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Bioorg Med Chem Lett. 2015 Nov 15;25(22):5097-101. doi: 10.1016/j.bmcl.2015.10.014. Epub 2015 Oct 8.

Constituents of the seeds of Cassia tora with inhibitory activity on soluble expoxide hydrolease.

Author information

1
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
2
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.
3
Department of Horticultural Environment, National Institute of Horticultural and Herbal Science, RDA, Wanju 565-852, Republic of Korea.
4
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea. Electronic address: yhk@cnu.ac.kr.

Abstract

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.

KEYWORDS:

Cassia tora; Leguminosae; Molecular docking; Soluble epoxide hydrolase; Uncompetitive behavior

PMID:
26483136
DOI:
10.1016/j.bmcl.2015.10.014
[Indexed for MEDLINE]

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