Biotransformation of cadinane sesquiterpenes by Beauveria bassiana ATCC 7159
Incubation of cadina-4,10(15)-dien-3-one with Beauveria bassiana ATCC 7159 has resulted in the production of nine novel sesquiterpenes. These metabolites were identified as (4S)-cadin-10(15)-en-3-one, (4S)-3α-hydroxycadin-10(15)-ene, (4R)-3α-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadin-10(15)-ene,...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2000-05, Vol.54 (1), p.39-45 |
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| creator | Buchanan, Greg O Williams, Lawrence A.D Reese, Paul B |
| description | Incubation of cadina-4,10(15)-dien-3-one with
Beauveria bassiana ATCC 7159 has resulted in the production of nine novel sesquiterpenes. These metabolites were identified as (4S)-cadin-10(15)-en-3-one, (4S)-3α-hydroxycadin-10(15)-ene, (4R)-3α-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadina-10(15),12(14)-diene, (4S)-13-hydroxycadin-10(15)-en-3-one, (4S)-12-hydroxycadin-10(15)-en-3-one, (4R)-3β,14-dihydroxycadin-10(15)-ene and 3α-hydroxycadina-4,10(15)-diene. The allylic alcohol 3α-hydroxycadina-4,10(15)-diene was also biotransformed to afford cadina-4,10(15)-dien-3-one, (4S)-cadin-10(15)-en-3-one and (4S)-12-hydroxycadin-10(15)-en-3-one. The insecticidal potential and phytotoxicity of the isolated metabolites have been evaluated. |
| doi_str_mv | 10.1016/S0031-9422(00)00024-8 |
| format | Article |
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Beauveria bassiana ATCC 7159 has resulted in the production of nine novel sesquiterpenes. These metabolites were identified as (4S)-cadin-10(15)-en-3-one, (4S)-3α-hydroxycadin-10(15)-ene, (4R)-3α-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadina-10(15),12(14)-diene, (4S)-13-hydroxycadin-10(15)-en-3-one, (4S)-12-hydroxycadin-10(15)-en-3-one, (4R)-3β,14-dihydroxycadin-10(15)-ene and 3α-hydroxycadina-4,10(15)-diene. The allylic alcohol 3α-hydroxycadina-4,10(15)-diene was also biotransformed to afford cadina-4,10(15)-dien-3-one, (4S)-cadin-10(15)-en-3-one and (4S)-12-hydroxycadin-10(15)-en-3-one. The insecticidal potential and phytotoxicity of the isolated metabolites have been evaluated.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/S0031-9422(00)00024-8</identifier><identifier>PMID: 10846745</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Animals ; Ascomycota - metabolism ; Beauveria bassiana ; Beauveria bassiana ATCC 7159 ; Biotransformation ; Brassicaceae - drug effects ; cadina-4,10-dien-3-one ; Cadinane ; cadinane sesquiterpenes ; Deuteromycotina ; Hyptis verticillata ; Insecticides - metabolism ; Insecticides - pharmacology ; Naphthalenes - metabolism ; Naphthalenes - pharmacology ; Seeds - drug effects ; Sesquiterpene ; sesquiterpene lactones ; sesquiterpenes ; Sesquiterpenes - metabolism ; Sesquiterpenes - pharmacology</subject><ispartof>Phytochemistry (Oxford), 2000-05, Vol.54 (1), p.39-45</ispartof><rights>2000 Elsevier Science Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c392t-5977331dd525c7b36daedde5d4dc94602a4626738b0dc871c5965372754a49dd3</citedby><cites>FETCH-LOGICAL-c392t-5977331dd525c7b36daedde5d4dc94602a4626738b0dc871c5965372754a49dd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0031-9422(00)00024-8$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10846745$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Buchanan, Greg O</creatorcontrib><creatorcontrib>Williams, Lawrence A.D</creatorcontrib><creatorcontrib>Reese, Paul B</creatorcontrib><title>Biotransformation of cadinane sesquiterpenes by Beauveria bassiana ATCC 7159</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Incubation of cadina-4,10(15)-dien-3-one with
Beauveria bassiana ATCC 7159 has resulted in the production of nine novel sesquiterpenes. These metabolites were identified as (4S)-cadin-10(15)-en-3-one, (4S)-3α-hydroxycadin-10(15)-ene, (4R)-3α-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadina-10(15),12(14)-diene, (4S)-13-hydroxycadin-10(15)-en-3-one, (4S)-12-hydroxycadin-10(15)-en-3-one, (4R)-3β,14-dihydroxycadin-10(15)-ene and 3α-hydroxycadina-4,10(15)-diene. The allylic alcohol 3α-hydroxycadina-4,10(15)-diene was also biotransformed to afford cadina-4,10(15)-dien-3-one, (4S)-cadin-10(15)-en-3-one and (4S)-12-hydroxycadin-10(15)-en-3-one. The insecticidal potential and phytotoxicity of the isolated metabolites have been evaluated.