Biotransformation of Caryophyllene Oxide by Botrytis cinerea

Biotransformation of caryophyllene oxide (1) with B. cinerea afforded 15 products (2−16). Ten of these (3−5, 7, 9−11, and 14−16) are reported here for the first time. The main reaction paths involved stereoselective epoxidation at C-8/C-13 and hydroxylation at C-7. A rearranged compound was found, w...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 1999-01, Vol.62 (1), p.41-44
Hauptverfasser:	Duran, Rosa, Corrales, Elena, Hernández-Galán, Rosario, Collado, Isidro G
Format:	Artikel
Sprache:	eng
Schlagworte:	AGENT PATHOGENE Bioconversions. Hemisynthesis BIODEGRADACION BIODEGRADATION Biological and medical sciences Biotechnology BOTRYTIS CINEREA CHEMICAL REACTIONS CHEMICAL STRUCTURE CHEMISTRY CHIMIE ENFERMEDADES FUNGOSAS EPOXIDATION ESPECTROMETRIA ESTRUCTURA QUIMICA Fundamental and applied biological sciences. Psychology FUNGAL DISEASES HYDROXYLATION MALADIE FONGIQUE METABOLITE METABOLITES METABOLITOS Methods. Procedures. Technologies MICROBIAL DEGRADATION ORGANISMOS PATOGENOS PATHOGENESE PATHOGENESIS PATHOGENS PATOGENESIS QUIMICA REACCIONES QUIMICAS REACTION CHIMIQUE SESQUITERPENES SESQUITERPENOIDE SESQUITERPENOIDS SESQUITERPENOS SPECTRAL ANALYSIS SPECTROMETRIE SPECTROMETRY STEREOCHEMISTRY STRUCTURE CHIMIQUE
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creator	Duran, Rosa Corrales, Elena Hernández-Galán, Rosario Collado, Isidro G
description	Biotransformation of caryophyllene oxide (1) with B. cinerea afforded 15 products (2−16). Ten of these (3−5, 7, 9−11, and 14−16) are reported here for the first time. The main reaction paths involved stereoselective epoxidation at C-8/C-13 and hydroxylation at C-7. A rearranged compound was found, which was a cyclization product 16 possessing the caryolane skeleton.
doi_str_mv	10.1021/np980104b
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Ten of these (3−5, 7, 9−11, and 14−16) are reported here for the first time. The main reaction paths involved stereoselective epoxidation at C-8/C-13 and hydroxylation at C-7. A rearranged compound was found, which was a cyclization product 16 possessing the caryolane skeleton.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np980104b</identifier><identifier>PMID: 9917279</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>AGENT PATHOGENE ; Bioconversions. Hemisynthesis ; BIODEGRADACION ; BIODEGRADATION ; Biological and medical sciences ; Biotechnology ; BOTRYTIS CINEREA ; CHEMICAL REACTIONS ; CHEMICAL STRUCTURE ; CHEMISTRY ; CHIMIE ; ENFERMEDADES FUNGOSAS ; EPOXIDATION ; ESPECTROMETRIA ; ESTRUCTURA QUIMICA ; Fundamental and applied biological sciences. Psychology ; FUNGAL DISEASES ; HYDROXYLATION ; MALADIE FONGIQUE ; METABOLITE ; METABOLITES ; METABOLITOS ; Methods. Procedures. Technologies ; MICROBIAL DEGRADATION ; ORGANISMOS PATOGENOS ; PATHOGENESE ; PATHOGENESIS ; PATHOGENS ; PATOGENESIS ; QUIMICA ; REACCIONES QUIMICAS ; REACTION CHIMIQUE ; SESQUITERPENES ; SESQUITERPENOIDE ; SESQUITERPENOIDS ; SESQUITERPENOS ; SPECTRAL ANALYSIS ; SPECTROMETRIE ; SPECTROMETRY ; STEREOCHEMISTRY ; STRUCTURE CHIMIQUE</subject><ispartof>Journal of natural products (Washington, D.C.), 1999-01, Vol.62 (1), p.41-44</ispartof><rights>Copyright © 1999 American Chemical Society and American Society of Pharmacognosy</rights><rights>1999 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a432t-71520750f75372be303296854efb4a58c9d6fb8cdbd2ce5d58120d6abd0411d23</citedby><cites>FETCH-LOGICAL-a432t-71520750f75372be303296854efb4a58c9d6fb8cdbd2ce5d58120d6abd0411d23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np980104b$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np980104b$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1689992$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9917279$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Duran, Rosa</creatorcontrib><creatorcontrib>Corrales, Elena</creatorcontrib><creatorcontrib>Hernández-Galán, Rosario</creatorcontrib><creatorcontrib>Collado, Isidro G</creatorcontrib><title>Biotransformation of Caryophyllene Oxide by Botrytis cinerea</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Biotransformation of caryophyllene oxide (1) with B. cinerea afforded 15 products (2−16). Ten of these (3−5, 7, 9−11, and 14−16) are reported here for the first time. The main reaction paths involved stereoselective epoxidation at C-8/C-13 and hydroxylation at C-7. A rearranged compound was found, which was a cyclization product 16 possessing the caryolane skeleton.