Wistin

Wistin Exerts an Anti-Inflammatory Effect via Nuclear Factor-kappaB and p38 Signaling Pathways in Lipopolysaccharide-Stimulated RAW264.7 Cells.[Pubmed:36080491]

Molecules. 2022 Sep 5;27(17):5719.

Inflammation is an immune response to cellular damage caused by various stimuli (internal or external) and is essential to human health. However, excessive inflammatory responses may be detrimental to the host. Considering that the existing drugs for the treatment of inflammatory diseases have various side effects, such as allergic reactions, stomach ulcers, and cardiovascular problems, there is a need for research on new anti-inflammatory agents with low toxicity and fewer side effects. As 4',6-dimethoxyisoflavone-7-O-beta-d-glucopyranoside (Wistin) is a phytochemical that belongs to an isoflavonoid family, we investigated whether Wistin could potentially serve as a novel anti-inflammatory agent. In this study, we found that Wistin significantly reduced the production of nitric oxide and intracellular reactive oxygen species in lipopolysaccharide-stimulated RAW 264.7 cells. Moreover, Wistin reduced the mRNA levels of pro-inflammatory enzymes (inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX-2)) and cytokines (interleukin (IL)-1beta and IL-6) and significantly reduced the protein expression of pro-inflammatory enzymes (iNOS and COX-2). Furthermore, Wistin reduced the activation of the nuclear factor-kappaB and p38 signaling pathways. Together, these results suggest that Wistin is a prospective candidate for the development of anti-inflammatory drugs.

Neuraminidase Inhibitors from the Roots of Caragana sinica.[Pubmed:32996697]

Chem Biodivers. 2020 Nov;17(11):e2000470.

Two new oligostilbenes, caragasinins D and E, along with four known compounds, kobophenol A, alpha-viniferin, Wistin, and 5-hydroxy-2-[(4-hydroxyphenyl)acetyl]-3-methoxybenzoic acid, were isolated from the roots of Caragana sinica. These compounds were spectroscopically analyzed for their structures and configurations and compared with existing data. The configurations of caragasinins D and E were elucidated by (1) H-NMR spectroscopy, CD spectroscopy, and time-dependent density-functional theory simulated ECD spectral data. All six compounds were evaluated for their inhibitory activity against neuraminidase (NA) from Clostridium perfringens. Among the tested compounds, 5-hydroxy-2-[(4-hydroxyphenyl)acetyl]-3-methoxybenzoic acid demonstrated statistically significant NA inhibitory activity, which was comparable to the positive control, mangiferin.

4',6-Dimethoxyisoflavone-7-O-beta-D-glucopyranoside (wistin) is a peroxisome proliferator-activated receptor alpha (PPARalpha) agonist in mouse hepatocytes.[Pubmed:29318455]

Mol Cell Biochem. 2018 Sep;446(1-2):35-41.

Peroxisome proliferator-activated receptors (PPARs) are ligand-dependent transcription factors that regulate lipid and glucose metabolism. PPARalpha mainly affects fatty acid metabolism, and its activation lowers lipid levels. PPARgamma is involved in the regulation of adipogenesis, insulin sensitivity, energy balance, and lipid biosynthesis. We have previously reported that 4',6-dimethoxyisoflavone-7-O-beta-D-glucopyranoside (Wistin) can activate PPARgamma. The purpose of the present study is to investigate the PPARalpha agonist activity of Wistin. Using a luciferase reporter assay system of PPARalpha in monkey COS7 kidney cells, we showed that Wistin could activate PPARalpha (P < 0.01 at 10 mug/mL) in a dose-dependent manner. Moreover, the addition of Wistin upregulated the expression of PPARalpha (P < 0.01 at 10 mug/mL) and PPARalpha target genes including carnitine palmitoyltransferase 1a (P < 0.05 at 10 mug/mL), acyl-CoA oxidase (P < 0.01 at 10 mug/mL), acyl-CoA synthase (P < 0.05 at 10 mug/mL), PPARgamma coactivator 1alpha (P < 0.05 at 10 mug/mL), uncoupling protein 2 (P < 0.05 at 1 mug/mL), and uncoupling protein 3 (P < 0.05 at 10 mug/mL), which are genes involved in lipid efflux and energy expenditure, in mouse primary hepatocytes. Furthermore, Wistin inhibited cellular triglyceride accumulation in hepatocytes (P < 0.05 at 10 mug/mL) in a dose-dependent manner. These results indicate that Wistin could suppress lipid accumulation through PPARalpha activation. The action of Wistin on PPARalpha could be of interest for the amelioration of lipid metabolic disorders. To the best of our knowledge, Wistin is the first reported isoflavonoid O-glycoside with PPARalpha agonist activity.

