The Microbiological Transformation of Two 15β-Hydroxy-ent-kaurene Diterpenes by Gibberella fujikuroi
The incubation of 15 beta -hydroxy-3-oxo-ent-kaur-16-ene (1) with the fungus Gibberella fujikuroi afforded 11 beta -hydroxy-3,15-dioxo-ent-kaurane (6), 11 beta ,15 beta -dihydroxy-3-oxo-ent-kaur-16-ene (8), 7 beta ,11 beta ,15 beta -trihydroxy-3-oxo-ent-kaur-16-ene (9), 7 alpha ,11 beta -dihydroxy-3...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2004-01, Vol.67 (1), p.64-69 |
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| creator | FRAGA, Braulio M. GUILLERMO, Ricardo HERNáNDEZ, Melchor G. |
| description | The incubation of 15 beta -hydroxy-3-oxo-ent-kaur-16-ene (1) with the fungus Gibberella fujikuroi afforded 11 beta -hydroxy-3,15-dioxo-ent-kaurane (6), 11 beta ,15 beta -dihydroxy-3-oxo-ent-kaur-16-ene (8), 7 beta ,11 beta ,15 beta -trihydroxy-3-oxo-ent-kaur-16-ene (9), 7 alpha ,11 beta -dihydroxy-3,15-dioxo-ent-kaurane (7), and 7 alpha ,11 beta ,15 beta -trihydroxy-3-oxo-ent-kaur-16-ene (10). The incubation of 15 beta -hydroxy-ent-kaur-2,16-diene (3) with the same fungus yielded 70 alpha ,11 beta -dihydroxy-15-oxo-ent-kaur-2-ene (12), 70 alpha ,11 beta ,15 beta -trihydroxy-ent-kaur-2,16-diene (13), 7 beta ,15 beta -dihydroxy-ent-kaur-2,16-dien-19,6-olide (14), 1 beta ,7 beta ,15 beta -trihydroxy-ent-kaur-2,16-dien-19-oic acid (15), 7 alpha ,11 beta ,16 alpha -trihydroxy-15-oxo-ent-kaur-2-ene (17), and 7 alpha ,15 beta ,17-trihydroxy-11 beta ,16 beta -epoxy-ent-kaur-2-ene (19). These results indicated that a 3-oxo group in ent-kaur-16-ene derivatives inhibits the oxidation at C-19, typical of the biosynthetic pathway of gibberellins and kaurenolides, while a 2,3-double bond or a 15 beta -OH does not. In both substrates a 15 beta -alcohol directs hydroxylations at C-11( beta ) and C-7( alpha ), while in those with a 2,3-double bond the functionalization of C-1( beta ) is favored. |
| doi_str_mv | 10.1021/np030363n |
| format | Article |
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The incubation of 15 beta -hydroxy-ent-kaur-2,16-diene (3) with the same fungus yielded 70 alpha ,11 beta -dihydroxy-15-oxo-ent-kaur-2-ene (12), 70 alpha ,11 beta ,15 beta -trihydroxy-ent-kaur-2,16-diene (13), 7 beta ,15 beta -dihydroxy-ent-kaur-2,16-dien-19,6-olide (14), 1 beta ,7 beta ,15 beta -trihydroxy-ent-kaur-2,16-dien-19-oic acid (15), 7 alpha ,11 beta ,16 alpha -trihydroxy-15-oxo-ent-kaur-2-ene (17), and 7 alpha ,15 beta ,17-trihydroxy-11 beta ,16 beta -epoxy-ent-kaur-2-ene (19). These results indicated that a 3-oxo group in ent-kaur-16-ene derivatives inhibits the oxidation at C-19, typical of the biosynthetic pathway of gibberellins and kaurenolides, while a 2,3-double bond or a 15 beta -OH does not. In both substrates a 15 beta -alcohol directs hydroxylations at C-11( beta ) and C-7( alpha ), while in those with a 2,3-double bond the functionalization of C-1( beta ) is favored.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np030363n</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; Gibberella fujikuroi ; Medical sciences ; Methods. Procedures. Technologies ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments</subject><ispartof>Journal of natural products (Washington, D.C.), 2004-01, Vol.67 (1), p.64-69</ispartof><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,782,786,27933,27934</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15429724$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>FRAGA, Braulio M.</creatorcontrib><creatorcontrib>GUILLERMO, Ricardo</creatorcontrib><creatorcontrib>HERNáNDEZ, Melchor G.</creatorcontrib><title>The Microbiological Transformation of Two 15β-Hydroxy-ent-kaurene Diterpenes by Gibberella fujikuroi</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The incubation of 15 beta -hydroxy-3-oxo-ent-kaur-16-ene (1) with the fungus Gibberella fujikuroi afforded 11 beta -hydroxy-3,15-dioxo-ent-kaurane (6), 11 beta ,15 beta -dihydroxy-3-oxo-ent-kaur-16-ene (8), 7 beta ,11 beta ,15 beta -trihydroxy-3-oxo-ent-kaur-16-ene (9), 7 alpha ,11 beta -dihydroxy-3,15-dioxo-ent-kaurane (7), and 7 alpha ,11 beta ,15 beta -trihydroxy-3-oxo-ent-kaur-16-ene (10). The incubation of 15 beta -hydroxy-ent-kaur-2,16-diene (3) with the same fungus yielded 70 alpha ,11 beta -dihydroxy-15-oxo-ent-kaur-2-ene (12), 70 alpha ,11 beta ,15 beta -trihydroxy-ent-kaur-2,16-diene (13), 7 beta ,15 beta -dihydroxy-ent-kaur-2,16-dien-19,6-olide (14), 1 beta ,7 beta ,15 beta -trihydroxy-ent-kaur-2,16-dien-19-oic acid (15), 7 alpha ,11 beta ,16 alpha -trihydroxy-15-oxo-ent-kaur-2-ene (17), and 7 alpha ,15 beta ,17-trihydroxy-11 beta ,16 beta -epoxy-ent-kaur-2-ene (19). These results indicated that a 3-oxo group in ent-kaur-16-ene derivatives inhibits the oxidation at C-19, typical of the biosynthetic pathway of gibberellins and kaurenolides, while a 2,3-double bond or a 15 beta -OH does not. In both substrates a 15 beta -alcohol directs hydroxylations at C-11( beta ) and C-7( alpha ), while in those with a 2,3-double bond the functionalization of C-1( beta ) is favored.