Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa
•New unusual cholestane and pregnane derivatives from Subergorgia suberosa.•Structures were elucidated by analyses of 2D NMR, IR, and HRMS.•Compounds were evaluated for antifouling activity. Two new unusual cholestane derivatives, pentacyclic steroid 16,22-epoxy-20β,23S-dihydroxycholest-1-ene-3-one...
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| Veröffentlicht in: | Steroids 2014-01, Vol.79, p.1-6 |
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| creator | Zhang, Jun Liang, Yan Wang, Kai-Ling Liao, Xiao-Jian Deng, Zhou Xu, Shi-Hai |
| description | •New unusual cholestane and pregnane derivatives from Subergorgia suberosa.•Structures were elucidated by analyses of 2D NMR, IR, and HRMS.•Compounds were evaluated for antifouling activity.
Two new unusual cholestane derivatives, pentacyclic steroid 16,22-epoxy-20β,23S-dihydroxycholest-1-ene-3-one (1) and 20β,23S-dihydroxycholest-1-ene-3,22-dione (2), along with two new pregnane derivatives, 15β,17α-dihydroxypregna-4,6-diene-3,20-dione (3) and 11α-hydroxypregna-4-ene-3,6,20-trione (4), were isolated from the South China Sea gorgonian coral Subergorgia suberosa. Their structures were established based on the extensive analyses of 2D NMR, IR, and HRMS. Antifouling tests against Balanus amphitrite larvae settlement indicated that 1 and 2 exhibited inhibitory effect with EC50 values of 5.3, and 14.5μg/mL, respectively. |
| doi_str_mv | 10.1016/j.steroids.2013.10.007 |
| format | Article |
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Two new unusual cholestane derivatives, pentacyclic steroid 16,22-epoxy-20β,23S-dihydroxycholest-1-ene-3-one (1) and 20β,23S-dihydroxycholest-1-ene-3,22-dione (2), along with two new pregnane derivatives, 15β,17α-dihydroxypregna-4,6-diene-3,20-dione (3) and 11α-hydroxypregna-4-ene-3,6,20-trione (4), were isolated from the South China Sea gorgonian coral Subergorgia suberosa. Their structures were established based on the extensive analyses of 2D NMR, IR, and HRMS. Antifouling tests against Balanus amphitrite larvae settlement indicated that 1 and 2 exhibited inhibitory effect with EC50 values of 5.3, and 14.5μg/mL, respectively.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2013.10.007</identifier><identifier>PMID: 24184487</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>20β,23S-Dihydroxycholest ; Animals ; Anthozoa - chemistry ; Antifouing ; Biofouling - prevention & control ; Cholestanes - chemistry ; Cholestanes - pharmacology ; Cholestenones - chemistry ; Cholestenones - pharmacology ; Dose-Response Relationship, Drug ; Gorgonian coral ; Larva - drug effects ; Larva - growth & development ; Magnetic Resonance Spectroscopy - methods ; Mass Spectrometry ; Molecular Structure ; Oceans and Seas ; Pentacyclic steroid ; Prednisone - analogs & derivatives ; Prednisone - chemistry ; Prednisone - pharmacology ; Pregnadienediols - chemistry ; Pregnadienediols - pharmacology ; Pregnanes - chemistry ; Pregnanes - pharmacology ; Spectrophotometry ; Stereoisomerism ; Steroids - chemistry ; Steroids - pharmacology ; Subergorgia suberosa ; Thoracica - drug effects ; Thoracica - growth & development</subject><ispartof>Steroids, 2014-01, Vol.79, p.1-6</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-c368t-e6eace23d1a737d558d09e156b0777f581c0377f75897db5c25d165d654c9f23</citedby><cites>FETCH-LOGICAL-c368t-e6eace23d1a737d558d09e156b0777f581c0377f75897db5c25d165d654c9f23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0039128X13002316$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24184487$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Jun</creatorcontrib><creatorcontrib>Liang, Yan</creatorcontrib><creatorcontrib>Wang, Kai-Ling</creatorcontrib><creatorcontrib>Liao, Xiao-Jian</creatorcontrib><creatorcontrib>Deng, Zhou</creatorcontrib><creatorcontrib>Xu, Shi-Hai</creatorcontrib><title>Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa</title><title>Steroids</title><addtitle>Steroids</addtitle><description>•New unusual cholestane and pregnane derivatives from Subergorgia suberosa.•Structures were elucidated by analyses of 2D NMR, IR, and HRMS.•Compounds were evaluated for antifouling activity.
