Chemistry:Tabersonine
Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also plants in the genus Voacanga[1]: 8 (both taxa belonging to the alkaloid-rich family Apocynaceae). Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase to form 16-hydroxytabersonine.[2] Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.
Biosynthesis
Tabersonine is an indole alkaloid whose immediate precursor in Catharanthus roseus (Madagascar periwinkle) is the compound dehydrosecodine. This is cyclised by the enzyme tabersonine synthase:[3][4]
- REDIRECT Template:Chemical reaction
The biosynthetic pathway to vindoline and vinblastine continues when tabersonine is hydroxylated by the enzyme tabersonine 16-hydroxylase, giving 16-hydroxytabersonine:[4]
- REDIRECT Template:Chemical reaction
See also
References
- ↑ Van Beek, T.A.; Verpoorte, R.; Svendsen, A.Baerheim; Leeuwenberg, A.J.M.; Bisset, N.G. (1984). "Tabernaemontana L. (Apocynaceae): A review of its taxonomy, phytochemistry, ethnobotany and pharmacology". Journal of Ethnopharmacology 10 (1): 1–156. doi:10.1016/0378-8741(84)90046-1. PMID 6371388.
- ↑ St-Pierre, B.; De Luca, V. (1995). "A Cytochrome P-450 Monooxygenase Catalyzes the First Step in the Conversion of Tabersonine to Vindoline in Catharanthus roseus". Plant Physiology 109 (1): 131–139. doi:10.1104/pp.109.1.131. PMID 12228585.
- ↑ Caputi, Lorenzo; Franke, Jakob; Farrow, Scott C. et al. (2018). "Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle". Science 360 (6394): 1235–1239. doi:10.1126/science.aat4100. PMID 29724909.
- ↑ 4.0 4.1 Demars, Matthew D.; o'Connor, Sarah E. (2024). "Evolution and diversification of carboxylesterase-like [4+2] cyclases in aspidosperma and iboga alkaloid biosynthesis". Proceedings of the National Academy of Sciences 121 (7). doi:10.1073/pnas.2318586121. PMID 38319969.
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