Isolation and absolute configuration of new bioactive marine steroids from Euryspongia n. sp
The apolar fraction of the crude alcoholic extract of the sponge Euryspongia n. sp. was shown to display anti-inflammatory activity. Bioassay guided chromatographic purification led to the isolation of a known compound petrosterol ( 1) of 3β-hydroxy-24-norchol-5-en-23-oic acid ( 2), which has never...
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| Veröffentlicht in: | Steroids 2005-12, Vol.70 (13), p.873-878 |
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| creator | Mandeau, Anne Debitus, Cecile Ariès, Marie-Françoise David, Bruno |
| description | The apolar fraction of the crude alcoholic extract of the sponge
Euryspongia n. sp. was shown to display anti-inflammatory activity. Bioassay guided chromatographic purification led to the isolation of a known compound petrosterol (
1) of 3β-hydroxy-24-norchol-5-en-23-oic acid (
2), which has never yet been found as a natural substance, and of a new steroid, 3β-hydroxy-26-norcampest-5-en-25-oic acid (
3). The absolute configurations of
2 and
3 were deduced from comparative
1H NMR data of the (
S)- and (
R)-phenylglycine methyl ester derivatives. These compounds were evaluated for their anti-inflammatory activity against 6-keto-prostaglandinF1α release in a human keratinocyte cell line HaCaT. |
| doi_str_mv | 10.1016/j.steroids.2005.05.006 |
| format | Article |
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Euryspongia n. sp. was shown to display anti-inflammatory activity. Bioassay guided chromatographic purification led to the isolation of a known compound petrosterol (
1) of 3β-hydroxy-24-norchol-5-en-23-oic acid (
2), which has never yet been found as a natural substance, and of a new steroid, 3β-hydroxy-26-norcampest-5-en-25-oic acid (
3). The absolute configurations of
2 and
3 were deduced from comparative
1H NMR data of the (
S)- and (
R)-phenylglycine methyl ester derivatives. These compounds were evaluated for their anti-inflammatory activity against 6-keto-prostaglandinF1α release in a human keratinocyte cell line HaCaT.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2005.05.006</identifier><identifier>PMID: 16081116</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>3β-Hydroxy-26-norcampest-5-en-25-oic acid ; 6-Ketoprostaglandin F1 alpha - metabolism ; Absolute configuration ; Animals ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - isolation & purification ; Anti-Inflammatory Agents - pharmacology ; Biological and medical sciences ; Cell Line ; Euryspongia n. sp ; Fundamental and applied biological sciences. Psychology ; Humans ; Keratinocytes - cytology ; Magnetic Resonance Spectroscopy ; Phenylglycine methyl ester ; Porifera - chemistry ; Stereoisomerism ; Steroids - chemistry ; Steroids - isolation & purification ; Steroids - pharmacology ; Sterols - isolation & purification ; Vertebrates: endocrinology</subject><ispartof>Steroids, 2005-12, Vol.70 (13), p.873-878</ispartof><rights>2005 Elsevier Inc.</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2005.05.006$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17266533$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16081116$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mandeau, Anne</creatorcontrib><creatorcontrib>Debitus, Cecile</creatorcontrib><creatorcontrib>Ariès, Marie-Françoise</creatorcontrib><creatorcontrib>David, Bruno</creatorcontrib><title>Isolation and absolute configuration of new bioactive marine steroids from Euryspongia n. sp</title><title>Steroids</title><addtitle>Steroids</addtitle><description>The apolar fraction of the crude alcoholic extract of the sponge
Euryspongia n. sp. was shown to display anti-inflammatory activity. Bioassay guided chromatographic purification led to the isolation of a known compound petrosterol (
1) of 3β-hydroxy-24-norchol-5-en-23-oic acid (
2), which has never yet been found as a natural substance, and of a new steroid, 3β-hydroxy-26-norcampest-5-en-25-oic acid (
3). The absolute configurations of
2 and
3 were deduced from comparative
1H NMR data of the (
S)- and (