</description><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Gibberella fujikuroi</subject><subject>Medical sciences</subject><subject>Methods. Procedures. Technologies</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNo9j81OAjEcxBujiYgefINe9FbtB223R4MCGowkrIm3TXf5rxaWLba7EV7LB_GZXAPxNJPML5MZhC4ZvWGUs9t6QwUVStRHqMckp0RRLo9RjzIliEjU4BSdxbiktMOM7CFIPwA_uyL43PnKv7vCVjgNto6lD2vbOF9jX-L0y2Mmf77JZLcIfrsjUDdkZdsANeB710DYdC7ifIfHLs8hQFVZXLZLt2qDd-fopLRVhIuD9tHr6CEdTsj0Zfw4vJsSxxPdEFjkwJUpldUJaLNIGFXdTlqIXOTaJloabU2imFbAhQLTJYVSC8mZkpZT0UfX-95N8J8txCZbu1j8banBtzFj2lBOpezAqwNoY_e47A4XLmab4NY27DImB9xoPug4sudcbGD7n9uwypQWWmbpbJ7N7t8mZj5KsyfxC7y-dZI</recordid><startdate>20040123</startdate><enddate>20040123</enddate><creator>FRAGA, Braulio M.</creator><creator>GUILLERMO, Ricardo</creator><creator>HERNáNDEZ, Melchor G.</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>BSCLL</scope><scope>IQODW</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20040123</creationdate><title>The Microbiological Transformation of Two 15β-Hydroxy-ent-kaurene Diterpenes by Gibberella fujikuroi</title><author>FRAGA, Braulio M. ; GUILLERMO, Ricardo ; HERNáNDEZ, Melchor G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i287t-edbe269f6a78e79d81060300c3b3b7a87597a986176e236e90c3c66d52165a203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Gibberella fujikuroi</topic><topic>Medical sciences</topic><topic>Methods. Procedures. Technologies</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FRAGA, Braulio M.</creatorcontrib><creatorcontrib>GUILLERMO, Ricardo</creatorcontrib><creatorcontrib>HERNáNDEZ, Melchor G.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>FRAGA, Braulio M.</au><au>GUILLERMO, Ricardo</au><au>HERNáNDEZ, Melchor G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Microbiological Transformation of Two 15β-Hydroxy-ent-kaurene Diterpenes by Gibberella fujikuroi</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2004-01-23</date><risdate>2004</risdate><volume>67</volume><issue>1</issue><spage>64</spage><epage>69</epage><pages>64-69</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>The incubation of 15 beta -hydroxy-3-oxo-ent-kaur-16-ene (1) with the fungus Gibberella fujikuroi afforded 11 beta -hydroxy-3,15-dioxo-ent-kaurane (6), 11 beta ,15 beta -dihydroxy-3-oxo-ent-kaur-16-ene (8), 7 beta ,11 beta ,15 beta -trihydroxy-3-oxo-ent-kaur-16-ene (9), 7 alpha ,11 beta -dihydroxy-3,15-dioxo-ent-kaurane (7), and 7 alpha ,11 beta ,15 beta -trihydroxy-3-oxo-ent-kaur-16-ene (10). The incubation of 15 beta -hydroxy-ent-kaur-2,16-diene (3) with the same fungus yielded 70 alpha ,11 beta -dihydroxy-15-oxo-ent-kaur-2-ene (12), 70 alpha ,11 beta ,15 beta -trihydroxy-ent-kaur-2,16-diene (13), 7 beta ,15 beta -dihydroxy-ent-kaur-2,16-dien-19,6-olide (14), 1 beta ,7 beta ,15 beta -trihydroxy-ent-kaur-2,16-dien-19-oic acid (15), 7 alpha ,11 beta ,16 alpha -trihydroxy-15-oxo-ent-kaur-2-ene (17), and 7 alpha ,15 beta ,17-trihydroxy-11 beta ,16 beta -epoxy-ent-kaur-2-ene (19). These results indicated that a 3-oxo group in ent-kaur-16-ene derivatives inhibits the oxidation at C-19, typical of the biosynthetic pathway of gibberellins and kaurenolides, while a 2,3-double bond or a 15 beta -OH does not. In both substrates a 15 beta -alcohol directs hydroxylations at C-11( beta ) and C-7( alpha ), while in those with a 2,3-double bond the functionalization of C-1( beta ) is favored.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><doi>10.1021/np030363n</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Fundamental and applied biological sciences. Psychology General pharmacology Gibberella fujikuroi Medical sciences Methods. Procedures. Technologies Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments |
| title | The Microbiological Transformation of Two 15β-Hydroxy-ent-kaurene Diterpenes by Gibberella fujikuroi |
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