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7-Nor-ergosterolide, a Pentalactone-Containing Norsteroid and Related Steroids from the Marine-Derived Endophytic Aspergillus ochraceus EN-31
7-Nor-ergosterolide (1), a rare 7-norsteroid with an unusual pentalactone B-ring system, and two new steroid derivatives, 3β,11α-dihydroxyergosta-8,24(28)-dien-7-one (2) and 3β-hydroxyergosta-8,24(28)-dien-7-one (3), were characterized from the culture extract of Aspergillus ochraceus EN-31, an endo...
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Published in: | Journal of natural products (Washington, D.C.) D.C.), 2010-11, Vol.73 (11), p.1780-1784 |
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container_title | Journal of natural products (Washington, D.C.) |
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creator | Cui, Chuan-Ming Li, Xiao-Ming Meng, Li Li, Chun-Shun Huang, Cai-Guo Wang, Bin-Gui |
description | 7-Nor-ergosterolide (1), a rare 7-norsteroid with an unusual pentalactone B-ring system, and two new steroid derivatives, 3β,11α-dihydroxyergosta-8,24(28)-dien-7-one (2) and 3β-hydroxyergosta-8,24(28)-dien-7-one (3), were characterized from the culture extract of Aspergillus ochraceus EN-31, an endophytic fungus isolated from the marine brown alga Sargassum kjellmanianum. In addition, nine known related steroids were isolated and identified. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configuration of the new steroids (1−3) was determined by application of the modified Mosher’s method. Compound 1, which represents the first example of a 7-nor-ergosteroid possessing a pentalactone B-ring system in a naturally occurring steroid, displayed cytotoxicity against NCI-H460, SMMC-7721, and SW1990 cell lines with IC50 values of 5.0, 7.0, and 28.0 μg/mL, respectively. Compound 2 also displayed cytotoxicity against the SMMC-7721 cell line with an IC50 value of 28.0 μg/mL. |
doi_str_mv | 10.1021/np100386q |
format | article |
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In addition, nine known related steroids were isolated and identified. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configuration of the new steroids (1−3) was determined by application of the modified Mosher’s method. Compound 1, which represents the first example of a 7-nor-ergosteroid possessing a pentalactone B-ring system in a naturally occurring steroid, displayed cytotoxicity against NCI-H460, SMMC-7721, and SW1990 cell lines with IC50 values of 5.0, 7.0, and 28.0 μg/mL, respectively. Compound 2 also displayed cytotoxicity against the SMMC-7721 cell line with an IC50 value of 28.0 μg/mL.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np100386q</identifier><identifier>PMID: 21043476</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Antineoplastic Agents - chemistry ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Aspergillus ochraceus - chemistry ; Biological and medical sciences ; Drug Screening Assays, Antitumor ; General pharmacology ; Humans ; Inhibitory Concentration 50 ; Marine Biology ; Medical sciences ; Molecular Structure ; Norsteroids - chemistry ; Norsteroids - isolation & purification ; Norsteroids - pharmacology ; Nuclear Magnetic Resonance, Biomolecular ; Phaeophyceae - microbiology ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Stereoisomerism</subject><ispartof>Journal of natural products (Washington, D.C.), 2010-11, Vol.73 (11), p.1780-1784</ispartof><rights>Copyright © 2010 American Chemical Society and American Society of Pharmacognosy and American Society of Pharmacognosy</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-76dfb66b14edc75def301d46315a4d8487636cc7067f2f4b946421b8eb1e6a9f3</citedby><cites>FETCH-LOGICAL-a410t-76dfb66b14edc75def301d46315a4d8487636cc7067f2f4b946421b8eb1e6a9f3</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=23504332$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21043476$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cui, Chuan-Ming</creatorcontrib><creatorcontrib>Li, Xiao-Ming</creatorcontrib><creatorcontrib>Meng, Li</creatorcontrib><creatorcontrib>Li, Chun-Shun</creatorcontrib><creatorcontrib>Huang, Cai-Guo</creatorcontrib><creatorcontrib>Wang, Bin-Gui</creatorcontrib><title>7-Nor-ergosterolide, a Pentalactone-Containing Norsteroid and Related Steroids from the Marine-Derived Endophytic Aspergillus ochraceus EN-31</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>7-Nor-ergosterolide (1), a rare 7-norsteroid with an unusual pentalactone B-ring system, and two new steroid derivatives, 3β,11α-dihydroxyergosta-8,24(28)-dien-7-one (2) and 3β-hydroxyergosta-8,24(28)-dien-7-one (3), were characterized from the culture extract of Aspergillus ochraceus EN-31, an endophytic fungus isolated from the marine brown alga Sargassum kjellmanianum. In addition, nine known related steroids were isolated and identified. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configuration of the new steroids (1−3) was determined by application of the modified Mosher’s method. Compound 1, which represents the first example of a 7-nor-ergosteroid possessing a pentalactone B-ring system in a naturally occurring steroid, displayed cytotoxicity against NCI-H460, SMMC-7721, and SW1990 cell lines with IC50 values of 5.0, 7.0, and 28.0 μg/mL, respectively. Compound 2 also displayed cytotoxicity against the SMMC-7721 cell line with an IC50 value of 28.0 μg/mL.