Structural and biosynthetic studies of botrycinereic acid, a new cryptic metabolite from the fungus Botrytis cinerea
2022
Pinto, Ana | Barúa, Javier | Almeida, Marilia | Viaud, Muriel | Zorrilla, David | Collado, Isidro | Macías-Sánchez, Antonio | Durán-Patrón, Rosa | Universidad de Cádiz = University of Cádiz (UCA) | BIOlogie et GEstion des Risques en agriculture (BIOGER) ; Université Paris-Saclay-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE) | MCIURTI2018097356-B-C21 | CONACYT-ParaguayPVCT18332 | ANR-17-EURE-0007,SPS-GSR,Ecole Universitaire de Recherche de Sciences des Plantes de Paris-Saclay(2017)
International audience
显示更多 [+] 显示较少 [-]英语. 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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