Constituents of the seeds of Cassia tora with inhibitory activity on soluble expoxide hydrolease.
Efforts to extract soluble epoxide hydrolase (sEH) inhibitors from food sources through bioactivity-guided fractionation of Cassia tora seed extracts led to the isolation of one new compound, 1, and 15 known compounds, 2-16. Structural elucidations were performed using 1D/2D NMR spectroscopy and mass spectrometry. Compounds 1, 3, 4, 6, 10, 11, and 13-16 exhibited inhibitory activities on sEH with IC50 values of 2.2±2.1-40.6±3.4 μM. Compound 13 was particularly active and exhibited a reversible-uncompetitive behavior in enzyme kinetic studies. A binding site on the enzyme for compound 13 was also predicted by Autodock 4.2 simulations.
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
Ga Young
GY
Lee
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea; Department of Horticultural Environment, National Institute of Horticultural and Herbal Science, RDA, Wanju 565-852, Republic of Korea.
Jang Hoon
JH
Kim
Department of Horticultural Environment, National Institute of Horticultural and Herbal Science, RDA, Wanju 565-852, Republic of Korea.
Seung-Kook
SK
Choi
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea. Electronic address: yhk@cnu.ac.kr.
Young Ho
YH
Kim
D000880:Anthraquinones / Q000302:isolation & purification / Q000494:pharmacology*; D002366:Cassia; D004791:Enzyme Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D004851:Epoxide Hydrolases / Q000037:antagonists & inhibitors*; D005470:Fluorometry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D062105:Molecular Docking Simulation; D012639:Seeds
D000880:Anthraquinones; D004791:Enzyme Inhibitors; C000609684:cassitoroside; D004851:Epoxide Hydrolases
Cassia tora; Leguminosae; Molecular docking; Soluble epoxide hydrolase; Uncompetitive behavior