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Irisolidone
Irisolidone
ChemFaces products have been cited in many studies from excellent and top scientific journals
Product Name Irisolidone
Price:
CAS No.: 2345-17-7
Catalog No.: CFN93085
Molecular Formula: C17H14O6
Molecular Weight: 314.29 g/mol
Purity: >=98%
Type of Compound: Flavonoids
Physical Desc.: Powder
Source: The herbs of Pueraia lobata
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS
Similar structural: Comparison
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Related Screening Libraries
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Biological Activity
Description: Irisolidone is a potent volume-regulated anion channel (VRAC) current inhibitor, it exhibits high efficacy for VRAC blockade with IC50s of 5-13 uM. Irisolidone shows anti-inflammatory, anti-platelet aggregation, hepatoprotective, and α-amylase inhibitory activities, it may attenuate ethanol-induced gastritis by inhibiting the infiltration of immune cells, particularly neutrophils, through the regulation of CXCL-4 or IL-8 secretion. Irisolidone shows potent inhibitory activity against Helicobacter pylori. Irisolidone also shows antiproliferative activity against amelanotic melanoma cells.
Targets: IL Receptor | NF-kB | TNF-α | COX | IkB | PGE | NO | BChE | AChR | ATPase | Potassium Channel | IKK | VRAC
In vitro:
Pflugers Arch. 2018 Jun 30.
Natural and synthetic flavonoids, novel blockers of the volume-regulated anion channels, inhibit endothelial cell proliferation.[Pubmed: 29961148]
Natural flavonoids are ubiquitous in dietary plants and vegetables and have been proposed to have antiviral, antioxidant, cardiovascular protective, and anticancer effects. Volume-regulated anion channels (VRACs), which are essential for cell volume regulation, have been proposed to play a key role in cell proliferation and migration, apoptosis, transepithelial transport, and cancer development.
METHODS AND RESULTS:
In this study, we screened a group of 53 structurally related natural flavonoids and three synthetic flavonoids for their inhibitory activities on VRAC currents. A whole-cell patch technique was used to record VRAC currents in the human embryonic kidney (HEK) 293 and human umbilical vein endothelial (HUVEC) cells. The 5'-bromo-2-deoxyuridine (BrdU) assay technique was used to investigate cell proliferation. At 100 μM, 34 of 53 compounds significantly inhibited hypotonic extrasolution-induced VRAC currents by > 50% in HEK293 cells. Among these compounds, luteolin, baicalein, eupatorin, galangin, quercetin, fisetin, karanjin, Dh-morin, genistein, Irisolidone, and prunetin exhibited the highest efficacy for VRAC blockade (the mean inhibition > 80%) with IC50s of 5-13 μM and Emaxs of about 87-99%. We also studied the effects of three synthetic flavonoids on VRAC currents in HEK293 cells. Flavoxate showed high inhibition efficacy toward VRAC currents (IC50 = 2.3 ± 0.3 μM; Emax = 91.8% ± 2.7%). Finally, these flavonoids inhibited endogenous VRAC currents and cell proliferation in endothelial cells.
CONCLUSIONS:
This study demonstrates that natural and synthetic flavonoids are potent VRAC current inhibitors, and VRAC inhibition by flavonoids might be responsible for their anti-angiogenic effects.
J Asian Nat Prod Res. 2009 Jun;11(6):471-81.
Inhibitory activity of isoflavones of Pueraria flowers on nitric oxide production from lipopolysaccharide-activated primary rat microglia.[Pubmed: 20183278 ]
Microglial activation plays an important role in alcohol-induced neuroinflammation. In search for natural medicines that may be of therapeutic potential for alcoholism, two new natural isoflavone glycosides, 6-hydroxybiochanin A-6,7-di-O-beta-d-glucopyranoside (1) and 6-hydroxygenistein-7-O-beta-d-glucopyranoside (2), were isolated from the ethanolic extract of the flowers of Pueraria thomsonii Benth., together with the seven known isoflavones, genistein (3), tectorigenin (4), Irisolidone (5), genistin (7), tectoridin (8), tectorigenin-7-O-beta-d-xylosyl-(1 --> 6)-beta-d-glucopyranoside (9), and 6-hydroxygenistein-6,7-di-O-beta-d-glucopyranoside (11). Moreover, gehuain (6) and kakkalide (10) were obtained from the flowers of Pueraria lobata (Willd.) Ohwi.
