The formation of sesquiterpenoid presilphiperfolane and cameroonane metabolites in the Bcbot4 null mutant of Botrytis cinerea

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dc.creatorGabriel Franco dos Santos
dc.creatorJavier Moraga
dc.creatorJacqueline Aparecida Takahashi
dc.creatorMuriel Viaud
dc.creatorJames R. Hanson
dc.creatorRosario Hernández Galán
dc.creatorIsidro González Collado
dc.date.accessioned2023-10-11T22:19:06Z
dc.date.accessioned2025-09-08T23:22:45Z
dc.date.available2023-10-11T22:19:06Z
dc.date.issued2017-06-15
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.1039/C7OB01088E
dc.identifier.issn1477-0520
dc.identifier.urihttps://hdl.handle.net/1843/59430
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofOrganic & Biomolecular Chemistry
dc.rightsAcesso Aberto
dc.subjectSesquiterpenos
dc.subjectQuímica
dc.subjectFungos
dc.subject.otherSesquiterpenos
dc.subject.otherQuímica
dc.subject.otherFungos
dc.titleThe formation of sesquiterpenoid presilphiperfolane and cameroonane metabolites in the Bcbot4 null mutant of Botrytis cinerea
dc.typeArtigo de periódico
local.citation.epage5363
local.citation.issue25
local.citation.spage5357
local.citation.volume15
local.description.resumoBotrytis cinerea is a polyphagous fungal parasite which causes serious damage to more than 200 plant species and consequent economic losses for commercial crops. This pathogen produces two families of phytotoxins, the botryanes and botcinins, which are involved in the infection mechanism. The B. cinerea genome has provided a complete picture of the genes involved in the biosynthesis of its secondary metabolites. The botrydial biosynthetic gene cluster has been identified. This cluster consists of seven genes, where the genes BcBOT1, BcBOT3 and BcBOT4 encode three mono-oxygenases. A study of the Bcbot4Δ null mutant revealed that this mono-oxygenase was involved in the hydroxylation at C-4 of the probotryane skeleton (C-11 of the presilphiperfolane skeleton). A detailed study of the Bcbot4Δ null mutant has been undertaken in order to study the metabolic fate of the presilphiperfolan-8-ol intermediate biosynthesized by this organism and in particular by this strain. As a result three new presilphiperfolanes and three new cameroonanes have been identified. The results suggest that the absence of the oxygen function at C-11 of the presilphiperfolane skeleton permits rearrangement to a cameroonane whilst hydroxylation at C-11 precludes this rearrangement. It is possible that the interactions of the C-11 hydroxylated derivatives perturb the stereo-electronic requirements for the migration of the C-11:C-7 sigma bond to C-8.
local.identifier.orcidhttp://orcid.org/0000-0002-4155-6238
local.identifier.orcidhttp://orcid.org/0000-0001-6383-924X
local.identifier.orcidhttp://orcid.org/0000-0002-8831-1609
local.identifier.orcidhttp://orcid.org/0000-0001-8341-0555
local.identifier.orcidhttp://orcid.org/0000-0003-1887-4796
local.identifier.orcidhttp://orcid.org/0000-0002-8612-0593
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://pubs.rsc.org/en/content/articlelanding/2017/OB/C7OB01088E

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