ArticleNature chemical biology2015
Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy.
Article in Nature chemical biology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 63 papers.
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63 citing papers in PubMed, 159 citations in OpenAlex.
- Biosynthetic mechanism and ecological function of chirality in Solanum steroidal alkaloids.Nature communications · 2026Article
- Uncovering the molecular basis of high morphinan product efficiency in opium poppy through Multi-omics integrated analysis with multi-capsules.Plant molecular biology · 2026Article
- Enzymatic epimerization of monoterpene indole alkaloids in kratom.Nature chemical biology · 2026Article
- Biosynthesis of the α-D-mannosidase inhibitor (-)-Swainsonine.Nature chemical biology · 2026Article
- A chromosome-level Mitragyna parvifolia genome unveils spirooxindole alkaloid diversification and mitraphylline biosynthesis.The Plant cell · 2025Article
- A Tight-Knit Family: The Medium-Chain Dehydrogenase/Reductases of Monoterpene Indole Alkaloid Biosynthesis.Biochemistry · 2025Review
- From data to discovery: leveraging big data in plant natural products biosynthesis research.The Plant journal : for cell and molecular biology · 2025Review
- Wounding and Phospholipase C Inhibition: Evaluation of the Alkaloid Profiling in Opium Poppy.Plants (Basel, Switzerland) · 2025Article
- Genome-Wide Identification and Functional Analysis of the Norcoclaurine Synthase Gene Family inInternational journal of molecular sciences · 2025Article
- Metabolic profiling and transcriptome analysis of Sinomenium acutum provide insights into the biosynthesis of structurally diverse benzylisoquinoline alkaloids.Scientific reports · 2025Article
- Engineering Saccharomyces cerevisiae for medical applications.Microbial cell factories · 2025Review
- Molecular and expression analyses indicate the role of fusion transcripts in mediating abiotic stress responses in chickpea.Frontiers in plant science · 2025Article
- DNA methylation orchestrates secondary metabolite biosynthesis and transport in Papaver somniferum.PloS one · 2025Article
- Cloning, heterologous expression, and expression analysis of SinSyn7 gene from Sinomenium acutum.PloS one · 2025Article
- Expanding the repertoire of imine reductases by mining divergent biosynthetic pathways for promiscuous reactivity.Chem catalysis · 2024Article
- The landscape of fusion transcripts in plants: a new insight into genome complexity.BMC plant biology · 2024Article
- Tuning architectural organization of eukaryotic P450 system to boost bioproduction in Escherichia coli.Nature communications · 2024Article
- Two ubiquitous aldo-keto reductases in the genus Papaver support a patchwork model for morphine pathway evolution.Communications biology · 2024Article
- Lineage-Specific CYP80 Expansion and Benzylisoquinoline Alkaloid Diversity in Early-Diverging Eudicots.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Regulation of T16H subcellular localization for promoting its catalytic efficiency in yeast cells.Biotechnology letters · 2024Article
3 more citing papers are in PubMed but not listed here.
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The gateway to morphine biosynthesis in opium poppy (Papaver somniferum) is the stereochemical inversion of (S)-reticuline since the enzyme yielding the first committed intermediate salutaridine is specific for (R)-reticuline. A fusion between a cytochrome P450 (CYP) and an aldo-keto reductase (AKR) catalyzes the S-to-R epimerization of reticuline via 1,2-dehydroreticuline. The reticuline epimerase (REPI) fusion was detected in opium poppy and in Papaver bracteatum, which accumulates thebaine. In contrast, orthologs encoding independent CYP and AKR enzymes catalyzing the respective synthesis and reduction of 1,2-dehydroreticuline were isolated from Papaver rhoeas, which does not accumulate morphinan alkaloids. An ancestral relationship between these enzymes is supported by a conservation of introns in the gene fusions and independent orthologs. Suppression of REPI transcripts using virus-induced gene silencing in opium poppy reduced levels of (R)-reticuline and morphinan alkaloids and increased the overall abundance of (S)-reticuline and its O-methylated derivatives. Discovery of REPI completes the isolation of genes responsible for known steps of morphine biosynthesis.
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