Isocucurbic Acid Derivatives and Soluble Epoxide Hydroxylase Inhibitors from the Flowers of Chrysanthemum indicum L. |
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| Authors: | Bui Thi Thu Trang Jang Hoon Kim Bui Thi Thuy Luyen |
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| Institution: | 1. Faculty of Chemical Technology, Hanoi University of Industry, 298 Cau Dien, Minh Khai, Bac Tu Liem, Hanoi, 10000 Vietnam;2. Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA, Eumseong, 27709 Korea;3. Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hoan Kiem, Hanoi, 10000 Vietnam |
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| Abstract: | Soluble epoxide hydrolase (sEH) inhibitory activity guided fractionation and isolation of two new isocucurbic acid derivatives ( 1 and 2 ) and nine known compounds ( 3 – 11 ) from the flowers of Chrysanthemum indicum L. Their structures were elucidated on the basis of spectroscopic data interpretation and comparison with those reported in previous studies. Luteolin ( 3 ), acacetin-7-O-β-D-glucopyranoside ( 6 ), and methyl 3,4-di-O-caffeoylquinate ( 10 ) displayed sEH inhibitory activities with IC50 values ranging from 13.7±3.6 to 20.8±0.4 μM. Enzyme kinetic analysis revealed that 3 , 6 , and 10 were non-competitive inhibitors with Ki values of 14.8±0.5, 31.2±0.8, and 3.9±0.2 μM, respectively. Additionally, molecular docking studies indicated compound 10 had the ability to form six hydrogen bonds at sEH active site, resulting binding energy as low as ?9.58 Kcal/mol. |
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| Keywords: | Chrysanthemum indicum isocucurbic acid derivative flavonoid quinic acid derivative soluble epoxide hydrolase inhibitor |
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