Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C25H32N2O6.ClH |
| Molecular Weight | 492.992 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC[C@@]12C=CCN3CC[C@@]4([C@H]13)[C@@H](N(C)C5=C4C=CC(OC)=C5)[C@](O)([C@@H]2OC(C)=O)C(=O)OC
InChI
InChIKey=WKBKCMCWVKDZQX-AWARSVQWSA-N
InChI=1S/C25H32N2O6.ClH/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;1H/t19-,20+,21+,23+,24+,25-;/m0./s1
Vindoline (VDL) is an indole alkaloid, possessing hypoglycemic and vasodilator effects, and it is also the prodrug of many vinca alkaloids. Vindoline as one of the alkaloids is highly present in
young leaves and twigs of Catharanthus roseus, and oral administration of vindoline (100 mg/kg) had an acute hypoglycemic effect on rats. Vindoline acted as a Kv2.1 inhibitor able to reduce the voltage-dependent outward potassium currents finally enhancing insulin secretion. It protected β-cells from the cytokines-induced apoptosis following its inhibitory role in Kv2.1. Moreover, vindoline (20mg/kg) treatment significantly improved glucose homeostasis in db/db mice and STZ/HFD-induced type 2 diabetic rats, as reflected by its functions in increasing plasma insulin concentration, protecting the pancreatic β-cells from damage, decreasing fasting blood glucose and glycated hemoglobin (HbA1c), improving OGTT and reducing plasma triglyceride (TG).
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast. | 2015-05-12 |
|
| Natural product vindoline stimulates insulin secretion and efficiently ameliorates glucose homeostasis in diabetic murine models. | 2013-10-28 |
|
| Vindoline synthesis in in vitro shoot cultures of Catharanthus roseus. | 2004-04 |
|
| Effects of Near-Ultraviolet Light on Alkaloid Production in Catharanthus roseus Plants. | 1993-02 |
Sample Use Guides
Daily oral treatment with vindoline (20mg/kg) to diabetic mice/rats for 4 weeks, body weight and blood glucose were determined every week, oral glucose tolerance test (OGTT) was performed after 4 weeks.
Route of Administration:
Oral
Vindoline dose-dependently
inhibited the sustained outward K+ current by IC50 of 31 uM in MIN6 cells, preincubated with nifedipine (10 uM). Vindoline efficiently reduced K+ current by IC50 of 43 uM in Kv2.1 over-expressing CHO cells. MIN6 cells were pretreated with vindoline (20 or 50 uM for 4 h), followed by incubation with apoptotic cytokines or vindoline (20 or 50 uM for another 24 h). The percentage of
the apoptotic MIN6 cells represented by FITC-AnnexinV was 9.41%
under normal condition, and the percentage became 26.36% with
treatment of apoptotic cytokines for 24 h, while vindoline (50 uM)
decreased the percentage of apoptotic cells by 16.45% in vindolinetreated
MIN6 cells.
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5826-69-7
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CH4X1G69D3
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m11455
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20831630
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SUBSTANCE RECORD
