ArticleThe Journal of biological chemistry2013
Dioxygenases catalyze O-demethylation and O,O-demethylenation with widespread roles in benzylisoquinoline alkaloid metabolism in opium poppy.
Article in The Journal of biological chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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25 citing papers in PubMed, 63 citations in OpenAlex.
- Network-based identification of hub transcription factors associated with benzylisoquinoline alkaloid biosynthesis inBiochemistry and biophysics reports · 2025Article
- Metabolic profiling and transcriptome analysis of Sinomenium acutum provide insights into the biosynthesis of structurally diverse benzylisoquinoline alkaloids.Scientific reports · 2025Article
- Functional evolution and diversification of CYP82D subfamily members have shaped flavonoid diversification in the genus Scutellaria.Plant communications · 2025Article
- Transcriptomic and Proteomics Analysis of a Lipid-Loaded HepaRG Model for Steatosis Reveals Altered Regulation in Lipid and Xenobiotic Metabolism.Current drug metabolism · 2025Article
- Two ubiquitous aldo-keto reductases in the genus Papaver support a patchwork model for morphine pathway evolution.Communications biology · 2024Article
- Genome-wide characterization of 2OGD superfamily for mining of susceptibility factors responding to various biotic stresses inPhysiology and molecular biology of plants : an international journal of functional plant biology · 2023Article
- Synthesis of 5,6-Dihydrophenanthridines via Palladium-Catalyzed Intramolecular Dehydrogenative Coupling of Two Aryl C-H Bonds.Molecules (Basel, Switzerland) · 2023Article
- Systematic analysis and expression of Gossypium 2ODD superfamily highlight the roles of GhLDOXs responding to alkali and other abiotic stress in cotton.BMC plant biology · 2023Article
- Biosynthesis and synthetic biology of psychoactive natural products.Chemical Society reviews · 2021Review
- Over 100 Million Years of Enzyme Evolution Underpinning the Production of Morphine in the Papaveraceae Family of Flowering Plants.Plant communications · 2020Article
- Enabling microbial syringol conversion through structure-guided protein engineering.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
- Unleashing the Synthetic Power of Plant Oxygenases: From Mechanism to Application.Plant physiology · 2019Review
- Identification and metabolite profiling of alkaloids in aerial parts of Papaver rhoeas by liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry.Journal of separation science · 2018Article
- A three enzyme system to generate the Strychnos alkaloid scaffold from a central biosynthetic intermediate.Nature communications · 2017Article
- Common origin of methylenedioxy ring degradation and demethylation in bacteria.Scientific reports · 2017Article
- Studies on the formation of formaldehyde during 2-ethylhexyl 4-(dimethylamino)benzoate demethylation in the presence of reactive oxygen and chlorine species.Environmental science and pollution research international · 2017Article
- Salinity stress induces the production of 2-(2-phenylethyl)chromones and regulates novel classes of responsive genes involved in signal transduction in Aquilaria sinensis calli.BMC plant biology · 2016Article
- Catalytic strategies of the non-heme iron dependent oxygenases and their roles in plant biology.Current opinion in chemical biology · 2016Review
- Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants.BMC plant biology · 2015Article
- Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy.Nature chemical biology · 2015Article
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2 authors at 1 institution in 1 country.
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Abstract
In opium poppy, the antepenultimate and final steps in morphine biosynthesis are catalyzed by the 2-oxoglutarate/Fe(II)-dependent dioxygenases, thebaine 6-O-demethylase (T6ODM) and codeine O-demethylase (CODM). Further investigation into the biochemical functions of CODM and T6ODM revealed extensive and unexpected roles for such enzymes in the metabolism of protopine, benzo[c]phenanthridine, and rhoeadine alkaloids. When assayed with a wide range of benzylisoquinoline alkaloids, CODM, T6ODM, and the functionally unassigned paralog DIOX2, renamed protopine O-dealkylase, showed novel and efficient dealkylation activities, including regio- and substrate-specific O-demethylation and O,O-demethylenation. Enzymes catalyzing O,O-demethylenation, which cleave a methylenedioxy bridge leaving two hydroxyl groups, have previously not been reported in plants. Similar cleavage of methylenedioxy bridges on substituted amphetamines is catalyzed by heme-dependent cytochromes P450 in mammals. Preferred substrates for O,O-demethylenation by CODM and protopine O-dealkylase were protopine alkaloids that serve as intermediates in the biosynthesis of benzo[c]phenanthridine and rhoeadine derivatives. Virus-induced gene silencing used to suppress the abundance of CODM and/or T6ODM transcripts indicated a direct physiological role for these enzymes in the metabolism of protopine alkaloids, and they revealed their indirect involvement in the formation of the antimicrobial benzo[c]phenanthridine sanguinarine and certain rhoeadine alkaloids in opium poppy.
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