- Hydrolysis of soybean isoflavonoid glycosides by Dalbergia β-glucosidases
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Two β-glucosidases from the legumes Dalbergia cochinchinensis and Dalbergia nigrescens were compared for their ability to hydrolyze isoflavonoid glycosides from soybean. Both D. nigrescens and D. cochinchinensis β-glucosidases could hydrolyze conjugated soybean glycosides, but D. nigrescens β-glucosidase hydrolyzed both conjugated and nonconjugated glycosides in crude soybean extract more rapidly. The kinetic properties K m, kcat, and kcat/Km of the Dalbergia β-glucosidases toward conjugated isoflavonoid glycosides, determined using high-performance liquid chromatography, confirmed the higher efficiency of the D. nigrescens β-glucosidase in hydrolyzing these substrates. The D. nigrescens β-glucosidase could also efficiently hydrolyze isoflavone glycosides in soy flour suspensions, suggesting its application to increase free isoflavones in soy products.
- Chuankhayan, Phimonphan,Rimlumduan, Thipwarin,Svasti, Jisnuson,Ketudat Cairns, James R.
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- Deglycosylation of isoflavonoid glycosides from maackia amurensis cell culture by β-D-glucosidase from littorina sitkana hepatopancrease
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Maakia amurensis (strain A-18) cell culture synthesizes a significant quantity of isoflavonoids, a large part of which consists of isoflavone glucosides and malonylglucosides. β-D-Hydrolase enzyme complexes from the marine mollusk Littorina sitkana and the marine mycelial fungus P. canescens were used to obtain isoflavones from their conjugated forms. The specificity of β-D-glucanases from L. sitkana for various glycosides was studied. The deglycosylation efficiency depended on the aglycon structure. The deglycosylated fraction of isoflavonoids obtained from M. amurensis cell culture exhibited antitumor activity.
- Kusaikin,Zakharenko,Ermakova,Veselova,Grigoruk,Fedoreev,Zvyagintseva
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- Anti-inflammatory isoflavonoids from the stems of Derris scandens
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Fractionation of the aqueous extract of Derris scandens stems extract using tests for eicosanoid inhibition resulted in the isolation of three isoflavonoids, genistein, its 7-O-α-rhamno(1→6)-β-glucosyl glycoside, a new compound, and two known isoprenyl derivatives 3′-γ,γ-dimethylallylweighteone and scandenin. The isoprenylated compounds showed a high inhibitory effect on eicosanoid production in vitro but HPLC analysis showed that the genistein accounted for most of the activity of the total extract. Antioxidant studies showed that genistein and the isoprenylated compounds showed activity comparable to standard antioxidants. Genistein and its glycoside demonstrated no cytotoxicity in the MTT test but the prenylated compounds showed some toxicity and also increased LDH release from polymorphonucleocytes, at concentrations much greater than would be encountered in an aqueous extract of D. scandens.
- Laupattarakasem, Pisamai,Houghton, Peter J.,Hoult, J. Robin S.
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- A novel method for the highly efficient biotransformation of genistein from genistin using a high-speed counter-current chromatography bioreactor
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Genistein, an important soybean isoflavone compound, has gained attention for its significant properties. Compared with the glycone form of genistin, low content of genistein limits the use in food and pharmaceutical fields. In this study, a novel bioreactor with high-speed counter-current chromatography (HSccc) was built for the highly efficient biotransformation of genistein from genistin. The solvent system for the bioreactor was selected according to the KD values. The selected solvent system was evaluated by the enzyme activity of β-glucosidase. An ethyl acetate/buffer solution was selected as the preferred solvent system for the HSccc bioreactor. Optimum reactor parameters were selected according to the retention of the stationary phase. The HSccc bioreactor was operated using different flow rates, and 2.0 mL min-1 was chosen as the optimal flow rate with a conversion rate of over 90% within 24 h; the novel bioreactor easily immobilized and recycled the enzyme and could be applied in the preparation of genistein.
