Inhibition potential of phenolic constituents from the aerial parts of <i>Tetrastigma hemsleyanum</i> against soluble epoxide hydrolase and nitric oxide synthase

Wang, Cai Yi; Lee, Soo Kon; Jang, Hyun‐Jae; Su, Xiang Dong; Wang, Hengshan; Kim, Young Ho; Yang, Seo Young

doi:10.1080/14756366.2019.1584621

Cited by 13 publications

(17 citation statements)

References 25 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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“…Previous studies demonstrated that the extract of S. hexaphylla leaves has an anti-inflammatory effect through suppression of nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) expression [5,15]. A phytochemical investigation of S. hexaphylla led to the isolation of two compounds, 3-O- (2). Their structures were determined by the analysis of their spectroscopic data, IR, NMR, ESI-MS and chemical reaction.…”

Section: Discussionmentioning

confidence: 99%

“…Thus, it is often necessary to suppress macrophage activation to prevent chronic inflammatory disorders. Medicinal herbs have been identified as rich sources of natural products with anti-inflammatory activities [2].…”

Section: Introductionmentioning

confidence: 99%

Enhancement of an In Vivo Anti-Inflammatory Activity of Oleanolic Acid through Glycosylation Occurring Naturally in Stauntonia hexaphylla

et al. 2020

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Stauntonia hexaphylla (Lardizabalaceae) has been used as a traditional herbal medicine in Korea and China for its anti-inflammatory and analgesic properties. As part of a bioprospecting program aimed at the discovery of new bioactive compounds from Korean medicinal plants, a phytochemical study of S. hexaphylla leaves was carried out leading to isolation of two oleanane-type triterpene saponins, 3-O-[β-d-glucopyranosyl (1→2)-α-l-arabinopyranosyl] oleanolic acid-28-O-[β-d-glucopyranosyl (1→6)-β-d-glucopyranosyl] ester (1) and 3-O-α-l-arabinopyranosyl oleanolic acid-28-O-[β-d-glucopyranosyl (1→6)-β-d-glucopyranosyl] ester (2). Their structures were established unambiguously by spectroscopic methods such as one- and two-dimensional nuclear magnetic resonance and infrared spectroscopies, high-resolution electrospray ionization mass spectrometry and chemical reactions. Their anti-inflammatory activities were examined for the first time with an animal model for the macrophage-mediated inflammatory response as well as a cell-based assay using an established macrophage cell line (RAW 264.7) in vitro. Together, it was concluded that the saponin constituents, when they were orally administered, exerted much more potent activities in vivo than their sapogenin core even though both the saponins and the sapogenin molecule inhibited the RAW 264.7 cell activation comparably well in vitro. These results imply that saponins from S. hexaphylla leaves have a definite advantage in the development of oral medications for the control of inflammatory responses.

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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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Inhibition potential of phenolic constituents from the aerial parts of Tetrastigma hemsleyanum against soluble epoxide hydrolase and nitric oxide synthase

Cited by 13 publications

References 25 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

Enhancement of an In Vivo Anti-Inflammatory Activity of Oleanolic Acid through Glycosylation Occurring Naturally in Stauntonia hexaphylla

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

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