</description><subject>Animals</subject><subject>Ascomycota - metabolism</subject><subject>Beauveria bassiana</subject><subject>Beauveria bassiana ATCC 7159</subject><subject>Biotransformation</subject><subject>Brassicaceae - drug effects</subject><subject>cadina-4,10-dien-3-one</subject><subject>Cadinane</subject><subject>cadinane sesquiterpenes</subject><subject>Deuteromycotina</subject><subject>Hyptis verticillata</subject><subject>Insecticides - metabolism</subject><subject>Insecticides - pharmacology</subject><subject>Naphthalenes - metabolism</subject><subject>Naphthalenes - pharmacology</subject><subject>Seeds - drug effects</subject><subject>Sesquiterpene</subject><subject>sesquiterpene lactones</subject><subject>sesquiterpenes</subject><subject>Sesquiterpenes - metabolism</subject><subject>Sesquiterpenes - pharmacology</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtOwzAQRS0EglL4BFBWCBaBcfyKV6iteEmVWFDWlmNPJKM2KXaC1L8nEITYsZrNuXNnDiFnFK4pUHnzAsBornlRXAJcAUDB83KPTGipWM4UwD6Z_CJH5DiltwESQspDckSh5FJxMSHLeWi7aJtUt3Fju9A2WVtnzvrQ2AazhOm9Dx3GLTaYsmqXzdH2HxiDzSqbUrCNzWarxSJTVOgTclDbdcLTnzklr_d3q8Vjvnx-eFrMlrljuuhyoZVijHovCuFUxaS36D0Kz73TXEJhuSykYmUF3pWKOqGlYKpQgluuvWdTcjHu3cb2vcfUmU1IDtfr4eS2T4YqwTQv9QCKEXSxTSlibbYxbGzcGQrmS6P51mi-HBkA863RlEPu_Kegrzbo_6RGbwNwOwI4vPkRMJrkAjYOfYjoOuPb8E_FJ7wDgGE</recordid><startdate>20000501</startdate><enddate>20000501</enddate><creator>Buchanan, Greg O</creator><creator>Williams, Lawrence A.D</creator><creator>Reese, Paul B</creator><general>Elsevier Ltd</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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>20000501</creationdate><title>Biotransformation of cadinane sesquiterpenes by Beauveria bassiana ATCC 7159</title><author>Buchanan, Greg O ; Williams, Lawrence A.D ; Reese, Paul B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c392t-5977331dd525c7b36daedde5d4dc94602a4626738b0dc871c5965372754a49dd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Animals</topic><topic>Ascomycota - metabolism</topic><topic>Beauveria bassiana</topic><topic>Beauveria bassiana ATCC 7159</topic><topic>Biotransformation</topic><topic>Brassicaceae - drug effects</topic><topic>cadina-4,10-dien-3-one</topic><topic>Cadinane</topic><topic>cadinane sesquiterpenes</topic><topic>Deuteromycotina</topic><topic>Hyptis verticillata</topic><topic>Insecticides - metabolism</topic><topic>Insecticides - pharmacology</topic><topic>Naphthalenes - metabolism</topic><topic>Naphthalenes - pharmacology</topic><topic>Seeds - drug effects</topic><topic>Sesquiterpene</topic><topic>sesquiterpene lactones</topic><topic>sesquiterpenes</topic><topic>Sesquiterpenes - metabolism</topic><topic>Sesquiterpenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Buchanan, Greg O</creatorcontrib><creatorcontrib>Williams, Lawrence A.D</creatorcontrib><creatorcontrib>Reese, Paul B</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Buchanan, Greg O</au><au>Williams, Lawrence A.D</au><au>Reese, Paul B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biotransformation of cadinane sesquiterpenes by Beauveria bassiana ATCC 7159</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2000-05-01</date><risdate>2000</risdate><volume>54</volume><issue>1</issue><spage>39</spage><epage>45</epage><pages>39-45</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Incubation of cadina-4,10(15)-dien-3-one with
Beauveria bassiana ATCC 7159 has resulted in the production of nine novel sesquiterpenes. These metabolites were identified as (4S)-cadin-10(15)-en-3-one, (4S)-3α-hydroxycadin-10(15)-ene, (4R)-3α-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadin-10(15)-ene, (4S)-3β-hydroxycadina-10(15),12(14)-diene, (4S)-13-hydroxycadin-10(15)-en-3-one, (4S)-12-hydroxycadin-10(15)-en-3-one, (4R)-3β,14-dihydroxycadin-10(15)-ene and 3α-hydroxycadina-4,10(15)-diene. The allylic alcohol 3α-hydroxycadina-4,10(15)-diene was also biotransformed to afford cadina-4,10(15)-dien-3-one, (4S)-cadin-10(15)-en-3-one and (4S)-12-hydroxycadin-10(15)-en-3-one. The insecticidal potential and phytotoxicity of the isolated metabolites have been evaluated.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>10846745</pmid><doi>10.1016/S0031-9422(00)00024-8</doi><tpages>7</tpages></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Animals Ascomycota - metabolism Beauveria bassiana Beauveria bassiana ATCC 7159 Biotransformation Brassicaceae - drug effects cadina-4,10-dien-3-one Cadinane cadinane sesquiterpenes Deuteromycotina Hyptis verticillata Insecticides - metabolism Insecticides - pharmacology Naphthalenes - metabolism Naphthalenes - pharmacology Seeds - drug effects Sesquiterpene sesquiterpene lactones sesquiterpenes Sesquiterpenes - metabolism Sesquiterpenes - pharmacology |
| title | Biotransformation of cadinane sesquiterpenes by Beauveria bassiana ATCC 7159 |
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