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3',4',7-Trihydroxyisoflavone

(Synonyms: 3',4',7-三羟基异黄酮) 目录号 : GC40618

A natural isoflavone

3',4',7-Trihydroxyisoflavone Chemical Structure

Cas No.:485-63-2

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25mg
¥599.00
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50mg
¥1,020.00
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100mg
¥1,669.00
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250mg
¥3,730.00
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产品描述

3',4',7-Trihydroxyisoflavone is a natural isoflavonoid that has antioxidant activity. It can be produced by the metabolism of daidzein or daidzin . 3',4',7-Trihydroxyisoflavone inhibits several signaling pathways in cells, including tyrosinase-mediated melanin formation (IC50 = 5.2 µM), casein kinase II-mediated phosphorylation of 60S acidic ribosomal P proteins, and cyclin-dependent, kinase-regulated cell proliferation.

Chemical Properties

Cas No. 485-63-2 SDF
别名 3',4',7-三羟基异黄酮
Canonical SMILES OC1=CC=C(C(C(C2=CC(O)=C(O)C=C2)=CO3)=O)C3=C1
分子式 C15H10O5 分子量 270.2
溶解度 DMF: 20 mg/ml,DMF:PBS (pH 7.2) (1:4): 0.1 mg/ml,DMSO: 10 mg/ml,Ethanol: 1 mg/ml 储存条件 Store at -20°C
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1 mM 3.701 mL 18.5048 mL 37.0096 mL
5 mM 0.7402 mL 3.701 mL 7.4019 mL
10 mM 0.3701 mL 1.8505 mL 3.701 mL
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Research Update

Regioselective hydroxylation of isoflavones by Streptomyces avermitilis MA-4680

J Biosci Bioeng 2009 Jul;108(1):41-6.PMID:19577190DOI:10.1016/j.jbiosc.2009.02.021.

Screening of bacterial whole cells was performed for regioselective hydroxylation of daidzein and genistein. Among the strains examined, Streptomyces avermitilis MA-4680 showed high ortho-dihydroxylation activity to produce 3',4',7-Trihydroxyisoflavone and 3',4',5,7-tetrahydroxyisoflavone from daidzein (4',7-dihydroxyisoflavone) and genistein (4',5,7-trihydroxyisoflavone), respectively. Using 100 mg cells (wet wt.) and 1% (v/v) Triton X100 in 1 ml of total reaction volume, where 100 microl of the substrate solution (0.5 mM in 10% (v/v) mixed solvent of DMSO:MeOH = 3:7) was added to 900 microl of potassium phosphate buffer (100 mM, pH 7.2), a 16% molar conversion yield of 3',4',7-Trihydroxyisoflavone was obtained from 0.5 mM daidzein after 24 h of reaction time at 28 degrees C and 200 rpm. Ketoconazole significantly (ca. 90%) inhibited the ortho-hydroxylation activity of daidzein, suggesting that cytochrome P450 enzymes putatively play roles in regiospecific daidzein hydroxylation. The analysis of the reaction products was determined by gas chromatography/mass spectrometry (GC/MS) and (1)H NMR.

Production of a novel O-methyl-isoflavone by regioselective sequential hydroxylation and O-methylation reactions in Streptomyces avermitilis host system

Biotechnol Bioeng 2013 Oct;110(10):2591-9.PMID:23592181DOI:10.1002/bit.24931.

Distinct isoflavone O-methyltransferases (IOMTs) from Streptomyces species were isolated and expressed using S. avermitilis host system. Previously reported isoflavone 7-O-methyltransferases (I7OMTs, E.C. 2.1.1.150) and two putative O-methyltransferases (OMTs) from Saccharopolyspora erythraea were selected by comparative sequence grouping and expressed in S. avermitilisΔSaOMT2 under the control of constitutive ermE promoter. During whole-cell biotransformation of 4',7-dihydroxyisoflavone (daidzein) by constructed recombinant strains, production of O-methylated daidzein was investigated. S. avermitilisΔSaOMT2::SeOMT3 (SeOMT3) produced 7-methoxy-4'-hydroxyisoflavone (7-OMD) with 4.5% of low conversion yield due to competitive oxidation reactions. However, SeOMT3 could produce a novel 4',7-dihydroxy-3'-methoxyisoflavone (3'-OMD) (<1%) resulted from subsequent 3'-O-methylation of 3',4',7-Trihydroxyisoflavone (3'-OHD) which was a hydroxylated product catalyzed by oxygenases. Although external addition of SAM did not change the conversion yield of O-methylation reaction, co-expression of SAM synthetase gene (metK) with SeOMT3 greatly induced the regiospecific O-methylation reaction at 3'-hydroxyl group with final conversion of 12.1% using 0.1 mM of daidzein.

Inhibitory effects of isoflavonoids on rat prostate testosterone 5α-reductase

J Acupunct Meridian Stud 2012 Dec;5(6):319-22.PMID:23265084DOI:10.1016/j.jams.2012.07.022.

