Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis

Detalhes bibliográficos
Autor(a) principal: Ishikawa,Noemia Kazue
Data de Publicação: 2013
Outros Autores: Tahara,Satoshi, Namatame,Tomohiro, Farooq,Afgan, Fukushi,Yukiharu
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Brazilian Journal of Microbiology
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822013000400037
Resumo: Enokipodins A, B, C, and D are antimicrobial sesquiterpenes isolated from the mycelial culture medium of Flammulina velutipes, an edible mushroom. The presence of a quaternary carbon stereocenter on the cyclopentane ring makes enokipodins A-D attractive synthetic targets. In this study, nine different cytochrome P450 inhibitors were used to trap the biosynthetic intermediates of highly oxygenated cuparene-type sesquiterpenes of F. velutipes. Of these, 1-aminobenzotriazole produced three less-highly oxygenated biosynthetic intermediates of enokipodins A-D; these were identified as (S)-(-)-cuparene-1,4-quinone and epimers at C-3 of 6-hydroxy-6-methyl-3-(1,2,2-trimethylcyclopentyl)-2-cyclohexen-1-one. One of the epimers was found to be a new compound.
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spelling Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesisAntimicrobial compoundcuparene-1,4-quinoneedible mushroomenokitakeFlammulina velutipesEnokipodins A, B, C, and D are antimicrobial sesquiterpenes isolated from the mycelial culture medium of Flammulina velutipes, an edible mushroom. The presence of a quaternary carbon stereocenter on the cyclopentane ring makes enokipodins A-D attractive synthetic targets. In this study, nine different cytochrome P450 inhibitors were used to trap the biosynthetic intermediates of highly oxygenated cuparene-type sesquiterpenes of F. velutipes. Of these, 1-aminobenzotriazole produced three less-highly oxygenated biosynthetic intermediates of enokipodins A-D; these were identified as (S)-(-)-cuparene-1,4-quinone and epimers at C-3 of 6-hydroxy-6-methyl-3-(1,2,2-trimethylcyclopentyl)-2-cyclohexen-1-one. One of the epimers was found to be a new compound.Sociedade Brasileira de Microbiologia2013-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822013000400037Brazilian Journal of Microbiology v.44 n.4 2013reponame:Brazilian Journal of Microbiologyinstname:Sociedade Brasileira de Microbiologia (SBM)instacron:SBM10.1590/S1517-83822013000400037info:eu-repo/semantics/openAccessIshikawa,Noemia KazueTahara,SatoshiNamatame,TomohiroFarooq,AfganFukushi,Yukiharueng2014-03-27T00:00:00Zoai:scielo:S1517-83822013000400037Revistahttps://www.scielo.br/j/bjm/ONGhttps://old.scielo.br/oai/scielo-oai.phpbjm@sbmicrobiologia.org.br||mbmartin@usp.br1678-44051517-8382opendoar:2014-03-27T00:00Brazilian Journal of Microbiology - Sociedade Brasileira de Microbiologia (SBM)false
dc.title.none.fl_str_mv Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis
title Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis
spellingShingle Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis
Ishikawa,Noemia Kazue
Antimicrobial compound
cuparene-1,4-quinone
edible mushroom
enokitake
Flammulina velutipes
title_short Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis
title_full Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis
title_fullStr Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis
title_full_unstemmed Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis
title_sort Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis
author Ishikawa,Noemia Kazue
author_facet Ishikawa,Noemia Kazue
Tahara,Satoshi
Namatame,Tomohiro
Farooq,Afgan
Fukushi,Yukiharu
author_role author
author2 Tahara,Satoshi
Namatame,Tomohiro
Farooq,Afgan
Fukushi,Yukiharu
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Ishikawa,Noemia Kazue
Tahara,Satoshi
Namatame,Tomohiro
Farooq,Afgan
Fukushi,Yukiharu
dc.subject.por.fl_str_mv Antimicrobial compound
cuparene-1,4-quinone
edible mushroom
enokitake
Flammulina velutipes
topic Antimicrobial compound
cuparene-1,4-quinone
edible mushroom
enokitake
Flammulina velutipes
description Enokipodins A, B, C, and D are antimicrobial sesquiterpenes isolated from the mycelial culture medium of Flammulina velutipes, an edible mushroom. The presence of a quaternary carbon stereocenter on the cyclopentane ring makes enokipodins A-D attractive synthetic targets. In this study, nine different cytochrome P450 inhibitors were used to trap the biosynthetic intermediates of highly oxygenated cuparene-type sesquiterpenes of F. velutipes. Of these, 1-aminobenzotriazole produced three less-highly oxygenated biosynthetic intermediates of enokipodins A-D; these were identified as (S)-(-)-cuparene-1,4-quinone and epimers at C-3 of 6-hydroxy-6-methyl-3-(1,2,2-trimethylcyclopentyl)-2-cyclohexen-1-one. One of the epimers was found to be a new compound.
publishDate 2013
dc.date.none.fl_str_mv 2013-12-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822013000400037
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1517-83822013000400037
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S1517-83822013000400037
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Microbiologia
publisher.none.fl_str_mv Sociedade Brasileira de Microbiologia
dc.source.none.fl_str_mv Brazilian Journal of Microbiology v.44 n.4 2013
reponame:Brazilian Journal of Microbiology
instname:Sociedade Brasileira de Microbiologia (SBM)
instacron:SBM
instname_str Sociedade Brasileira de Microbiologia (SBM)
instacron_str SBM
institution SBM
reponame_str Brazilian Journal of Microbiology
collection Brazilian Journal of Microbiology
repository.name.fl_str_mv Brazilian Journal of Microbiology - Sociedade Brasileira de Microbiologia (SBM)
repository.mail.fl_str_mv bjm@sbmicrobiologia.org.br||mbmartin@usp.br
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