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Plant Physiol, August 2000, Vol. 123, pp. 1437-1448
Transgenic Tobacco and Arabidopsis Plants Expressing the Two
Multifunctional Sorghum Cytochrome P450 Enzymes, CYP79A1 and
CYP71E1, Are Cyanogenic and Accumulate Metabolites Derived from
Intermediates in Dhurrin Biosynthesis1
Søren
Bak,
Carl Erik
Olsen,
Barbara Ann
Halkier, and
Birger
Lindberg
Møller*
Plant Biochemistry Laboratory, Department of Plant Biology (S.B.,
B.A.H., B.L.M.), Department of Chemistry (C.E.O.), and Center of
Molecular Plant Physiology (PlaCe) (S.B., C.E.O., B.A.H., B.L.M.),
Royal Veterinary and Agricultural University, DK-1871 Frederiksberg C,
Copenhagen, Denmark
Novel cyanogenic plants have been generated by the
simultaneous expression of the two multifunctional sorghum
(Sorghum bicolor [L.] Moench) cytochrome P450 enzymes
CYP79A1 and CYP71E1 in tobacco (Nicotiana tabacum cv
Xanthi) and Arabidopsis under the regulation of the constitutive 35S
promoter. CYP79A1 and CYP71E1 catalyze the conversion of the parent
amino acid tyrosine to p-hydroxymandelonitrile, the
aglycone of the cyanogenic glucoside dhurrin. CYP79A1 catalyzes the
conversion of tyrosine to p-hydroxyphenylacetaldoxime
and CYP71E1, the subsequent conversion to
p-hydroxymandelonitrile. p-Hydroxymandelonitrile is labile and dissociates into
p-hydroxybenzaldehyde and hydrogen cyanide, the same
products released from dhurrin upon cell disruption as a result of pest
or herbivore attack. In transgenic plants expressing CYP79A1 as well as
CYP71E1, the activity of CYP79A1 is higher than that of CYP71E1,
resulting in the accumulation of several
p-hydroxyphenylacetaldoxime-derived products in the
addition to those derived from p-hydroxymandelonitrile. Transgenic tobacco and Arabidopsis plants expressing only CYP79A1 accumulate the same p-hydroxyphenylacetaldoxime-derived
products as transgenic plants expressing both sorghum cytochrome P450
enzymes. In addition, the transgenic CYP79A1 Arabidopsis plants
accumulate large amounts of
p-hydroxybenzylglucosinolate. In transgenic
Arabidopsis expressing CYP71E1, this enzyme and the enzymes of the
pre-existing glucosinolate pathway compete for the
p-hydroxyphenylacetaldoxime as substrate, resulting in
the formation of small amounts of
p-hydroxybenzylglucosinolate. Cyanogenic glucosides are
phytoanticipins, and the present study demonstrates the feasibility of
expressing cyanogenic compounds in new plant species by gene transfer
technology to improve pest and disease resistance.
1
This work was supported by the Danish National
Research Foundation.
*
Corresponding author; e-mail blm{at}kvl.dk; fax 45-35283333.
© 2000 American Society of Plant Physiologists
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