title: Inhibition of soluble epoxide hydrolase activity by compounds isolated from the aerial parts of Glycosmis stenocarpa.
abstract: The aim of this study is to search for soluble epoxide hydrolase (sEH) inhibitors from natural plants, bioassay-guided fractionation of lipophilic n-hexane and chloroform layers of an extract of the aerial parts of Glycosmis stenocarpa led to the isolation of 12 compounds (1-12) including murrayafoline-A (1), isomahanine (2), bisisomahanine (3), saropeptate (4), (24 S)-ergost-4-en-3,6-dione (5), stigmasta-4-en-3,6-dion (6), stigmast-4-en-3-one (7), β-sitosterol (8), 24-methylpollinastanol (9), trans-phytol (10), neosarmentol III (11) and (+)-epiloliolide (12). Their structures were elucidated on the basis of spectroscopic data. Among them, neosarmentol III (11) was isolated from nature for the first time. All the isolated compounds were evaluated for their inhibitory activity against sEH. Among isolated carbazole-type compounds, isomahanine (2) and bisisomahanine (3) were identified as a potent inhibitor of sEH, with IC50 values of 22.5 ± 1.7 and 7.7 ± 1.2 µM, respectively. Moreover, the inhibitory action of 2 and 3 represented mixed-type enzyme inhibition.
authors.affiliation: a College of Pharmacy, Chungnam National University , Daejeon , Republic of Korea .|b Virology Unit, Department of Horticultural Environment , National Institute of Horticultural and Herbal Science, RDA , Jeollabuk-Do , Republic of Korea .
authors.forename: Jang Hoon
authors.initials: JH
authors.lastname: Kim
authors.affiliation: a College of Pharmacy, Chungnam National University , Daejeon , Republic of Korea .
authors.forename: Abubaker M A
authors.initials: AM
authors.lastname: Morgan
authors.affiliation: a College of Pharmacy, Chungnam National University , Daejeon , Republic of Korea .|c Institute of Marine Biochemistry , and.
authors.forename: Bui Huu
authors.initials: BH
authors.lastname: Tai
authors.affiliation: d Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology , Hanoi , Vietnam.
authors.forename: Doan Thi
authors.initials: DT
authors.lastname: Van
authors.affiliation: d Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology , Hanoi , Vietnam.
authors.forename: Nguyen Manh
authors.initials: NM
authors.lastname: Cuong
authors.affiliation: a College of Pharmacy, Chungnam National University , Daejeon , Republic of Korea .
authors.forename: Young Ho
authors.initials: YH
authors.lastname: Kim
mesh_terms: D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004851:Epoxide Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006801:Humans; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry*; D027821:Rutaceae / Q000737:chemistry*; D012995:Solubility; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D004851:Epoxide Hydrolases
keywords: Bisisomahanine mixed-type; Glycosmis stenocarpa; Rutaceae; soluble epoxide hydrolase