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Synthesis and hypoglycemic activity of esterified-derivatives of mangiferin / 中国天然药物
Chinese Journal of Natural Medicines (English Ed.) ; (6): 296-301, 2013.
Article in English | WPRIM | ID: wpr-812689
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.
Subject(s)
Full text: Available Index: WPRIM (Western Pacific) Main subject: Molecular Structure / Chemistry / Islets of Langerhans / Xanthones / Diabetes Mellitus, Experimental / Drug Therapy / Esterification / Hypoglycemic Agents Limits: Animals / Humans / Male Language: English Journal: Chinese Journal of Natural Medicines (English Ed.) Year: 2013 Type: Article

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Full text: Available Index: WPRIM (Western Pacific) Main subject: Molecular Structure / Chemistry / Islets of Langerhans / Xanthones / Diabetes Mellitus, Experimental / Drug Therapy / Esterification / Hypoglycemic Agents Limits: Animals / Humans / Male Language: English Journal: Chinese Journal of Natural Medicines (English Ed.) Year: 2013 Type: Article