</description><subject>AGENT PATHOGENE</subject><subject>Bioconversions. Hemisynthesis</subject><subject>BIODEGRADACION</subject><subject>BIODEGRADATION</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>BOTRYTIS CINEREA</subject><subject>CHEMICAL REACTIONS</subject><subject>CHEMICAL STRUCTURE</subject><subject>CHEMISTRY</subject><subject>CHIMIE</subject><subject>ENFERMEDADES FUNGOSAS</subject><subject>EPOXIDATION</subject><subject>ESPECTROMETRIA</subject><subject>ESTRUCTURA QUIMICA</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>FUNGAL DISEASES</subject><subject>HYDROXYLATION</subject><subject>MALADIE FONGIQUE</subject><subject>METABOLITE</subject><subject>METABOLITES</subject><subject>METABOLITOS</subject><subject>Methods. Procedures. Technologies</subject><subject>MICROBIAL DEGRADATION</subject><subject>ORGANISMOS PATOGENOS</subject><subject>PATHOGENESE</subject><subject>PATHOGENESIS</subject><subject>PATHOGENS</subject><subject>PATOGENESIS</subject><subject>QUIMICA</subject><subject>REACCIONES QUIMICAS</subject><subject>REACTION CHIMIQUE</subject><subject>SESQUITERPENES</subject><subject>SESQUITERPENOIDE</subject><subject>SESQUITERPENOIDS</subject><subject>SESQUITERPENOS</subject><subject>SPECTRAL ANALYSIS</subject><subject>SPECTROMETRIE</subject><subject>SPECTROMETRY</subject><subject>STEREOCHEMISTRY</subject><subject>STRUCTURE CHIMIQUE</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><recordid>eNp9kUtvEzEUhS0EKiGw4AcgzQIQLAau7fFLYkMiaJEqFdR0w8by-AEuk3FqT6Tm3-MoUbpBrO7ifDr3nnMReonhAwaCP44bJQFD1z9CM8wItBwIe4xmgDltqeTdU_SslFsAoKDYGTpTCgsi1Ax9WsQ0ZTOWkPLaTDGNTQrN0uRd2vzeDYMffXN1H51v-l2zqOhuiqWxcfTZm-foSTBD8S-Oc45uvn5ZLS_ay6vzb8vPl63pKJlasT9JMAiCUUF6T4ESxSXrfOg7w6RVjodeWtc7Yj1zTGICjpveQYexI3SO3h18NzndbX2Z9DoW64fBjD5ti8aS1TyiI6yib_-PCsKYkLyC7w-gzamU7IPe5LiuuTUGvS9Vn0qt7Kuj6bZfe3cijy1W_fVRN8WaIdQ-bSwPhlwqpfYx2gMWy-TvT7LJfzQXVDC9-n6tf-DFT35xDnr1sDaYpM2vXC1vrnG1gtpLfeUcvTnoxhZ9m7Z5rE_4x_l_AQidoQw</recordid><startdate>19990101</startdate><enddate>19990101</enddate><creator>Duran, Rosa</creator><creator>Corrales, Elena</creator><creator>Hernández-Galán, Rosario</creator><creator>Collado, Isidro G</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</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><scope>7X8</scope></search><sort><creationdate>19990101</creationdate><title>Biotransformation of Caryophyllene Oxide by Botrytis cinerea</title><author>Duran, Rosa ; Corrales, Elena ; Hernández-Galán, Rosario ; Collado, Isidro G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a432t-71520750f75372be303296854efb4a58c9d6fb8cdbd2ce5d58120d6abd0411d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>AGENT PATHOGENE</topic><topic>Bioconversions. Hemisynthesis</topic><topic>BIODEGRADACION</topic><topic>BIODEGRADATION</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>BOTRYTIS CINEREA</topic><topic>CHEMICAL REACTIONS</topic><topic>CHEMICAL STRUCTURE</topic><topic>CHEMISTRY</topic><topic>CHIMIE</topic><topic>ENFERMEDADES FUNGOSAS</topic><topic>EPOXIDATION</topic><topic>ESPECTROMETRIA</topic><topic>ESTRUCTURA QUIMICA</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>FUNGAL DISEASES</topic><topic>HYDROXYLATION</topic><topic>MALADIE FONGIQUE</topic><topic>METABOLITE</topic><topic>METABOLITES</topic><topic>METABOLITOS</topic><topic>Methods. Procedures. 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Nat. Prod</addtitle><date>1999-01-01</date><risdate>1999</risdate><volume>62</volume><issue>1</issue><spage>41</spage><epage>44</epage><pages>41-44</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Biotransformation of caryophyllene oxide (1) with B. cinerea afforded 15 products (2−16). Ten of these (3−5, 7, 9−11, and 14−16) are reported here for the first time. The main reaction paths involved stereoselective epoxidation at C-8/C-13 and hydroxylation at C-7. A rearranged compound was found, which was a cyclization product 16 possessing the caryolane skeleton.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>9917279</pmid><doi>10.1021/np980104b</doi><tpages>4</tpages></addata></record>
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source	ACS_美国化学学会期刊（与NSTL共建）
subjects	AGENT PATHOGENE Bioconversions. Hemisynthesis BIODEGRADACION BIODEGRADATION Biological and medical sciences Biotechnology BOTRYTIS CINEREA CHEMICAL REACTIONS CHEMICAL STRUCTURE CHEMISTRY CHIMIE ENFERMEDADES FUNGOSAS EPOXIDATION ESPECTROMETRIA ESTRUCTURA QUIMICA Fundamental and applied biological sciences. Psychology FUNGAL DISEASES HYDROXYLATION MALADIE FONGIQUE METABOLITE METABOLITES METABOLITOS Methods. Procedures. Technologies MICROBIAL DEGRADATION ORGANISMOS PATOGENOS PATHOGENESE PATHOGENESIS PATHOGENS PATOGENESIS QUIMICA REACCIONES QUIMICAS REACTION CHIMIQUE SESQUITERPENES SESQUITERPENOIDE SESQUITERPENOIDS SESQUITERPENOS SPECTRAL ANALYSIS SPECTROMETRIE SPECTROMETRY STEREOCHEMISTRY STRUCTURE CHIMIQUE
title	Biotransformation of Caryophyllene Oxide by Botrytis cinerea
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