METHODS AND RESULTS:
The structures of the new compounds were elucidated by UV, IR, HR-MS, and 1D and 2D NMR spectroscopic methods. Compounds 3-5 substantially inhibited the lipopolysaccharide-induced nitric oxide release from primary cultured rat cortical microglia (IC50: 1.3-9.3 microM). The inhibitory effects of compounds 6, 8, 9, and 11 (IC50: 38-62 microM) were significant but weaker than the above aglycones. However, compounds 1, 2, 7, and 10 showed little inhibitory activity. With regard to the structure-activity relationships of the isoflavonoids for the inhibition of microglial activation, the glycosylation at the C-7 hydroxyl group reduces the inhibitory activity. The methoxylation of 4'-hydroxyl group of 7-glycosylated isoflavonoids reduces the inhibitory activity, while the methoxyl group at the 6-position enhances the activity.
CONCLUSIONS:
The results suggest that isoflavonoids of Pueraria flowers may be of therapeutic potential in alcoholism related to microglial activation.
Fitoterapia. 2009 Jan;80(1):62-7.
Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents.[Pubmed: 19000749 ]
The present study describes for the first time the in vitro properties of Iris pseudopumila flowers and rhizomes extracts and their constituents.
METHODS AND RESULTS:
The methanolic extract of rhizomes showed significant anti-inflammatory activity through inhibition of NO production in the murine monocytic macrophage cell line RAW 264.7. Among the isolated compounds, those which most effectively inhibited LPS-induced NO production were Irisolidone and 7-methyl-tectorigenin-4'-O-[beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside], with IC(50) values of 23.6 microM and 29.4 microM respectively. Isoorientin and isovitexin exhibited the most promising activity against AChE with IC(50) of 26.8 microM and 36.4 microM, respectively. The same compounds exhibited also the higher activity against BChE.
Arch Pharm Res. 2008 Jul;31(7):886-90.
Anti-platelet effects of flavonoids and flavonoid-glycosides from Sophora japonica.[Pubmed: 18704331 ]

METHODS AND RESULTS:
A methanol extract of Sophora japonica was subjected to anti-platelet activity guided fractionation affording the isolation of four flavonoids and six flavonoid-glycosides: biochanin A (1), Irisolidone (2), genistein (3), sissotrin (4), sophorabioside (5), genistin (6), tectoridin (7), apigenin (8), quercitrin (9), and rutin (10). The structure of each compound was determined by a variety of spectroscopic methods.
CONCLUSIONS:
Among the compounds, 1, 3, and 7 showed approximately 2.5-6.5 fold greater inhibitory effects on arachidonic acid (AA) and U46619 induced platelet aggregation (IC50: 19.9 and 99.8 microM; 20.3 and 53.8 microM; 25.9 and 123.4 microM, respectively) than acetylsalicylic acid (ASA, IC50: 63.0 and 350.0 microM). Compound 2 was an approximately 22-40 fold stronger inhibitor than ASA on AA and U46619 induced aggregation (IC50: 1.6 and 15.6 microM, respectively).
Planta Med. 2001 Mar;67(2):161-3.
In vitro anti-Helicobacter pylori activity of irisolidone isolated from the flowers and rhizomes of Pueraria thunbergiana.[Pubmed: 11301866 ]

METHODS AND RESULTS:
The inhibitory effect of isoflavones isolated from the flowers and rhizomes of Pueraria thunbergiana (Leguminosae) on the growth of Helicobacter pylori (HP) was investigated. Isoflavone glycosides did not inhibit the growth of HP. However, their aglycones, Irisolidone, tectorigenin and genistein, inhibited HP growth.
