ArticleThe Journal of biological chemistry2016
Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy.
Article in The Journal of biological chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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24 citing papers in PubMed, 52 citations in OpenAlex.
- A Golgi-localized N-methyltransferase and reversible aldo-keto reductases coordinate dual terminal routes in galanthamine biosynthesis.The Plant journal : for cell and molecular biology · 2026Article
- Biosynthesis of benzylisoquinoline alkaloids and its evolution in plants.Plant communications · 2026Review
- Genome-wide identification and characterization of methyltransferase involved in benzylisoquinoline alkaloids biosynthesis fromChinese herbal medicines · 2026Article
- Gene duplication and clustering underlie the conservation and diversification of benzylisoquinoline alkaloid biosynthesis in plants.Nature communications · 2025Article
- Advances in the biosynthesis of naturally occurring benzylisoquinoline alkaloids.Frontiers in plant science · 2025Review
- Comparative metabolite analysis of Piper sarmentosum organs approached by LC-MS-based metabolic profiling.Natural products and bioprospecting · 2024Article
- Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002-2020).Chemical reviews · 2023Review
- The Potential ofMolecules (Basel, Switzerland) · 2023Review
- Functional Diversification and Structural Origins of Plant Natural Product Methyltransferases.Molecules (Basel, Switzerland) · 2022Review
- Antioxidant, Antidiabetic, Anticholinergic, and Antiglaucoma Effects of Magnofluorine.Molecules (Basel, Switzerland) · 2022Article
- Article
- Analysis of the Coptis chinensis genome reveals the diversification of protoberberine-type alkaloids.Nature communications · 2021Article
- EngineeringaBIOTECH · 2021Review
- Full-length transcriptome analysis of Coptis deltoidea and identification of putative genes involved in benzylisoquinoline alkaloids biosynthesis based on combined sequencing platforms.Plant molecular biology · 2020Article
- Isolation and characterization of twoThe Journal of biological chemistry · 2020Article
- Novel findings to the biosynthetic pathway of magnoflorine and taspine through transcriptomic and metabolomic analysis of Croton draco (Euphorbiaceae).BMC plant biology · 2019Article
- Structure-function studies of tetrahydroprotoberberineThe Journal of biological chemistry · 2019Article
- Molecular Origins of Functional Diversity in Benzylisoquinoline Alkaloid Methyltransferases.Frontiers in plant science · 2019Review
- Benzylisoquinoline Alkaloids Biosynthesis in Sacred Lotus.Molecules (Basel, Switzerland) · 2018Review
- Transcriptome Profiling of Two Ornamental and MedicinalInternational journal of molecular sciences · 2018Article
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2 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Benzylisoquinoline alkaloids are a large group of plant-specialized metabolites displaying an array of biological and pharmacological properties associated with numerous structural scaffolds and diverse functional group modification. N-Methylation is one of the most common tailoring reactions, yielding tertiary and quaternary pathway intermediates and products. Two N-methyltransferases accepting (i) early 1-benzylisoquinoline intermediates possessing a secondary amine and leading to the key branch-point intermediate (S)-reticuline and (ii) downstream protoberberines containing a tertiary amine and forming quaternary intermediates destined for phthalideisoquinolines and antimicrobial benzo[c]phenanthridines were previously characterized. We report the isolation and characterization of a phylogenetically related yet functionally distinct N-methyltransferase (NMT) from opium poppy (Papaver somniferum) that primarily accepts 1-benzylisoquinoline and aporphine substrates possessing a tertiary amine. The preferred substrates were the R and S conformers of reticuline and the aporphine (S)-corytuberine, which are proposed intermediates in the biosynthesis of magnoflorine, a quaternary aporphine alkaloid common in plants. Suppression of the gene encoding reticuline N-methyltransferase (RNMT) using virus-induced gene silencing in opium poppy resulted in a significant decrease in magnoflorine accumulation and a concomitant increase in corytuberine levels in roots. RNMT transcript levels were also most abundant in roots, in contrast to the distribution of transcripts encoding other NMTs, which occur predominantly in aerial plant organs. The characterization of a third functionally unique NMT involved in benzylisoquinoline alkaloid metabolism will facilitate the establishment of structure-function relationships among a large group of related enzymes.
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