- Wang, Daijie,Khan, Muhammad Shafiq,Cui, Li,Song, Xiangyun,Zhu, Heng,Ma, Tianyu,Li, Xiaoyu,Sun, Rong
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- Chevalierinoside B and C: Two new isoflavonoid glycosides from the stem bark of Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri Beille)
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Chevalierinosides B (1) and C (2), two new isoflavonoid glycosides, characterized as biochanin A 7-O-[β-d-apiofuranosyl-(1→2)-β-d- glucopyranoside] and genistein 7-O-[β-d-apiofuranosyl-(1→2)-β-d- glucopyranoside], together with the known isoflavonoids, chevalierinoside A (3) and genistein 7-O-β-d-glucopyranoside (4), kaempferol 3-O-β-d- glucopyranoside (5) and triterpenes, friedelin (6), betulinic acid (7), 30-oxobetulinic acid (8), 30-hydroxybetulinic acid (9), were isolated from the stem bark of Antidesma laciniatum Muell. Arg. (syn. Antidesma chevalieri Beille). Their structures were established by direct interpretation of their spectral data, mainly HR-TOFESIMS, 1D-NMR (1H, 13C and DEPT) and 2D-NMR (COSY, NOESY, TOCSY, HSQC and HMBC), and by comparison with the literature.
- Djouossi, Marie Geneviève,Mabou, Florence Déclaire,Foning Tebou, Perrin Lanversin,Ngnokam, David,Tapondjou, Leon A.,Harakat, Dominique,Voutquenne-Nazabadioko, Laurence
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- First finding of Daidzein 7-O-phosphate and Genistein 7-O-phosphate that are hydrolyzed by sulfatase
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Attempted structural assignment of two water soluble isoflavone analogs of Daidzein and Genistein, was initially assumed to be the corresponding sulfates on the basis of the facts that these analogs were hydrolyzed by sulfatase; however, they were eventua
- Kanakubo, Akira,Koga, Kazushi,Isobe, Minoru,Fushimi, Tatsushi,Saitoh, Takanobu,Ohshima, Yoshifumi,Tsukamoto, Yoshinori
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- Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation
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In this study, polyhydroxyisoflavones that directly prevent the aggregation of both amyloid β (Aβ) and tau were expediently synthesized via divergent Pd(0)-catalyzed Suzuki-Miyaura coupling and then biologically evaluated. By preliminary structure–activity relationship studies using thioflavin T (ThT) assays, an ortho-catechol containing isoflavone scaffold was proven to be crucial for preventing both Aβ aggregation and tau-mediated neurofibrillary tangle formation. Additional TEM experiment confirmed that ortho-catechol containing isoflavone 4d significantly prevented the aggregation of both Aβ and tau. To investigate the mode of action (MOA) of 4d, which possesses an ortho-catechol moiety, 1H-15N HSQC NMR analysis was thoroughly performed and the result indicated that 4d could directly inhibit both the formation of Aβ42 fibrils and the formation of tau-derived neurofibrils, probably through the catechol-mediated nucleation of tau. Finally, 4d was demonstrated to alleviate cognitive impairment and pathologies related to Alzheimer's disease in a 5XFAD transgenic mouse model.
- Do, Ji Min,Gee, Min Sung,Inn, Kyung-Soo,Kim, Jong-Ho,Kim, Nam Kwon,Kim, Nam-Jung,Lee, Hyun Woo,Lee, Jong Kil,Seo, Min-Duk,Seong, Ji Hye,Son, Seung Hwan,Yoo, Hyung-Seok,Yoo, Ji-Na
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- Continuous flow microchannel synthesis process of flavonoid compounds
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The invention provides a continuous flow microchannel synthesis process of flavonoid compounds. According to the process, hesperidin and iodine elementary substance are used as raw materials and react in a continuous flow microchannel reactor in the presence of a reaction solvent to synthesize the flavonoid compound as shown in a formula A. Compared with a traditional kettle-type preparation process, the process disclosed by the invention has the advantages that the preparation time is obviously shortened, and the conversion rate of raw materials and the yield of products are obviously improved; and especially, when the diosmin is prepared under optimal process conditions of continuous flow microchannel synthesis, the conversion rate of the raw material hesperidin is as high as 96.48%, and the yield of the product diosmin is as high as 81.96%. The continuous flow micro-channel synthesis process provided by the invention is beneficial to realizing safe, efficient and rapid industrial production of flavonoid compounds, and has a wide application prospect.
