Tabersonine
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| IUPAC name
Methyl 2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate | |
| Systematic IUPAC name
Methyl (3aR,3a1S,10bR)-3a-ethyl-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.022.378 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C21H24N2O2 | |
| Molar mass | 336.435 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]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]
The biosynthetic pathway to vindoline and vinblastine continues when tabersonine is hydroxylated by the enzyme tabersonine 16-hydroxylase, giving 16-hydroxytabersonine:[4]
See also
[edit]References
[edit]- ↑ 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. PMC 157569. 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.
- 1 2 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) e2318586121. doi:10.1073/pnas.2318586121. PMID 38319969.