Three New Alkaloids from the Leaves of Uncaria rhynchophylla
Three new alkaloids, 2′‐O‐β‐D‐glucopyranosyl‐11‐hydroxyvincoside lactam (1), 22‐O‐demethyl‐22‐O‐β‐D‐glucopyranosylisocorynoxeine (2), and (4S)‐corynoxeine N‐oxide (3) were isolated from the leaves of Uncaria rhynchophylla, together with four known tetracyclic oxindole or indole alkaloids, isocorynox...
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| Veröffentlicht in: | Helvetica chimica acta 2009-08, Vol.92 (8), p.1575-1585 |
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| container_title | Helvetica chimica acta |
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| creator | Ma, Bin Wu, Chun-Fu Yang, Jing-Yu Wang, Rui Kano, Yoshihiro Yuan, Dan |
| description | Three new alkaloids, 2′‐O‐β‐D‐glucopyranosyl‐11‐hydroxyvincoside lactam (1), 22‐O‐demethyl‐22‐O‐β‐D‐glucopyranosylisocorynoxeine (2), and (4S)‐corynoxeine N‐oxide (3) were isolated from the leaves of Uncaria rhynchophylla, together with four known tetracyclic oxindole or indole alkaloids, isocorynoxeine N‐oxide (4), rhynchophylline N‐oxide (5), isorhynchophylline N‐oxide (6), and dihydrocorynantheine (7), and an indole alkaloid glycoside, strictosidine (8). The structures of 1–3 were elucidated by spectroscopic methods including UV, IR, ESI‐TOF‐MS, 1D‐ and 2D‐NMR, as well as CD experiments. The activity assay showed that 8 (IC50=8.3 μM) exhibited potent inhibitory activity on lipopolysaccharide(LPS)‐induced nitrogen monoxide (NO) release in N9 microglia cells. However, only weak inhibitory activities were observed for 1–7 (IC50>100 μM for 1–6 or >30 μM for 7). |
| doi_str_mv | 10.1002/hlca.200900021 |
| format | Article |
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The structures of 1–3 were elucidated by spectroscopic methods including UV, IR, ESI‐TOF‐MS, 1D‐ and 2D‐NMR, as well as CD experiments. The activity assay showed that 8 (IC50=8.3 μM) exhibited potent inhibitory activity on lipopolysaccharide(LPS)‐induced nitrogen monoxide (NO) release in N9 microglia cells. However, only weak inhibitory activities were observed for 1–7 (IC50>100 μM for 1–6 or >30 μM for 7).</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.200900021</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>(4S)-Corynoxeine N-oxide ; 11-hydroxy ; Alkaloids ; Glucosides ; Isocorynoxeinic acids ; Uncaria rhynchophylla ; Vincoside lactams ; Vincoside lactams, 11‐hydroxy</subject><ispartof>Helvetica chimica acta, 2009-08, Vol.92 (8), p.1575-1585</ispartof><rights>Copyright © 2009 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3931-ba78c7a295d959c4b04343f5358e43e86e63a7be01fa11c31a8f7024143eb6a03</citedby><cites>FETCH-LOGICAL-c3931-ba78c7a295d959c4b04343f5358e43e86e63a7be01fa11c31a8f7024143eb6a03</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.200900021$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.200900021$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Ma, Bin</creatorcontrib><creatorcontrib>Wu, Chun-Fu</creatorcontrib><creatorcontrib>Yang, Jing-Yu</creatorcontrib><creatorcontrib>Wang, Rui</creatorcontrib><creatorcontrib>Kano, Yoshihiro</creatorcontrib><creatorcontrib>Yuan, Dan</creatorcontrib><title>Three New Alkaloids from the Leaves of Uncaria rhynchophylla</title><title>Helvetica chimica acta</title><addtitle>HCA</addtitle><description>Three new alkaloids, 2′‐O‐β‐D‐glucopyranosyl‐11‐hydroxyvincoside lactam (1), 22‐O‐demethyl‐22‐O‐β‐D‐glucopyranosylisocorynoxeine (2), and (4S)‐corynoxeine N‐oxide (3) were isolated from the leaves of Uncaria rhynchophylla, together with four known tetracyclic oxindole or indole alkaloids, isocorynoxeine N‐oxide (4), rhynchophylline N‐oxide (5), isorhynchophylline N‐oxide (6), and dihydrocorynantheine (7), and an indole alkaloid glycoside, strictosidine (8). The structures of 1–3 were elucidated by spectroscopic methods including UV, IR, ESI‐TOF‐MS, 1D‐ and 2D‐NMR, as well as CD experiments. The activity assay showed that 8 (IC50=8.3 μM) exhibited potent inhibitory activity on lipopolysaccharide(LPS)‐induced nitrogen monoxide (NO) release in N9 microglia cells. However, only weak inhibitory activities were observed for 1–7 (IC50>100 μM for 1–6 or >30 μM for 7).