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Isothiocyanate Sesquiterpenes from a Sponge of the Genus Axinyssa
The chemical study of a sponge of the genus Axinyssa collected in the Gulf of California has led to the isolation of the new bicyclic sesquiterpenes axinisothiocyanates A−L (1−12) together with the known compounds (1R,6S,7S,10S)-10-isothiocyanato-4-amorphene (13), (4R*,5R*,7S*,10R*)-4-isocyanoeudesm...
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| Published in: | Journal of natural products (Washington, D.C.) D.C.), 2008-04, Vol.71 (4), p.608-614 |
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| Main Authors: | , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a405t-6956fabc7104bbbbdc5380574875b71931ae4e293f68d14df812a633d5e6eaa3 |
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| cites | cdi_FETCH-LOGICAL-a405t-6956fabc7104bbbbdc5380574875b71931ae4e293f68d14df812a633d5e6eaa3 |
| container_end_page | 614 |
| container_issue | 4 |
| container_start_page | 608 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 71 |
| creator | Zubía, Eva Ortega, María J Hernández-Guerrero, Claudia J Carballo, J. Luis |
| description | The chemical study of a sponge of the genus Axinyssa collected in the Gulf of California has led to the isolation of the new bicyclic sesquiterpenes axinisothiocyanates A−L (1−12) together with the known compounds (1R,6S,7S,10S)-10-isothiocyanato-4-amorphene (13), (4R*,5R*,7S*,10R*)-4-isocyanoeudesm-11-ene, (−)-epipolasin A, and (+)-aristolone. The structures of the new metabolites have been established by spectroscopic techniques, including the analysis of pyridine-induced 1H NMR chemical shifts. The cytotoxic activity has been tested against three human tumor cell lines. |
| doi_str_mv | 10.1021/np070593s |
| format | article |
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The cytotoxic activity has been tested against three human tumor cell lines.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np070593s</identifier><identifier>PMID: 18288806</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; axinisothiocyanate ; Axinyssa ; Biological and medical sciences ; cadinane sesquiterpenes ; California ; chemical structure ; cultured cells ; cytotoxicity ; Drug Screening Assays, Antitumor ; General aspects ; General pharmacology ; Humans ; isothiocyanates ; Isothiocyanates - chemistry ; Isothiocyanates - isolation & purification ; Isothiocyanates - pharmacology ; Medical sciences ; medicinal properties ; Molecular Structure ; Oceans and Seas ; Pharmacognosy. 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Drug treatments ; Porifera ; Porifera - chemistry ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; sesquiterpenoids ; spectral analysis ; stereochemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2008-04, Vol.71 (4), p.608-614</ispartof><rights>Copyright © 2008 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-6956fabc7104bbbbdc5380574875b71931ae4e293f68d14df812a633d5e6eaa3</citedby><cites>FETCH-LOGICAL-a405t-6956fabc7104bbbbdc5380574875b71931ae4e293f68d14df812a633d5e6eaa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20301980$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18288806$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zubía, Eva</creatorcontrib><creatorcontrib>Ortega, María J</creatorcontrib><creatorcontrib>Hernández-Guerrero, Claudia J</creatorcontrib><creatorcontrib>Carballo, J. Luis</creatorcontrib><title>Isothiocyanate Sesquiterpenes from a Sponge of the Genus Axinyssa</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The chemical study of a sponge of the genus Axinyssa collected in the Gulf of California has led to the isolation of the new bicyclic sesquiterpenes axinisothiocyanates A−L (1−12) together with the known compounds (1R,6S,7S,10S)-10-isothiocyanato-4-amorphene (13), (4R*,5R*,7S*,10R*)-4-isocyanoeudesm-11-ene, (−)-epipolasin A, and (+)-aristolone. The structures of the new metabolites have been established by spectroscopic techniques, including the analysis of pyridine-induced 1H NMR chemical shifts. The cytotoxic activity has been tested against three human tumor cell lines.