LL-Z1272alpha epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae
A novel metabolite, LL-Z1272alpha epoxide, structurally related to ascochlorin, was isolated from the cultured mycelium of Ascochyta viciae J-29, a mutant derived from A. viciae Libert. The structure was elucidated on the basis of spectroscopic data. The epoxide is proposed to be enzymatically forme...
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| Veröffentlicht in: | Journal of antibiotics 2009-10, Vol.62 (10), p.571-574 |
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| container_issue | 10 |
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| container_title | Journal of antibiotics |
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| creator | Hosono, Kuniaki Ogihara, Jun Ohdake, Takamichi Masuda, Setsuko |
| description | A novel metabolite, LL-Z1272alpha epoxide, structurally related to ascochlorin, was isolated from the cultured mycelium of Ascochyta viciae J-29, a mutant derived from A. viciae Libert. The structure was elucidated on the basis of spectroscopic data. The epoxide is proposed to be enzymatically formed from LL-Z1272alpha and is a precursor of ascochlorin, an antiviral and antitumor antibiotic. The conversion of the epoxide to ascochlorin by cyclization of its farnesyl chain to a cyclohexanone ring is similar to that of squalene 2, 3-oxide to sterols. Unlike ascochlorin, the new metabolite had no growth inhibitory activity against Candida albicans in the paper-disc agar diffusion assay. |
| doi_str_mv | 10.1038/ja.2009.80 |
| format | Article |
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The structure was elucidated on the basis of spectroscopic data. The epoxide is proposed to be enzymatically formed from LL-Z1272alpha and is a precursor of ascochlorin, an antiviral and antitumor antibiotic. The conversion of the epoxide to ascochlorin by cyclization of its farnesyl chain to a cyclohexanone ring is similar to that of squalene 2, 3-oxide to sterols. Unlike ascochlorin, the new metabolite had no growth inhibitory activity against Candida albicans in the paper-disc agar diffusion assay.</description><identifier>ISSN: 0021-8820</identifier><identifier>DOI: 10.1038/ja.2009.80</identifier><identifier>PMID: 19680284</identifier><language>eng</language><publisher>Japan</publisher><subject>Alkenes - chemistry ; Alkenes - metabolism ; Ascomycota - classification ; Ascomycota - genetics ; Ascomycota - growth & development ; Ascomycota - metabolism ; Benzaldehydes - chemistry ; Benzaldehydes - isolation & purification ; Benzaldehydes - metabolism ; Candida albicans - drug effects ; Candida albicans - growth & development ; Chemistry, Physical ; Culture Media ; Epoxy Compounds - chemistry ; Epoxy Compounds - isolation & purification ; Epoxy Compounds - metabolism ; Magnetic Resonance Spectroscopy ; Microbial Sensitivity Tests - methods ; Mutation ; Phenols - chemistry ; Phenols - metabolism ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - metabolism</subject><ispartof>Journal of antibiotics, 2009-10, Vol.62 (10), p.571-574</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19680284$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hosono, Kuniaki</creatorcontrib><creatorcontrib>Ogihara, Jun</creatorcontrib><creatorcontrib>Ohdake, Takamichi</creatorcontrib><creatorcontrib>Masuda, Setsuko</creatorcontrib><title>LL-Z1272alpha epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae</title><title>Journal of antibiotics</title><addtitle>J Antibiot (Tokyo)</addtitle><description>A novel metabolite, LL-Z1272alpha epoxide, structurally related to ascochlorin, was isolated from the cultured mycelium of Ascochyta viciae J-29, a mutant derived from A. viciae Libert. The structure was elucidated on the basis of spectroscopic data. The epoxide is proposed to be enzymatically formed from LL-Z1272alpha and is a precursor of ascochlorin, an antiviral and antitumor antibiotic. The conversion of the epoxide to ascochlorin by cyclization of its farnesyl chain to a cyclohexanone ring is similar to that of squalene 2, 3-oxide to sterols. Unlike ascochlorin, the new metabolite had no growth inhibitory activity against Candida albicans in the paper-disc agar diffusion assay.