CONCLUSIONS:
Among them, Irisolidone had the most potent inhibitory activity against HP and its MIC was 12.5-25 micrograms/ml. Genistein only weakly inhibited the urease of HP and H+/K(+)-ATPase of rat stomach: its IC50 were 0.43 and 0.89 mg/ml, respectively.
In vivo:
Mol Nutr Food Res. 2017 Feb;61(2).
Irisolidone attenuates ethanol-induced gastric injury in mice by inhibiting the infiltration of neutrophils.[Pubmed: 27546737]
This study was designed to determine whether Irisolidone and its glycoside kakkalide, which are the major constituents of the flower of Pueraria lobata (Kudzu) can attenuate ethanol-induced gastritic injury in mice.
METHODS AND RESULTS:
Irisolidone and kakkalide inhibited IL-8 secretion and NF-κB activation in lipopolysaccharide-stimulated KATO III cells. Therefore, we investigated their protective effects against ethanol-induced gastric injury in mice. Pretreatment with kakkalide or Irisolidone decreased the area of hemorrhagic ulcerative lesions caused by ethanol and suppressed stomach myeloperoxidase activity, CXCL4 secretion, and NF-κB activation. The ameliorating effect of Irisolidone was more potent than that of kakkalide.
CONCLUSIONS:
Irisolidone may attenuate ethanol-induced gastritis by inhibiting the infiltration of immune cells, particularly neutrophils, through the regulation of CXCL-4 or IL-8 secretion.
Biol Pharm Bull. 2005 Mar;28(3):531-3.
Hepatoprotective effects of irisolidone on tert-butyl hyperoxide-induced liver injury.[Pubmed: 15744084]
To clarify the hepatoprotective effects of kakkalide and its metabolite Irisolidone by human fecal microflora, their effects on tert-butyl hydroperoxide (t-BHP)-injured HepG2 cells and mice were investigated.
METHODS AND RESULTS:
Irisolidone protected HepG2 cells against cytotoxicity induced by t-BHP. However, kakkalide did not protect cytotoxicity. When kakkalide 100 mg/kg was orally administered to mice injured by t-BHP, it significantly inhibited the increase in plasma alanine aminotransferase and aspartate aminotransferase activities by 84% and 85% of t-BHP-treated control group, respectively. The inhibitory effect of kakkalide is much more potent than that of silybin, a hepatoprotective agent. However, intraperitoneally administered kakkalide did not exhibit hepatoprotective activity. When Irisolidone was intraperitoneally administered to mice, it exhibited potent hepatoprotective activity.
CONCLUSIONS:
Based on these findings, Irisolidone can be hepatoprotective and kakkalide may be a prodrug transformed to Irisolidone.
Irisolidone Description
Source: The herbs of Pueraia lobata
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

Cell. 2018 Jan 11;172(1-2):249-261.e12.
doi: 10.1016/j.cell.2017.12.019.
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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1818 mL 15.9089 mL 31.8177 mL 63.6355 mL 79.5444 mL
5 mM 0.6364 mL 3.1818 mL 6.3635 mL 12.7271 mL 15.9089 mL
10 mM 0.3182 mL 1.5909 mL 3.1818 mL 6.3635 mL 7.9544 mL
50 mM 0.0636 mL 0.3182 mL 0.6364 mL 1.2727 mL 1.5909 mL
100 mM 0.0318 mL 0.1591 mL 0.3182 mL 0.6364 mL 0.7954 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Kinase Assay:
Inflammation. 2011 Oct;34(5):344-51.
Kakkalide and its metabolite irisolidone ameliorate carrageenan-induced inflammation in mice by inhibiting NF-κB pathway.[Pubmed: 20686830]
The anti-inflammatory activities of kakkalide, a major constituent of the flower of Pueraria thunbergiana, and Irisolidone, a metabolite of kakkalide produced by intestinal microflora, against carrageenan-induced inflammation in air pouches on the backs of mice and in lipopolysaccharide (LPS)-stimulated peritoneal macrophages were investigated.
