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 En
| WPRIM
| ID: wpr-812689
Responsible library:
WPRO
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.
Full text:
1
Index:
WPRIM
Main subject:
Molecular Structure
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Chemistry
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Islets of Langerhans
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Xanthones
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Diabetes Mellitus, Experimental
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Drug Therapy
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Esterification
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Hypoglycemic Agents
Limits:
Animals
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Humans
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Male
Language:
En
Journal:
Chinese Journal of Natural Medicines (English Ed.)
Year:
2013
Type:
Article