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Securigenin glycosides as hypoglycemic principles of Securigera securidaca seeds

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Abstract

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.

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Acknowledgements

This research was a part of PhD thesis and it was supported by Tehran University of Medical Sciences and Health Services Grants (Nos. 11981 and 13726).

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Authors and Affiliations

  1. Department of Pharmacognosy, Faculty of Pharmacy and Medicinal Plant Research Center, Tehran University of Medical Sciences, Tehran, 14174-14411, Iran

    Zahra Tofighi, Saied Goodarzi, Abbas Hadjiakhoondi & Narguess Yassa

  2. Department of Pharmacognosy, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran

    Fahimeh Moradi-Afrapoli

  3. Department of Pharmaceutical Sciences, University of Basel, Klingelberg Strasse 50, 4056, Basel, Switzerland

    Fahimeh Moradi-Afrapoli, Samad Nejad Ebrahimi & Matthias Hamburger

  4. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran

    Samad Nejad Ebrahimi

  5. Inorganic Chemistry, Department of Chemistry, University of Basel, 4056, Basel, Switzerland

    Markus Neuburger

  6. Department of Toxicology and Pharmacology, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, 14155-6451, Iran

    Mohammad Abdollahi

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  1. Zahra Tofighi
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  2. Fahimeh Moradi-Afrapoli
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  9. Narguess Yassa
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Correspondence to Narguess Yassa.

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Tofighi, Z., Moradi-Afrapoli, F., Ebrahimi, S.N. et al. Securigenin glycosides as hypoglycemic principles of Securigera securidaca seeds. J Nat Med 71, 272–280 (2017). https://doi.org/10.1007/s11418-016-1060-7

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  • DOI: https://doi.org/10.1007/s11418-016-1060-7

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