Caragasinin C: a new oligostilbene from the roots of Caragana sinica.[Pubmed:28347167]

J Asian Nat Prod Res. 2017 Nov;19(11):1143-1147.

A new oligostilbene, caragasinin C (1), and seven known compounds, betulinic acid (2), 4-hydroxybenzaldehyde (3), (‒)-medicarpin (4), Wistin (5), (2E,4S)-4-hydroxy-2-nonenoic acid (6), pallidol (7), and (+)-alpha-viniferin (8), were isolated from the roots of Caragana sinica. The structure of caragasinin C was established on the basis of spectroscopic techniques, including HRESIMS, 1D and 2D-NMR.

4',6-dimethoxyisoflavone-7-O-beta-D-glucopyranoside (wistin) is a peroxisome proliferator-activated receptor gamma (PPARgamma) agonist that stimulates adipocyte differentiation.[Pubmed:27071611]

Anim Sci J. 2016 Nov;87(11):1347-1351.

Peroxisome proliferator-activated receptor gamma (PPARgamma) is a ligand-dependent transcription factor that directly activates the expression of adipocyte-specific genes, and is universally accepted as the master regulator for adipocyte differentiation. Using a PPARgamma luciferase reporter assay system, we showed that 4',6-dimethoxyisoflavone-7-O-beta-D-glucopyranoside (Wistin) dose-dependently activates PPARgamma. Treatment with Wistin enhanced the marker of adipocyte differentiation, such as triglyceride accumulation in 3T3-L1 cells. Real-time quantitative polymerase chain reaction showed that Wistin increased the expression of PPARgamma2 messenger RNA. Moreover, the addition of Wistin upregulated the expression of PPARgamma-target genes, aP2 and adiponectin in 3T3-L1 cells. To our knowledge, Wistin is the first isoflavonoid O-glycoside that exhibits PPARgamma agonist activity.

[Isoflavones and flavans from Millettia nitida var. hirsutissima].[Pubmed:26591526]

Zhongguo Zhong Yao Za Zhi. 2015 Jun;40(12):2363-6.

The current study to separate and identify constituents from Millettia nitida var. hirsutissima. The compounds from Millettia nitida var. hirsutissima were isolated by means of various chromatographic techniques such as column chromatography over ODS and Sephadex LH-20, preparative HPLC, and the structures of these isolated compounds were identified through spectroscopic analyses. Nine isoflavonoids and two flavans were isolated and identified as 5-O-methy genistein (1), 7-hydroxy-3',4'-dimethoxyisoflavone (2), ononin (3), catechin (4), formononetin (5), genistein (6), calycosin (7), (-)-gallocatechin (8), sissotrin (9), Wistin (10), daidzin (11). Compounds 1, 2, 9 are obtained from the genus Millettia for the first time,and compounds 4, 8 are isolated from this plant for the first time.

[A novel isoflavone glycoside from Caragana alaica].[Pubmed:11696899]

Bioorg Khim. 2000 Nov;26(11):877-80.

3-O-Rhamnopyranosylisorhamnetin, 3-O-glucopyranosylisorhamnetin, 7-O-galactopyranosylluteolin, quercitrin isoquercitrin, Wistin, and a novel isoflavonoid, 3'-hydroxy-6,4'-dimethoxy-7-O-beta-D-glucopyranosylisoflavone, were isolated from the aerial parts of Caragana alaica. Of these, the previously described compounds were identified on the basis of their physicochemical and spectral characteristics, whereas the spectral analysis and conversion to a known compound, cladrastin, allowed the structural elucidation of the novel isoflavone glycoside.