Antifungal Activity and Biotransformation of Diisophorone by Botrytis cinerea
Diisophorone (1) was tested against two strains of the necrotrophic plant pathogen Botrytis cinerea. Fungal sensitivity varied according to the strain. B. cinera 2100 was more sensitive than B. cinerea UCA992: its mycelial growth was significantly inhibited at concentrations of 50 ppm and above. Al...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2005-07, Vol.53 (15), p.6035-6039 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Daoubi, Mourad Deligeorgopoulou, Athina Macías-Sánchez, Antonio J Hernández-Galán, Rosario Hitchcock, Peter B Hanson, James R Collado, Isidro G |
| description | Diisophorone (1) was tested against two strains of the necrotrophic plant pathogen Botrytis cinerea. Fungal sensitivity varied according to the strain. B. cinera 2100 was more sensitive than B. cinerea UCA992: its mycelial growth was significantly inhibited at concentrations of 50 ppm and above. Although diisophorone (1) showed an effective control of B. cinerea, a detoxification mechanism was present. The detoxification of racemic diisophorone (1) by B. cinerea was investigated. Incubation with two strains of B. cinerea gave one and four biotransformation products (2 − 5), respectively. Their structures were established as the known 8β-hydroxydiisophorone (2), 6α-hydroxydiisophorone (3), 6β-hydroxydiisophorone (4) and 8β,14β-dihydroxydiisophorone (5) on the basis of their spectroscopic data, including two-dimensional NMR analysis [heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser enhancement spectroscopy (NOESY)] and an X-ray crystallographic study. Keywords: Biotransformation; diisophorone; Botrytis cinerea; antifungal activity |
| doi_str_mv | 10.1021/jf050600n |
| format | Article |
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Fungal sensitivity varied according to the strain. B. cinera 2100 was more sensitive than B. cinerea UCA992: its mycelial growth was significantly inhibited at concentrations of 50 ppm and above. Although diisophorone (1) showed an effective control of B. cinerea, a detoxification mechanism was present. The detoxification of racemic diisophorone (1) by B. cinerea was investigated. Incubation with two strains of B. cinerea gave one and four biotransformation products (2 − 5), respectively. Their structures were established as the known 8β-hydroxydiisophorone (2), 6α-hydroxydiisophorone (3), 6β-hydroxydiisophorone (4) and 8β,14β-dihydroxydiisophorone (5) on the basis of their spectroscopic data, including two-dimensional NMR analysis [heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser enhancement spectroscopy (NOESY)] and an X-ray crystallographic study. Keywords: Biotransformation; diisophorone; Botrytis cinerea; antifungal activity</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf050600n</identifier><identifier>PMID: 16028992</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>antifungal properties ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Biotransformation ; Botrytis - drug effects ; Botrytis - growth & development ; Botrytis - metabolism ; Botrytis cinerea ; chemical structure ; Cyclohexanones - chemistry ; Cyclohexanones - metabolism ; Cyclohexanones - pharmacology ; diisophorone ; Fundamental and applied biological sciences. Psychology ; fungicide resistance ; fungicides ; Fungicides, Industrial - metabolism ; Fungicides, Industrial - pharmacology ; Hydroxylation ; Magnetic Resonance Spectroscopy ; metabolic detoxification ; metabolism ; metabolites ; Methods. Procedures. Technologies ; Molecular Structure ; Mycelium - growth & development ; nuclear magnetic resonance spectroscopy ; plant pathogenic fungi ; Plants - microbiology ; X-ray diffraction</subject><ispartof>Journal of agricultural and food chemistry, 2005-07, Vol.53 (15), p.6035-6039</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a436t-9e8c4e457a497857fc71e1a5596830b1361c4d1e633d0e57973dea84569dc87a3</citedby><cites>FETCH-LOGICAL-a436t-9e8c4e457a497857fc71e1a5596830b1361c4d1e633d0e57973dea84569dc87a3</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/jf050600n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf050600n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16981311$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16028992$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Daoubi, Mourad</creatorcontrib><creatorcontrib>Deligeorgopoulou, Athina</creatorcontrib><creatorcontrib>Macías-Sánchez, Antonio