Codeinone reductase isoforms with differential stability, efficiency and product selectivity in opium poppy

The Plant Journal : for Cell and Molecular Biology
Mehran DastmalchiPeter J Facchini

Abstract

Codeinone reductase (COR) catalyzes the reversible NADPH-dependent reduction of codeinone to codeine as the penultimate step of morphine biosynthesis in opium poppy (Papaver somniferum). COR also irreversibly reduces neopinone, which forms by spontaneous isomerization in aqueous solution from codeinone, to neopine. In a parallel pathway involving 3-O-desmethylated analogs, COR converts morphinone to morphine, and neomorphinone to neomorphine. Similar to neopine, neomorphine formation by COR is irreversible. Neopine is a minor substrate for codeine O-demethylase (CODM) yielding morphine. In the plant, neopine levels are low and neomorphine has not been detected. Silencing of CODM leads to accumulation of upstream metabolites, such as codeine and thebaine, but does not result in a shift towards higher relative concentrations of neopine, suggesting a plant mechanism for limiting neopine production. In yeast (Saccharomyces cerevisiae) engineered to produce opiate alkaloids, the catalytic properties of COR lead to accumulation of neopine and neomorphine as major products. An isoform (COR-B) was isolated from opium poppy chemotype Bea's Choice that showed higher catalytic activity compared with previously characterized CORs, and it y...Continue Reading

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Citations

Mar 20, 2019·Nature Chemical Biology·Mehran DastmalchiPeter J Facchini
Aug 11, 2020·Journal of Industrial Microbiology & Biotechnology·Natali OzberPeter J Facchini
Jul 24, 2020·Chembiochem : a European Journal of Chemical Biology·Jeremy S MorrisPeter J Facchini
Jan 2, 2021·Forensic Science International : Synergy·Nicole S Jones, Jeffrey H Comparin

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