Vincoline

Vincoline is an alkaloid isolated from Catharanthus roseus.[1] In a mouse model, it has been found to stimulate insulin secretion.[2]

Vincoline
Names
IUPAC name
Methyl (20S)-2-hydroxy-6,7-didehydro-3α,20-epoxy-2β,5α,12β,19α-aspidospermidine-3β-carboxylate
Systematic IUPAC name
Methyl (3aS,3a1S,4S,6R,6aS,11bR)-6a-hydroxy-4-methyl-6a,7,12,13-tetrahydro-1H,3a1H,4H,6H-3a,6-methanoindolizino[1′,8′:4,5,6]oxepino[3,4-b]indole-6-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C21H24N2O4/c1-13-18-8-5-10-23-11-9-19(16(18)23)14-6-3-4-7-15(14)22-21(19,25)20(12-18,27-13)17(24)26-2/h3-8,13,16,22,25H,9-12H2,1-2H3/t13-,16-,18-,19+,20-,21-/m0/s1
    Key: YOQNZWXFGROKGY-KVKBDHCBSA-N
  • InChI=1/C21H24N2O4/c1-13-18-8-5-10-23-11-9-19(16(18)23)14-6-3-4-7-15(14)22-21(19,25)20(12-18,27-13)17(24)26-2/h3-8,13,16,22,25H,9-12H2,1-2H3/t13-,16-,18-,19+,20-,21-/m0/s1
    Key: YOQNZWXFGROKGY-KVKBDHCBBE
  • C[C@H]1[C@]23C[C@@](O1)([C@]4([C@@]5([C@H]2N(CC5)CC=C3)c6ccccc6N4)O)C(=O)OC
Properties
C21H24N2O4
Molar mass 368.433 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

References
  1. Aynilian, GH; Weiss, SG; Cordell, GA; Abraham, DJ; Crane, FA; Farnsworth, NR (1974). "Catharanthus alkaloids. XXIX. Isolation and structure elucidation of vincoline". Journal of Pharmaceutical Sciences. 63 (4): 536–8. doi:10.1002/jps.2600630409. PMID 4828700.
  2. Yao, XG; Chen, F; Li, P; Quan, L; Chen, J; Yu, L; Ding, H; Li, C; Chen, L; Gao, Z; Wan, P; Hu, L; Jiang, H; Shen, X (2013). "Natural product vindoline stimulates insulin secretion and efficiently ameliorates glucose homeostasis in diabetic murine models". Journal of Ethnopharmacology. 150 (1): 285–97. doi:10.1016/j.jep.2013.08.043. PMID 24012527.
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