐α‐L‐arabinopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐28‐O‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐[β‐D‐galactopyranosyl‐(1→2)]‐α‐L‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2‐hydroxymethyl‐6‐methyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D‐glucopyranosylechinocystic acid (2). The complete 1H and 13C assignments of saponins 1 and 2 were achieved on the basis of 2D NMR spectra including HMQC‐TOCSY, TOCSY, 1H–1H COSY, HMBC, ROESY and HMQC spectra. Copyright © 2002 John Wiley & Sons, Ltd.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/mrc.1061</doi><tpages>5</tpages></addata></record> |
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subjects | 13C NMR 1H NMR 2D NMR Gledistsia dolavayi Franch gledistside A gledistside B Leguminosae NMR NMR complete assignments triterpenoid saponin |
title | Two new complex triterpenoid saponins from Gledistsia dolavayi Franch |
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