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Paragraph 0050-0059; 0061
(2021/06/22)
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- Cytosine N-isoflavone compound as well as preparation method and application thereof
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The invention relates to a cytosine N-isoflavone compound as well as a preparation method and application thereof. The compound has a structural formula as shown in the specification, wherein R1 is selected from one of hydroxyl, alkoxy, amido or halo, R2 is selected from one of hydrogen, alkyl or aryl, and R3 is selected from one or a combination of several of hydroxyl, alkoxy, amido or halo. Compared with the prior art, the cytosine N-isoflavone compound has the characteristic that an isoflavone compound serving as a structural unit is spliced to N on the 12th position of cytosine by using acombined synthesis technology, so that a series of cytosine-isoflavone derivatives are synthesized, and a novel active pharmacological action is exerted.
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- Synthesis, Characterization, and Antioxidant Activities of Genistein, Biochanin A, and Their Analogues
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A series of naturally occurring genistein (3) and biochanin A (4) compounds and their analogues were synthesized from phloroglucinol. The structures of all the synthesized compounds were established by the combined use of 1HNMR, 13CNMR, IR spectral data, and mass spectrometry; their antioxidant activities were investigated. Most of the synthesized compounds show moderate-to-high activity; only two compounds exhibit no significant activity.
- Hamza Sherif, Salah,Gebreyohannes, BerihuTekluu
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- Technical Process for Preparation of Genistein
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Development and scale-up of the synthetic process for genistein preparation are described. The process was designed with consideration for environmental and economical aspects and optimized in a laboratory scale. In a scale up, on every step quantity of the environmentally unfriendly substrates or solvents was reduced without compromising the quality of the final product, and the waste load was significantly diminished. The optimal duration times of the individual stages were determined, and the number of operations was reduced, leading to lowering of energy consumption. Elaborated process secures good yield and quality expected for pharmaceutical substances.
- Filip, Katarzyna,Kleczkowska-Plichta, Ewa,Ara?ny, Zbigniew,Grynkiewicz, Grzegorz,Polowczyk, Magdalena,Gabarski, Krzysztof,Trzcińska, Kinga
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p. 1354 - 1362
(2016/07/23)
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- Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones
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In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS.+ and DPPH. radicals with SC50 values of 11.3±0.3 and 9.4±0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9±4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.
- Lu, Tzy-Ming,Ko, Horng-Huey,Ng, Lean-Teik,Hsieh, Yen-Pin
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p. 963 - 979
(2015/06/25)
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- Novel synthesis of 3-phenyl-chromen-4-ones using n-heterocyclic carbene as organocatalyst: An efficient domino catalysis type approach
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Herein is reported a simple and efficient synthesis of isoflavones starting from various substituted phenacyl bromides and salicylaldehydes in presence of NHC. The mechanism involved domino catalysis type approach with consumption and regeneration of catalyst in two catalytic cycles. This method proved to be very lucrative and gives very good yield. The method described here represents an environmentally benign alternative to classical approach.
- Mishra, Priya,Singh, Sarita,Ankit, Preyas,Fatma, Shahin,Singh, Divya,Singh, Jagdamba
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p. 1070 - 1076
(2013/07/28)
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- A new isoflavone from Blepharis ciliaris of an Egyptian origin
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A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6″-O-E-caffeoyl-β-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3″-acetyl-6″-E-p-coumaroyl- β-d-glucopyranoside) (5), naringenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (6), apigenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.
