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Applied and Environmental Microbiology, June 2003, p. 3165-3169, Vol. 69, No. 6
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.6.3165-3169.2003

Identification of Intermediate and Branch Metabolites Resulting from Biotransformation of 2-Benzoxazolinone by Fusarium verticillioides

A. E. Glenn,1* F. I. Meredith,1 W. H. Morrison III,2 and C. W. Bacon1

Toxicology and Mycotoxin Research Unit,1 Quality Assessment Research Unit, Russell Research Center, USDA Agricultural Research Service, Athens, Georgia 306042

Received 11 October 2002/ Accepted 27 February 2003

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 apparently is not a major virulence factor but may enhance the ecological fitness of the fungus during colonization of maize stubble and field debris.

* Corresponding author. Mailing address: USDA, ARS, P.O. Box 5677, Russell Research Center, Athens, GA 30604-5677. Phone: (706) 546-3119. Fax: (706) 546-3116. E-mail: aglenn{at}saa.ars.usda.gov.

Applied and Environmental Microbiology, June 2003, p. 3165-3169, Vol. 69, No. 6
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.6.3165-3169.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.



This article has been cited by other articles:

  • Saunders, M., Kohn, L. M. (2008). Host-Synthesized Secondary Compounds Influence the In Vitro Interactions between Fungal Endophytes of Maize. Appl. Environ. Microbiol. 74: 136-142 [Abstract] [Full Text]  


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