Securigenin glycosides as hypoglycemic principles of Securigera securidaca seeds

Tofighi, Zahra and Moradi-Afrapoli, Fahimeh and Ebrahimi, Samad Nejad and Goodarzi, Saied and Hadjiakhoondi, Abbas and Neuburger, Markus and Hamburger, Matthias and Abdollahi, Mohammad and Yassa, Narguess. (2017) Securigenin glycosides as hypoglycemic principles of Securigera securidaca seeds. Journal of Natural Medicines, 71 (1). pp. 272-280.

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Seeds of Securigera securidaca (Fabaceae) are used in Iranian folk medicine as an antidiabetic treatment. In this study, the antihyperglycemic activity of chloroform and methanol fractions (CF and MF) from S. securidaca seed extract was investigated and their bioactive constituents were identified. The antidiabetic effects of fractions were assessed by streptozocin-induced diabetic Naval Medical Research Institute mice. The hypoglycemic activity of MF at 100 mg/kg and CF at 400 mg/kg was comparable with glibenclamide (3 mg/kg). MF at 400 mg/kg and CF at 600 mg/kg showed equal hypoglycemic responses to 12.5 IU/kg insulin ( P > 0.05). Three cardiac glycosides were isolated as active constituents responsible for the hypoglycemic activity. Securigenin-3 - O - β - glucopyranosyl - (1 → 4) - β - xylopyranoside ( 1 ) was a major compound in seeds. Securigenin-3 - O - inositol - (1 → 3) - β - glucopyranosyl - (1 → 4) - β - xylopyranoside ( 2 ) and securigenin-3 - O - α - rhamnopyranosyl - (1 → 4) - α - glucopyranoside ( 3 ) were found as new natural products. When 1–3 were tested at 10 mg/kg there was a significant reduction of blood glucose levels in diabetic mice, comparable to that of 3 mg/kg glibenclamide ( P > 0.05). The hypoglycemic effect was due to an increase in insulin secretion; the insulin levels in the diabetic mice significantly improved and were comparable with those in healthy animals ( P > 0.05). Compounds responsible for the hypoglycemic properties of S. securidaca seeds were identified as cardiac glycosides and were found to act via an increase of insulin levels in a diabetic mouse model.
Faculties and Departments:05 Faculty of Science > Departement Chemie
UniBasel Contributors:Ebrahimi, Samad Nejad and Neuburger, Markus and Hamburger, Matthias
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:30 May 2018 06:45
Deposited On:24 Jan 2018 11:16

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