ArticleAngewandte Chemie (International ed. in English)2025
Oxidative Rearrangements of the Alkaloid Intermediate Geissoschizine.
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Cell-Specific Expression and Cellular Compartmental Regulation in Camptothecin Biosynthesis.Plant biotechnology journal · 2026Article
- Unified Chemical Synthesis of Corynanthe-Sarpagine-Ajmaline Type Monoterpene Indole Alkaloids: A Biomimetic Approach.JACS Au · 2025Article
- Evolution of CYP71D drives the diversification of monoterpene indole alkaloid biosynthesis in Gentianales.Plant communications · 2025Article
- Oxidative Rearrangements of the Alkaloid Intermediate Geissoschizine.Angewandte Chemie (International ed. in English) · 2025Article
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7 authors.
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Abstract
Plants can generate structural diversity by enzymatic rearrangement of a central intermediate. 19E-geissoschizine is one such chemically versatile intermediate that plays a central role in the biosynthesis of monoterpene indole alkaloids such as strychnine, ibogaine, and vinblastine. Here we report how 19E-geissoschizine undergoes oxidative transformations to generate four distinct alkaloid scaffolds through the action of three biosynthetic enzymes. Using in vitro enzymatic assays and gene silencing, we demonstrate how these three cytochrome P450 enzymes in the medicinal plant Catharanthus roseus transform 19E-geissoschizine into strychnos, sarpagan, akuammiline-type, and mavacurane-type alkaloids. We use mutational analysis to show how minimal changes to the active site of these similar enzymes modulate product specificity. This work highlights how substrate reactivity and enzyme mutations work synergistically to generate chemical diversity.
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