3-Hydroxy-16-methoxy-2,3-dihydrotabersonine

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
3-Hydroxy-16-methoxy-2,3-dihydrotabersonine
3-Hydroxy-16-methoxy-2,3-dihydrotabersonine.svg
Names
IUPAC name
Methyl (2β,3β,5α,12β,19α)-3-hydroxy-16-methoxy-6,7-didehydroaspidospermidine-3-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
Properties
C22H28N2O4
Molar mass 384.48 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine is a terpene indole alkaloid produced by Catharanthus roseus. The metabolite is a substrate for 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase (NMT) which transfers a methyl group to the nitrogen of the indole ring forming desacetoxyvindoline.[1] The enzyme catalyzing the formation of 3-hydroxy-16-methoxy-2,3-dihydrotabersonine from 16-methoxytabersonine is currently unknown, but is a result of hydration of the double bond connecting the 6 and 13 position carbons.[2] [3]

References[edit]

  1. ^ Dethier and De Luca (1993) Partial purification of an N-methyltransferase involved in vindoline biosynthesis in Catharanthus roseus. Phytochemistry. 32(3). 673-678
  2. ^ Liscombe, Usera and O’connor (2010) Homolog of tocopherol C methyltransferases catalyzes N methylation in anticancer alkaloid biosynthesis. Proceedings of the National Academy of Sciences. 107(44). 18793-18798
  3. ^ O'connor and Maresh (2006) Chemistry and biology of monoterpene indole alkaloid biosynthesis. Natural Product Reports. 23(4). 532-547