Novel Sorbicillin Analogues from the Marine Fungus Trichoderma sp. Associated with the Seastar Acanthaster Planci
Two novel sorbicillinoid analogues, (4'Z)-sorbicillin (1) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[(E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2',3'-dihyd...
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| Veröffentlicht in: | Natural product communications 2012-10, Vol.7 (10), p.1337-1340 |
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| creator | Lan, Wen-Jian Zhao, Yang Xie, Zhong-Liang Liang, Li-Zhen Shao, Wei-Yan Zhu, Long-Ping Yang, De-Po Zhu, Xiao-Feng Li, Hou-Jin |
| description | Two novel sorbicillinoid analogues, (4'Z)-sorbicillin (1) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[(E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2',3'-dihydrosorbicillin (5), were isolated from the culture broth of the fungus Trichoderma sp. associated with the seastar Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. Compound 1 was the first example with a Z-configuration of the C-4'/C-5’ double bond in the sorbyl side chain. Compounds 2 and 3 were uncommon monomeric sorbicillinoids with a cyclic sorbyl chain. 2, 3 and 5 showed moderate cytotoxic activities against various cancer cell lines. |
| doi_str_mv | 10.1177/1934578X1200701022 |
| format | Article |
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Associated with the Seastar Acanthaster Planci</title><source>SAGE Open Access</source><creator>Lan, Wen-Jian ; Zhao, Yang ; Xie, Zhong-Liang ; Liang, Li-Zhen ; Shao, Wei-Yan ; Zhu, Long-Ping ; Yang, De-Po ; Zhu, Xiao-Feng ; Li, Hou-Jin</creator><creatorcontrib>Lan, Wen-Jian ; Zhao, Yang ; Xie, Zhong-Liang ; Liang, Li-Zhen ; Shao, Wei-Yan ; Zhu, Long-Ping ; Yang, De-Po ; Zhu, Xiao-Feng ; Li, Hou-Jin</creatorcontrib><description>Two novel sorbicillinoid analogues, (4'Z)-sorbicillin (1) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[(E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2',3'-dihydrosorbicillin (5), were isolated from the culture broth of the fungus Trichoderma sp. associated with the seastar Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. Compound 1 was the first example with a Z-configuration of the C-4'/C-5’ double bond in the sorbyl side chain. Compounds 2 and 3 were uncommon monomeric sorbicillinoids with a cyclic sorbyl chain. 2, 3 and 5 showed moderate cytotoxic activities against various cancer cell lines.</description><identifier>ISSN: 1934-578X</identifier><identifier>EISSN: 1555-9475</identifier><identifier>DOI: 10.1177/1934578X1200701022</identifier><identifier>PMID: 23157004</identifier><language>eng</language><publisher>Los Angeles, CA: SAGE Publications</publisher><subject>Animals ; Antibiotics, Antineoplastic - chemistry ; Antibiotics, Antineoplastic - pharmacology ; Cell Line, Tumor ; Chromans - chemistry ; Chromans - pharmacology ; Circular Dichroism ; Drug Screening Assays, Antitumor ; Humans ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Molecular Conformation ; Resorcinols - chemistry ; Resorcinols - pharmacology ; Spectrometry, Mass, Electrospray Ionization ; Starfish - microbiology ; Tetrazolium Salts ; Thiazoles ; Trichoderma - chemistry</subject><ispartof>Natural product communications, 2012-10, Vol.7 (10), p.1337-1340</ispartof><rights>2012 SAGE Publications Inc.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c387t-51513df02807c2e2fbb28b20a27ae9aa8b1c5048c0207624294579214d80b7083</citedby><cites>FETCH-LOGICAL-c387t-51513df02807c2e2fbb28b20a27ae9aa8b1c5048c0207624294579214d80b7083</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://journals.sagepub.com/doi/pdf/10.1177/1934578X1200701022$$EPDF$$P50$$Gsage$$H</linktopdf><linktohtml>$$Uhttps://journals.sagepub.com/doi/10.1177/1934578X1200701022$$EHTML$$P50$$Gsage$$H</linktohtml><link.rule.ids>314,780,784,21966,27853,27924,27925,44945,45333</link.rule.ids><linktorsrc>$$Uhttps://journals.sagepub.com/doi/full/10.1177/1934578X1200701022?utm_source=summon&utm_medium=discovery-provider$$EView_record_in_SAGE_Publications$$FView_record_in_$$GSAGE_Publications</linktorsrc><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23157004$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lan, Wen-Jian</creatorcontrib><creatorcontrib>Zhao, Yang</creatorcontrib><creatorcontrib>Xie, Zhong-Liang</creatorcontrib><creatorcontrib>Liang, Li-Zhen</creatorcontrib><creatorcontrib>Shao, Wei-Yan</creatorcontrib><creatorcontrib>Zhu, Long-Ping</creatorcontrib><creatorcontrib>Yang, De-Po</creatorcontrib><creatorcontrib>Zhu, Xiao-Feng</creatorcontrib><creatorcontrib>Li, Hou-Jin</creatorcontrib><title>Novel Sorbicillin Analogues from the Marine Fungus Trichoderma sp. Associated with the Seastar Acanthaster Planci</title><title>Natural product communications</title><addtitle>Nat Prod Commun</addtitle><description>Two novel sorbicillinoid analogues, (4'Z)-sorbicillin (1) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[(E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2',3'-dihydrosorbicillin (5), were isolated from the culture broth of the fungus Trichoderma sp. associated with the seastar Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. Compound 1 was the first example with a Z-configuration of the C-4'/C-5’ double bond in the sorbyl side chain. Compounds 2 and 3 were uncommon monomeric sorbicillinoids with a cyclic sorbyl chain. 