16-Hydroxytabersonine
Appearance
(Redirected from 16-hydroxytabersonine)
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Names | |
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IUPAC name
Methyl 16-hydroxy-2,3,6,7-tetradehydro-5α,12β,19α-aspidospermidine-3-carboxylate
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Systematic IUPAC name
Methyl (3aR,3a1S,10bR)-3a-ethyl-8-hydroxy-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate | |
Other names
11-Hydroxytabersonine
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C21H24N2O3 | |
Molar mass | 352.434 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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16-Hydroxytabersonine is a terpene indole alkaloid produced by the plant Catharanthus roseus. The metabolite is an intermediate in the formation of vindoline, a precursor needed for formation of the pharmaceutically valuable vinblastine and vincristine. 16-hydroxytabersonine is formed from the hydroxylation of tabersonine by tabersonine 16-hydroxylase (T16H). Tabersonine 16-O-methyltransferase (16OMT) methylates the hydroxylated 16 position to form 16-methoxytabersonine.[1]
References
[edit]- ^ Levac, Dylan; Murata, Jun; Kim, Won S.; De Luca, Vincenzo (2008). "Application of carborundum abrasion for investigating the leaf epidermis: Molecular cloning of Catharanthus roseus 16-hydroxytabersonine-16-O-methyltransferase". The Plant Journal. 53 (2): 225–236. doi:10.1111/j.1365-313X.2007.03337.x. PMID 18053006.