- El-Shanawany, Mohamed A.,Sayed, Hanaa M.,Ibrahim, Sabrin R. M.,Fayed, Marwa A. A.,Radwan, Mohamed M.,Ross, Samir A.
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p. 2346 - 2350
(2013/07/26)
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- 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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scheme or table
p. 1535 - 1541
(2012/05/07)
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- Total synthesis of the pyranoisoflavone kraussianone 1 and related isoflavones
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The first total synthesis of the pyranoisoflavone kraussianone 1 (1) is described. The key steps involved the Suzuki-Miyaura reaction for the construction of the isoflavone core and the regioselective formation of the dimethylpyran scaffolds to the phloroglucinol (ring A) and resorcinol (ring B) moieties of kraussianone 1 (1). This route also provided access to the related isoflavones eriosemaone D (2) and genistein (3) via simple structural modifications.
- Selepe, Mamoalosi A.,Drewes, Siegfried E.,Van Heerden, Fanie R.
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experimental part
p. 1680 - 1685
(2011/02/21)
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- Novel synthesis of the isoflavone genistein
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Genistein was efficiently synthesized from (2,4,6-trihydroxyphenyl)ethanone by a novel five-step procedure involving the formation of an enamino ketone, followed by ring closure and a Suzuki coupling reaction using palladium acetate and poly(ethylene glycol). Georg Thieme Verlag Stuttgart.
- Denis, Jeffrey D. St.,Gordon Iv, James S.,Carroll, Vincent M.,Priefer, Ronny
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experimental part
p. 1590 - 1592
(2010/06/21)
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- Synthesis of Talosin A and B, two bioactive isoflavonoid glycosides
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Talosin A and B, namely genistein 7-O-α-L-6-deoxy-talopyranoside and genistein 4',7-di-O-α-L-6-deoxytalopyranoside, which show excellent antifungal and anti-inflammatory activities, were synthesized concisely.
- Wu, Zhongtao,Lian, Gaoyana,Yu, Biao,Wang, Zhenzhongc,Zhao, Yiwuc,Xiao, Wei
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p. 1725 - 1730
(2011/07/07)
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- A Versatile Microbial System for Biosynthesis of Novel Polyphenols with Altered Estrogen Receptor Binding Activity
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Isoflavonoids possess enormous potential for human health with potential impact on heart disease and cancer, and some display striking affinities for steroid receptors. Synthesized primarily by legumes, isoflavonoids are present in low and variable abundance within complex mixtures, complicating efforts to assess their clinical potential. To satisfy the need for controlled, efficient, and flexible biosynthesis of isoflavonoids, a three-enzyme system has been constructed in yeast that can convert natural and synthetic flavanones into their corresponding isoflavones in practical quantities. Based on the determination of the substrate requirements of isoflavone synthase, a series of natural and nonnatural isoflavones were prepared and their binding affinities for the human estrogen receptors (ERα and ERβ) were determined. Structure activity relationships are suggested based on changes to binding affinities related to small variations on the isoflavone structure.
- Chemler, Joseph A.,Lim, Chin Giaw,Daiss, John L.,Koffas, Mattheos A.G.
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experimental part
p. 392 - 401
(2011/06/28)
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- 7-Hydroxy-benzopyran-4-one derivatives: A novel pharmacophore of peroxisome proliferator-activated receptor α and -γ (PPARα and γ) dual agonists
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Design, synthesis, and in vitro bioevaluation of a new class of potential dual PPARα and γ agonists discovered through a structure-driven design paradigm are described. The 7-hydroxy-benzopyran-4-one moiety (includes flavones, flavanones, and isoflavones) is the key pharmacophore of these novel molecules, exhibiting similarity to the core structure of both fibrates and thiazolidinediones. New lead PPAR ligands were identified from "natraceuticals" and synthetic analogues. In total, 77 molecules, including chalcones, flavones, flavanones, isoflavones, and pyrazole derivatives, were screened and structure-activity relationship studies of the dual agonists undertaken. Compounds 68, 70, 72, and 76 were identified as novel and potent dual PPARα and γ agonists. These novel molecules may have the potential to be the future leads in PPAR-related disorders, including type II diabetes mellitus and metabolic syndrome. 2009 American Chemical Society.
