Desacetoxyvindoline

Desacetoxyvindoline
Names
IUPAC name
Methyl (2β,3β,5α,12β,19α)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Other names
Deacetoxyvindoline
Identifiers
3D model (Jmol) Interactive image
ChemSpider 388838
PubChem 439783
Properties
C23H30N2O4
Molar mass 398.50 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

Desacetoxyvindoline is a terpene idole alkaloid produced by the plant Catharanthus roseus. Desacetoxyvindoline is a product formed by the methylation of the nitrogen on the indole ring by the enzyme 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase (NMT).[1] The metabolite is a substrate for desacetoxyvindoline 4-hydroxylase (D4H) which catalyzes a hydroxylation to yield deacetylvindoline.[2]

References

  1. 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
  2. Vazquez-Flota, De Carolis, Alarco and De Luca (1997) Molecular cloning and characterization of desacetoxyvindoline-4-hydroxylase, a 2-oxoglutarate dependent-dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus (L.) G. Don. Plant Molecular Biology. 34(6). 935-948
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