ArticleNature chemical biology2025
Ipecac alkaloid biosynthesis in two evolutionarily distant plants.
Article in Nature chemical biology, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- The roles and mechanisms of natural compounds in preventing and treating viral reproductive disorders in major economic livestock.Virulence · 2026Review
- Discovery of a Plant Pictet-Spenglerase With R-Stereoselectivity.Angewandte Chemie (International ed. in English) · 2026Article
- Herbgenomics: Unraveling natural product biosynthesis in traditional Chinese medicine.Chinese herbal medicines · 2026Article
- Biodiversity-Driven Natural Products and Bioactive Metabolites.Plants (Basel, Switzerland) · 2025Review
- The missing link in the iridoid puzzle.Nature plants · 2025Article
- Discovery of iridoid cyclase completes the iridoid pathway in asterids.Nature plants · 2025Article
- A Tight-Knit Family: The Medium-Chain Dehydrogenase/Reductases of Monoterpene Indole Alkaloid Biosynthesis.Biochemistry · 2025Review
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16 authors.
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Abstract
Ipecac alkaloids are medicinal monoterpenoid-derived tetrahydroisoquinoline alkaloids found in two distantly related plants: Carapichea ipecacuanha (Gentianales) and Alangium salviifolium (Cornales). Here we provide evidence suggesting that both plants initiate ipecac alkaloid biosynthesis through a nonenzymatic Pictet-Spengler reaction and we elucidate the biosynthetic fate of both the 1R and 1S stereoisomers that are produced in this nonstereoselective reaction. Although the biosynthesis of the 1S-derived protoemetine proceeds according to the same chemical logic in both species, each plant uses a distinct monoterpene precursor. Phylogenetic analyses show examples of independent pathway evolution through parallel and convergently evolved enzymes. This work provides insight into how nature can capitalize on highly reactive starting substrates and the manner in which multistep pathways can arise and lays the foundation for metabolic engineering of these important medicinal compounds.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the Socratic graph.