Cytotoxic 9,11-secosteroids from the South China Sea gorgonian Subergorgia suberosa
•Ten new 9,11-secosteroids were isolated from the gorgonian Subergorgia suberosa.•Their structures were elucidated by analysis of MS, 1D and 2D NMR data.•All the isolates possess the same 3β,6α,11-trihydroxy-7-en-9-one-5α-9,11- secosteroidal nucleus.•Compounds 9 and 10 showed significant cytotoxic a...
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| Veröffentlicht in: | Steroids 2013-09, Vol.78 (9), p.845-850 |
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| creator | Zhang, Gang Tang, Xuli Cheng, Canling Gong, Kaikai Zhang, Xingwang Zhu, Hongyan Wu, Rongcui Li, Pinglin Li, Guoqiang |
| description | •Ten new 9,11-secosteroids were isolated from the gorgonian Subergorgia suberosa.•Their structures were elucidated by analysis of MS, 1D and 2D NMR data.•All the isolates possess the same 3β,6α,11-trihydroxy-7-en-9-one-5α-9,11- secosteroidal nucleus.•Compounds 9 and 10 showed significant cytotoxic activities..
Ten new 9,11-secosteroids, subergorgols A–J (1–10), including two pairs of epimers (3/4, and 6/7), along with three known analogues (11–13) were isolated from the South China Sea gorgonian Subergorgia suberosa. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with the literature data. The cytotoxicities in vitro against three selected human tumor cell lines for all the compounds were evaluated. Compound 9 showed significant cytotoxicities toward both K562 and MDA-MB-231 cell lines with IC50 values of 5.5 and 6.2μM, respectively, and compound 10 also showed inhibitory activity against K562 cell line with an IC50 value of 6.5μM. |
| doi_str_mv | 10.1016/j.steroids.2013.05.009 |
| format | Article |
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Ten new 9,11-secosteroids, subergorgols A–J (1–10), including two pairs of epimers (3/4, and 6/7), along with three known analogues (11–13) were isolated from the South China Sea gorgonian Subergorgia suberosa. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with the literature data. The cytotoxicities in vitro against three selected human tumor cell lines for all the compounds were evaluated. Compound 9 showed significant cytotoxicities toward both K562 and MDA-MB-231 cell lines with IC50 values of 5.5 and 6.2μM, respectively, and compound 10 also showed inhibitory activity against K562 cell line with an IC50 value of 6.5μM.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2013.05.009</identifier><identifier>PMID: 23688970</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>9,11-Secosteroids ; Animals ; Anthozoa - chemistry ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; China ; Cytotoxicity ; Drug Screening Assays, Antitumor ; Gorgonian ; HeLa Cells ; Humans ; Inhibitory Concentration 50 ; K562 Cells ; Magnetic Resonance Spectroscopy ; Models, Molecular ; Molecular Conformation ; Oceans and Seas ; Secosteroids - chemistry ; Secosteroids - pharmacology ; Sesquiterpenes - chemistry ; Sesquiterpenes - pharmacology ; Structural identification ; Structure-Activity Relationship ; Subergorgia suberosa</subject><ispartof>Steroids, 2013-09, Vol.78 (9), p.845-850</ispartof><rights>2013 Elsevier Inc.</rights><rights>Copyright © 2013 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c434t-2e9aab30f3d6c0dcd95ead8dc5b07d82dde6ec2aca8dfe1b4905aacffbc458443</citedby><cites>FETCH-LOGICAL-c434t-2e9aab30f3d6c0dcd95ead8dc5b07d82dde6ec2aca8dfe1b4905aacffbc458443</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.steroids.2013.05.009$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23688970$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Gang</creatorcontrib><creatorcontrib>Tang, Xuli</creatorcontrib><creatorcontrib>Cheng, Canling</creatorcontrib><creatorcontrib>Gong, Kaikai</creatorcontrib><creatorcontrib>Zhang, Xingwang</creatorcontrib><creatorcontrib>Zhu, Hongyan</creatorcontrib><creatorcontrib>Wu, Rongcui</creatorcontrib><creatorcontrib>Li, Pinglin</creatorcontrib><creatorcontrib>Li, Guoqiang</creatorcontrib><title>Cytotoxic 9,11-secosteroids from the South China Sea gorgonian Subergorgia suberosa</title><title>Steroids</title><addtitle>Steroids</addtitle><description>•Ten new 9,11-secosteroids were isolated from the gorgonian Subergorgia suberosa.•Their structures were elucidated by analysis of MS, 1D and 2D NMR data.•All the isolates possess the same 3β,6α,11-trihydroxy-7-en-9-one-5α-9,11- secosteroidal nucleus.•Compounds 9 and 10 showed significant cytotoxic activities..
