1. Caffeoylquinic acid derivatives isolated from the aerial parts of Gynura divaricata and their yeast α-glucosidase and PTP1B inhibitory activity.
- Author
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Chen, Jian, Mangelinckx, Sven, Ma, Li, Wang, Zhengtao, Li, Weilin, and De Kimpe, Norbert
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ALTERNATIVE medicine , *BIOLOGICAL assay , *BIOLOGICAL models , *PHYSICAL & theoretical chemistry , *ENZYME inhibitors , *HYPOGLYCEMIC agents , *MEDICINAL plants , *PHYTOCHEMICALS , *PLANT extracts , *PILOT projects , *DESCRIPTIVE statistics , *IN vitro studies , *PHARMACODYNAMICS - Abstract
The phytochemical investigation of natural products of Gynura divaricata led to the isolation of eleven caffeoylquinic acid derivatives. They were characterized by spectrometric methods as 5- O -caffeoylquinic acid ( 1 ), 5- O - p -coumaroylquinic acid ( 2 ), 5- O -feruloylquinic acid ( 3 ), methyl 5- O -caffeoylquinate ( 4 ), 3,4-dicaffeoylquinic acid ( 5 ), 3,5-dicaffeoylquinic acid ( 6 ), 4,5-dicaffeoylquinic acid ( 7 ), methyl 3,4-dicaffeoylquinate ( 8 ), methyl 3,5-dicaffeoylquinate ( 9 ), methyl 4,5-dicaffeoylquinate ( 10 ) and ethyl 4,5-dicaffeoylquinate ( 11 ). The individual compounds were screened for the inhibition of yeast α-glucosidase and Protein Tyrosine Phosphatase 1B (PTP1B) using in vitro assays. Among the isolated compounds, 3,4-dicaffeoylquinic acid ( 5 ), 4,5-dicaffeoylquinic acid ( 7 ), methyl 3,4-dicaffeoylquinate ( 8 ) and methyl 4,5-dicaffeoylquinate ( 10 ) exhibited significant inhibitory activities against α-glucosidase. In addition, 5- O - p -coumaroylquinic acid ( 2 ), 3,5-dicaffeoylquinic acid ( 6 ) and 4,5-dicaffeoylquinic acid ( 7 ) had considerable inhibitory effect against PTP1B. Based on these findings, the caffeoylquinic acid derivatives were deduced to be potentially responsible for the anti-diabetic activity of G. divaricata . The preliminary structure–activity relationship study suggests that the number and positioning of caffeoyl groups in the quinic acid derivatives are important for both α-glucosidase and PTP1B inhibitory potency. Moreover, the corresponding methyl esters of some dicaffeoylquinic acids have enhanced inhibitory activity against yeast α-glucosidase. [ABSTRACT FROM AUTHOR]
- Published
- 2014
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