Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis
The lipid extract of the marine sponge Luffariella cf. variabilis from Mayotte (Indian Ocean) has proven to be an extraordinarily rich source of a wide variety of unusual steroids belonging to the 5α,8α-epidioxy sterol family. Ten epidioxy sterols have been identified: 5α,8α-epidioxycholesta-6,22-di...
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| Veröffentlicht in: | Canadian journal of chemistry 2000-07, Vol.78 (7), p.986-992 |
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| container_title | Canadian journal of chemistry |
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| creator | Gauvin, Anne Smadja, Jacqueline Aknin, Maurice Faure, Robert Gaydou, Emile-Marcel |
| description | The lipid extract of the marine sponge Luffariella cf. variabilis from Mayotte (Indian Ocean) has proven to be an extraordinarily rich source of a wide variety of unusual steroids belonging to the 5α,8α-epidioxy sterol family. Ten epidioxy sterols have been identified: 5α,8α-epidioxycholesta-6,22-dien-3β-ol, 5α,8α-epidioxycholest-6-en-3β-ol, 5α,8α-epidioxy-24(ξ)-methylcholesta-6,22-dien-3β-ol, 5α,8α-epidioxy-24(S)-methylcholest-6-en-3β-ol and its epimer (24R), 5α,8α-epidioxy-24(S)-ethylcholesta-6,22-dien-3β-ol and its epimer (24R), 5α,8α-epidioxy-24(S)-ethylcholest-6-en-3β-ol and its epimer (24R), along with 5α,8α-epidioxy-24(ξ)-methylcholesta-6,9(11),22-trien-3β-ol. Their structures were determined by nuclear magnetic resonance (
1
H,
13
C) and electron impact mass spectrometry. The mixture of the 10 steroids showed inhibitive activity against the human T-cell leukemia/lymphotropic virus type I (HTLV-I) and also displayed cytotoxic activity against the human breast cancer cell line (MCF
7
WT).Key words: Luffariella cf. variabilis, marine sponge, 5α,8α-epidioxy sterols, antitumor and antiviral activities. |
| doi_str_mv | 10.1139/v00-083 |
| format | Article |
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1
H,
13
C) and electron impact mass spectrometry. The mixture of the 10 steroids showed inhibitive activity against the human T-cell leukemia/lymphotropic virus type I (HTLV-I) and also displayed cytotoxic activity against the human breast cancer cell line (MCF
7
WT).Key words: Luffariella cf. variabilis, marine sponge, 5α,8α-epidioxy sterols, antitumor and antiviral activities.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v00-083</identifier><language>eng</language><ispartof>Canadian journal of chemistry, 2000-07, Vol.78 (7), p.986-992</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c138t-3e27e0dbf30c99251d34b2ca842caa494298dadc00b131821dfa5fd840e74e3f3</citedby><cites>FETCH-LOGICAL-c138t-3e27e0dbf30c99251d34b2ca842caa494298dadc00b131821dfa5fd840e74e3f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27907,27908</link.rule.ids></links><search><creatorcontrib>Gauvin, Anne</creatorcontrib><creatorcontrib>Smadja, Jacqueline</creatorcontrib><creatorcontrib>Aknin, Maurice</creatorcontrib><creatorcontrib>Faure, Robert</creatorcontrib><creatorcontrib>Gaydou, Emile-Marcel</creatorcontrib><title>Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis</title><title>Canadian journal of chemistry</title><description>The lipid extract of the marine sponge Luffariella cf. variabilis from Mayotte (Indian Ocean) has proven to be an extraordinarily rich source of a wide variety of unusual steroids belonging to the 5α,8α-epidioxy sterol family. Ten epidioxy sterols have been identified: 5α,8α-epidioxycholesta-6,22-dien-3β-ol, 5α,8α-epidioxycholest-6-en-3β-ol, 5α,8α-epidioxy-24(ξ)-methylcholesta-6,22-dien-3β-ol, 5α,8α-epidioxy-24(S)-methylcholest-6-en-3β-ol and its epimer (24R), 5α,8α-epidioxy-24(S)-ethylcholesta-6,22-dien-3β-ol and its epimer (24R), 5α,8α-epidioxy-24(S)-ethylcholest-6-en-3β-ol and its epimer (24R), along with 5α,8α-epidioxy-24(ξ)-methylcholesta-6,9(11),22-trien-3β-ol. Their structures were determined by nuclear magnetic resonance (
