Synthesis and hypoglycemic activity of esterified-derivatives of mangiferin.
10.1016/S1875-5364(13)60032-1
- Author:
Xue-Jian LI
1
;
Zheng-Cai DU
;
Yan HUANG
;
Bu-Ming LIU
;
Wen-Ji HU
;
Wen-Jie LU
;
Jia-Gang DENG
Author Information
1. School of Pharmaceutical Sciences, Guangxi Medical University, Nanning, China.
- Publication Type:Journal Article
- MeSH:
Animals;
Diabetes Mellitus, Experimental;
drug therapy;
Esterification;
Humans;
Hypoglycemic Agents;
administration & dosage;
chemical synthesis;
chemistry;
Islets of Langerhans;
drug effects;
Male;
Mice;
Molecular Structure;
Xanthones;
administration & dosage;
chemical synthesis;
chemistry
- From:
Chinese Journal of Natural Medicines (English Ed.)
2013;11(3):296-301
- CountryChina
- Language:English
-
Abstract:
AIM:To synthesize three novel esterified-derivatives of mangiferin and evaluate their hypoglycemic activities.
METHODS:Acetic, propionic, and butyric anhydride were reacted with mangiferin, respectively. The hypoglycemic activity of the derivatives was evaluated using a hyperglycemic mouse model induced by streptozotocin (STZ), and the islet cells were checked by biopsy inspection.
RESULTS:7, 2', 3', 4', 6'-penta-acetyl-mangiferin (PAM), 3, 6, 7, 2', 3', 4', 6'-hepta-propionyl-mangiferin (HPM) and 3, 6, 7, 2', 3', 4'-hexa-butyryl-mangiferin (HBM) were synthesized and their structures were identified by MS,(1)H, (13)C NMR, and 2D NMR. These three compounds were reported for the first time. PAM group (0.5, 0.25 mmol·kg(-1)), HPM group (0.5, 0.25 mmol·kg(-1)), and HBM group (0.5, 0.25, 0.125 mmol·kg(-1)) mice showed strong hypoglycemic activity (P < 0.01); mangiferin group (1, 0.5 mmol·kg(-1)), PAM group (0.125 mmol·kg(-1)) and HPM group (0.125 mmol·kg(-1)) showed marginal hypoglycemic activity (P < 0.05); mangiferin group (0.25 mmol·kg(-1)) had the potential for a hypoglycemic effect, although it did not demonstrate that statistically. In histological examination, the islet cells of the PAM, HPM, and HBM groups could recover from the STZ damage; islet cells of the mangiferin group could recover also, but less than the esterified-derivative groups.
CONCLUSION:Derivatives could repair the damaged islet cells, and had higher lipid-solubility and stronger hypoglycemic activity than mangiferin itself. There existed a structure activity effect, and a solubility effect relationship: the larger esterification moieties, or the higher lipid-solubility, the stronger the hypoglycemic activity (no ester → acetyl → propionyl → butyryl). Esterified derivatives of mangiferin are potential compounds for new anti-diabetes drugs.
