Plant Physiol. Journal of Pharmacology and Experimental Therapeutics
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Published on September 17, 2008; 10.1104/pp.108.125757

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Received July 7, 2008
Accepted September 14, 2008

A subclade of flavin-monooxygenases involved in aliphatic glucosinolate biosynthesis

Jing Li , Bjarne Gram Hansen , James A. Ober , Daniel J. Kliebenstein , and Barbara Ann Halkier *

Plant Biochemistry Laboratory, Department of Plant Biology and VKR Research Centre for Pro-Active Plants, Faculty of Life Sciences, University of Copenhagen, DK-1871 Frederiksberg C, Denmark; University of California-Davis, Department of Plant Sciences, Mail Stop 3, One Shields Ave, Davis, CA 95616-8780

* Corresponding author; email: bah{at}life.ku.dk.

Glucosinolates (GSLs) are amino acid-derived secondary metabolites with diverse biological activities dependent on chemical modifications of the side chain. We previously identified the flavin-monooxygenase FMOGS-OX1 as an enzyme in the biosynthesis of aliphatic GSLs in Arabidopsis thaliana that catalyzes the S-oxygenation of methylthioalkyl to methylsulfinylalkyl GSLs. Here, we report the fine-mapping of a QTL for the S-oxygenating activity in Arabidopsis. In this region, there are three FMOs that together with FMOGS-OX1 and a fifth FMO form what appears to be a crucifer-specific subclade. We report the identification of these four uncharacterized FMOs designated FMOGS-OX2-5. Biochemical characterization of the recombinant protein combined with the analysis of GSL content in knock-out mutants and over-expression lines show that FMOGS-OX2, FMOGS-OX3 and FMOGS-OX4 have broad substrate specificity and catalyze the conversion from methylthioalkyl GSL to the corresponding methylsulfinylalkyl GSL independent of chain-length. In contrast, FMOGS-OX5 shows substrate specificity towards the long-chain 8-methylthiooctyl GSL. Identification of the FMOGS-OX subclade will generate a better understanding of the evolution of biosynthetic activities and specificities in secondary metabolism and provides an important tool for breeding plants with improved cancer-prevention characteristics as provided by the methylsulfinylalkyl GSL.




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