J</creatorcontrib><creatorcontrib>Hernández-Galán, Rosario</creatorcontrib><creatorcontrib>Hitchcock, Peter B</creatorcontrib><creatorcontrib>Hanson, James R</creatorcontrib><creatorcontrib>Collado, Isidro G</creatorcontrib><title>Antifungal Activity and Biotransformation of Diisophorone by Botrytis cinerea</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Diisophorone (1) was tested against two strains of the necrotrophic plant pathogen Botrytis cinerea. Fungal sensitivity varied according to the strain. B. cinera 2100 was more sensitive than B. cinerea UCA992: its mycelial growth was significantly inhibited at concentrations of 50 ppm and above. Although diisophorone (1) showed an effective control of B. cinerea, a detoxification mechanism was present. The detoxification of racemic diisophorone (1) by B. cinerea was investigated. Incubation with two strains of B. cinerea gave one and four biotransformation products (2 − 5), respectively. Their structures were established as the known 8β-hydroxydiisophorone (2), 6α-hydroxydiisophorone (3), 6β-hydroxydiisophorone (4) and 8β,14β-dihydroxydiisophorone (5) on the basis of their spectroscopic data, including two-dimensional NMR analysis [heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser enhancement spectroscopy (NOESY)] and an X-ray crystallographic study. Keywords: Biotransformation; diisophorone; Botrytis cinerea; antifungal activity</description><subject>antifungal properties</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Biotransformation</subject><subject>Botrytis - drug effects</subject><subject>Botrytis - growth & development</subject><subject>Botrytis - metabolism</subject><subject>Botrytis cinerea</subject><subject>chemical structure</subject><subject>Cyclohexanones - chemistry</subject><subject>Cyclohexanones - metabolism</subject><subject>Cyclohexanones - pharmacology</subject><subject>diisophorone</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>fungicide resistance</subject><subject>fungicides</subject><subject>Fungicides, Industrial - metabolism</subject><subject>Fungicides, Industrial - pharmacology</subject><subject>Hydroxylation</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>metabolic detoxification</subject><subject>metabolism</subject><subject>metabolites</subject><subject>Methods. Procedures. Technologies</subject><subject>Molecular Structure</subject><subject>Mycelium - growth & development</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>plant pathogenic fungi</subject><subject>Plants - microbiology</subject><subject>X-ray diffraction</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MFuEzEQBmALgWgoHHgB2AtIHBZm1uu195iUQpFagZRUPVoTr7c4bOzU3kXN22OUqOXAyYf59M_4Z-w1wkeECj9tehDQAPgnbIaiglIgqqdsBnlYKtHgCXuR0gYAlJDwnJ1gA5Vq22rGruZ-dP3kb2ko5mZ0v924L8h3xcKFMZJPfYhbGl3wReiLz86lsPsZYvC2WO-LRTb70aXCOG-jpZfsWU9Dsq-O7ym7_nK-OrsoL79__XY2vyyp5s1YtlaZ2tZCUt3KfFJvJFokIdpGcVgjb9DUHdqG8w6skK3knSVVi6btjJLET9n7Q-4uhrvJplFvXTJ2GMjbMCWNEmSrlMjwwwGaGFKKtte76LYU9xpB_-1OP3SX7Ztj6LTe2u5RHsvK4N0RUDI09Lke49I_rlXIEbMrD86l0d4_zCn-0o3kUujVj6W-uVotYHVzoZfZvz34noKm25gzr5cVIAcElFzIx81kkt6EKfrc7n--8AezyJpb</recordid><startdate>20050727</startdate><enddate>20050727</enddate><creator>Daoubi, Mourad</creator><creator>Deligeorgopoulou, Athina</creator><creator>Macías-Sánchez, Antonio J</creator><creator>Hernández-Galán, Rosario</creator><creator>Hitchcock, Peter B</creator><creator>Hanson, James R</creator><creator>Collado, Isidro G</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><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>20050727</creationdate><title>Antifungal Activity and Biotransformation of Diisophorone by Botrytis cinerea</title><author>Daoubi, Mourad ; Deligeorgopoulou, Athina ; Macías-Sánchez, Antonio J ; Hernández-Galán, Rosario ; Hitchcock, Peter B ; Hanson, James R ; Collado, Isidro G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a436t-9e8c4e457a497857fc71e1a5596830b1361c4d1e633d0e57973dea84569dc87a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>antifungal