Desmethylglycitein
(Synonyms: 4',6,7-三羟基异黄酮; 4',6,7-Trihydroxyisoflavone) 目录号 : GC38482An active metabolite of daidzein
Cas No.:17817-31-1
Sample solution is provided at 25 µL, 10mM.
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- Purity: >98.00%
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6,7,4’-Trihydroxyisoflavone is an active metabolite of the phytoestrogen daidzein .1,2,3,4 It suppresses anchorage-dependent and -independent growth of HCT116 and DLD-1 colon cancer cells, as well as induces cell cycle arrest at the S and G2/M phases in HCT116 cells when used at concentrations ranging from 12.5 to 100 ?M.1 6,7,4'-Trihydroxyisoflavone (40 and 80 ?M) inhibits adipogenesis in 3T3-L1 preadipocytes induced by isobutylmethylxanthine, dexamethasone, and insulin (MDI).2 In vivo, 6,7,4'-trihydroxyisoflavone (5 mg/kg) reverses scopolamine-induced memory impairments and increases hippocampal brain-derived neurotrophic factor (BDNF) and CREB levels in mice.3 It also prevents LPS-induced bone loss in mice.4
1.Lee, D.E., Lee, K.W., Jung, S.K., et al.6,7,4'-Trihydroxyisoflavone inhibits HCT-116 human colon cancer cell proliferation by targeting CDK1 and CDK2Carcinogenesis32(4)629-635(2011) 2.Seo, S.G., Yang, H., Shin, S.H., et al.A metabolite of daidzein, 6,7,4'-trihydroxyisoflavone, suppresses adipogenesis in 3T3-L1 preadipocytes via ATP-competitive inhibition of PI3KMol. Nutr. Food Res.57(8)1446-1455(2013) 3.Ko, Y.-H., Kim, S.Y., Lee, S.-Y., et al.6,7,4'-Trihydroxyisoflavone, a major metabolite of daidzein, improves learning and memory via the cholinergic system and the p-CREB/BDNF signaling pathway in miceEur. J. Pharmacol.826140-147(2018) 4.Kim, E.-N., Kim, Y.G., Lee, J.-H., et al.6,7,4'-Trihydroxyflavone inhibits osteoclast formation and bone resorption in vitro and in vivoPhytother. Res.33(11)2948-2959(2019)
Cas No. | 17817-31-1 | SDF | |
别名 | 4',6,7-三羟基异黄酮; 4',6,7-Trihydroxyisoflavone | ||
Canonical SMILES | O=C1C(C2=CC=C(O)C=C2)=COC3=CC(O)=C(O)C=C13 | ||
分子式 | C15H10O5 | 分子量 | 270.24 |
溶解度 | DMSO: 125 mg/mL (462.55 mM) | 储存条件 | Store at 2-8°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 3.7004 mL | 18.5021 mL | 37.0041 mL |
5 mM | 0.7401 mL | 3.7004 mL | 7.4008 mL |
10 mM | 0.37 mL | 1.8502 mL | 3.7004 mL |
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% DMSO % % Tween 80 % saline | ||||||||||
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2.
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Molecular action of larvicidal flavonoids on ecdysteroidogenic glutathione S-transferase Noppera-bo in Aedes aegypti
BMC Biol 2022 Feb 17;20(1):43.PMID:35172816DOI:10.1186/s12915-022-01233-2.
Background: Mosquito control is a crucial global issue for protecting the human community from mosquito-borne diseases. There is an urgent need for the development of selective and safe reagents for mosquito control. Flavonoids, a group of chemical substances with variable phenolic structures, such as daidzein, have been suggested as potential mosquito larvicides with less risk to the environment. However, the mode of mosquito larvicidal action of flavonoids has not been elucidated. Results: Here, we report that several flavonoids, including daidzein, inhibit the activity of glutathione S-transferase Noppera-bo (Nobo), an enzyme used for the biosynthesis of the insect steroid hormone ecdysone, in the yellow fever mosquito Aedes aegypti. The crystal structure of the Nobo protein of Ae. aegypti (AeNobo) complexed with the flavonoids and its molecular dynamics simulation revealed that Glu113 forms a hydrogen bond with the flavonoid inhibitors. Consistent with this observation, substitution of Glu113 with Ala drastically reduced the inhibitory activity of the flavonoids against AeNobo. Among the identified flavonoid-type inhibitors, Desmethylglycitein (4',6,7-trihydroxyisoflavone) exhibited the highest inhibitory activity in vitro. Moreover, the inhibitory activities of the flavonoids correlated with the larvicidal activity, as Desmethylglycitein suppressed Ae. aegypti larval development more efficiently than daidzein. Conclusion: Our study demonstrates the mode of action of flavonoids on the Ae. aegypti Nobo protein at the atomic, enzymatic, and organismal levels.
UHPLC method for the simultaneous determination of β-blockers, isoflavones and their metabolites in human urine
J Chromatogr B Analyt Technol Biomed Life Sci 2011 Mar 15;879(9-10):615-26.PMID:21345747DOI:10.1016/j.jchromb.2011.01.026.
A rapid-resolution ultra high-performance liquid chromatography separation method (UHPLC) for the simultaneous determination of the following β-blockers: milrinone, sotalol, metoprolol, propranolol and carvedilol, and their metabolites: 5'-hydroxylphenyl-carvedilol, O-desmethylcarvedilol, 4-hydroxypropranolol, α-hydroxy-metoprolol, O-desmethyl-metoprolol; the following isoflavones: genistein, daidzein, glycitin, glycitein, puerarin and biochanin A; as well as their metabolites: dihydrogenistein, Desmethylglycitein, 8-hydroxygenistein, daidzein-7,4'-diglucoside, 8-hydroxydaidzein, dihydrobiochanin A in human urine was optimized. The analysed compounds were extracted from human urine by means of solid phase extraction (SPE). The effective UHPLC separation of the examined compounds was applied on a Hypersil GOLD™ (50 mm×2.1 mm, 1.9 μm) column with a gradient mobile phase system and a UV detector. The complete separation of all analytes was achieved within 8.0 min. The method was validated for the determination of the aforementioned substances in human urine. The linear ranges, limits of detection (LOD) and limits of quantification (LOQ) for β-blockers, isoflavones and their metabolites were determined. The intra- and inter-day precision (%C.V.) was less than 4.48%, and the intra-day and inter-day accuracy was less than 4.74%. The tested SPE sorbent proved that appropriate absolute recoveries can be obtained for Oasis HLB (Waters). The mean recovery of the analytes, using the new SPE procedure, amounted from 70.14% to 99.85%. The present paper reports, for the first time, the method for the determination of β-blockers, isoflavones and their metabolites in human urine samples. The newly developed method was suitably validated and successfully applied for the analysis of the certain of the aforementioned analytes in human urine samples obtained from the patients suffering cardiovascular disease.