(2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a New Amino Alcohol from the Caribbean Sponge Haliclona vansoesti
The Caribbean marine sponge Haliclona vansoesti was found to contain a high amount (5% dry wt) of a new analogue of 4-sphingenine, (2R,3R,7Z)-2-aminotetradec-7-ene-1,3-diol (1). Its structure was determined by detailed spectroscopic analysis. The relative configuration was deduced from the NMR data...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2000-07, Vol.63 (7), p.978-980 |
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| container_issue | 7 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 63 |
| creator | Devijver, C Salmoun, M Daloze, D Braekman, J. C De Weerdt, W. H De Kluijver, M. J Gomez, R |
| description | The Caribbean marine sponge Haliclona vansoesti was found to contain a high amount (5% dry wt) of a new analogue of 4-sphingenine, (2R,3R,7Z)-2-aminotetradec-7-ene-1,3-diol (1). Its structure was determined by detailed spectroscopic analysis. The relative configuration was deduced from the NMR data of the corresponding acetonide 5, while the absolute configuration was secured via protection of the primary alcohol and amino groups, and esterification of the secondary alcohol with Mosher's reagent. |
| doi_str_mv | 10.1021/np000081c |
| format | Article |
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The relative configuration was deduced from the NMR data of the corresponding acetonide 5, while the absolute configuration was secured via protection of the primary alcohol and amino groups, and esterification of the secondary alcohol with Mosher's reagent.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np000081c</identifier><identifier>PMID: 10924178</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>2-Aminotetradec-7-ene-1,3-diol ; alcohols ; Analytical, structural and metabolic biochemistry ; Animals ; Biological and medical sciences ; Fundamental and applied biological sciences. Psychology ; Haliclona vansoesti ; Molecular Structure ; natural products ; Other biological molecules ; Plant growth substances ; Porifera - chemistry ; Spectrum Analysis ; Sphingosine - analogs & derivatives ; Sphingosine - chemistry ; Sphingosine - isolation & purification</subject><ispartof>Journal of natural products (Washington, D.C.), 2000-07, Vol.63 (7), p.978-980</ispartof><rights>Copyright © 2000 American Chemical Society and American Society of Pharmacognosy</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-a3a74218135c500c580daecafaedce442608614e392e46f20604cf0e31c595923</citedby><cites>FETCH-LOGICAL-a411t-a3a74218135c500c580daecafaedce442608614e392e46f20604cf0e31c595923</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/np000081c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np000081c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1454582$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10924178$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Devijver, C</creatorcontrib><creatorcontrib>Salmoun, M</creatorcontrib><creatorcontrib>Daloze, D</creatorcontrib><creatorcontrib>Braekman, J. C</creatorcontrib><creatorcontrib>De Weerdt, W. H</creatorcontrib><creatorcontrib>De Kluijver, M. J</creatorcontrib><creatorcontrib>Gomez, R</creatorcontrib><title>(2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a New Amino Alcohol from the Caribbean Sponge Haliclona vansoesti</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The Caribbean marine sponge Haliclona vansoesti was found to contain a high amount (5% dry wt) of a new analogue of 4-sphingenine, (2R,3R,7Z)-2-aminotetradec-7-ene-1,3-diol (1). Its structure was determined by detailed spectroscopic analysis. The relative configuration was deduced from the NMR data of the corresponding acetonide 5, while the absolute configuration was secured via protection of the primary alcohol and amino groups, and esterification of the secondary alcohol with Mosher's reagent.</description><subject>2-Aminotetradec-7-ene-1,3-diol</subject><subject>alcohols</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Haliclona vansoesti</subject><subject>Molecular Structure</subject><subject>natural products</subject><subject>Other biological molecules</subject><subject>Plant growth substances</subject><subject>Porifera - chemistry</subject><subject>Spectrum Analysis</subject><subject>Sphingosine - analogs & derivatives</subject><subject>Sphingosine - chemistry</subject><subject>Sphingosine - isolation & purification</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U1v1DAQBmALgehSOPAHUA6AqLQGf8bJcbUqXVD5ULsIiYs160xoWsde7GyBf09KVoUDEr744EfvjGcIeczZS84EfxW2bDwVd3fIjGvBaMmEvktmjJeSyqpUB-RBzpejkazW98kBZ7VQ3FQz4l-Is7k8m5svR1TQRd-FOOCQoEFHDcWAlM8lbbro5wUU7_F78dsUC-_iRfRFm2JfDBdYLCF1mw1CKM63MXzFYgW-cz4GKK4h5Ih56B6Sey34jI_29yH59Pp4vVzR0w8nb5aLUwqK84GCBKMEr7jUTjPmdMUaQActYONQKVGyquQKZS1Qla1gJVOuZSi507WuhTwkz6fcbYrfdmNl23fZofcQMO6yNXyMKAX7L-TGlEabaoRHE3Qp5pywtdvU9ZB-Ws7szQ7s7Q5G-2Qfutv02Pwlp6GP4OkeQHbg2wTBdfmPU1rp6uYXdGJdHvDH7TOkK1saabRdfzy31Yl-91asV_bz6J9NHly2l3GXwjjjf_T3C1SvpUg</recordid><startdate>20000701</startdate><enddate>20000701</enddate><creator>Devijver, C</creator><creator>Salmoun, M</creator><creator>Daloze, D</creator><creator>Braekman, J. C</creator><creator>De Weerdt, W. H</creator><creator>De Kluijver, M. J</creator><creator>Gomez, R</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><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>8FD</scope><scope>F1W</scope><scope>FR3</scope><scope>H95</scope><scope>H99</scope><scope>L.F</scope><scope>L.G</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20000701</creationdate><title>(2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a New Amino Alcohol from the Caribbean Sponge Haliclona vansoesti</title><author>Devijver, C ; Salmoun, M ; Daloze, D ; Braekman, J. C ; De Weerdt, W. H ; De Kluijver, M. J ; Gomez, R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-a3a74218135c500c580daecafaedce442608614e392e46f20604cf0e31c595923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>2-Aminotetradec-7-ene-1,3-diol</topic><topic>alcohols</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Haliclona vansoesti</topic><topic>Molecular Structure</topic><topic>natural products</topic><topic>Other biological molecules</topic><topic>Plant growth substances</topic><topic>Porifera - chemistry</topic><topic>Spectrum Analysis</topic><topic>Sphingosine - analogs & derivatives</topic><topic>Sphingosine - chemistry</topic><topic>Sphingosine - isolation & purification</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Devijver, C</creatorcontrib><creatorcontrib>Salmoun, M</creatorcontrib><creatorcontrib>Daloze, D</creatorcontrib><creatorcontrib>Braekman, J. C</creatorcontrib><creatorcontrib>De Weerdt, W. H</creatorcontrib><creatorcontrib>De Kluijver, M. 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| ispartof | Journal of natural products (Washington, D.C.), 2000-07, Vol.63 (7), p.978-980 |
| issn | 0163-3864 1520-6025 |
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| source | MEDLINE; American Chemical Society Publications |
| subjects | 2-Aminotetradec-7-ene-1,3-diol alcohols Analytical, structural and metabolic biochemistry Animals Biological and medical sciences Fundamental and applied biological sciences. Psychology Haliclona vansoesti Molecular Structure natural products Other biological molecules Plant growth substances Porifera - chemistry Spectrum Analysis Sphingosine - analogs & derivatives Sphingosine - chemistry Sphingosine - isolation & purification |
| title | (2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a New Amino Alcohol from the Caribbean Sponge Haliclona vansoesti |
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