Two new unusual cholestane derivatives, pentacyclic steroid 16,22-epoxy-20β,23S-dihydroxycholest-1-ene-3-one (1) and 20β,23S-dihydroxycholest-1-ene-3,22-dione (2), along with two new pregnane derivatives, 15β,17α-dihydroxypregna-4,6-diene-3,20-dione (3) and 11α-hydroxypregna-4-ene-3,6,20-trione (4), were isolated from the South China Sea gorgonian coral Subergorgia suberosa. Their structures were established based on the extensive analyses of 2D NMR, IR, and HRMS. Antifouling tests against Balanus amphitrite larvae settlement indicated that 1 and 2 exhibited inhibitory effect with EC50 values of 5.3, and 14.5μg/mL, respectively.</description><subject>20β,23S-Dihydroxycholest</subject><subject>Animals</subject><subject>Anthozoa - chemistry</subject><subject>Antifouing</subject><subject>Biofouling - prevention & control</subject><subject>Cholestanes - chemistry</subject><subject>Cholestanes - pharmacology</subject><subject>Cholestenones - chemistry</subject><subject>Cholestenones - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>Gorgonian coral</subject><subject>Larva - drug effects</subject><subject>Larva - growth & development</subject><subject>Magnetic Resonance Spectroscopy - methods</subject><subject>Mass Spectrometry</subject><subject>Molecular Structure</subject><subject>Oceans and Seas</subject><subject>Pentacyclic steroid</subject><subject>Prednisone - analogs & derivatives</subject><subject>Prednisone - chemistry</subject><subject>Prednisone - pharmacology</subject><subject>Pregnadienediols - chemistry</subject><subject>Pregnadienediols - pharmacology</subject><subject>Pregnanes - chemistry</subject><subject>Pregnanes - pharmacology</subject><subject>Spectrophotometry</subject><subject>Stereoisomerism</subject><subject>Steroids - chemistry</subject><subject>Steroids - pharmacology</subject><subject>Subergorgia suberosa</subject><subject>Thoracica - drug effects</subject><subject>Thoracica - growth & development</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFUMtOwzAQtBCIlsIvVD5ySbCT-JEbVcVLqoREe-BmufamdZXGxU6Q-HsSteXKaUejmdndQWhKSUoJ5Q-7NLYQvLMxzQjNezIlRFygMZVCJkxycYnGhORlQjP5OUI3Me4IITwvs2s0ygoqi0KKMfqYNa2rfFe7ZoPPkbgKfo_bLeCl79otnm9do_ESNN74sPGN0w02PugaL7s1hIF0GscB-6hv0VWl6wh3pzlBq-en1fw1Wby_vM1ni8TkXLYJcNAGstxSLXJhGZOWlEAZXxMhRMUkNSTvgWCyFHbNTMYs5cxyVpiyyvIJuj_GHoL_6iC2au-igbrWDfguKlrwMqOUkbKX8qPU9PfFAJU6BLfX4UdRooY61U6df1dDnQPf19kbp6cd3XoP9s927q8XPB4F0D_67SCoaBw0BqwLYFplvftvxy8zm4py</recordid><startdate>201401</startdate><enddate>201401</enddate><creator>Zhang, Jun</creator><creator>Liang, Yan</creator><creator>Wang, Kai-Ling</creator><creator>Liao, Xiao-Jian</creator><creator>Deng, Zhou</creator><creator>Xu, Shi-Hai</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>201401</creationdate><title>Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa</title><author>Zhang, Jun ; Liang, Yan ; Wang, Kai-Ling ; Liao, Xiao-Jian ; Deng, Zhou ; Xu, Shi-Hai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-e6eace23d1a737d558d09e156b0777f581c0377f75897db5c25d165d654c9f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>20β,23S-Dihydroxycholest</topic><topic>Animals</topic><topic>Anthozoa - chemistry</topic><topic>Antifouing</topic><topic>Biofouling - prevention & control</topic><topic>Cholestanes - chemistry</topic><topic>Cholestanes - pharmacology</topic><topic>Cholestenones - chemistry</topic><topic>Cholestenones - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>Gorgonian