- Matin, Azadeh,Gavande, Navnath,Kim, Moon S.,Yang, Nancy X.,Salam, Noeris K.,Hanrahan, Jane R.,Roubin, Rebecca H.,Hibbs, David E.
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experimental part
p. 6835 - 6850
(2010/04/04)
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- Synthesis of Isoflavone
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The invention provides a process of manufacturing an isoflavone of the general formula 7 wherein R1, R2, R3, and R4 each independently are H, OH, or an alkoxy, provided at least one of R1, R2, R3, and R4 being OH, and one being alkoxy, or at least 2 groups being OH, comprising providing ketone (3) wherein R1, R2, R3, and R4 are as stated above, combining (3) with trialkylortho formate, and a Lewis or Bronsted acid to produce the isoflavone, precipitating the isoflavone.
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(2009/04/24)
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- PROCESS FOR THE MANUFACTURE OF HYDROXYLATED ISOFLAVONES
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A process for the preparation of hydroxylated isoflavones by reacting in a Hoesch reaction using an alkanoic acid alkyl ester as solvent a phenol with a phenylacetonitrile to yield a 1,2-diphenyl-ethanone and transforming the ethanone into an isoflavone by well-known methods.
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(2008/06/13)
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- Process for producing aglycon and flavor-improved food containing the aglycon by diglycosidase, and converting agent to be used in the process
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A physiologically active substance of aglycon type, in particular, aglycon isoflavone, can be efficiently produced, without resort to any acid/alkali treatment or fermentation and substantially without changing the physical properties of a material, by treating the material with a sufficient amount of diglycosidase for a sufficient period of time at an appropriate temperature and pH so that a physiologically active substance of glycoside type contained in the material can be converted into the physiologically active substance of aglycon type. Moreover, by using diglycosidase and/or a specific enzyme preparation, the aglycon content in a protein or protein-containing food can be increased and the flavor thereof can be improved.
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(2008/06/13)
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- MANUFACTURE OF ISOFLAVONES
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A process for manufacturing a hydroxylated isoflavone of the formula (I) given in the description comprises reacting an appropriately substituted 2-hydroxydeoxybenzoin of the formula (II), also given in the description, with a formic acid anhydride of the formula HCOOCOR3, wherein R3 signifies C2-20-alkyl or various other groups as given in the description, in the presence of a base or in a solvent which acts as a base, and if necessary promoting the ensuing hydrolysis of the so-produced acylated form of the hydroxylated isoflavone of the formula I by acidification. Of particular interest as products of this process are the 5,7-dihydroxyisoflavones, e.g. genistein (5,7,4'-trihydroxyisoflavone).Isoflavones display many useful biochemical effects.
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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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- Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover)
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Biochanin A and formononetin are the predominant isoflavones in red clover. In a previous study (J. Agric. Food Chem. 2002, 50, 4783-4790), it was demonstrated that human liver microsomes converted biochanin A and formononetin to genistein and daidzein. This paper now shows CYP1B1-catalyzed O-demethylation of biochanin A and formononetin to produce genistein and daidzein, respectively, which inhibit CYP1B1. Recombinant human CYP1A1 or CYP1B1 was incubated with biochanin A or formononetin. CYP1A1 catalyzed isoflavone 4′-O-demethylation and hydroxylations with similar efficiency, whereas CYP1B1 favored 4′-O-demethylation over hydroxylations. Three of the biochanin A metabolites (5,7,3′-trihydroxy-4′-methoxyisoflavone, 5,7,8-trihydroxy-4′-methoxyisoflavone, and 5,6,7-trihydroxy-4′- methoxyisoflavone) were characterized by 1H NMR spectroscopy and mass spectrometry. Daidzein (Ki = 3.7 μM) exhibited competitive inhibition of CYP1B1 7-ethoxyresorufin O-deethylase activity, and genistein (Ki = 1.9 μM) exhibited mixed inhibition. Biochanin A and/or formononetin may exert anticarcinogenic effects directly by acting as competitive substrates for CYP1B1 or indirectly through their metabolites daidzein and genistein, which inhibit CYP1B1.