1
H,
13
C) and electron impact mass spectrometry. The mixture of the 10 steroids showed inhibitive activity against the human T-cell leukemia/lymphotropic virus type I (HTLV-I) and also displayed cytotoxic activity against the human breast cancer cell line (MCF
7
WT).Key words: Luffariella cf. variabilis, marine sponge, 5α,8α-epidioxy sterols, antitumor and antiviral activities.</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNotkM1KxDAcxIMoWFfxFXLzYtZ_PkrToyx-LBS86LmkyT8a6TalqcV9rH2RfSYjeplh5jAMP0KuOaw5l_XdAsBAyxNScKWBSVHzU1IAgGYKlDgnFyl95liBKAtitin2Zg5xoNHTLkRj57AgLY-HW308MByDC_F7T9OMU-wT9VPc0fkD6c5MYUCaxji8I22-vM8F9r2h1q_pkoPpQh_SJTnzpk949e8r8vb48Lp5Zs3L03Zz3zDLpZ6ZRFEhuM5LsHUtSu6k6oQ1WmUxqlai1s44C9BxybXgzpvSO60AK4XSyxW5-du1U0xpQt-OU8gn9y2H9pdMm8m0mYz8AW_uWDg</recordid><startdate>20000701</startdate><enddate>20000701</enddate><creator>Gauvin, Anne</creator><creator>Smadja, Jacqueline</creator><creator>Aknin, Maurice</creator><creator>Faure, Robert</creator><creator>Gaydou, Emile-Marcel</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20000701</creationdate><title>Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis</title><author>Gauvin, Anne ; Smadja, Jacqueline ; Aknin, Maurice ; Faure, Robert ; Gaydou, Emile-Marcel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c138t-3e27e0dbf30c99251d34b2ca842caa494298dadc00b131821dfa5fd840e74e3f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gauvin, Anne</creatorcontrib><creatorcontrib>Smadja, Jacqueline</creatorcontrib><creatorcontrib>Aknin, Maurice</creatorcontrib><creatorcontrib>Faure, Robert</creatorcontrib><creatorcontrib>Gaydou, Emile-Marcel</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gauvin, Anne</au><au>Smadja, Jacqueline</au><au>Aknin, Maurice</au><au>Faure, Robert</au><au>Gaydou, Emile-Marcel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis</atitle><jtitle>Canadian journal of chemistry</jtitle><date>2000-07-01</date><risdate>2000</risdate><volume>78</volume><issue>7</issue><spage>986</spage><epage>992</epage><pages>986-992</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>The lipid extract of the marine sponge Luffariella cf. variabilis from Mayotte (Indian Ocean) has proven to be an extraordinarily rich source of a wide variety of unusual steroids belonging to the 5α,8α-epidioxy sterol family. Ten epidioxy sterols have been identified: 5α,8α-epidioxycholesta-6,22-dien-3β-ol, 5α,8α-epidioxycholest-6-en-3β-ol, 5α,8α-epidioxy-24(ξ)-methylcholesta-6,22-dien-3β-ol, 5α,8α-epidioxy-24(S)-methylcholest-6-en-3β-ol and its epimer (24R), 5α,8α-epidioxy-24(S)-ethylcholesta-6,22-dien-3β-ol and its epimer (24R), 5α,8α-epidioxy-24(S)-ethylcholest-6-en-3β-ol and its epimer (24R), along with 5α,8α-epidioxy-24(ξ)-methylcholesta-6,9(11),22-trien-3β-ol. Their structures were determined by nuclear magnetic resonance (
1
H,
13
C) and electron impact mass spectrometry. The mixture of the 10 steroids showed inhibitive activity against the human T-cell leukemia/lymphotropic virus type I (HTLV-I) and also displayed cytotoxic activity against the human breast cancer cell line (MCF
7
WT).Key words: Luffariella cf. variabilis, marine sponge, 5α,8α-epidioxy sterols, antitumor and antiviral activities.</abstract><doi>10.1139/v00-083</doi><tpages>7</tpages></addata></record> |
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| title | Isolation of bioactive 5α,8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis |
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