Triterpene Saponins in the Defensive Secretion of a Chrysomelid Beetle, Platyphora ligata
The secretion of the defensive glands of adults of the chrysomelid beetle Platyphora ligata from Panama has been shown to contain, besides chlorogenic acid (1) and a mixture of phosphatidylcholines, two new oleanane triterpene saponins, named ligatosides A and B. Their structures were established as...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2000-05, Vol.63 (5), p.646-649 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Plasman, V Braekman, J. C Daloze, D Luhmer, M Windsor, D Pasteels, J. M |
| description | The secretion of the defensive glands of adults of the chrysomelid beetle Platyphora ligata from Panama has been shown to contain, besides chlorogenic acid (1) and a mixture of phosphatidylcholines, two new oleanane triterpene saponins, named ligatosides A and B. Their structures were established as 3-O-β-d-glucuronopyranosyl-16α,23-dihydroxyoleanolic acid-28-O-2-(3,4-dimethoxybenzoyl)-β-d-glucopyranoside (2) and 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucuronopyranosyl-16α,23-dihydroxyoleanolic acid-28-O-2-(3,4-dimethoxybenzoyl)-β-d-glucopyranoside (3), respectively, by a combination of extensive 1D and 2D NMR methods (COSY, HMQC, HMBC, and TOCSY) and FABMS. This is the first report of triterpene saponins in the defensive secretion of an insect. |
| doi_str_mv | 10.1021/np990406t |
| format | Article |
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This is the first report of triterpene saponins in the defensive secretion of an insect.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np990406t</identifier><identifier>PMID: 10843577</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Chlorogenic Acid - analysis ; Chromatography, High Pressure Liquid ; Chromatography, Thin Layer ; Chrysomelidae ; Coleoptera - chemistry ; ligatosides ; Magnetic Resonance Spectroscopy ; oleanane triterpene saponins ; Panama ; Phosphatidylcholines - analysis ; Platyphora ligata ; Saponins - analysis ; Saponins - isolation & purification ; Spectrometry, Mass, Fast Atom Bombardment ; Spectrophotometry, Ultraviolet ; triterpene saponins ; Triterpenes - analysis ; Triterpenes - isolation & purification</subject><ispartof>Journal of natural products (Washington, D.C.), 2000-05, Vol.63 (5), p.646-649</ispartof><rights>Copyright © 2000 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a446t-69f2968da5afa0f376e01dacca3c3318b7863159963695652e9ac5f3e65ab5133</citedby><cites>FETCH-LOGICAL-a446t-69f2968da5afa0f376e01dacca3c3318b7863159963695652e9ac5f3e65ab5133</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np990406t$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np990406t$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10843577$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Plasman, V</creatorcontrib><creatorcontrib>Braekman, J. 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Their structures were established as 3-O-β-d-glucuronopyranosyl-16α,23-dihydroxyoleanolic acid-28-O-2-(3,4-dimethoxybenzoyl)-β-d-glucopyranoside (2) and 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucuronopyranosyl-16α,23-dihydroxyoleanolic acid-28-O-2-(3,4-dimethoxybenzoyl)-β-d-glucopyranoside (3), respectively, by a combination of extensive 1D and 2D NMR methods (COSY, HMQC, HMBC, and TOCSY) and FABMS. 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Their structures were established as 3-O-β-d-glucuronopyranosyl-16α,23-dihydroxyoleanolic acid-28-O-2-(3,4-dimethoxybenzoyl)-β-d-glucopyranoside (2) and 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucuronopyranosyl-16α,23-dihydroxyoleanolic acid-28-O-2-(3,4-dimethoxybenzoyl)-β-d-glucopyranoside (3), respectively, by a combination of extensive 1D and 2D NMR methods (COSY, HMQC, HMBC, and TOCSY) and FABMS. This is the first report of triterpene saponins in the defensive secretion of an insect.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>10843577</pmid><doi>10.1021/np990406t</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2000-05, Vol.63 (5), p.646-649 |
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| subjects | Animals Chlorogenic Acid - analysis Chromatography, High Pressure Liquid Chromatography, Thin Layer Chrysomelidae Coleoptera - chemistry ligatosides Magnetic Resonance Spectroscopy oleanane triterpene saponins Panama Phosphatidylcholines - analysis Platyphora ligata Saponins - analysis Saponins - isolation & purification Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Ultraviolet triterpene saponins Triterpenes - analysis Triterpenes - isolation & purification |
| title | Triterpene Saponins in the Defensive Secretion of a Chrysomelid Beetle, Platyphora ligata |
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