- Roberts, Dean W.,Doerge, Daniel R.,Churchwell, Mona I.,Da Costa, Goncalo Gamboa,Marques, M. Matilde,Tolleson, William H.
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p. 6623 - 6632
(2007/10/03)
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- COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH
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The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.
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Page/Page column 17
(2010/11/30)
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- Estrogens for treating ALS
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A method for preventing and treating ALS by administering a phytoestrogen, preferably genistein.
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- Partial purification and characterization of a soybean β-glucosidase with high specific activity towards isoflavone conjugates
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A β-glucosidase with high specific activity towards isoflavone conjugates was purified from soybean [Glycine max] roots by high salt extraction from a low speed centrifugal pellet and subsequent anion and cation exchange chromatography. Purification required stabilization throughout fractionation in 10% glycerol. The enzyme is most likely a dimer (approximate Mr 165 kDa) with potential subunits of Mr 80 and/or 75 kDa. The pH and temperature optima are pH 6 and 30 °C, respectively. The enzyme was highly heat-stable. Of the various potential effectors examined, silver and mercury ions were the most inhibitory. The IC50 of silver ions was increased from 140 μM to 14 mM in the presence of 250 μM β-mercaptoethanol. Glucono-δ-lactone was not strongly inhibitory (IC50 24 mM). The activity was highly active against isoflavone conjugates, with a specificity constant 160-1000 fold higher for isoflavone conjugates over the generic chromogenic substrate, p-nitrophenyl β-glucoside. The enzyme was inactive against the flavonol glycosides tested. The partially purified enzyme had similar Km and kcat towards 7-O-glucosyl- and 7-O-glucosyl-6″-malonyl-isoflavones, suggesting that it may be able to cleave the esterified glucosyl conjugate. We hypothesize that the enzyme is involved in the release of daidzein and genistein, both of which play central roles in soybean defense.
- Hsieh, Ming-Ching,Graham, Terrence L
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p. 995 - 1005
(2007/10/03)
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- Novel use of flavones
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A pharmaceutical composition for inhibiting COX-2 biosynthesis comprising a therapeutically effective amount of the compound of formula I and a pharmaceutrically acceptable carrier. wherein R1 and R4 represent either Hydrogen or together a bond R5, R6, R7, R8 represent independently of each other Hydrogen, Hydroxy or Methoxy; in addition R7 represents a sugar substituent like glucoside, rutinosid, manno gluco pyransyl, aprosylglucoside R2 and R3 represent Hydrogen, Hydroxy, Methoxy or wherein R2′, R3′, R4′, R5′ and R6′ are independently or each other Hydrogen, Hydroxy or Methoxy with the proviso, that R2 or R3 is represented by the optionally substituted Phenylring.
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- The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavone synthesis
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The yellow intermediate 4f produced during the reaction of the deoxybenzoin 3f with N,N'-dimethyl(chloromethylene)ammonium chloride in the presence of BF3*Et2O prior to the formation of the corresponding isoflavone was isolated for the first time and characterized by NMR, MS and single-crystal X-ray diffraction techniques. These yellow intermediates showed anticancer, nematicidal and mosquitocidal activities.
- Balasubramanian, Sreenivasan,Ward, Donald L.,Nair, Muraleedharan G.