</description><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Aspergillus ochraceus - chemistry</subject><subject>Biological and medical sciences</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Marine Biology</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Norsteroids - chemistry</subject><subject>Norsteroids - isolation & purification</subject><subject>Norsteroids - pharmacology</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Phaeophyceae - microbiology</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Stereoisomerism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNpt0MlOBCEQBmBiNDouB1_AcPFgIgoNTc8czTguiVtczh0aCgfTAy30mMxD-M6i43LxBFS-qgo_QruMHjFasGPfMUr5UL6uoAErC0okLcpVNKBMcpLrYgNtpvRCM6Kjch1tFIwKLio5QO8VuQmRQHwOqYcYWmfgECt8B75XrdJ98EDGIT-cd_4ZZ_zlnMHKG3wPrerB4IdlLWEbwwz3U8DXKrrcegrRvWUw8SZ000XvND5JXV7n2naecNDTqDTk2-SGcLaN1qxqE-x8n1vo6WzyOL4gV7fnl-OTK6IEoz2ppLGNlA0TYHRVGrCcMiMkZ6USZiiGleRS64rKyhZWNCMhRcGaITQMpBpZvoUOlnN1DClFsHUX3UzFRc1o_Rlp_RtptntL282bGZhf-ZNhBvvfQCWtWhuV1y79OV5myIs_p3SqX8I8-vzFfxZ-AEWSi-M</recordid><startdate>20101129</startdate><enddate>20101129</enddate><creator>Cui, Chuan-Ming</creator><creator>Li, Xiao-Ming</creator><creator>Meng, Li</creator><creator>Li, Chun-Shun</creator><creator>Huang, Cai-Guo</creator><creator>Wang, Bin-Gui</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><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>20101129</creationdate><title>7-Nor-ergosterolide, a Pentalactone-Containing Norsteroid and Related Steroids from the Marine-Derived Endophytic Aspergillus ochraceus EN-31</title><author>Cui, Chuan-Ming ; Li, Xiao-Ming ; Meng, Li ; Li, Chun-Shun ; Huang, Cai-Guo ; Wang, Bin-Gui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-76dfb66b14edc75def301d46315a4d8487636cc7067f2f4b946421b8eb1e6a9f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Aspergillus ochraceus - chemistry</topic><topic>Biological and medical sciences</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Marine Biology</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Norsteroids - chemistry</topic><topic>Norsteroids - isolation & purification</topic><topic>Norsteroids - pharmacology</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Phaeophyceae - microbiology</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cui, Chuan-Ming</creatorcontrib><creatorcontrib>Li, Xiao-Ming</creatorcontrib><creatorcontrib>Meng, Li</creatorcontrib><creatorcontrib>Li, Chun-Shun</creatorcontrib><creatorcontrib>Huang, Cai-Guo</creatorcontrib><creatorcontrib>Wang, Bin-Gui</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>CrossRef</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cui, Chuan-Ming</au><au>Li, Xiao-Ming</au><au>Meng, Li</au><au>Li, Chun-Shun</au><au>Huang, Cai-Guo</au><au>Wang, Bin-Gui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>7-Nor-ergosterolide, a Pentalactone-Containing Norsteroid and Related Steroids from the Marine-Derived Endophytic Aspergillus ochraceus EN-31</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2010-11-29</date><risdate>2010</risdate><volume>73</volume><issue>11</issue><spage>1780</spage><epage>1784</epage><pages>1780-1784</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>7-Nor-ergosterolide (1), a rare 7-norsteroid with an unusual pentalactone B-ring system, and two new steroid derivatives, 3β,11α-dihydroxyergosta-8,24(28)-dien-7-one (2) and 3β-hydroxyergosta-8,24(28)-dien-7-one (3), were characterized from the culture extract of Aspergillus ochraceus EN-31, an endophytic fungus isolated from the marine brown alga Sargassum kjellmanianum. In addition, nine known related steroids were isolated and identified. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The absolute configuration of the new steroids (1−3) was determined by application of the modified Mosher’s method. Compound 1, which represents the first example of a 7-nor-ergosteroid possessing a pentalactone B-ring system in a naturally occurring steroid, displayed cytotoxicity against NCI-H460, SMMC-7721, and SW1990 cell lines with IC50 values of 5.0, 7.0, and 28.0 μg/mL, respectively. Compound 2 also displayed cytotoxicity against the SMMC-7721 cell line with an IC50 value of 28.0 μg/mL.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>21043476</pmid><doi>10.1021/np100386q</doi><tpages>5</tpages></addata></record> |
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source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
subjects | Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Aspergillus ochraceus - chemistry Biological and medical sciences Drug Screening Assays, Antitumor General pharmacology Humans Inhibitory Concentration 50 Marine Biology Medical sciences Molecular Structure Norsteroids - chemistry Norsteroids - isolation & purification Norsteroids - pharmacology Nuclear Magnetic Resonance, Biomolecular Phaeophyceae - microbiology Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Stereoisomerism |
title | 7-Nor-ergosterolide, a Pentalactone-Containing Norsteroid and Related Steroids from the Marine-Derived Endophytic Aspergillus ochraceus EN-31 |
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