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BIOCHEMICAL PROCESSES AND MACROMOLECULAR STRUCTURES

A Novel 2-Oxoacid-Dependent Dioxygenase Involved in the Formation of the Goiterogenic 2-Hydroxybut-3-enyl Glucosinolate and Generalist Insect Resistance in Arabidopsis^[C],[W],[OA]

Plant Biochemistry Laboratory, Department of Plant Biology, VKR Centre for Pro-Active Plants, Faculty of Life Sciences, University of Copenhagen, DK–1871 Frederiksberg C, Denmark (B.G.H., B.A.H.); Department of Plant Sciences and Plant Biology Graduate Group, University of California, Davis, California 95616–8746 (R.E.K., J.A.O., V.M.L., D.J.K.); Max Planck Institute for Chemical Ecology, D–07745 Jena, Germany (V.M.L., T.M.-O., J.G., D.J.K.); and Department of Biology, Duke University, Durham, North Carolina 27708 (T.M.-O.)

Glucosinolates are secondary metabolites found almost exclusively in the order Brassicales. They are synthesized from a variety of amino acids and can have numerous side chain modifications that control biological function. We investigated the biosynthesis of 2-hydroxybut-3-enyl glucosinolate, which has biological activities including toxicity to Caenorhabditis elegans, inhibition of seed germination, induction of goiter disease in mammals, and production of bitter flavors in Brassica vegetable crops. Arabidopsis (Arabidopsis thaliana) accessions contain three different patterns of 2-hydroxybut-3-enyl glucosinolate accumulation (present in leaves and seeds, seeds only, or absent) corresponding to three different alleles at a single locus, GSL-OH. Fine-scale mapping of the GSL-OH locus identified a 2-oxoacid-dependent dioxygenase encoded by At2g25450 required for the formation of both 2R- and 2S-2-hydroxybut-3-enyl glucosinolate from the precursor 3-butenyl glucosinolate precursor. Naturally occurring null mutations and T-DNA insertional mutations in At2g25450 exhibit a complete absence of 2-hydroxybut-3-enyl glucosinolate accumulation. Analysis of herbivory by the generalist lepidopteran Trichoplusia ni showed that production of 2-hydroxybut-3-enyl glucosinolate provides increased resistance. These results show that At2g25450 is necessary for the hydroxylation of but-3-enyl glucosinolate to 2-hydroxybut-3-enyl glucosinolate in planta and that this metabolite increases resistance to generalist herbivory.

The author responsible for distribution of materials integral to the findings presented in this article in accordance with the policy described in the Instructions for Authors (www.plantphysiol.org) is: Daniel J. Kliebenstein (kliebenstein{at}ucdavis.edu).

^[C] Some figures in this article are displayed in color online but in black and white in the print edition.

^[W] The online version of this article contains Web-only data.

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www.plantphysiol.org/cgi/doi/10.1104/pp.108.129981

^* Corresponding author; e-mail kliebenstein{at}ucdavis.edu.

Received September 17, 2008; accepted October 17, 2008; published October 22, 2008.