| Literature DB >> 24316226 |
Thu-Thuy T Dang1, Peter J Facchini2.
Abstract
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 (Km=4.63±0.71 μM) 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.Entities:
Keywords: BIA; Benzylisoquinoline alkaloid; CID; CPR; CYP; Cytochrome P450; ESI; GAPDH; LC–MS/MS; Methylenedioxy bridge; Noscapine biosynthesis; Papaver somniferum; SOMT; TNMT; TRV; VIGS; Virus-induced gene silencing; benzylisoquinoline alkaloid; collision-induced dissociation; cytochrome P450; cytochrome P450 reductase; electrospray ionization; glyceraldehyde 3-phosphate dehydrogenase; liquid chromatography–tandem mass spectrometry; scoulerine 9-O-methyltransferase; tetrahydroprotoberberine N-methyltransferase; tobacco rattle virus; virus-induced gene silencing
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Year: 2013 PMID： 24316226 DOI： 10.1016/j.febslet.2013.11.037
Source DB: PubMed Journal: FEBS Lett ISSN： 0014-5793 Impact factor: 4.124