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
InChI InChI=1S/C23H30N2O4/c1-5-21-9-6-11-25-12-10-22(18(21)25)16-8-7-15(28-3)13-17(16)24(2)19(22)23(27,14-21)20(26)29-4/h6-9,13,18-19,27H,5,10-12,14H2,1-4H3/t18-,19+,21-,22+,23+/m0/s1 Key: WNKDGPXNFMMOEJ-RNJSZURPSA-N InChI=1/C23H30N2O4/c1-5-21-9-6-11-25-12-10-22(18(21)25)16-8-7-15(28-3)13-17(16)24(2)19(22)23(27,14-21)20(26)29-4/h6-9,13,18-19,27H,5,10-12,14H2,1-4H3/t18-,19+,21-,22+,23+/m0/s1 Key: WNKDGPXNFMMOEJ-RNJSZURPBV
SMILES CC[C@]12C[C@@]([C@H]3[C@@]4([C@H]1N(CC4)CC=C2)c5ccc(cc5N3C)OC)(C(=O)OC)O
Properties
Chemical formula	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