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p. 567 - 570
(2007/10/03)
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- An efficient 'one pot'synthesis of isoflavones
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Initial formation of deoxybenzoin 3 from phenyl acetic acid 1 and phenol 2 in the presence of BF3.Et2O followed by its treatment at room temperature with N, N'-dimethyl (chloromethylene) ammonium chloride, generated by reacting PCl5 with DMF provides a mild and efficient route for a 'one pot' synthesis of Isoflavones in high yields.
- Balasubramanian, Sreenivasan,Nair, Muraleedharan G.
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p. 469 - 484
(2007/10/03)
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- Compositions and treatments for reducing potential unwanted side effects associated with long-term administration of androgenic testosterone precursors
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A method for reducing potential adverse effects of androgenic testosterone precursors by interfering with production or action of testosterone and estrogen metabolites by nutrient combinations is described. Although androgenic testosterone precursors themselves have little or no toxicity, there is the potential for their metabolites, estradiol and dihydrotestosterone, to enhance or cause hormone-responsive illnesses such as breast or prostatic cancer, benign prostatic hyperplasia, or hirsutism or acne in women. The use of the invented nutrient combinations reduces the formation or action of estradiol and dihydrotestosterone, thereby reducing potential adverse effects from increased production of these hormones following androgenic testosterone precursor administration. This may be accomplished without negating the effects of testosterone on muscle anabolism. The nutrient combinations include androstenedione, DHEA, pregnenolone, androstenediols, norandrostenedione and norandrostenediols, and natural products which reduce estrogen effects in the estrogen-responsive tissues, and substances to reduce formation of dihydrotestosterone from testosterone in prostate tissue.
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- Process for the isolation and purification of isoflavones
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The present invention relates to a process for the isolation and purification of isoflavones from a number of different biomass sources. More particularly, the present invention relates to a three-step process whereby a biomass containing isoflavones with a solvent thereby forming an extract that is subsequently fractionated using a reverse phase matrix in combination with a step gradient elution, wherein the resulting fractions eluted from the column contain specific isoflavones that are later crystallized. The purified isoflavone glycosides may then be hydrolyzed to their respective aglycone.
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- Study of sophoricoside derivatives with the aid of lanthanoid shift reagents
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Acylated and methylated derivatives of sophoricoside and of genistein have been synthesized, and their interaction in solution with the lanthanoid shift reagent (LSR) Eu(FOD)3 has been studied. For 5-O-alkyl derivatives of genistein an anomalous broadening of the 1H NMR signals was observed in the presence of the LSR, which is explained by the formation with the LSR of a chelate having a low rate of dissociation. The temperature and concentration dependencies of the paramagnetic broadenings of the signals have been studied.
- Turov,Bondarenko,Khilya
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p. 535 - 538
(2007/10/03)
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- Microwave-Mediated Synthesis of Anticarcinogenic Isoflavones from Soybeans
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Soybean isoflavonoids, 7,4'-dihydroxyisoflavone (daidzein), 7-hydroxy-4'-methoxyisoflavone (formononetin), 5,7,4'-trihydroxyisoflavone (genistein), and 5,7-dihydroxy-4'-methoxyisoflavone (biochanin A), were synthesized in high yields by cyclization of their corresponding ketones in a conventional microwave oven. Keywords: Microwave synthesis; isoflavones; daidzein; genistein; formononetin; biochanin A
- Chang, Yu-Chen,Nair, Muraleedharan G.,Santell, Ross C.,Helferich, William G.