2, 3 and 5 showed moderate cytotoxic activities against various cancer cell lines.</description><subject>Animals</subject><subject>Antibiotics, Antineoplastic - chemistry</subject><subject>Antibiotics, Antineoplastic - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Chromans - chemistry</subject><subject>Chromans - pharmacology</subject><subject>Circular Dichroism</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Molecular Conformation</subject><subject>Resorcinols - chemistry</subject><subject>Resorcinols - pharmacology</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Starfish - microbiology</subject><subject>Tetrazolium Salts</subject><subject>Thiazoles</subject><subject>Trichoderma - chemistry</subject><issn>1934-578X</issn><issn>1555-9475</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtOwzAQRS0EAlT6AyyQl2zSjicxdpYV4iWVhwRI7CLHcVqjJC52AuLvcWlhg8RsPItzr8aHkGMGE8aEmLI8zbiQLwwBBDBA3CGHjHOe5Jngu3GPQLImDsg4hFeII2UGWb5PDjBlXABkh-Ttzr2bhj46X1ptm8Z2dNapxi0GE2jtXUv7paG3ytvO0MuhWwyBPnmrl64yvlU0rCZ0FoLTVvWmoh-2X34nHo0KvfJ0plXXL-NuPH1oVKftEdmrVRPMePuOyPPlxdP5dTK_v7o5n80TnUrRJ5xxllY1oASh0WBdlihLBIVCmVwpWTLNIZMaEMQZZphHHTmyrJJQCpDpiJxuelfevcXf9EVrgzZNPMK4IRTRohSYn0mMKG5Q7V0I3tTFyttW-c-CwZoTxV_bMXSy7R_K1lS_kR-3EZhugKAWpnh1g49iw3-VX8gRhuw</recordid><startdate>201210</startdate><enddate>201210</enddate><creator>Lan, Wen-Jian</creator><creator>Zhao, Yang</creator><creator>Xie, Zhong-Liang</creator><creator>Liang, Li-Zhen</creator><creator>Shao, Wei-Yan</creator><creator>Zhu, Long-Ping</creator><creator>Yang, De-Po</creator><creator>Zhu, Xiao-Feng</creator><creator>Li, Hou-Jin</creator><general>SAGE Publications</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>201210</creationdate><title>Novel Sorbicillin Analogues from the Marine Fungus Trichoderma sp. Associated with the Seastar Acanthaster Planci</title><author>Lan, Wen-Jian ; Zhao, Yang ; Xie, Zhong-Liang ; Liang, Li-Zhen ; Shao, Wei-Yan ; Zhu, Long-Ping ; Yang, De-Po ; Zhu, Xiao-Feng ; Li, Hou-Jin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c387t-51513df02807c2e2fbb28b20a27ae9aa8b1c5048c0207624294579214d80b7083</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Animals</topic><topic>Antibiotics, Antineoplastic - chemistry</topic><topic>Antibiotics, Antineoplastic - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Chromans - chemistry</topic><topic>Chromans - pharmacology</topic><topic>Circular Dichroism</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Molecular Conformation</topic><topic>Resorcinols - chemistry</topic><topic>Resorcinols - pharmacology</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Starfish - microbiology</topic><topic>Tetrazolium Salts</topic><topic>Thiazoles</topic><topic>Trichoderma - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lan, Wen-Jian</creatorcontrib><creatorcontrib>Zhao, Yang</creatorcontrib><creatorcontrib>Xie, Zhong-Liang</creatorcontrib><creatorcontrib>Liang, Li-Zhen</creatorcontrib><creatorcontrib>Shao, Wei-Yan</creatorcontrib><creatorcontrib>Zhu, Long-Ping</creatorcontrib><creatorcontrib>Yang, De-Po</creatorcontrib><creatorcontrib>Zhu, Xiao-Feng</creatorcontrib><creatorcontrib>Li, Hou-Jin</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>Natural product communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Lan, Wen-Jian</au><au>Zhao, Yang</au><au>Xie, Zhong-Liang</au><au>Liang, Li-Zhen</au><au>Shao, Wei-Yan</au><au>Zhu, Long-Ping</au><au>Yang, De-Po</au><au>Zhu, Xiao-Feng</au><au>Li, Hou-Jin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Sorbicillin Analogues from the Marine Fungus Trichoderma sp. Associated with the Seastar Acanthaster Planci</atitle><jtitle>Natural product communications</jtitle><addtitle>Nat Prod Commun</addtitle><date>2012-10</date><risdate>2012</risdate><volume>7</volume><issue>10</issue><spage>1337</spage><epage>1340</epage><pages>1337-1340</pages><issn>1934-578X</issn><eissn>1555-9475</eissn><abstract>Two novel sorbicillinoid analogues, (4'Z)-sorbicillin (1) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[(E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2',3'-dihydrosorbicillin (5), were isolated from the culture broth of the fungus Trichoderma sp. associated with the seastar Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. Compound 1 was the first example with a Z-configuration of the C-4'/C-5’ double bond in the sorbyl side chain. 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| subjects | Animals Antibiotics, Antineoplastic - chemistry Antibiotics, Antineoplastic - pharmacology Cell Line, Tumor Chromans - chemistry Chromans - pharmacology Circular Dichroism Drug Screening Assays, Antitumor Humans Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Conformation Resorcinols - chemistry Resorcinols - pharmacology Spectrometry, Mass, Electrospray Ionization Starfish - microbiology Tetrazolium Salts Thiazoles Trichoderma - chemistry |
| title | Novel Sorbicillin Analogues from the Marine Fungus Trichoderma sp. Associated with the Seastar Acanthaster Planci |
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