METHODS AND RESULTS:
Kakkalide and Irisolidone down-regulated the gene expression of cytokines [tumor necrosis factor alpha (TNF-α) and interleukin-1 beta (IL-1β)] and cyclooxygenase-2 (COX-2) and the production of pro-inflammatory cytokines, TNF-α and IL-1β, and inflammatory mediators, NO and prostaglandin E(2) (PGE(2)), in LPS-stimulated peritoneal macrophages. These agents also inhibited the phosphorylation of IκB-α and the nuclear translocation of nuclear factor-kappa B (NF-κB). Orally administered kakkalide and Irisolidone significantly reduced carrageenan-induced inflammatory markers, leukocyte number, and protein amount in the exudates of the air pouch. These constituents also inhibited PGE(2) production and COX-2 inducible nitric oxide synthase, IL-1β, and TNF-α expression. These agents also inhibited NF-κB activation. The anti-inflammatory effects of Irisolidone were more potent than those of kakkalide.
CONCLUSIONS:
Based on these findings, kakkalide and Irisolidone may inhibit inflammatory reactions via NF-κB pathway, and Irisolidone, a metabolite of kakkalide, may more potently inhibit these inflammatory reactions.
Cell Research:
Z Naturforsch C. 2009 Jul-Aug;64(7-8):490-4.
Antiproliferative activity on human cancer cell lines after treatment with polyphenolic compounds isolated from Iris pseudopumila flowers and rhizomes.[Pubmed: 19791498]
The present study describes the antiproliferative properties of Iris pseudopumila flowers and rhizomes extracts and fourteen constituents isolated from them.
METHODS AND RESULTS:
The in vitro cytotoxic activity assay against two human cancer cell lines, large lung carcinoma (CORL-23) and amelanotic melanoma (C32), showed that the most antiproliferative extract was the MeOH extract from flowers with a percentage of inhibition of 50.9 at 100 microg/ml against amelanotic melanoma cells. The most antiproliferative compounds against amelanotic melanoma cells were kaempferol-3-O-beta-D-glucopyranoside and Irisolidone with a percentage of inhibition of 100 and 96.6, respectively, and against large lung carcinoma cells with a percentage of inhibition of 82.1 and 84.6, respectively. Significant activity on the amelanotic melanoma cell line was also showed by irigenin-7-O-beta-D-glucopyranoside, with a percentage of inhibition of 89.3. The compounds isovitexin and isoorientin-6-O''-beta-D-glucopyranoside showed a selective activity against amelanotic melanoma cells with a percentage of inhibition of 83.2 and 79.8, respectively.
Structure Identification:
Bioorg Chem. 2017 Feb;70:192-198.
8-Hydroxyirilone 5-methyl ether and 8-hydroxyirilone, new antioxidant and α-amylase inhibitors isoflavonoids from Iris germanica rhizomes.[Pubmed: 28069265]
Iris species are well recognized as wealthy sources of isoflavonoids.
METHODS AND RESULTS:
In the present study, phytochemical investigation of the rhizomes of Iris germanica (Iridaceae) procure the isolation of two new isoflavonoids namely, 8-hydroxyirilone 5-methyl ether (2) and 8-hydroxyirilone (3), along with eight known isoflavonoids: irilone 4'-methyl ether (1), irilone (4), Irisolidone (5), irigenin S (6), irigenin (7), irilone 4'-O-β-d-glucopyranoside (8), iridin S (9), and iridin (10). The isolated flavonoids were structurally characterized with the assist of comprehensive spectroscopic analyses (UV, IR, 1D and 2D NMR, and HRMS) and comparing with the published data. They were estimated for their antioxidant and antidaibetic capacities using DPPH and α-amylase inhibition assays, respectively.
CONCLUSIONS:
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