ArticleThe Journal of biological chemistry2012
Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis.
Article in The Journal of biological chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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23 citing papers in PubMed, 69 citations in OpenAlex.
- Genome-Wide Identification and Functional Verification of CoreInternational journal of molecular sciences · 2026Article
- Biosynthesis of benzylisoquinoline alkaloids and its evolution in plants.Plant communications · 2026Review
- Advances in artificial biosynthesis of bioactive plant natural products.Current opinion in biotechnology · 2026Review
- Sanguinarine-Chelerythrine fromPharmaceutics · 2025Article
- Advances in the biosynthesis of naturally occurring benzylisoquinoline alkaloids.Frontiers in plant science · 2025Review
- De novo production of protoberberine and benzophenanthridine alkaloids through metabolic engineering of yeast.Nature communications · 2024Article
- Screening and Genomic Analysis of Alkaloid-Producing Endophytic FungusMicroorganisms · 2024Article
- Characterization of CYP82 genes involved in the biosynthesis of structurally diverse benzylisoquinoline alkaloids in Corydalis yanhusuo.Plant molecular biology · 2024Article
- Opium alkaloids, biosynthesis, pharmacology and association with cancer occurrence.Open biology · 2023Review
- De novo biosynthesis of berberine and halogenated benzylisoquinoline alkaloids in Saccharomyces cerevisiae.Communications chemistry · 2023Article
- California poppy (Frontiers in plant science · 2023Review
- Biosynthesis of tetrahydropapaverine and semisynthesis of papaverine in yeast.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- A computational workflow for the expansion of heterologous biosynthetic pathways to natural product derivatives.Nature communications · 2021Article
- EngineeringaBIOTECH · 2021Review
- Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.Chemical reviews · 2018Review
- Mining of the Uncharacterized Cytochrome P450 Genes Involved in Alkaloid Biosynthesis in California Poppy Using a Draft Genome Sequence.Plant & cell physiology · 2018Article
- Identification and Characterization of Daurichromenic Acid Synthase Active in Anti-HIV Biosynthesis.Plant physiology · 2017Article
- Modulation of benzylisoquinoline alkaloid biosynthesis by heterologous expression of CjWRKY1 in Eschscholzia californica cells.PloS one · 2017Article
- Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy.The Journal of biological chemistry · 2016Article
- Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants.BMC plant biology · 2015Article
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6 authors at 2 institutions in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Benzylisoquinoline alkaloids are a diverse class of plant specialized metabolites that includes the analgesic morphine, the antimicrobials sanguinarine and berberine, and the vasodilator papaverine. The two-electron oxidation of dihydrosanguinarine catalyzed by dihydrobenzophenanthridine oxidase (DBOX) is the final step in sanguinarine biosynthesis. The formation of the fully conjugated ring system in sanguinarine is similar to the four-electron oxidations of (S)-canadine to berberine and (S)-tetrahydropapaverine to papaverine. We report the isolation and functional characterization of an opium poppy (Papaver somniferum) cDNA encoding DBOX, a flavoprotein oxidase with homology to (S)-tetrahydroprotoberberine oxidase and the berberine bridge enzyme. A query of translated opium poppy stem transcriptome databases using berberine bridge enzyme yielded several candidate genes, including an (S)-tetrahydroprotoberberine oxidase-like sequence selected for heterologous expression in Pichia pastoris. The recombinant enzyme preferentially catalyzed the oxidation of dihydrosanguinarine to sanguinarine but also converted (RS)-tetrahydropapaverine to papaverine and several protoberberine alkaloids to oxidized forms, including (RS)-canadine to berberine. The K(m) values of 201 and 146 μm for dihydrosanguinarine and the protoberberine alkaloid (S)-scoulerine, respectively, suggested high concentrations of these substrates in the plant. Virus-induced gene silencing to reduce DBOX transcript levels resulted in a corresponding reduction in sanguinarine, dihydrosanguinarine, and papaverine accumulation in opium poppy roots in support of DBOX as a multifunctional oxidative enzyme in BIA metabolism.
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