</description><subject>Alkenes - chemistry</subject><subject>Alkenes - metabolism</subject><subject>Ascomycota - classification</subject><subject>Ascomycota - genetics</subject><subject>Ascomycota - growth & development</subject><subject>Ascomycota - metabolism</subject><subject>Benzaldehydes - chemistry</subject><subject>Benzaldehydes - isolation & purification</subject><subject>Benzaldehydes - metabolism</subject><subject>Candida albicans - drug effects</subject><subject>Candida albicans - growth & development</subject><subject>Chemistry, Physical</subject><subject>Culture Media</subject><subject>Epoxy Compounds - chemistry</subject><subject>Epoxy Compounds - isolation & purification</subject><subject>Epoxy Compounds - metabolism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Microbial Sensitivity Tests - methods</subject><subject>Mutation</subject><subject>Phenols - chemistry</subject><subject>Phenols - metabolism</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - metabolism</subject><issn>0021-8820</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo10LtOw0AQBdAtQCQ8Gj4AbUeDw-wrXpdRxEuyRJMqjTXeHSuO7Kzx2oj8PQZCNRrdo9HVMHYrYCFA2cc9LiRAtrBwxuYAUiTWSpixyxj3ACpVqb1gM5EtLUir52yb58lWyFRi0-2QUxe-ak8PHHnXkxv7GHoeKo7RBbdrQl8fpiD40ZHn5XFi7TjgYfgxq19zHJB_1q5GumbnFTaRbk7zim2enzbr1yR_f3lbr_KkM0YnpIQ3hrxXziBq7zMN065FRU7YJVSoy9SVpamcs-AMibKEbOkEyQxNhuqK3f-dnXp9jBSHoq2jo6bBA4UxFqnSAoy2YpJ3JzmWLfmi6-sW-2Px_w31DfWyXto</recordid><startdate>200910</startdate><enddate>200910</enddate><creator>Hosono, Kuniaki</creator><creator>Ogihara, Jun</creator><creator>Ohdake, Takamichi</creator><creator>Masuda, Setsuko</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>200910</creationdate><title>LL-Z1272alpha epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae</title><author>Hosono, Kuniaki ; Ogihara, Jun ; Ohdake, Takamichi ; Masuda, Setsuko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p554-e31d55edd3c5aa4dd94055e41fec1860fa4b7cbb5fcc80c5e1bb096c1e29a59a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alkenes - chemistry</topic><topic>Alkenes - metabolism</topic><topic>Ascomycota - classification</topic><topic>Ascomycota - genetics</topic><topic>Ascomycota - growth & development</topic><topic>Ascomycota - metabolism</topic><topic>Benzaldehydes - chemistry</topic><topic>Benzaldehydes - isolation & purification</topic><topic>Benzaldehydes - metabolism</topic><topic>Candida albicans - drug effects</topic><topic>Candida albicans - growth & development</topic><topic>Chemistry, Physical</topic><topic>Culture Media</topic><topic>Epoxy Compounds - chemistry</topic><topic>Epoxy Compounds - isolation & purification</topic><topic>Epoxy Compounds - metabolism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Microbial Sensitivity Tests - methods</topic><topic>Mutation</topic><topic>Phenols - chemistry</topic><topic>Phenols - metabolism</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hosono, Kuniaki</creatorcontrib><creatorcontrib>Ogihara, Jun</creatorcontrib><creatorcontrib>Ohdake, Takamichi</creatorcontrib><creatorcontrib>Masuda, Setsuko</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hosono, Kuniaki</au><au>Ogihara, Jun</au><au>Ohdake, Takamichi</au><au>Masuda, Setsuko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>LL-Z1272alpha epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae</atitle><jtitle>Journal of antibiotics</jtitle><addtitle>J Antibiot (Tokyo)</addtitle><date>2009-10</date><risdate>2009</risdate><volume>62</volume><issue>10</issue><spage>571</spage><epage>574</epage><pages>571-574</pages><issn>0021-8820</issn><abstract>A novel metabolite, LL-Z1272alpha epoxide, structurally related to ascochlorin, was isolated from the cultured mycelium of Ascochyta viciae J-29, a mutant derived from A. viciae Libert. The structure was elucidated on the basis of spectroscopic data. The epoxide is proposed to be enzymatically formed from LL-Z1272alpha and is a precursor of ascochlorin, an antiviral and antitumor antibiotic. The conversion of the epoxide to ascochlorin by cyclization of its farnesyl chain to a cyclohexanone ring is similar to that of squalene 2, 3-oxide to sterols. Unlike ascochlorin, the new metabolite had no growth inhibitory activity against Candida albicans in the paper-disc agar diffusion assay.</abstract><cop>Japan</cop><pmid>19680284</pmid><doi>10.1038/ja.2009.80</doi><tpages>4</tpages></addata></record> |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Alma/SFX Local Collection |
| subjects | Alkenes - chemistry Alkenes - metabolism Ascomycota - classification Ascomycota - genetics Ascomycota - growth & development Ascomycota - metabolism Benzaldehydes - chemistry Benzaldehydes - isolation & purification Benzaldehydes - metabolism Candida albicans - drug effects Candida albicans - growth & development Chemistry, Physical Culture Media Epoxy Compounds - chemistry Epoxy Compounds - isolation & purification Epoxy Compounds - metabolism Magnetic Resonance Spectroscopy Microbial Sensitivity Tests - methods Mutation Phenols - chemistry Phenols - metabolism Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - metabolism |
| title | LL-Z1272alpha epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae |
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