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

Kim, Young Ho; Kim, Hyo Young; Kang, Si Yong; Jin, Chang Hyun

doi:10.3390/molecules22091432

Cited by 10 publications

(4 citation statements)

References 18 publications

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“…Some of flavonoids, isolated and identified from the genera Scutellaria , Tetrastigma , Epimedium , Apios , Kaempferia , Boscia , and so on, exhibited sEH inhibitory potencies (Figure ). ,,− …”

Section: Seh Inhibitorsmentioning

confidence: 99%

Discovery of Soluble Epoxide Hydrolase Inhibitors from Chemical Synthesis and Natural Products

et al. 2020

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Soluble epoxide hydrolase (sEH) is an α/β hydrolase fold protein and widely distributed in numerous organs including the liver, kidney, and brain. The inhibition of sEH can effectively maintain endogenous epoxyeicosatrienoic acids (EETs) levels and reduce dihydroxyeicosatrienoic acids (DHETs) levels, resulting in therapeutic potentials for cardiovascular, central nervous system, and metabolic diseases. Therefore, since the beginning of this century, the development of sEH inhibitors is a hot research topic. A variety of potent sEH inhibitors have been developed by chemical synthesis or isolated from natural sources. In this review, we mainly summarized the interconnected aspects of sEH with cardiovascular, central nervous system, and metabolic diseases and then focus on representative inhibitors, which would provide some useful guidance for the future development of potential sEH inhibitors.

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Section: Seh Inhibitorsmentioning

confidence: 99%

Discovery of Soluble Epoxide Hydrolase Inhibitors from Chemical Synthesis and Natural Products

et al. 2020

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“…From these 1D- and 2D-NMR data, compound 1 was determined to be 3,7,4′-trihydroxy-5-methoxycoumaronochromone, although a compound with the same skeleton has been isolated recently from A. americana , but its configuration was not determined. This substance showed a great difference in optical rotation value ([α] 20 D +44.0, MeOH) when compared to compound 1 ([α] 22 D −184.6, MeOH), confirming that 1 has a new structure . A few other coumaronochromone analogues bearing a hydroxy group at the C-3 position have been reported from several plant sources, but their stereostructures have not been reported. − This is the first study to determine the absolute configuration of a 3-hydroxycoumaronochromone derivative.…”

Section: Resultsmentioning

confidence: 84%

“…Edible tubers have been used as food sources by American Indians because of their high nutritional value and health benefits . Nutritional studies have reported the composition of fatty acids, amino acids, carbohydrates, and starch in A. americana tubers. − In pharmacological studies, it has been reported that A. americana is effective in reducing hypertension, hyperlipidemia, cancer, and diabetes. − Several investigations on its secondary metabolites have indicated that isoflavone compounds isolated from this plant are associated with biological activities such as antioxidant, estrogen agonistic, α-glucosidase inhibitory, antiandrogenic, and soluble epoxide hydrolase inhibitory effects. − A conjugated saponin has also been reported to occur in A. americana tubers …”

mentioning

confidence: 99%

Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

et al. 2018

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Apios americana is an important food crop producing edible tubers with high nutritional and medicinal values and is widely cultivated in many countries. Despite its usefulness, research on its secondary metabolites and biological activities has been limited. In the present study, a new coumaronochromone, (2 R,3 S)-3,7,4'-trihydroxy-5-methoxycoumaronochromone (1), and two new isoflavone glucosides, 7,2',4'-trihydroxy-5-methoxyisoflavone-4'- O-β-d-glucopyranoside (3) and 5,7,4'-trihydroxyisoflavone-7- O-β-d-gentiotrioside (5), were isolated from the tubers of A. americana via chromatographic separation. Seventeen known compounds (2, 4, and 6-20) were also obtained from this plant part. The chemical structures of 1, 3, and 5 were determined by the interpretation of spectroscopic data. The absolute structure of the new compound 1 was established from experimental and calculated electronic circular dichroism spectra. This is the first study to determine the absolute configuration of a 3-hydroxycoumaronochromone derivative. The potential anti-inflammatory activity of the 20 isolates obtained was evaluated by measuring their inhibitory effects on nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 macrophages. Among the isolates, seven compounds (1, 3, 6-8, 15, and 20) showed substantial inhibition of nitric oxide production in RAW 264.7 cells, with the most active being compound 1 (IC value of 0.38 ± 0.04 μM).

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“…In addition, several studies have reported that the lectin shows immunostimulatory activity [ 20 , 21 , 22 ]. In addition to its immunostimulatory activity, Apios has been reported to exhibit anti-hypertension, sEH inhibitory, anti-cancer, and anti-inflammatory activities [ 23 , 24 , 25 ]. Sohn et al [ 24 ] have reported that Apios exerts a protective effect against LPS- and H1N1-induced acute lung injury by reducing inflammation in the lung.…”

Section: Discussionmentioning

confidence: 99%

Anti-Inflammatory Effect of Lupinalbin A Isolated from Apios americana on Lipopolysaccharide-Treated RAW264.7 Cells

Kim

So³

et al. 2018

Molecules

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Apios americana, a leguminous plant, is used as food in some countries. Although the biological activities of Apios extract have been reported, there have been no reports about the anti-inflammatory mechanism of lupinalbin A on the RAW264.7 cells. In this study, we investigated the anti-inflammatory effect of A. americana lupinalbin A on lipopolysaccharide (LPS)-treated RAW264.7 cells. Lupinalbin A significantly inhibited nitric oxide production and inducible nitric oxide synthase expression in LPS-treated RAW264.7 cells. The expression of cytokines, including interleukin-6, tumor necrosis factor-α, and chemokine of monocyte chemoattractant protein, was reduced under lupinalbin A exposure in LPS-treated RAW264.7 cells. In addition, lupinalbin A significantly decreased LPS-induced interferon (IFN)-β production and STAT1 protein levels in RAW264.7 cells. Taken together, these results suggest that A. americana lupinalbin A exerts anti-inflammatory effects via the inhibition of pro-inflammatory cytokines and blocking of IFN-β/STAT1 pathway activation.

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

Cited by 10 publications

References 18 publications

Discovery of Soluble Epoxide Hydrolase Inhibitors from Chemical Synthesis and Natural Products

Discovery of Soluble Epoxide Hydrolase Inhibitors from Chemical Synthesis and Natural Products

Chemical Constituents of Apios americana Tubers and Their Inhibitory Activities on Nitric Oxide Production in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

Anti-Inflammatory Effect of Lupinalbin A Isolated from Apios americana on Lipopolysaccharide-Treated RAW264.7 Cells

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