The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi

The microbiological transformation of the diterpene ent-15B,16B-epoxy-14a-hydroxykaurane into ent-14a,15B-dihydroxy-11a,16a-epoxykaurane, ent-7a,14a,15B-trihydroxy-11a,16a-epoxykaurane and ent-7B,14a,15B-trihydroxy-11a,16a-epoxykaurane has been carried out using the fungus Gibberella fujikuroi. The...

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Authors: Fraga, Braulio M., Hernández, Melchor G., García-Tellado, Fernando, González, Pedro, Perales, Áurea
Format: article
Publication Date:1993
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/21860
Online Access:http://hdl.handle.net/10261/21860
Access Level:Open access
Keyword:Gibberella fujikuroi
Microbiological transformations
Diterpenes
ent-15B,16B-epoxy-14a-hydroxykaurane
Sideroxol
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repository_id_str
spelling The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroiFraga, Braulio M.Hernández, Melchor G.García-Tellado, FernandoGonzález, PedroPerales, ÁureaGibberella fujikuroiMicrobiological transformationsDiterpenesent-15B,16B-epoxy-14a-hydroxykauraneSideroxolThe microbiological transformation of the diterpene ent-15B,16B-epoxy-14a-hydroxykaurane into ent-14a,15B-dihydroxy-11a,16a-epoxykaurane, ent-7a,14a,15B-trihydroxy-11a,16a-epoxykaurane and ent-7B,14a,15B-trihydroxy-11a,16a-epoxykaurane has been carried out using the fungus Gibberella fujikuroi. The incubation with this fungus of sideroxol (ent-7a,18-dihydroxy-15B,16B-epoxykaurane) gave as main products ent-7a,15B,18-trihydroxy-11a,16a-epoxykaurane and ent-7a,13,18-trihydroxy-15a,16a-epoxykaurane. Some of these compounds were identified as their acetate derivatives. The presence of the 15a,16a-epoxy group in these two substrates inhibits transformations involving oxidation at C-19 and favours the hydroxylation at C-11(B).This work has been supported by the DGICYT, Ministry of Education and Science, Spain, grant PR87-255. We thank Dr. J. R. Hanson (University of Sussex, U.K.) for cultures of Gibberella fujikuroi and Prof. García-Granados (Universidad de Granada) for a sample of pusillatriol.Peer reviewedElsevierMinisterio de Educación y Ciencia (España)201020101993info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501243357 bytesapplication/pdfhttp://hdl.handle.net/10261/21860reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglésinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/218602026-05-22T06:33:51Z
dc.title.none.fl_str_mv The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi
title The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi
spellingShingle The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi
Fraga, Braulio M.
Gibberella fujikuroi
Microbiological transformations
Diterpenes
ent-15B,16B-epoxy-14a-hydroxykaurane
Sideroxol
title_short The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi
title_full The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi
title_fullStr The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi
title_full_unstemmed The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi
title_sort The biotransformation of two ent-15B,16B-epoxy-kaurane derivatives by Gibberella fujikuroi
dc.creator.none.fl_str_mv Fraga, Braulio M.
Hernández, Melchor G.
García-Tellado, Fernando
González, Pedro
Perales, Áurea
author Fraga, Braulio M.
author_facet Fraga, Braulio M.
Hernández, Melchor G.
García-Tellado, Fernando
González, Pedro
Perales, Áurea
author_role author
author2 Hernández, Melchor G.
García-Tellado, Fernando
González, Pedro
Perales, Áurea
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Educación y Ciencia (España)
dc.subject.none.fl_str_mv Gibberella fujikuroi
Microbiological transformations
Diterpenes
ent-15B,16B-epoxy-14a-hydroxykaurane
Sideroxol
topic Gibberella fujikuroi
Microbiological transformations
Diterpenes
ent-15B,16B-epoxy-14a-hydroxykaurane
Sideroxol
description The microbiological transformation of the diterpene ent-15B,16B-epoxy-14a-hydroxykaurane into ent-14a,15B-dihydroxy-11a,16a-epoxykaurane, ent-7a,14a,15B-trihydroxy-11a,16a-epoxykaurane and ent-7B,14a,15B-trihydroxy-11a,16a-epoxykaurane has been carried out using the fungus Gibberella fujikuroi. The incubation with this fungus of sideroxol (ent-7a,18-dihydroxy-15B,16B-epoxykaurane) gave as main products ent-7a,15B,18-trihydroxy-11a,16a-epoxykaurane and ent-7a,13,18-trihydroxy-15a,16a-epoxykaurane. Some of these compounds were identified as their acetate derivatives. The presence of the 15a,16a-epoxy group in these two substrates inhibits transformations involving oxidation at C-19 and favours the hydroxylation at C-11(B).
publishDate 1993
dc.date.none.fl_str_mv 1993
2010
2010
dc.type.none.fl_str_mv info:eu-repo/semantics/article
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format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/21860
url http://hdl.handle.net/10261/21860
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 243357 bytes
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
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