R)-phenylglycine methyl ester derivatives. These compounds were evaluated for their anti-inflammatory activity against 6-keto-prostaglandinF1α release in a human keratinocyte cell line HaCaT.</description><subject>3β-Hydroxy-26-norcampest-5-en-25-oic acid</subject><subject>6-Ketoprostaglandin F1 alpha - metabolism</subject><subject>Absolute configuration</subject><subject>Animals</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - isolation & purification</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Euryspongia n. sp</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Humans</subject><subject>Keratinocytes - cytology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Phenylglycine methyl ester</subject><subject>Porifera - chemistry</subject><subject>Stereoisomerism</subject><subject>Steroids - chemistry</subject><subject>Steroids - isolation & purification</subject><subject>Steroids - pharmacology</subject><subject>Sterols - isolation & purification</subject><subject>Vertebrates: endocrinology</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkd9LJDEMx8txcq7e_QvSF-9txrazbadvJ-IvEHxR8EEonTaVLrPtXjuj-N_bZXcRAknIJyHJF6EzSlpKqLhYtWWCnIIrLSOEt1sj4gda0F72De-F_IkWhHSqoax_OUYnpaxIJTrFfqFjKkhPKRUL9Hpf0mimkCI20WEz1HSeANsUfXib866UPI7wgYeQjJ3CO-C1ySECPuyAfU5rfD3nz7JJ8S0YHFtcNr_RkTdjgT97f4qeb66fru6ah8fb-6vLhwaYElPjQElO5HLgTlpKlkB6Bpwq4Qe2VIY5RgeglgyeO98R4aDGjivleV8bfHeK_u7mbnL6P0OZ9DoUC-NoIqS5aNFLoYSUFTzbg_OwBqc3OdRLPvXhHxU43wOmWDP6bKIN5ZuTTAjedZX7t-OgnvUeIOtiA0QLLmSwk3YpaEr0Viq90oc36a1UemtViC-B8YmM</recordid><startdate>20051201</startdate><enddate>20051201</enddate><creator>Mandeau, Anne</creator><creator>Debitus, Cecile</creator><creator>Ariès, Marie-Françoise</creator><creator>David, Bruno</creator><general>Elsevier Inc</general><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20051201</creationdate><title>Isolation and absolute configuration of new bioactive marine steroids from Euryspongia n. sp</title><author>Mandeau, Anne ; Debitus, Cecile ; Ariès, Marie-Françoise ; David, Bruno</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-e296t-de975074b5d7c104e082e5196fb249a2d21be1c0bf5df306dec0bd599f587c1f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>3β-Hydroxy-26-norcampest-5-en-25-oic acid</topic><topic>6-Ketoprostaglandin F1 alpha - metabolism</topic><topic>Absolute configuration</topic><topic>Animals</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - isolation & purification</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Euryspongia n. sp</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Humans</topic><topic>Keratinocytes - cytology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Phenylglycine methyl ester</topic><topic>Porifera - chemistry</topic><topic>Stereoisomerism</topic><topic>Steroids - chemistry</topic><topic>Steroids - isolation & purification</topic><topic>Steroids - pharmacology</topic><topic>Sterols - isolation & purification</topic><topic>Vertebrates: endocrinology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mandeau, Anne</creatorcontrib><creatorcontrib>Debitus, Cecile</creatorcontrib><creatorcontrib>Ariès, Marie-Françoise</creatorcontrib><creatorcontrib>David, Bruno</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mandeau, Anne</au><au>Debitus, Cecile</au><au>Ariès, Marie-Françoise</au><au>David, Bruno</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation and absolute configuration of new bioactive marine steroids from Euryspongia n. sp</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2005-12-01</date><risdate>2005</risdate><volume>70</volume><issue>13</issue><spage>873</spage><epage>878</epage><pages>873-878</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>The apolar fraction of the crude alcoholic extract of the sponge
Euryspongia n. sp. was shown to display anti-inflammatory activity. Bioassay guided chromatographic purification led to the isolation of a known compound petrosterol (
1) of 3β-hydroxy-24-norchol-5-en-23-oic acid (
2), which has never yet been found as a natural substance, and of a new steroid, 3β-hydroxy-26-norcampest-5-en-25-oic acid (
3). The absolute configurations of
2 and
3 were deduced from comparative
1H NMR data of the (
S)- and (
R)-phenylglycine methyl ester derivatives. These compounds were evaluated for their anti-inflammatory activity against 6-keto-prostaglandinF1α release in a human keratinocyte cell line HaCaT.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>16081116</pmid><doi>10.1016/j.steroids.2005.05.006</doi><tpages>6</tpages></addata></record> |
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| ispartof | Steroids, 2005-12, Vol.70 (13), p.873-878 |
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| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | 3β-Hydroxy-26-norcampest-5-en-25-oic acid 6-Ketoprostaglandin F1 alpha - metabolism Absolute configuration Animals Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - isolation & purification Anti-Inflammatory Agents - pharmacology Biological and medical sciences Cell Line Euryspongia n. sp Fundamental and applied biological sciences. Psychology Humans Keratinocytes - cytology Magnetic Resonance Spectroscopy Phenylglycine methyl ester Porifera - chemistry Stereoisomerism Steroids - chemistry Steroids - isolation & purification Steroids - pharmacology Sterols - isolation & purification Vertebrates: endocrinology |
| title | Isolation and absolute configuration of new bioactive marine steroids from Euryspongia n. sp |
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