Six New Triterpenoid Glycosides from Gynostemma pentaphyllum
Six new triterpenoid glycosides, gynosaponins I–VI (1–6, resp.), together with three known compounds, ginseng Rb1 (7), gypenoside XLIX (8), and gylongiposide I (9), were isolated from the aerial parts of Gynostemma pentaphyllum. Based on ESI‐MS, IR, 1D‐ and 2D‐NMR data (HMQC, HMBC, COSY, and TOCSY),...
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Veröffentlicht in: | Helvetica chimica acta 2009-12, Vol.92 (12), p.2737-2745 |
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description | Six new triterpenoid glycosides, gynosaponins I–VI (1–6, resp.), together with three known compounds, ginseng Rb1 (7), gypenoside XLIX (8), and gylongiposide I (9), were isolated from the aerial parts of Gynostemma pentaphyllum. Based on ESI‐MS, IR, 1D‐ and 2D‐NMR data (HMQC, HMBC, COSY, and TOCSY), the structures of the new compounds were determined as (3β,12β,20S)‐trihydroxydammar‐24‐ene 20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (1), (3β,12β,20S)‐trihydroxydammar‐24‐ene 20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (2), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐β‐glucopyranosyl‐20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (3), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐β‐glucopyranosyl‐20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (4), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐{[β‐glucopyranosyl‐(1→2)]‐β‐glucopyranosyl}‐20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (5), and (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐{[β‐glucopyranosyl‐(1→2)]‐β‐glucopyranosyl}‐20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (6). |
doi_str_mv | 10.1002/hlca.200900100 |
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Based on ESI‐MS, IR, 1D‐ and 2D‐NMR data (HMQC, HMBC, COSY, and TOCSY), the structures of the new compounds were determined as (3β,12β,20S)‐trihydroxydammar‐24‐ene 20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (1), (3β,12β,20S)‐trihydroxydammar‐24‐ene 20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (2), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐β‐glucopyranosyl‐20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (3), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐β‐glucopyranosyl‐20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (4), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐{[β‐glucopyranosyl‐(1→2)]‐β‐glucopyranosyl}‐20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (5), and (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐{[β‐glucopyranosyl‐(1→2)]‐β‐glucopyranosyl}‐20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (6).</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.200900100</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>Glycosides ; Gynosaponins I - VI ; Gynostemma pentaphyllum ; Triterpenoid glycosides</subject><ispartof>Helvetica chimica acta, 2009-12, Vol.92 (12), p.2737-2745</ispartof><rights>Copyright © 2009 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3270-ad58856a8fcbd9d2e95c334a7e18d5d35eafc1428d538eed2a9ddf647e4c45a73</citedby><cites>FETCH-LOGICAL-c3270-ad58856a8fcbd9d2e95c334a7e18d5d35eafc1428d538eed2a9ddf647e4c45a73</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%2Fhlca.200900100$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.200900100$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27915,27916,45565,45566</link.rule.ids></links><search><creatorcontrib>Liu, Jie-Qing</creatorcontrib><creatorcontrib>Wang, Cui-Fang</creatorcontrib><creatorcontrib>Chen, Jian-Chao</creatorcontrib><creatorcontrib>Tu, Shang-Hui</creatorcontrib><creatorcontrib>Gu, Hong-Fei</creatorcontrib><creatorcontrib>Hu, Wen-Xiang</creatorcontrib><creatorcontrib>Qiu, Ming-Hua</creatorcontrib><title>Six New Triterpenoid Glycosides from Gynostemma pentaphyllum</title><title>Helvetica chimica acta</title><addtitle>HCA</addtitle><description>Six new triterpenoid glycosides, gynosaponins I–VI (1–6, resp.), together with three known compounds, ginseng Rb1 (7), gypenoside XLIX (8), and gylongiposide I (9), were isolated from the aerial parts of Gynostemma pentaphyllum. Based on ESI‐MS, IR, 1D‐ and 2D‐NMR data (HMQC, HMBC, COSY, and TOCSY), the structures of the new compounds were determined as (3β,12β,20S)‐trihydroxydammar‐24‐ene 20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (1), (3β,12β,20S)‐trihydroxydammar‐24‐ene 20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (2), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐β‐glucopyranosyl‐20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (3), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐β‐glucopyranosyl‐20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (4), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐{[β‐glucopyranosyl‐(1→2)]‐β‐glucopyranosyl}‐20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (5), and (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐{[β‐glucopyranosyl‐(1→2)]‐β‐glucopyranosyl}‐20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (6).