Identification of intermediate and branch metabolites resulting from biotransformation of 2-benzoxazolinone by Fusarium verticillioides.

Applied and Environmental Microbiology
A E GlennC W Bacon

Abstract

Detoxification of the maize (Zea mays) antimicrobial compound 2-benzoxazolinone by the fungal endophyte Fusarium verticillioides involves two genetic loci, FDB1 and FDB2, and results in the formation of N-(2-hydroxyphenyl)malonamic acid. Intermediate and branch metabolites were previously suggested to be part of the biotransformation pathway. Evidence is presented here in support of 2-aminophenol as the intermediate metabolite and 2-acetamidophenol as the branch metabolite, which was previously designated as BOA-X. Overall, 2-benzoxazolinone metabolism involves hydrolysis (FDB1) to produce 2-aminophenol, which is then modified (FDB2) by addition of a malonyl group to produce N-(2-hydroxyphenyl)malonamic acid. If the modification is prevented due to genetic mutation (fbd2), then 2-acetamidophenol may accumulate as a result of addition of an acetyl group to 2-aminophenol. This study resolves the overall chemistry of the 2-benzoxazolinone detoxification pathway, and we hypothesize that biotransformation of the related antimicrobial 6-methoxy-2-benzoxazolinone to produce N-(2-hydroxy-4-methoxyphenyl)malonamic acid also occurs via the same enzymatic modifications. Detoxification of these antimicrobials by F. verticillioides apparent...Continue Reading

References

Oct 1, 1996·Phytochemistry·Y Hashimoto, K Shudo
Mar 6, 2002·Molecular Plant-microbe Interactions : MPMI·A E GlennC W Bacon
Oct 1, 1992·Journal of Chemical Ecology·R W Gagliardo, W S Chilton

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Citations

Jun 2, 2006·Journal of Chemical Ecology·Hisashi Kato-Noguchi, Francisco A Macías
Nov 13, 2007·Applied and Environmental Microbiology·Megan Saunders, Linda M Kohn
May 17, 2012·Fungal Genetics and Biology : FG & B·Alma E Rodriguez EstradaGeorgiana May
May 9, 2014·The Journal of Nutrition·Kati HanhinevaKaisa Poutanen
May 30, 2020·Current Microbiology·Chuansheng LiuShaohua Wu
Nov 10, 2020·Molecular Plant-microbe Interactions : MPMI·Rabea SchweigerArtemio Mendoza-Mendoza
Dec 30, 2021·Journal of Agricultural and Food Chemistry·Feifei HouWei Huang

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