Ten new 9,11-secosteroids, subergorgols A–J (1–10), including two pairs of epimers (3/4, and 6/7), along with three known analogues (11–13) were isolated from the South China Sea gorgonian Subergorgia suberosa. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with the literature data. The cytotoxicities in vitro against three selected human tumor cell lines for all the compounds were evaluated. Compound 9 showed significant cytotoxicities toward both K562 and MDA-MB-231 cell lines with IC50 values of 5.5 and 6.2μM, respectively, and compound 10 also showed inhibitory activity against K562 cell line with an IC50 value of 6.5μM.</description><subject>9,11-Secosteroids</subject><subject>Animals</subject><subject>Anthozoa - chemistry</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>China</subject><subject>Cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Gorgonian</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>K562 Cells</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Oceans and Seas</subject><subject>Secosteroids - chemistry</subject><subject>Secosteroids - pharmacology</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Structural identification</subject><subject>Structure-Activity Relationship</subject><subject>Subergorgia suberosa</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFUMlOwzAQtRCIlsIvVD5yIGGc1b6BKjYJiUNA4mY59qR11cbFThD9e1K15cppZqS3zHuETBnEDFhxu4xDh95ZE-IEWBpDHgOIEzJmvORRzovylIwBUhGxhH-OyEUISwAoUpGck1GSFpyLEsakmm0717kfq6m4YSwKqN1RmTberWm3QFq5vlvQ2cK2ilao6Nz5uWutamnV1-h3p1U07HYX1CU5a9Qq4NVhTsjH48P77Dl6fXt6md2_RjpLsy5KUChVp9CkptBgtBE5KsONzmsoDU-MwQJ1orTipkFWZwJypXTT1DrLeZalE3K9191499Vj6OTaBo2rlWrR9UGyDApWlgKSAVrsoXp4MHhs5MbbtfJbyUDuCpVLeYwtd4VKyOVQ6ECcHjz6eo3mj3ZscADc7QE4JP226GXQFluNxnrUnTTO_ufxC7zfjRY</recordid><startdate>20130901</startdate><enddate>20130901</enddate><creator>Zhang, Gang</creator><creator>Tang, Xuli</creator><creator>Cheng, Canling</creator><creator>Gong, Kaikai</creator><creator>Zhang, Xingwang</creator><creator>Zhu, Hongyan</creator><creator>Wu, Rongcui</creator><creator>Li, Pinglin</creator><creator>Li, Guoqiang</creator><general>Elsevier Inc</general><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>20130901</creationdate><title>Cytotoxic 9,11-secosteroids from the South China Sea gorgonian Subergorgia suberosa</title><author>Zhang, Gang ; Tang, Xuli ; Cheng, Canling ; Gong, Kaikai ; Zhang, Xingwang ; Zhu, Hongyan ; Wu, Rongcui ; Li, Pinglin ; Li, Guoqiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c434t-2e9aab30f3d6c0dcd95ead8dc5b07d82dde6ec2aca8dfe1b4905aacffbc458443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>9,11-Secosteroids</topic><topic>Animals</topic><topic>Anthozoa - chemistry</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>China</topic><topic>Cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Gorgonian</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>K562 Cells</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Oceans and Seas</topic><topic>Secosteroids - chemistry</topic><topic>Secosteroids - pharmacology</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Structural identification</topic><topic>Structure-Activity Relationship</topic><topic>Subergorgia suberosa</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Gang</creatorcontrib><creatorcontrib>Tang, Xuli</creatorcontrib><creatorcontrib>Cheng, Canling</creatorcontrib><creatorcontrib>Gong, Kaikai</creatorcontrib><creatorcontrib>Zhang, Xingwang</creatorcontrib><creatorcontrib>Zhu, Hongyan</creatorcontrib><creatorcontrib>Wu, Rongcui</creatorcontrib><creatorcontrib>Li, Pinglin</creatorcontrib><creatorcontrib>Li, Guoqiang</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Gang</au><au>Tang, Xuli</au><au>Cheng, Canling</au><au>Gong, Kaikai</au><au>Zhang, Xingwang</au><au>Zhu, Hongyan</au><au>Wu, Rongcui</au><au>Li, Pinglin</au><au>Li, Guoqiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic 9,11-secosteroids from the South China Sea gorgonian Subergorgia suberosa</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2013-09-01</date><risdate>2013</risdate><volume>78</volume><issue>9</issue><spage>845</spage><epage>850</epage><pages>845-850</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><abstract>•Ten new 9,11-secosteroids were isolated from the gorgonian Subergorgia suberosa.•Their structures were elucidated by analysis of MS, 1D and 2D NMR data.•All the isolates possess the same 3β,6α,11-trihydroxy-7-en-9-one-5α-9,11- secosteroidal nucleus.•Compounds 9 and 10 showed significant cytotoxic activities..
Ten new 9,11-secosteroids, subergorgols A–J (1–10), including two pairs of epimers (3/4, and 6/7), along with three known analogues (11–13) were isolated from the South China Sea gorgonian Subergorgia suberosa. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with the literature data. The cytotoxicities in vitro against three selected human tumor cell lines for all the compounds were evaluated. Compound 9 showed significant cytotoxicities toward both K562 and MDA-MB-231 cell lines with IC50 values of 5.5 and 6.2μM, respectively, and compound 10 also showed inhibitory activity against K562 cell line with an IC50 value of 6.5μM.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>23688970</pmid><doi>10.1016/j.steroids.2013.05.009</doi><tpages>6</tpages></addata></record> |
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| subjects | 9,11-Secosteroids Animals Anthozoa - chemistry Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology China Cytotoxicity Drug Screening Assays, Antitumor Gorgonian HeLa Cells Humans Inhibitory Concentration 50 K562 Cells Magnetic Resonance Spectroscopy Models, Molecular Molecular Conformation Oceans and Seas Secosteroids - chemistry Secosteroids - pharmacology Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Structural identification Structure-Activity Relationship Subergorgia suberosa |
| title | Cytotoxic 9,11-secosteroids from the South China Sea gorgonian Subergorgia suberosa |
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