</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>axinisothiocyanate</subject><subject>Axinyssa</subject><subject>Biological and medical sciences</subject><subject>cadinane sesquiterpenes</subject><subject>California</subject><subject>chemical structure</subject><subject>cultured cells</subject><subject>cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>isothiocyanates</subject><subject>Isothiocyanates - chemistry</subject><subject>Isothiocyanates - isolation & purification</subject><subject>Isothiocyanates - pharmacology</subject><subject>Medical sciences</subject><subject>medicinal properties</subject><subject>Molecular Structure</subject><subject>Oceans and Seas</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Porifera</subject><subject>Porifera - chemistry</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>sesquiterpenoids</subject><subject>spectral analysis</subject><subject>stereochemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNptkMFu2zAMhoVhw5plO-wFNl82oAdvlGTJ8jEt1rRAgQ1ItqvA2HTrLpFc0Qaat5-LBOlluvCgjz_JT4iPEr5JUPJ76KEEU2l-JWbSKMgtKPNazEBanWtnizPxjvkBADRU5q04k04558DOxOKG43DfxXqPAQfKVsSPYzdQ6ikQZ22KuwyzVR_DHWWxzYZ7ypYURs4WT13YM-N78abFLdOHY52L9dWP9eV1fvtzeXO5uM2xADPktjK2xU1dSig202tqox2YsnCl2ZSy0hKpIFXp1rpGFk3rpEKrdWPIEqKei6-H2D7Fx5F48LuOa9puMVAc2dtKFlpN_XNxfgDrFJkTtb5P3Q7T3kvwz7r8SdfEfjqGjpsdNS_k0c8EfDkCyDVu24Sh7vjEqUmorBxMXH7gOh7o6fSP6a-3pS6NX_9a-T_qwi5dceWfl_x84FuMHu_SlPl7pUBqgEpCqeXLZKzZP8QxhUnuf074B-RtlaY</recordid><startdate>20080401</startdate><enddate>20080401</enddate><creator>Zubía, Eva</creator><creator>Ortega, María J</creator><creator>Hernández-Guerrero, Claudia J</creator><creator>Carballo, J. Luis</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</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><scope>7X8</scope></search><sort><creationdate>20080401</creationdate><title>Isothiocyanate Sesquiterpenes from a Sponge of the Genus Axinyssa</title><author>Zubía, Eva ; Ortega, María J ; Hernández-Guerrero, Claudia J ; Carballo, J. Luis</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-6956fabc7104bbbbdc5380574875b71931ae4e293f68d14df812a633d5e6eaa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>axinisothiocyanate</topic><topic>Axinyssa</topic><topic>Biological and medical sciences</topic><topic>cadinane sesquiterpenes</topic><topic>California</topic><topic>chemical structure</topic><topic>cultured cells</topic><topic>cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>isothiocyanates</topic><topic>Isothiocyanates - chemistry</topic><topic>Isothiocyanates - isolation & purification</topic><topic>Isothiocyanates - pharmacology</topic><topic>Medical sciences</topic><topic>medicinal properties</topic><topic>Molecular Structure</topic><topic>Oceans and Seas</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Porifera</topic><topic>Porifera - chemistry</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>sesquiterpenoids</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zubía, Eva</creatorcontrib><creatorcontrib>Ortega, María J</creatorcontrib><creatorcontrib>Hernández-Guerrero, Claudia J</creatorcontrib><creatorcontrib>Carballo, J. 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| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2008-04, Vol.71 (4), p.608-614 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69143229 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Animals Antineoplastic agents Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology axinisothiocyanate Axinyssa Biological and medical sciences cadinane sesquiterpenes California chemical structure cultured cells cytotoxicity Drug Screening Assays, Antitumor General aspects General pharmacology Humans isothiocyanates Isothiocyanates - chemistry Isothiocyanates - isolation & purification Isothiocyanates - pharmacology Medical sciences medicinal properties Molecular Structure Oceans and Seas Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Porifera Porifera - chemistry Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology sesquiterpenoids spectral analysis stereochemistry |
| title | Isothiocyanate Sesquiterpenes from a Sponge of the Genus Axinyssa |
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