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J. Biol. Chem., Vol. 276, Issue 14, 11078-11085, April 6, 2001
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From the Glucosinolates are natural plant products that
have received rising attention due to their role in interactions
between pests and crop plants and as chemical protectors against
cancer. Glucosinolates are derived from amino acids and have aldoximes
as intermediates. We report that cytochrome P450 CYP79F1 catalyzes
aldoxime formation in the biosynthesis of aliphatic glucosinolates in
Arabidopsis thaliana. Using recombinant CYP79F1
functionally expressed in Escherichia coli, we show that
both dihomomethionine and trihomomethionine are metabolized by CYP79F1
resulting in the formation of 5-methylthiopentanaldoxime and
6-methylthiohexanaldoxime, respectively.
5-methylthiopentanaldoxime is the precursor of the major
glucosinolates in leaves of A. thaliana, i.e.
4-methylthiobutylglucosinolate and 4-methylsulfinylbutylglucosinolate, and a variety of other glucosinolates in Brassica sp.
Transgenic A. thaliana with cosuppression of CYP79F1 have a
reduced content of aliphatic glucosinolates and a highly increased
level of dihomomethionine and trihomomethionine. The transgenic plants
have a morphological phenotype showing loss of apical dominance and
formation of multiple axillary shoots. Our data provide the first
evidence that a cytochrome P450 catalyzes the
N-hydroxylation of chain-elongated methionine homologues to
the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates.
Cytochrome P450 CYP79F1 from Arabidopsis Catalyzes the Conversion
of Dihomomethionine and Trihomomethionine to the Corresponding
Aldoximes in the Biosynthesis of Aliphatic Glucosinolates*
§,§,
,, and§**
Plant Biochemistry Laboratory, Department of
Plant Biology, ¶ Department of Chemistry, and § Center
for Molecular Plant Physiology (PlaCe), The Royal Veterinary and
Agricultural University, Thorvaldsensvej 40, DK-1871 Frederiksberg C,
Copenhagen, Denmark and the Integrated Approach to Crop
Research-Rothamsted, Harpenden, Hertfordshire AL5 2JQ, United
Kingdom
*
Financial support by the National Danish Research Foundation
to PlaCe, Center for Molecular Plant Physiology, is gratefully acknowledged. Integrated Approach to Crop Research-Rothamsted receives
grant-aided support from the Biotechnology and Biological Sciences
Research Council of the United Kingdom.The costs of publication of this
article were defrayed in part by the
payment of page charges. The article
must therefore be hereby marked
"advertisement" in accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
Copyright © 2001 by The American Society for Biochemistry and Molecular Biology, Inc.
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