Nobilisides A - C, three new triterpene glycosides from the sea cucumber Holothuria nobilis
Abstract Three new triterpene glycosides, named nobilisides A (1), B (2) and C (3), were isolated from the sea cucumber HOLOTHURIA NOBILIS Selenka. Their structures were deduced by extensive spectral analysis and chemical evidence. Compounds 1 and 3 are non-sulfated monoglycosides while 2 is a sulfa...
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| Veröffentlicht in: | Planta medica 2006-08, Vol.72 (10), p.932-935 |
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| container_title | Planta medica |
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| creator | Wu, J Yi, Y.H Wu, H.M Zou, Z.R Lin, H.W |
| description | Abstract
Three new triterpene glycosides, named nobilisides A (1), B (2) and C (3), were isolated from the sea cucumber HOLOTHURIA NOBILIS Selenka. Their structures were deduced by extensive spectral analysis and chemical evidence. Compounds 1 and 3 are non-sulfated monoglycosides while 2 is a sulfated diglycoside. The presence of two conjugated double bonds [22E,24-diene and 7,9(11)-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides, while 2 and 3 possess the same 22,25-epoxy moiety as their side chains. All three glycosides exhibited significant cytotoxicity against human tumor cell lines. |
| doi_str_mv | 10.1055/s-2006-931603 |
| format | Article |
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Three new triterpene glycosides, named nobilisides A (1), B (2) and C (3), were isolated from the sea cucumber HOLOTHURIA NOBILIS Selenka. Their structures were deduced by extensive spectral analysis and chemical evidence. Compounds 1 and 3 are non-sulfated monoglycosides while 2 is a sulfated diglycoside. The presence of two conjugated double bonds [22E,24-diene and 7,9(11)-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides, while 2 and 3 possess the same 22,25-epoxy moiety as their side chains. All three glycosides exhibited significant cytotoxicity against human tumor cell lines.</description><identifier>ISSN: 0032-0943</identifier><identifier>EISSN: 1439-0221</identifier><identifier>DOI: 10.1055/s-2006-931603</identifier><identifier>PMID: 16732529</identifier><identifier>CODEN: PLMEAA</identifier><language>eng</language><publisher>Stuttgart: Thieme</publisher><subject>Animals ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - toxicity ; Biological and medical sciences ; Cell Line, Tumor ; chemical structure ; General pharmacology ; glycosides ; Glycosides - chemistry ; Glycosides - isolation & purification ; Glycosides - toxicity ; Holothuria - chemistry ; Holothuroidea ; Humans ; Letter ; Medical sciences ; nobilisides ; Nuclear Magnetic Resonance, Biomolecular ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Saponins - chemistry ; Saponins - isolation & purification ; Saponins - toxicity ; secondary metabolites ; spectral analysis ; Triterpenes - chemistry ; Triterpenes - isolation & purification ; Triterpenes - toxicity ; triterpenoids</subject><ispartof>Planta medica, 2006-08, Vol.72 (10), p.932-935</ispartof><rights>Georg Thieme Verlag KG Stuttgart · New York</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c382t-177c074bd1d3ae4db2557ff92222f33cc1cf64e33fdc55151844c08b25b7e9dc3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-931603.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2006-931603$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3004,3005,27901,27902,54534,54535</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18716273$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16732529$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, J</creatorcontrib><creatorcontrib>Yi, Y.H</creatorcontrib><creatorcontrib>Wu, H.M</creatorcontrib><creatorcontrib>Zou, Z.R</creatorcontrib><creatorcontrib>Lin, H.W</creatorcontrib><title>Nobilisides A - C, three new triterpene glycosides from the sea cucumber Holothuria nobilis</title><title>Planta medica</title><addtitle>Planta Med</addtitle><description>Abstract
Three new triterpene glycosides, named nobilisides A (1), B (2) and C (3), were isolated from the sea cucumber HOLOTHURIA NOBILIS Selenka. Their structures were deduced by extensive spectral analysis and chemical evidence. Compounds 1 and 3 are non-sulfated monoglycosides while 2 is a sulfated diglycoside. The presence of two conjugated double bonds [22E,24-diene and 7,9(11)-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides, while 2 and 3 possess the same 22,25-epoxy moiety as their side chains. All three glycosides exhibited significant cytotoxicity against human tumor cell lines.