ArticleProceedings of the National Academy of Sciences of the United States of America2012
Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 107 citations in OpenAlex.
- A Comprehensive Review on the Biosynthesis of Tropane Alkaloids.Molecules (Basel, Switzerland) · 2026Review
- Convergence and parallelism in the evolution of plant metabolism.Journal of integrative plant biology · 2026Review
- Unveiling the Complexities of Medications, Substance Abuse, and Plants for Recreational and Narcotic Purposes: An In-Depth Analysis.Pharmacy (Basel, Switzerland) · 2025Review
- Two ubiquitous aldo-keto reductases in the genus Papaver support a patchwork model for morphine pathway evolution.Communications biology · 2024Article
- The chromosome-scale genome and the genetic resistance machinery against insect herbivores of the Mexican toloache, Datura stramonium.G3 (Bethesda, Md.) · 2024Article
- Multiple independent losses of the biosynthetic pathway for two tropane alkaloids in the Solanaceae family.Nature communications · 2023Article
- Genomic and structural basis for evolution of tropane alkaloid biosynthesis.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Understanding how plants produce cocaine.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Elucidation of tropane alkaloid biosynthesis inProceedings of the National Academy of Sciences of the United States of America · 2022Article
- Catalytic innovation underlies independent recruitment of polyketide synthases in cocaine and hyoscyamine biosynthesis.Nature communications · 2022Article
- Fruity, sticky, stinky, spicy, bitter, addictive, and deadly: evolutionary signatures of metabolic complexity in the Solanaceae.Natural product reports · 2022Review
- Transcriptome analysis of the pulp of citrus fruitlets suggests that domestication enhanced growth processes and reduced chemical defenses increasing palatability.Frontiers in plant science · 2022Article
- Function-based classification of hazardous biological sequences: Demonstration of a new paradigm for biohazard assessments.Frontiers in bioengineering and biotechnology · 2022Article
- Structural studies of codeinone reductase reveal novel insights into aldo-keto reductase function in benzylisoquinoline alkaloid biosynthesis.The Journal of biological chemistry · 2021Article
- Biosynthesis and synthetic biology of psychoactive natural products.Chemical Society reviews · 2021Review
- Diversity in Chemical Structures and Biological Properties of Plant Alkaloids.Molecules (Basel, Switzerland) · 2021Review
- Dissection of Dynamic Transcriptome Landscape of Leaf, Bract, and Lupulin Gland in Hop (International journal of molecular sciences · 2019Article
- Metabolic diversification of nitrogen-containing metabolites by the expression of a heterologous lysine decarboxylase gene in Arabidopsis.The Plant journal : for cell and molecular biology · 2019Article
- Erythroxylum in Focus: An Interdisciplinary Review of an Overlooked Genus.Molecules (Basel, Switzerland) · 2019Review
- Engineering a microbial biosynthesis platform for de novo production of tropane alkaloids.Nature communications · 2019Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
The pharmacologically important tropane alkaloids have a scattered distribution among angiosperm families, like many other groups of secondary metabolites. To determine whether tropane alkaloids have evolved repeatedly in different lineages or arise from an ancestral pathway that has been lost in most lines, we investigated the tropinone-reduction step of their biosynthesis. In species of the Solanaceae, which produce compounds such as atropine and scopolamine, this reaction is known to be catalyzed by enzymes of the short-chain dehydrogenase/reductase family. However, in Erythroxylum coca (Erythroxylaceae), which accumulates cocaine and other tropane alkaloids, no proteins of the short-chain dehydrogenase/reductase family were found that could catalyze this reaction. Instead, purification of E. coca tropinone-reduction activity and cloning of the corresponding gene revealed that a protein of the aldo-keto reductase family carries out this reaction in E. coca. This protein, designated methylecgonone reductase, converts methylecgonone to methylecgonine, the penultimate step in cocaine biosynthesis. The protein has highest sequence similarity to other aldo-keto reductases, such as chalcone reductase, an enzyme of flavonoid biosynthesis, and codeinone reductase, an enzyme of morphine alkaloid biosynthesis. Methylecgonone reductase reduces methylecgonone (2-carbomethoxy-3-tropinone) stereospecifically to 2-carbomethoxy-3β-tropine (methylecgonine), and has its highest activity, protein level, and gene transcript level in young, expanding leaves of E. coca. This enzyme is not found at all in root tissues, which are the site of tropane alkaloid biosynthesis in the Solanaceae. This evidence supports the theory that the ability to produce tropane alkaloids has arisen more than once during the evolution of the angiosperms.
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