properties</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Biotransformation</topic><topic>Botrytis - drug effects</topic><topic>Botrytis - growth & development</topic><topic>Botrytis - metabolism</topic><topic>Botrytis cinerea</topic><topic>chemical structure</topic><topic>Cyclohexanones - chemistry</topic><topic>Cyclohexanones - metabolism</topic><topic>Cyclohexanones - pharmacology</topic><topic>diisophorone</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>fungicide resistance</topic><topic>fungicides</topic><topic>Fungicides, Industrial - metabolism</topic><topic>Fungicides, Industrial - pharmacology</topic><topic>Hydroxylation</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>metabolic detoxification</topic><topic>metabolism</topic><topic>metabolites</topic><topic>Methods. Procedures. Technologies</topic><topic>Molecular Structure</topic><topic>Mycelium - growth & development</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>plant pathogenic fungi</topic><topic>Plants - microbiology</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Daoubi, Mourad</creatorcontrib><creatorcontrib>Deligeorgopoulou, Athina</creatorcontrib><creatorcontrib>Macías-Sánchez, Antonio J</creatorcontrib><creatorcontrib>Hernández-Galán, Rosario</creatorcontrib><creatorcontrib>Hitchcock, Peter B</creatorcontrib><creatorcontrib>Hanson, James R</creatorcontrib><creatorcontrib>Collado, Isidro G</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><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>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Daoubi, Mourad</au><au>Deligeorgopoulou, Athina</au><au>Macías-Sánchez, Antonio J</au><au>Hernández-Galán, Rosario</au><au>Hitchcock, Peter B</au><au>Hanson, James R</au><au>Collado, Isidro G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antifungal Activity and Biotransformation of Diisophorone by Botrytis cinerea</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2005-07-27</date><risdate>2005</risdate><volume>53</volume><issue>15</issue><spage>6035</spage><epage>6039</epage><pages>6035-6039</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Diisophorone (1) was tested against two strains of the necrotrophic plant pathogen Botrytis cinerea. Fungal sensitivity varied according to the strain. B. cinera 2100 was more sensitive than B. cinerea UCA992: its mycelial growth was significantly inhibited at concentrations of 50 ppm and above. Although diisophorone (1) showed an effective control of B. cinerea, a detoxification mechanism was present. The detoxification of racemic diisophorone (1) by B. cinerea was investigated. Incubation with two strains of B. cinerea gave one and four biotransformation products (2 − 5), respectively. Their structures were established as the known 8β-hydroxydiisophorone (2), 6α-hydroxydiisophorone (3), 6β-hydroxydiisophorone (4) and 8β,14β-dihydroxydiisophorone (5) on the basis of their spectroscopic data, including two-dimensional NMR analysis [heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser enhancement spectroscopy (NOESY)] and an X-ray crystallographic study. Keywords: Biotransformation; diisophorone; Botrytis cinerea; antifungal activity</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16028992</pmid><doi>10.1021/jf050600n</doi><tpages>5</tpages></addata></record> |
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| subjects | antifungal properties Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Biotransformation Botrytis - drug effects Botrytis - growth & development Botrytis - metabolism Botrytis cinerea chemical structure Cyclohexanones - chemistry Cyclohexanones - metabolism Cyclohexanones - pharmacology diisophorone Fundamental and applied biological sciences. Psychology fungicide resistance fungicides Fungicides, Industrial - metabolism Fungicides, Industrial - pharmacology Hydroxylation Magnetic Resonance Spectroscopy metabolic detoxification metabolism metabolites Methods. Procedures. Technologies Molecular Structure Mycelium - growth & development nuclear magnetic resonance spectroscopy plant pathogenic fungi Plants - microbiology X-ray diffraction |
| title | Antifungal Activity and Biotransformation of Diisophorone by Botrytis cinerea |
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