</description><subject>Animals</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - toxicity</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>chemical structure</subject><subject>General pharmacology</subject><subject>glycosides</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - isolation & purification</subject><subject>Glycosides - toxicity</subject><subject>Holothuria - chemistry</subject><subject>Holothuroidea</subject><subject>Humans</subject><subject>Letter</subject><subject>Medical sciences</subject><subject>nobilisides</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Saponins - chemistry</subject><subject>Saponins - isolation & purification</subject><subject>Saponins - toxicity</subject><subject>secondary metabolites</subject><subject>spectral analysis</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - isolation & purification</subject><subject>Triterpenes - toxicity</subject><subject>triterpenoids</subject><issn>0032-0943</issn><issn>1439-0221</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp10D1PwzAQBmALgWgpjKzghQ3DnZ3EzVhVQJEqGKATQ-Q4ZxqUj8pOhPj3pEolJm655dF7upexS4Q7hDi-D0ICJCJVmIA6YlOMVCpASjxmUwAlBaSRmrCzEL4AMEoBTtkEE61kLNMp-3hp87IqQ1lQ4Asu-PKWd1tPxBv65p0vO_I7aoh_Vj-2HZnzbT0g4oEMt73t65w8X7VV2217XxrejJnn7MSZKtDFYc_Y5vHhfbkS69en5-ViLayay06g1hZ0lBdYKENRkcs41s6lchinlLVoXRKRUq6wcYwxzqPIwnxguaa0sGrGxJhrfRuCJ5ftfFkb_5MhZPuSspDtS8rGkgZ_Nfpdn9dU_OlDKwO4OQATrKmcN40tw5-ba0yk3gfdjq7bllRT9tX2vhk-_ffu9cidaTPz6YfIzZsEVIAIGkGqXz4shaA</recordid><startdate>20060801</startdate><enddate>20060801</enddate><creator>Wu, J</creator><creator>Yi, Y.H</creator><creator>Wu, H.M</creator><creator>Zou, Z.R</creator><creator>Lin, H.W</creator><general>Thieme</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20060801</creationdate><title>Nobilisides A - C, three new triterpene glycosides from the sea cucumber Holothuria nobilis</title><author>Wu, J ; Yi, Y.H ; Wu, H.M ; Zou, Z.R ; Lin, H.W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c382t-177c074bd1d3ae4db2557ff92222f33cc1cf64e33fdc55151844c08b25b7e9dc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - toxicity</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>chemical structure</topic><topic>General pharmacology</topic><topic>glycosides</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - isolation & purification</topic><topic>Glycosides - toxicity</topic><topic>Holothuria - chemistry</topic><topic>Holothuroidea</topic><topic>Humans</topic><topic>Letter</topic><topic>Medical sciences</topic><topic>nobilisides</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Saponins - chemistry</topic><topic>Saponins - isolation & purification</topic><topic>Saponins - toxicity</topic><topic>secondary metabolites</topic><topic>spectral analysis</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - isolation & purification</topic><topic>Triterpenes - toxicity</topic><topic>triterpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, J</creatorcontrib><creatorcontrib>Yi, Y.H</creatorcontrib><creatorcontrib>Wu, H.M</creatorcontrib><creatorcontrib>Zou, Z.R</creatorcontrib><creatorcontrib>Lin, H.W</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Planta medica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, J</au><au>Yi, Y.H</au><au>Wu, H.M</au><au>Zou, Z.R</au><au>Lin, H.W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nobilisides A - C, three new triterpene glycosides from the sea cucumber Holothuria nobilis</atitle><jtitle>Planta medica</jtitle><addtitle>Planta Med</addtitle><date>2006-08-01</date><risdate>2006</risdate><volume>72</volume><issue>10</issue><spage>932</spage><epage>935</epage><pages>932-935</pages><issn>0032-0943</issn><eissn>1439-0221</eissn><coden>PLMEAA</coden><abstract>Abstract
Three new triterpene glycosides, named nobilisides A (1), B (2) and C (3), were isolated from the sea cucumber HOLOTHURIA NOBILIS Selenka. Their structures were deduced by extensive spectral analysis and chemical evidence. Compounds 1 and 3 are non-sulfated monoglycosides while 2 is a sulfated diglycoside. The presence of two conjugated double bonds [22E,24-diene and 7,9(11)-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides, while 2 and 3 possess the same 22,25-epoxy moiety as their side chains. All three glycosides exhibited significant cytotoxicity against human tumor cell lines.</abstract><cop>Stuttgart</cop><cop>New York, NY</cop><pub>Thieme</pub><pmid>16732529</pmid><doi>10.1055/s-2006-931603</doi><tpages>4</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; Thieme Connect Journals |
| subjects | Animals Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - toxicity Biological and medical sciences Cell Line, Tumor chemical structure General pharmacology glycosides Glycosides - chemistry Glycosides - isolation & purification Glycosides - toxicity Holothuria - chemistry Holothuroidea Humans Letter Medical sciences nobilisides Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Saponins - chemistry Saponins - isolation & purification Saponins - toxicity secondary metabolites spectral analysis Triterpenes - chemistry Triterpenes - isolation & purification Triterpenes - toxicity triterpenoids |
| title | Nobilisides A - C, three new triterpene glycosides from the sea cucumber Holothuria nobilis |
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