</description><subject>Glycosides</subject><subject>Gynosaponins I - VI</subject><subject>Gynostemma pentaphyllum</subject><subject>Triterpenoid glycosides</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFj11LwzAUhoMoOKe3XvcPdOajaRrwZhTthDIFJ_MuxOSURdt1JJOt_96MyfDOq8N7eJ8XHoRuCZ4QjOndqjV6QjGWGMd8hkaEU5rSXPBzNIq_IsVEvl-iqxA-caxJLEbo_tXtkznskoV3W_AbWPfOJlU7mD44CyFpfN8l1bDuwxa6TiexsdWb1dC23901umh0G-Dm947R2-PDopyl9XP1VE7r1DAqcKotLwqe66IxH1ZaCpIbxjItgBSWW8ZBN4ZkNAZWAFiqpbVNngnITMa1YGM0Oe4a34fgoVEb7zrtB0WwOrirg7s6uUdAHoGda2H4p61mdTn9y6ZH1kXj_YnV_kvlggmulvNKlS-8XszmS8XYD2OEbkE</recordid><startdate>200912</startdate><enddate>200912</enddate><creator>Liu, Jie-Qing</creator><creator>Wang, Cui-Fang</creator><creator>Chen, Jian-Chao</creator><creator>Tu, Shang-Hui</creator><creator>Gu, Hong-Fei</creator><creator>Hu, Wen-Xiang</creator><creator>Qiu, Ming-Hua</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200912</creationdate><title>Six New Triterpenoid Glycosides from Gynostemma pentaphyllum</title><author>Liu, Jie-Qing ; Wang, Cui-Fang ; Chen, Jian-Chao ; Tu, Shang-Hui ; Gu, Hong-Fei ; Hu, Wen-Xiang ; Qiu, Ming-Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3270-ad58856a8fcbd9d2e95c334a7e18d5d35eafc1428d538eed2a9ddf647e4c45a73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Glycosides</topic><topic>Gynosaponins I - VI</topic><topic>Gynostemma pentaphyllum</topic><topic>Triterpenoid glycosides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Jie-Qing</creatorcontrib><creatorcontrib>Wang, Cui-Fang</creatorcontrib><creatorcontrib>Chen, Jian-Chao</creatorcontrib><creatorcontrib>Tu, Shang-Hui</creatorcontrib><creatorcontrib>Gu, Hong-Fei</creatorcontrib><creatorcontrib>Hu, Wen-Xiang</creatorcontrib><creatorcontrib>Qiu, Ming-Hua</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Jie-Qing</au><au>Wang, Cui-Fang</au><au>Chen, Jian-Chao</au><au>Tu, Shang-Hui</au><au>Gu, Hong-Fei</au><au>Hu, Wen-Xiang</au><au>Qiu, Ming-Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Six New Triterpenoid Glycosides from Gynostemma pentaphyllum</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>2009-12</date><risdate>2009</risdate><volume>92</volume><issue>12</issue><spage>2737</spage><epage>2745</epage><pages>2737-2745</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><abstract>Six new triterpenoid glycosides, gynosaponins I–VI (1–6, resp.), together with three known compounds, ginseng Rb1 (7), gypenoside XLIX (8), and gylongiposide I (9), were isolated from the aerial parts of Gynostemma pentaphyllum. Based on ESI‐MS, IR, 1D‐ and 2D‐NMR data (HMQC, HMBC, COSY, and TOCSY), the structures of the new compounds were determined as (3β,12β,20S)‐trihydroxydammar‐24‐ene 20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (1), (3β,12β,20S)‐trihydroxydammar‐24‐ene 20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (2), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐β‐glucopyranosyl‐20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (3), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐β‐glucopyranosyl‐20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (4), (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐{[β‐glucopyranosyl‐(1→2)]‐β‐glucopyranosyl}‐20‐O‐[α‐rhamnopyranosyl‐(1→2)]‐β‐glucopyranoside (5), and (3β,12β,20S)‐trihydroxydammar‐24‐ene 3‐O‐{[β‐glucopyranosyl‐(1→2)]‐β‐glucopyranosyl}‐20‐O‐[α‐rhamnopyranosyl‐(1→2)] [α‐rhamnopyranosyl‐(1→3)]‐β‐glucopyranoside (6).</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/hlca.200900100</doi><tpages>9</tpages></addata></record> |
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subjects | Glycosides Gynosaponins I - VI Gynostemma pentaphyllum Triterpenoid glycosides |
title | Six New Triterpenoid Glycosides from Gynostemma pentaphyllum |
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