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Chembiochem. 2015 Aug 17;16(12):1782-90. doi: 10.1002/cbic.201500247. Epub 2015 Jul 3.

Investigations into the Biosynthesis, Regulation, and Self-Resistance of Toxoflavin in Pseudomonas protegens Pf-5.

Author information

1
College of Pharmacy, Oregon State University, 203 Pharmacy Building, Corvallis, OR 97331 (USA). benjamin.philmus@oregonstate.edu.
2
Agricultural Research Service, US Department of Agriculture, 3420 N.W. Orchard Avenue, Corvallis, OR 97330 (USA).
3
Department of Botany and Plant Pathology, Oregon State University, 2082 Cordley Hall, Corvallis, OR 97331 (USA).
4
Department of Microbial Ecology, Netherlands Institute of Ecology, Droevendaalsesteeg 10, 6708 PB Wageningen (The Netherlands).
5
Institute of Biology, Leiden University, Sylviusweg 72, 2333 BE Leiden (The Netherlands).
6
Department of Chemistry, Texas A&M University, College Station, TX 77843 (USA).
7
Agricultural Research Service, US Department of Agriculture, 3420 N.W. Orchard Avenue, Corvallis, OR 97330 (USA). joyce.loper@ars.usda.gov.
8
Department of Botany and Plant Pathology, Oregon State University, 2082 Cordley Hall, Corvallis, OR 97331 (USA). joyce.loper@ars.usda.gov.

Abstract

Pseudomonas spp. are prolific producers of natural products from many structural classes. Here we show that the soil bacterium Pseudomonas protegens Pf-5 is capable of producing trace levels of the triazine natural product toxoflavin (1) under microaerobic conditions. We evaluated toxoflavin production by derivatives of Pf-5 with deletions in specific biosynthesis genes, which led us to propose a revised biosynthetic pathway for toxoflavin that shares the first two steps with riboflavin biosynthesis. We also report that toxM, which is not present in the well-characterized cluster of Burkholderia glumae, encodes a monooxygenase that degrades toxoflavin. The toxoflavin degradation product of ToxM is identical to that of TflA, the toxoflavin lyase from Paenibacillus polymyxa. Toxoflavin production by P. protegens causes inhibition of several plant-pathogenic bacteria, and introduction of toxM into the toxoflavin-sensitive strain Pseudomonas syringae DC3000 results in resistance to toxoflavin.

KEYWORDS:

biocontrol; natural products; secondary metabolism; triazine

PMID:
26077901
DOI:
10.1002/cbic.201500247
[Indexed for MEDLINE]

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