coral</topic><topic>Larva - drug effects</topic><topic>Larva - growth & development</topic><topic>Magnetic Resonance Spectroscopy - methods</topic><topic>Mass Spectrometry</topic><topic>Molecular Structure</topic><topic>Oceans and Seas</topic><topic>Pentacyclic steroid</topic><topic>Prednisone - analogs & derivatives</topic><topic>Prednisone - chemistry</topic><topic>Prednisone - pharmacology</topic><topic>Pregnadienediols - chemistry</topic><topic>Pregnadienediols - pharmacology</topic><topic>Pregnanes - chemistry</topic><topic>Pregnanes - pharmacology</topic><topic>Spectrophotometry</topic><topic>Stereoisomerism</topic><topic>Steroids - chemistry</topic><topic>Steroids - pharmacology</topic><topic>Subergorgia suberosa</topic><topic>Thoracica - drug effects</topic><topic>Thoracica - growth & development</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Jun</creatorcontrib><creatorcontrib>Liang, Yan</creatorcontrib><creatorcontrib>Wang, Kai-Ling</creatorcontrib><creatorcontrib>Liao, Xiao-Jian</creatorcontrib><creatorcontrib>Deng, Zhou</creatorcontrib><creatorcontrib>Xu, Shi-Hai</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, Jun</au><au>Liang, Yan</au><au>Wang, Kai-Ling</au><au>Liao, Xiao-Jian</au><au>Deng, Zhou</au><au>Xu, Shi-Hai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2014-01</date><risdate>2014</risdate><volume>79</volume><spage>1</spage><epage>6</epage><pages>1-6</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><abstract>•New unusual cholestane and pregnane derivatives from Subergorgia suberosa.•Structures were elucidated by analyses of 2D NMR, IR, and HRMS.•Compounds were evaluated for antifouling activity.
Two new unusual cholestane derivatives, pentacyclic steroid 16,22-epoxy-20β,23S-dihydroxycholest-1-ene-3-one (1) and 20β,23S-dihydroxycholest-1-ene-3,22-dione (2), along with two new pregnane derivatives, 15β,17α-dihydroxypregna-4,6-diene-3,20-dione (3) and 11α-hydroxypregna-4-ene-3,6,20-trione (4), were isolated from the South China Sea gorgonian coral Subergorgia suberosa. Their structures were established based on the extensive analyses of 2D NMR, IR, and HRMS. Antifouling tests against Balanus amphitrite larvae settlement indicated that 1 and 2 exhibited inhibitory effect with EC50 values of 5.3, and 14.5μg/mL, respectively.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>24184487</pmid><doi>10.1016/j.steroids.2013.10.007</doi><tpages>6</tpages></addata></record> |
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| subjects | 20β,23S-Dihydroxycholest Animals Anthozoa - chemistry Antifouing Biofouling - prevention & control Cholestanes - chemistry Cholestanes - pharmacology Cholestenones - chemistry Cholestenones - pharmacology Dose-Response Relationship, Drug Gorgonian coral Larva - drug effects Larva - growth & development Magnetic Resonance Spectroscopy - methods Mass Spectrometry Molecular Structure Oceans and Seas Pentacyclic steroid Prednisone - analogs & derivatives Prednisone - chemistry Prednisone - pharmacology Pregnadienediols - chemistry Pregnadienediols - pharmacology Pregnanes - chemistry Pregnanes - pharmacology Spectrophotometry Stereoisomerism Steroids - chemistry Steroids - pharmacology Subergorgia suberosa Thoracica - drug effects Thoracica - growth & development |
| title | Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa |
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