- Hydrolysis of isoflavone glycosides by a thermostable β-glucosidase from pyrococcus furiosus
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The recombinant β-glucosidase from the hyperthermophilic archaeon Pyrococcus furiosus was purified with a specific activity of 330 U/mg for genistin by His-trap chromatography. The specific activity of the purified enzyme followed the order genistin > daidzin > glycitin> malonyl glycitin > malonyl daidzin > malonyl genistin. The hydrolytic activity for genistin was highest at pH 6.0 and 95 °C with a half-life of 59 h, a K m of 0.5 mM, and a kcat of 6050 1/s. The enzyme completely hydrolyzed 1.0 mM genistin, daidzin, and glycitin within 100, 140, and 180 min, respectively. The soybean flour extract at 7.5% (w/v) contained 1.0 mM genistin, 0.9 mM daidzin, and 0.3 mM glycitin. Genistin, daidzin, and glycitin in the soybean flour extract were completely hydrolyzed after 60, 75, and 120 min, respectively. Of the reported β-glucosidases, P. furiosus β -glucosidase exhibited the highest thermostability, kcat, k cat/Km, yield, and productivity for hydrolyzing genistin. These results suggest that this enzyme may be useful for the industrial hydrolysis of isoflavone glycosides.
- Yeom, Soo-Jin,Kim, Bi-Na,Kim, Yeong-Su,Oh, Deok-Kun
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- A new isoflavone glycoside from the stem bark of Sophora japonica
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A new isoflavone glycoside, 6-methoxy-7-hydroxy-4′-O-β-d- glucosyl isoflavone, glycitein-4′-O-β-d-glucoside (10), along with nine known flavonoids, were isolated from the stem bark of Sophora japonica. The structures of these compounds were determined by analysis of spectroscopic data (1D -, 2D - NMR and HRMS). The inhibitory effects of all the isolated compounds on aldose reductase were evaluated in vitro. Among these compounds, daidzein (1), puerol A (4), and paratensein-7-O-glucoside (9) exhibited potent inhibitory effects, with IC50 values of 3.2, 6.4, and 1.9 μM, respectively.
- Park, Hyun Young,Kim, Soo Hee,Kim, Gi Beom,Sim, Jae Young,Lim, Soon Sung,Kim, Myong Jo,Chun, Wanjoo,Kwon, Yong Soo
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- A simple synthesis of 7,4′-dihydroxy-6-methoxyisoflavone, glycitein, the third soybean isoflavone
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4-Methoxyresorcinol (3) was synthesized as the precursor for glycitein (6) synthesis by the oxidation of 3-hydroxy-4-methoxybenzaldehyde (1) to the aryl formate with H2O2 and a catalytic amount of SeO2. Glycitein (6) was synthesized by cyclization of 2,4,4′-trihydroxy-5-methoxydeoxybenzoin (5) with N,N-dimethylformamide, boron trifluoride diethyl ether, and methanesulfonyl chloride in a microwave oven.
- Lang'at-Thoruwa, Caroline,Song, Tong T.,Hu, Jiang,Simons, Andrean L.,Murphy, Patricia A.
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- Invention relates to a soybean in the process of synthesis method
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The present invention relates to organic chemical and technical field of drug synthesis, relates to a soybean flavins and its analogue synthetic method, the soybean flavins that 6 - methoxy - 4', 7 - dihydroxy isoflavone. The invention push-type apparatus shown synthetic route, to synthesize soybean flavins that 6 - methoxy - 4', 7 - dihydroxy isoflavone and its analogs, synthetic route of the present invention high yield, the operation is simple, mild condition, suitable for large-scale preparation.
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- Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities
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Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10') were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1- diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12-54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E-I) and their biphenyl-ketone derivatives (10E-H) also showed a high activity (ED50=50=26-32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3'-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10') by metabolism or biotransformation.
- Goto, Hideyuki,Terao, Yoshiyasu,Akai, Shuji
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experimental part
p. 346 - 360
(2009/12/27)
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- Anti-inflammatory mechanisms of isoflavone metabolites in lipopolysaccharide-stimulated microglial cells
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The microglial activation plays an important role in neurodegenerative diseases by producing several proinflammatory cytokines and nitric oxide (NO). We found that three types of isoflavones and their metabolites that are transformed by the human intestin
- Park, Jin-Sun,Woo, Moon-Sook,Kim, Dong-Hyun,Hyun, Jin-Won,Kim, Won-Ki,Lee, Jae-Chul,Kim, Hee-Sun
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p. 1237 - 1245
(2008/01/27)
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- Isoflavan and isoflavene compounds and their use as angiogenesis inhibitors
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The present invention is directed to the use of a group of isoflavan and isoflav-3-ene compounds having the formula wherein R1 and R2 independently have the meaning of a hydroxy group, or a group that decreases the metabolism or increases the bioavailability of the compound, and the dotted line means an optional double bond, for the treatment of pathological conditions associated with or dependent on enhanced or abnormal angiogenesis in a mammal. The invention also concerns a group of novel isoflavan and isoflav-3-ene compounds.
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(2008/06/13)
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- METHOD FOR PURIFYING AND SEPARATING SOY ISOFLAVONES
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A method for purifying isoflavones glycosides of genistin and daidzin from impurities present in a soy isoflavones concentrate. The method includes digesting a soy isoflavones concentrate with an acidic solution and separating insoluble solids from the acidic solution, wherein the solids are enriched in genistin and comprise glycosides of genistin and daidzin.
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- SYNTHESIS OF 13C-LABELLED ESTROGEN ANALOGUES
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There is provided a method of producing novel 13C-labelled estrogen analogues. The method preferably proceeds via an intermediate A or B or which is a mixture of (A) or (B): wherein a13C atom is located at one or more of positions 1, 2, 3 or 4 and wherein R is an optionally substituted alkane, alkene, alkyne or aryl group. Preferably R is -CH2Ph. An alternative preferred intermediate compound is 13C-resorcinol.
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- Synthesis of 4′,7-dihydroxy-6-methoxyisoflavone 7-O-β-D-glucopyranoside (glycitin)
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The aglycone glycitein (1) of the title glucoside glycitin (2) was prepared by oxidative rearrangement of the fully protected chalcone 4 by Tl(NO3)3 in MeOH into 5 followed by deprotection and ring closure. Its glucosylation with α-acetobromoglucose and subsequent saponification gave 2 as the main product. VCH Verlagsgesellschaft mbH, 1996.
- Nogradi, Mihaly,Szoellosy, Aron
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p. 1651 - 1652
(2007/10/03)
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- O-methylation of flavonoids by cell-free extracts of calamondin orange
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Cell-free extracts of calamondin orange (Citrus mitis) catalysed the O-methylation of almost all hydroxyls of a number of flavonoids, indicating the existence in citrus tissues of ortho, meta, para and 3-O-methyltransferases. The latter, hitherto unreported enzyme, catalysed the formation of 3-O-methyl ethers of galangin and quercetin. The stepwise O-methylation of a number of compounds, especially quercetin and quercetagetin, tends to suggest a coordinated sequence of O-methylations on the surface of a multienzyme complex. The methyl acceptor abilities of the flavonoid substrates used are discussed in relation to their hydroxyl substitution patterns and their negative electron density distribution.
- Brunet, Gunter,Ibrahim, Ragai K.
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p. 741 - 746
(2007/10/02)
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