</description><subject>(4S)-Corynoxeine N-oxide</subject><subject>11-hydroxy</subject><subject>Alkaloids</subject><subject>Glucosides</subject><subject>Isocorynoxeinic acids</subject><subject>Uncaria rhynchophylla</subject><subject>Vincoside lactams</subject><subject>Vincoside lactams, 11‐hydroxy</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFj1FLwzAUhYMoOKevPucPdN4kTdOAL3PoJpT5sjHfwm2W0LpuHclQ--_tmAzffLoc7vkOfITcMxgxAP5QNRZHHEBDn9gFGTDJecIzJS_JAIDlCTD9fk1uYvzoK1qDGpDHRRWco3P3RcfNBpu2XkfqQ7ulh8rRwuGni7T1dLmzGGqkoep2tmr3Vdc0eEuuPDbR3f3eIVm-PC8ms6R4m75OxkVihRYsKVHlViHXcq2ltmkJqUiFl0LmLhUuz1wmUJUOmEfGrGCYewU8Zf2zzBDEkIxOuza0MQbnzT7UWwydYWCO7ubobs7uPaBPwFfduO6ftpkVk_FfNjmxdTy47zOLYWMyJZQ0q_nUPC2msEplYebiBzMBa7Y</recordid><startdate>200908</startdate><enddate>200908</enddate><creator>Ma, Bin</creator><creator>Wu, Chun-Fu</creator><creator>Yang, Jing-Yu</creator><creator>Wang, Rui</creator><creator>Kano, Yoshihiro</creator><creator>Yuan, Dan</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200908</creationdate><title>Three New Alkaloids from the Leaves of Uncaria rhynchophylla</title><author>Ma, Bin ; Wu, Chun-Fu ; Yang, Jing-Yu ; Wang, Rui ; Kano, Yoshihiro ; Yuan, Dan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3931-ba78c7a295d959c4b04343f5358e43e86e63a7be01fa11c31a8f7024143eb6a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>(4S)-Corynoxeine N-oxide</topic><topic>11-hydroxy</topic><topic>Alkaloids</topic><topic>Glucosides</topic><topic>Isocorynoxeinic acids</topic><topic>Uncaria rhynchophylla</topic><topic>Vincoside lactams</topic><topic>Vincoside lactams, 11‐hydroxy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ma, Bin</creatorcontrib><creatorcontrib>Wu, Chun-Fu</creatorcontrib><creatorcontrib>Yang, Jing-Yu</creatorcontrib><creatorcontrib>Wang, Rui</creatorcontrib><creatorcontrib>Kano, Yoshihiro</creatorcontrib><creatorcontrib>Yuan, Dan</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>Ma, Bin</au><au>Wu, Chun-Fu</au><au>Yang, Jing-Yu</au><au>Wang, Rui</au><au>Kano, Yoshihiro</au><au>Yuan, Dan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Three New Alkaloids from the Leaves of Uncaria rhynchophylla</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>2009-08</date><risdate>2009</risdate><volume>92</volume><issue>8</issue><spage>1575</spage><epage>1585</epage><pages>1575-1585</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><abstract>Three new alkaloids, 2′‐O‐β‐D‐glucopyranosyl‐11‐hydroxyvincoside lactam (1), 22‐O‐demethyl‐22‐O‐β‐D‐glucopyranosylisocorynoxeine (2), and (4S)‐corynoxeine N‐oxide (3) were isolated from the leaves of Uncaria rhynchophylla, together with four known tetracyclic oxindole or indole alkaloids, isocorynoxeine N‐oxide (4), rhynchophylline N‐oxide (5), isorhynchophylline N‐oxide (6), and dihydrocorynantheine (7), and an indole alkaloid glycoside, strictosidine (8). The structures of 1–3 were elucidated by spectroscopic methods including UV, IR, ESI‐TOF‐MS, 1D‐ and 2D‐NMR, as well as CD experiments. The activity assay showed that 8 (IC50=8.3 μM) exhibited potent inhibitory activity on lipopolysaccharide(LPS)‐induced nitrogen monoxide (NO) release in N9 microglia cells. However, only weak inhibitory activities were observed for 1–7 (IC50>100 μM for 1–6 or >30 μM for 7).</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/hlca.200900021</doi><tpages>11</tpages></addata></record> |
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| ispartof | Helvetica chimica acta, 2009-08, Vol.92 (8), p.1575-1585 |
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| language | eng |
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| source | Wiley Online Library All Journals |
| subjects | (4S)-Corynoxeine N-oxide 11-hydroxy Alkaloids Glucosides Isocorynoxeinic acids Uncaria rhynchophylla Vincoside lactams Vincoside lactams, 11‐hydroxy |
| title | Three New Alkaloids from the Leaves of Uncaria rhynchophylla |
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