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1. (Article ID: 12482)
Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA
Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid
Journal of Biological Chemistry 275(43) (2000)
33712-33717
Glucosinolates are natural plant products known as flavor compounds, cancer-preventing agents, and biopesticides. We report cloning and characterization of the cytochrome P450 CYP79B2 fromArabidopsis. Heterologous expression of CYP79B2 in Escherichia coli shows that CYP79B2 catalyzes the conversion of tryptophan to indole-3-acetaldoxime. Recombinant CYP79B2 has a K m of 21 μm and aV max of 7.78 nmol/h/ml culture. Inhibitor studies show that CYP79B2 is different from a previously described enzyme activity that converts tryptophan to indole-3-acetaldoxime (Ludwig-Müller, J., and Hilgenberg, W. (1990)Phytochemistry, 29, 1397–1400). CYP79B2 is wound-inducible and expressed in leaves, stem, flowers, and roots, with the highest expression in roots. Arabidopsis overexpressing CYP79B2 has increased levels of indole glucosinolates, which strongly indicates that CYP79B2 is involved in indole glucosinolate biosynthesis. Our data show that oxime production by CYP79s is not restricted to those amino acids that are precursors for cyanogenic glucosides. Our data are consistent with the hypothesis that indole glucosinolates have evolved from cyanogenesis. Indole-3-acetaldoxime is a precursor of the plant hormone indole-3-acetic acid, which suggests that CYP79B2 might function in biosynthesis of indole-3-acetic acid. Identification of CYP79B2 provides an important tool for modification of the indole glucosinolate content to improve nutritional value and pest resistance.
Escherichia coli, Arabidopsis, enzymatic conversion, glucosinolates, P450 CYP79B2
NCBI PubMed ID: 10922360Publication DOI: 10.1074/jbc.M001667200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: halkier
biobase.dk
Institutions: Plant Biochemistry Laboratory, Department of Plant Biology, The Royal Veterinary and Agricultural University, Copenhagen, Denmark, Center for Molecular Plant Physiology (Place), The Royal Veterinary and Agricultural University, Copenhagen, Denmark
Methods: DNA sequencing, GC-MS, DNA techniques, HPLC, cloning, gene expression, Northern blotting
The publication contains the following compound(s):
- Compound ID: 32382
Structure type: monomer
Trivial name: glucobrassicin
Compound class: glycoside, glucosinolate
Reference(s) to other database(s): GenDB:AF069495
- Compound ID: 32383
|
b-D-Glcp-(1-1)-Subst4Me
Subst = 4-hydroxyglucobrassicin aglycon |
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Structure type: monomer
Trivial name: 4-hydroxyglucobrassicin
Compound class: glycoside, glucosinolate
Reference(s) to other database(s): GenDB:AF069495
- Compound ID: 32384
Structure type: monomer
Trivial name: neoglucobrassicin
Compound class: glycoside, glucosinolate
Reference(s) to other database(s): GenDB:AF069495
- Compound ID: 32385
Structure type: monomer
Trivial name: glucoraphanin
Compound class: glycoside, glucosinolate
Reference(s) to other database(s): GenDB:AF069495
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