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Published on October 22, 2008; 10.1104/pp.108.129981

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Received September 17, 2008
Accepted October 17, 2008

A novel 2-oxoacid-dependent dioxygenase involved in the formation of the goiterogenic 2-hydroxybut-3-enyl glucosinolate and generalist insect resistance in Arabidopsis thaliana

Bjarne G. Hansen , Rachel E. Kerwin , James A. Ober , Virginia M. Lambrix , Thomas Mitchell-Olds , Jonathan Gershenzon , Barbara A. Halkier , and Daniel J. Kliebenstein *

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; University of California, Department of Plant Sciences, and Plant Biology Graduate Group, One Shields Ave., Davis, CA 95616-8746; Max Planck Institute for Chemical Ecology, Hans-Knoll-Strasse 8, D-07745, Jena, Germany; Department of Biology, Duke University, Durham, NC 27708, USA

* Corresponding author; email: kliebenstein{at}ucdavis.edu.

Glucosinolates are secondary metabolites found almost exclusive 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 C. elegans, inhibition of seed germination, induction of goiter disease in mammals and production of bitter flavors in Brassica vegetable crops. Arabidopsis 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 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.




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DanielJ. Kliebenstein
Advancing Genetic Theory and Application by Metabolic Quantitative Trait Loci Analysis
PLANT CELL, June 1, 2009; 21(6): 1637 - 1646.
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