Vindoline
Vindoline is a semi-synthetic vinca alkaloid originally found in Catharanthus that exhibits anti-diabetic and antacid activities; it is an intermediate in the synthesis of vinblastine. Unlike other vinca alkaloids, vindoline is only weakly cytotoxic, binding poorly to tubulin. Vindoline increases glucose-stimulated insulin release and inhibits Kv2.1 K+ channels, decreasing outward K+ current and lowering blood glucose, Hb1Ac, and triglyceride levels in animal models of diabetes. Vindoline also inhibits H+/K+ ATPases, potentially decreasing gastric acid secretion.
References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/1897899
Cas No. |
2182-14-1 |
---|---|
Purity |
≥98% |
Formula |
C25H32N2O6 |
Formula Wt. |
456.53 |
Chemical Name |
(2β,3β,4β,5α,12β,19α)-4-(Acetyloxy)-6,7-didehydro- 3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carboxylic acid methyl ester |
Synonym |
Vindolin; NSC 91994 |
Melting Point |
164-165°C |
Solubility |
Soluble in chloroform or ethanol. |
Appearance |
White Powder |
Yao XG, Chen F, Li P, et al. Natural product vindoline stimulates insulin secretion and efficiently ameliorates glucose homeostasis in diabetic murine models. J Ethnopharmacol. 2013 Oct 28;150(1):285-97. PMID: 24012527.
Freitas CS, Baggio CH, Mayer B, et al. Inhibition of gastric H+, K(+)-ATPase activity by compounds from medicinal plants. Nat Prod Commun. 2011 Sep;6(9):1253-4. PMID: 21941891.
Sertel S, Fu Y, Zu Y, et al. Molecular docking and pharmacogenomics of vinca alkaloids and their monomeric precursors, vindoline and catharanthine. Biochem Pharmacol. 2011 Mar 15;81(6):723-35. PMID: 21219884.