Identification, characterization, kinetics, and molecular docking of flavonoid constituents from Archidendron clypearia (Jack.) Nielsen leaves and twigs

Thao, Nguyen Phuong; Luyen, Bui Thi Thuy; Kim, Young Ho; Jo, Ah Reum; Dat, Nguyen Tien; Kiệm, Phan Văn; Minh, Châu Văn

doi:10.1016/j.bmc.2016.05.034

Cited by 27 publications

(17 citation statements)

References 26 publications

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“…In recent studies, we revealed that flavonoids and triterpenoids have inhibitory activity against sEH [ 11 , 12 , 13 ]. A flavonoid glycoside ( 1 ) and triterpenoids ( 2 – 4 ) were purified from the fruit of M. domestica .…”

Section: Resultsmentioning

confidence: 99%

“…Recently, triterpenoids from Cimicifuga dahurica Maxim. [ 11 ], flavonoids from Tetrastigma hemsleyanum [ 12 ], and flavonoid glycosides [ 13 ] have been reported as noncompetitive agents blocking the catalytic activity of sEH [ 12 , 13 ]. In the present study, flavonoid and triterpenoid compounds were isolated from apples, and their structures were identified using spectroscopic methods.…”

Section: Introductionmentioning

confidence: 99%

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Inhibitory Activity of Quercetin 3-O-Arabinofuranoside and 2-Oxopomolic Acid Derived from Malus domestica on Soluble Epoxide Hydrolase

et al. 2020

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Flavonoids and triterpenoids were revealed to be the potential inhibitors on soluble epoxide hydrolase (sEH). The aim of this study is to reveal sEH inhibitors from Fuji apples. A flavonoid and three triterpenoids derived from the fruit of Malus domestica were identified as quercetin-3-O-arabinoside (1), ursolic acid (2), corosolic acid (3), and 2-oxopomolic acid (4). They had half-maximal inhibitory concentration of the inhibitors (IC50) values of 39.3 ± 3.4, 84.5 ± 9.5, 51.3 ± 4.9, and 11.4 ± 2.7 μM, respectively, on sEH. The inhibitors bound to allosteric sites of enzymes in mixed (1) and noncompetitive modes (2–4). Molecular simulations were carried out for inhibitors 1 and 4 to calculate the binding force of ligands to receptors. The inhibitors bound to the left (1) and right (4) pockets next to the enzyme’s active site. Based on analyses of their molecular docking and dynamics, it was shown that inhibitors 1 and 4 can stably bind sEH at 1 bar and 300 K. Finally, inhibitors 1 and 4 are promising candidates for further studies using cell-based assays and in vivo cardiovascular tests.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Inhibitory Activity of Quercetin 3-O-Arabinofuranoside and 2-Oxopomolic Acid Derived from Malus domestica on Soluble Epoxide Hydrolase

et al. 2020

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“…Molecular dynamics simulation was performed as previously reported, with few modifications [ 18 ]. The topology files of the ligand and receptor were built as GROMOS 53A6 force-field by prodrg and Gromacs 4.6.5, respectively.…”

Section: Methodsmentioning

confidence: 99%

Soluble Epoxide Hydrolase Inhibitory Activity of Components Isolated from Apios americana Medik

Kim

Kang

et al. 2017

Molecules

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A new compound 1, 5-methoxy-2,5,7,4′-tetrahydroxy-coumaronochromone, along with seven known compounds (2–8), were isolated from Apios americana using open column chromatography. Their structures were established based on an analysis of 1D and 2D NMR, and MS spectra. Among these, two compounds 1 and 2 showed inhibitory activity on soluble epoxide hydrolase (sEH) at a concentration below 50 μM. The respective competitive (1) and mixed (2) inhibitors were revealed to have Ki values of 21.0 ± 0.8 and 14.5 ± 1.5 μM, based on the Dixon plot. The potential inhibitor (2) was visually presented in a predicted binding pose in the receptor by molecular docking. Additionally, molecular dynamics were performed for a detailed understanding of their complex by Gromacs 4.6.5 package.

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“…The concentrated extracts were dissolved in distilled water and successively divided in n-hexane, chloroform, ethyl acetate, and BuOH fractions. Recently, our studies have revealed that some flavonoids showed inhibitory activity against sEH [13,14]. Purified compounds 1-3 were evaluated for binding strength and type of enzyme in vitrofor insight into the sEH inhibition.…”

Section: Isolation Identification and Enzyme Assaymentioning

confidence: 99%

Inhibitory Activity of Flavonoids, Chrysoeriol and Luteolin-7-O-Glucopyranoside, on Soluble Epoxide Hydrolase from Capsicum chinense

Kim

Jin

2020

Biomolecules

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Three flavonoids derived from the leaves of Capsicum chinense Jacq. were identified as chrysoeriol (1), luteolin-7-O-glucopyranoside (2), and isorhamnetin-7-O-glucopyranoside (3). They had IC50 values of 11.6±2.9, 14.4±1.5, and 42.7±3.5 µg/mL against soluble epoxide hydrolase (sEH), respectively. The three inhibitors (1–3) were found to non-competitively bind into the allosteric site of the enzyme with Ki values of 10.5 ± 3.2, 11.9 ± 2.8 and 38.0 ± 4.1 µg/mL, respectively. The potential inhibitors 1 and 2 were located at the left edge ofa U-tube shape that contained the enzyme active site. Additionally, we observed changes in several factors involved in the binding of these complexes under 300 K and 1 bar. Finally, it was confirmed that each inhibitor, 1 and 2, could be complexed with sEH by the “induced fit” and “lock-and-key” models.

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Identification, characterization, kinetics, and molecular docking of flavonoid constituents from Archidendron clypearia (Jack.) Nielsen leaves and twigs

Cited by 27 publications

References 26 publications

Inhibitory Activity of Quercetin 3-O-Arabinofuranoside and 2-Oxopomolic Acid Derived from Malus domestica on Soluble Epoxide Hydrolase

Inhibitory Activity of Quercetin 3-O-Arabinofuranoside and 2-Oxopomolic Acid Derived from Malus domestica on Soluble Epoxide Hydrolase

Soluble Epoxide Hydrolase Inhibitory Activity of Components Isolated from Apios americana Medik

Inhibitory Activity of Flavonoids, Chrysoeriol and Luteolin-7-O-Glucopyranoside, on Soluble Epoxide Hydrolase from Capsicum chinense

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