Vindoline

Vindoline is a chemical precursor to vinblastine.[1] Vindoline is formed through biosynthesis from Tabersonine.

Vindoline
Names
IUPAC name
Methyl 3β,4β-dihydroxy-16-methoxy-1-methyl-6,7-didehydro-2β,5α,12β,19α-aspidospermidine-3α-carboxylate
Systematic IUPAC name
Methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.871
EC Number
  • 218-558-0
UNII
  • InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
    Key: CXBGOBGJHGGWIE-ACSXSLCXSA-N
  • InChI=1/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
    Key: CXBGOBGJHGGWIE-ACSXSLCXBW
  • CC[C@@]12C=CCN3[C@@H]1[C@@]4(CC3)c5ccc(cc5N([C@H]4C([C@@H]2OC(=O)C)(C(=O)OC)O)C)OC
Properties
C25H32N2O6
Molar mass 456.539 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

See also

References
  1. Liu, J; Zhu, J; Tang, L; Wen, W; Lv, S; Yu, R (2014). "Enhancement of vindoline and vinblastine production in suspension-cultured cells of Catharanthus roseus by artemisinic acid elicitation". World Journal of Microbiology and Biotechnology. 30 (1): 175–80. doi:10.1007/s11274-013-1432-z. PMID 23864440.


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