Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Identification of Soluble Epoxide Hydrolase Inhibitors from the Seeds of Passiflora edulis Cultivated in Vietnam

  • Cuong, To Dao (Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST)) ;
  • Anh, Hoang Thi Ngoc (Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST)) ;
  • Huong, Tran Thu (Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST)) ;
  • Khanh, Pham Ngoc (Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST)) ;
  • Ha, Vu Thi (Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST)) ;
  • Hung, Tran Manh (Department of Biomedical Sciences, Institute for Research and Executive Education (VNUK), The University of Danang) ;
  • Kim, Young Ho (College of Pharmacy, Chungnam National University) ;
  • Cuong, Nguyen Manh (Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology (VAST))
  • Received : 2019.08.28
  • Accepted : 2019.10.21
  • Published : 2019.12.31
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Abstract

Soluble epoxide hydrolases (sEH) are enzymes present in all living organisms, metabolize epoxy fatty acids to 1,2-diols. sEH in the metabolism of polyunsaturated fatty acids plays a key role in inflammation. In addition, the endogenous lipid mediators in cardiovascular disease are also broken down to diols by the action of sEH that enhanced cardiovascular protection. In this study, sEH inhibitory guided fractionation led to the isolation of five phenolic compounds trans-resveratrol (1), trans-piceatannol (2), sulfuretin (3), (+)-balanophonin (4), and cassigarol E (5) from the ethanol extract of the seeds of Passiflora edulis Sims cultivated in Vietnam. The chemical structures of isolated compounds were determined by the interpretation of NMR spectral data, mass spectra, and comparison with data from the literature. The soluble epoxide hydrolase (sEH) inhibitory activity of isolated compounds was evaluated. Among them, trans-piceatannol (2) showed the most potent inhibitory activity on sEH with an IC50 value of 3.4 μM. This study marks the first time that sulfuretin (3) was isolated from Passiflora edulis as well as (+)-balanophonin (4), and cassigarol E (5) were isolated from Passiflora genus.

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