Journal
FEBS LETTERS
Volume 588, Issue 1, Pages 198-204Publisher
WILEY
DOI: 10.1016/j.febslet.2013.11.037
Keywords
Benzylisoquinoline alkaloid; Methylenedioxy bridge; Cytochrome P450; Noscapine biosynthesis; Virus-induced gene silencing; Papaver somniferum
Funding
- Genome Canada
- Genome Alberta
- Government of Alberta
- Natural Sciences and Engineering Research Council of Canada
- Canada Foundation for Innovation - Leaders Opportunity Fund
- Alberta Innovates Technology Futures Graduate Scholarship
- University of Calgary
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Noscapine biosynthesis in opium poppy is thought to occur via N-methylcanadine, which would be produced through 9-O-methylation of (S)-scoulerine, methylenedioxy bridge formation on (S)-tetrahydrocolumbamine, and N-methylation of (S)-canadine. Only scoulerine 9-O-methyltransferase has been functionally characterized. We report the isolation and characterization of a cytochrome P450 (CYP719A21) from opium poppy that converts (S)-tetrahydrocolumbamine to (S)-canadine. Recombinant CYP719A21 displayed strict substrate specificity and high affinity (K-m = 4.63 +/- 0.71 mu M) for (S)-tetrahydrocolumbamine. Virus-induced gene silencing of CYP719A21 caused a significant increase in (S)-tetrahydrocolumbamine accumulation and a corresponding decrease in the levels of putative downstream intermediates and noscapine in opium poppy plants. (C) 2013 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.
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