Structural and biosynthetic studies of botrycinereic acid, a new cryptic metabolite from the fungus Botrytis cinerea - Archive ouverte HAL Access content directly
Journal Articles Bioorganic Chemistry Year : 2022

Structural and biosynthetic studies of botrycinereic acid, a new cryptic metabolite from the fungus Botrytis cinerea

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Abstract

Chemical epigenetic manipulation of Botrytis cinerea strain B05.10 with the histone deacetylase inhibitor SAHA led to the isolation of a new cryptic metabolite, botrycinereic acid (22a). This compound was also overproduced by inactivating the stc2 gene, which encodes an unknown sesquiterpene cyclase. Its structure and absolute configuration were determined by extensive spectroscopic NMR and HRESIMS studies, and electronic circular dichroism calculations. Its biosynthesis was studied by feeding 2H and 13C isotopically labeled precursors to B. cinerea Deltastc2 mutant. A detailed analysis of the labeling and coupling patterns into botrycinereic acid (22a) revealed that this compound derives from l-phenylalanine and l-leucine.
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hal-03712908 , version 1 (04-07-2022)

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Attribution - NonCommercial - NoDerivatives - CC BY 4.0

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Ana Pinto, Javier Barúa, Marilia Almeida, Muriel Viaud, David Zorrilla, et al.. Structural and biosynthetic studies of botrycinereic acid, a new cryptic metabolite from the fungus Botrytis cinerea. Bioorganic Chemistry, 2022, 127, pp.105979. ⟨10.1016/j.bioorg.2022.105979⟩. ⟨hal-03712908⟩
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