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Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis
Sanguinarine is a benzo[. c]phenenthridine alkaloid with potent antimicrobial properties found commonly in plants of the Papaveraceae, including the roots of opium poppy (. Papaver somniferum). Sanguinarine is formed from the central 1-benzylisoquinoline intermediate (. S)-reticuline via the protoberberine alkaloid (. S)-scoulerine, which undergoes five enzymatic oxidations and an N-methylation. The first four oxidations from (. S)-scoulerine are catalyzed by cytochromes P450, whereas the final conversion involves a flavoprotein oxidase. All but one gene in the biosynthetic pathway from (. S)-reticuline to sanguinarine has been identified. In this communication, we report the isolation and characterization of (. S)-. cis-. N-methylstylopine 14-hydroxylase (MSH) from opium poppy based on the transcriptional induction in elicitor-treated cell suspension cultures and root-specific expression of the corresponding gene. Along with protopine 6-hydroxylase, which catalyzes the subsequent and penultimate step in sanguinarine biosynthesis, MSH is a member of the CYP82N subfamily of cytochromes P450. The full-length MSH cDNA was expressed in Saccharomyces cerevisiae and the recombinant microsomal protein was tested for enzymatic activity using 25 benzylisoquinoline alkaloids representing a wide range of structural subgroups. The only enzymatic substrates were the N-methylated protoberberine alkaloids N-methylstylopine and N-methylcanadine, which were converted to protopine and allocryptopine, respectively.
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Reference£º
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem