ArticleAngewandte Chemie (International ed. in English)2017
Dual Catalytic Activity of a Cytochrome P450 Controls Bifurcation at a Metabolic Branch Point of Alkaloid Biosynthesis in Rauwolfia serpentina.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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19 citing papers in PubMed, 53 citations in OpenAlex.
- Cytochrome P450 gene family: cross-pathway functional conservation, novel catalytic reactions, and synthetic biology-driven applications in plant secondary metabolism.Frontiers in plant science · 2026Review
- Stereochemical insights into sarpagan and akuammiline alkaloid biosynthesis.The New phytologist · 2025Article
- From data to discovery: leveraging big data in plant natural products biosynthesis research.The Plant journal : for cell and molecular biology · 2025Review
- Three cytochrome P450 enzymes consecutively catalyze the biosynthesis of furanoclerodane precursors in Salvia species.Plant communications · 2025Article
- Plants Utilize a Protection/Deprotection Strategy in Limonoid Biosynthesis: A "Missing Link" Carboxylesterase Boosts Yields and Provides Insights into Furan Formation.Journal of the American Chemical Society · 2024Article
- Updates on Mechanisms of Cytochrome P450 Catalysis of Complex Steroid Oxidations.International journal of molecular sciences · 2024Review
- A chromosome-scale genome assembly of Rauvolfia tetraphylla facilitates identification of the complete ajmaline biosynthetic pathway.Plant communications · 2024Article
- Characterization of CYP82 genes involved in the biosynthesis of structurally diverse benzylisoquinoline alkaloids in Corydalis yanhusuo.Plant molecular biology · 2024Article
- Mining and functional characterization of NADPH-cytochrome P450 reductases of the DNJ biosynthetic pathway in mulberry leaves.BMC plant biology · 2024Article
- Discovery of a cytochrome P450 enzyme catalyzing the formation of spirooxindole alkaloid scaffold.Frontiers in plant science · 2023Article
- Phylogeny-Aware Chemoinformatic Analysis of Chemical Diversity in Lamiaceae Enables Iridoid Pathway Assembly and Discovery of Aucubin Synthase.Molecular biology and evolution · 2022Article
- Discovery and Characterization of Oxidative Enzymes Involved in Monoterpenoid Indole Alkaloid Biosynthesis.Methods in molecular biology (Clifton, N.J.) · 2022Article
- Discovering and harnessing oxidative enzymes for chemoenzymatic synthesis and diversification of anticancer camptothecin analogues.Communications chemistry · 2021Article
- Cytochrome P450 Enzymes as Key Drivers of Alkaloid Chemical Diversification in Plants.Frontiers in plant science · 2021Review
- Expanding the Diversity of Plant Monoterpenoid Indole Alkaloids Employing Human Cytochrome P450 3A4.Chembiochem : a European journal of chemical biology · 2020Article
- The evolutionary origins of the cat attractant nepetalactone in catnip.Science advances · 2020Article
- Streamlining Natural Products Biomanufacturing With Omics and Machine Learning Driven Microbial Engineering.Frontiers in bioengineering and biotechnology · 2020Review
- Transcriptome analysis of phosphorus stress responsiveness in the seedlings of Dongxiang wild rice (Oryza rufipogon Griff.).Biological research · 2018Article
- Dual Catalytic Activity of a Cytochrome P450 Controls Bifurcation at a Metabolic Branch Point of Alkaloid Biosynthesis in Rauwolfia serpentina.Angewandte Chemie (International ed. in English) · 2017Article
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4 authors at 1 institution in 1 country.
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Abstract
Plants create tremendous chemical diversity from a single biosynthetic intermediate. In plant-derived ajmalan alkaloid pathways, the biosynthetic intermediate vomilenine can be transformed into the anti-arrhythmic compound ajmaline, or alternatively, can isomerize to form perakine, an alkaloid with a structurally distinct scaffold. Here we report the discovery and characterization of vinorine hydroxylase, a cytochrome P450 enzyme that hydroxylates vinorine to form vomilenine, which was found to exist as a mixture of rapidly interconverting epimers. Surprisingly, this cytochrome P450 also catalyzes the non-oxidative isomerization of the ajmaline precursor vomilenine to perakine. This unusual dual catalytic activity of vinorine hydroxylase thereby provides a control mechanism for the bifurcation of these alkaloid pathway branches. This discovery highlights the unusual catalytic functionality that has evolved in plant pathways.
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