Testosterone 5α-reductase inhibitors represent important therapeutic drugs for use against androgen-dependent diseases such as benign prostatic hyperplasia, male pattern baldness, and acne. We have searched for inhibitors of rat prostate testosterone 5α-reductase in the cultured broths of many kinds of soil bacteria, and have found that cultured soybean-casein digest broths of certain bacterial strains have a potent inhibitory effect on the enzyme. We tested 10 selected isoflavonoids, including isoflavones and O-methylated isoflavones, for inhibitory effects on rat prostate testosterone 5α-reductase to determine the important structural elements for inhibition of the enzyme. Genistein, biochanin A, equol, and 3',4',7-Trihydroxyisoflavone showed considerably higher inhibitory effects whereas daidzein, formononetin, glycitein, prunetin, ipriflavone, and 4',7-dimethoxyisoflavone showed lower inhibitory effects. The IC(50) values of genistein, biochanin A, equol, 3',4',7-Trihydroxyisoflavone, and riboflavin, a positive control, for rat prostate testosterone 5α-reductase were 710 μm, 140 μm, 370 μm, 690 μm, and 17 μm, respectively. Daidzein, genistein, biochanin A, formononetin, and equol are already known to be testosterone 5α-reductase inhibitors, but this is the first characterization of 3',4',7-Trihydroxyisoflavone as an inhibitor of the enzyme.

Biotransformation of Daidzein, Genistein, and Naringenin by Streptomyces Species Isolated from High-Altitude Soil of Nepal

Int J Microbiol 2021 Jun 19;2021:9948738.PMID:34249126DOI:10.1155/2021/9948738.

Flavonoids have achieved widespread importance in pharmaceutical, food, and cosmetics industries. Furthermore, modification of these naturally occurring flavonoids to structurally diverse compounds through whole cell biotransformation with enhanced biological activities has numerous biotechnological applications. The present study investigated the biotransformation potential of Streptomyces species isolated from a high-altitude-soil sample towards selected flavonoid molecules. The biotransformed metabolites were confirmed by comparing the HPLC chromatogram with authentic compounds and LC-MS/MS analysis. Of these isolates, Streptomyces species G-18 (Accession number: MW663767.1) catalyzed isoflavone molecules daidzein and genistein to produce hydroxylated products at 24 h of reaction condition in a whole cell system. The hydroxylation of daidzein (4',7-dihydroxyisoflavone) was confirmed at 3'-position of the B ring to produce 3',4',7-Trihydroxyisoflavone. In addition, Streptomyces species G-14 (Accession number: MW663770.1) and Streptomyces species S4L (Accession number: MW663769.1) also revealed the transformation of daidzein (4',7-dihydroxyisoflavone) to hydroxy daidzein at a distinct position than that of G-18 isolates, whereas thee Streptomyces species S4L reaction mixture with naringenin as a substrate also revealed the hydroxylated product. Our results demonstrated that microorganisms isolated from different ecological niches have broad application.

Pharmacological chaperones increase residual β-galactocerebrosidase activity in fibroblasts from Krabbe patients

Mol Genet Metab 2014 Aug;112(4):294-301.PMID:24913062DOI:10.1016/j.ymgme.2014.05.009.

Krabbe disease or globoid cell leukodystrophy is a degenerative, lysosomal storage disease resulting from the deficiency of β-galactocerebrosidase activity. This enzyme catalyzes the lysosomal hydrolysis of galactocerebroside and psychosine. Krabbe disease is inherited as an autosomal recessive trait, and many of the 70 disease-causing mutations identified in the GALC gene are associated with protein misfolding. Recent studies have shown that enzyme inhibitors can sometimes translocate misfolded polypeptides to their appropriate target organelle bypassing the normal cellular quality control machinery and resulting in enhanced activity. In search for pharmacological chaperones that could rescue the β-galactocerebrosidase activity, we investigated the effect of α-Lobeline or 3',4',7-Trihydroxyisoflavone on several patient-derived fibroblast cell lines carrying missense mutations, rather than on transduced cell lines. Incubation of these cell lines with α-lobeline or 3',4',7-Trihydroxyisoflavone leads to an increase of β-galacocerebrosidase activity in p.G553R + p.G553R, in p.E130K + p.N295T and in p.G57S + p.G57S mutant forms over the critical threshold. The low but sustained expression of β-galactocerebrosidase induced by these compounds is a promising result; in fact, it is known that residual enzyme activity of only 15-20% is sufficient for clinical efficacy. The molecular interaction of the two chaperones with β-galactocerebrosidase is also supported by in silico analysis. Collectively, our combined in silico-in vitro approach indicate α-lobeline and 3',4',7-Trihydroxyisoflavone as two potential pharmacological chaperones for the treatment or improvement of quality of life in selected Krabbe disease patients.