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p. 1869 - 1871
(2007/10/02)
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- Structural Studies on Bioactive Compounds. 23. Synthesis of Polyhydroxylated 2-Phenylbenzothiazoles and a Comparison of Their Cytotoxicities and Pharmacological Properties with Genistein and Quercetin
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A series of polyhydroxylated 2-phenylbenzothiazoles 3 has been prepared by demethylation of the precursor methoxylated 2-phenylbenzothiazoles 9.The key step in the construction of the benzothiazole nucleus involves a Jacobson cyclization of methoxylated thiobenzanilides 8.The target compounds inhibit WiDr human colon tumor cells and MCF-7 human mammary tumor cells in vitro with IC50 values in the low micromolar range, but the activity against MCF-7 cells is not related to estrogen receptor-binding affinity.None of the compounds showed selective cytotoxicity againstAbelson virus-transformed ANN-1 cells encoded with the pp120gag-abl tyrosine kinase compared with the parental 3T3 line.Compounds were only marginally inhibitory to the EGF receptor-associated protein tyrosine kinase from a membrane preparation of A431 cells.The most active compound was 4,6-dihydroxy-2-(4-hydroxyphenyl)benzothiazole (3b) which has the same overall hydroxyl substitution pattern as genistein (1a).The compounds were weakly cytotoxic for an EGF receptor, overexpressing cell line HN5, but when tested for differential toxicity against the EGF receptor tyrosine kinase or the PDGF receptor tyrosine kinase in a standard mitogenesis assay utilizing human fibroplasts, no discrimination was observed.In this assay, the compounds inhibited DNA synthesis when added to cells during S phase.This suggests that inhibition could not be interpreted in terms of tyrosine kinase inactivation but more likely as a relatively broad specificity for the ATP-binding domain of other kinases such as thymidine kinase.
- Stevens, Malcolm F. G.,McCall, Carol J.,Lelieveld, Peter,Alexander, Peter,Richter, Audrey,Davies, Donna E.
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p. 1689 - 1695
(2007/10/02)
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- Syntheses of Isoflavones and Isoflavone Glycosides, and Their Inhibitory Activity against Bovine Liver &β-Galactosidase
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To clarify the relationship between the structure and inhibitory action toward β-D-galactosidase (EC 3.2.1.21) of isoflavones and isoflavone glycosides, a number of polyhydroxyisoflavones, and the α-L-rhamnosides and β-L-quinovosides of daidzein and genistein were synthesized.Among the polyhydroxyisoflavones, 2',3',4',7-tetrahydroxyisoflavone showed the strongest inhibitory activity (Ki = 26 * 10-6 M).Among the glycosides, all the L-rhamnosides were strong inhibitors, of which genistein 4',7-di-O-α-L-rhamnoside was the strongest (Ki = 4.44 * 10-6 M), while all the isoflavone β-L-quinovosides were considerably weak or possessed no inhibition.
- Nishiyama, Kiyotoshi,Esaki, Sachiko,Deguchi, Ikuko,Sugiyama, Naoko,Kamiya, Shintaro
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p. 107 - 114
(2007/10/02)
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- Expedient Synthesis of Polyhydroxyisoflavones
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A general and direct synthesis of polyhydroxy isoflavones (3-phenyl-4H-1-benzopyran-4-ones) starting from the corresponding unprotected phenols and arylacetic acids is described.The aryl rings may carry additional alkyl, methoxy and/or halogeno groups.Intermediate polyhydroxydeoxybenzoins (1,2-diphenylethanones) can also be isolated in good yields.
- Waehaelae, Kristiina,Hase, Tapio A.
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p. 3005 - 3008
(2007/10/02)
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- FLAVONOID 5-GLUCOSIDES FROM PRUNUS CERASUS BARK AND THEIR CHARACTERISTIC WEAK GLYCOSIDIC BONDING
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Pinostrobin 5-glucoside, a novel flavanone glycoside, was isolated from the bark of Prunus cerasus.As it was not found in P. avium, the substance is useful to distinguish these two species.Apigenin 5-glucoside, genkwanin 5-glucoside and neosakuranin were also isolated from the bark of P. cerasus.They occur in both species as minor components.These 5-glucosides together with genistein 5-glucoside, prunetin 5-glucoside, sakuranin, tectochrysin 5-glucoside and luteolin 5-glucoside were hydrolysed in malic acid.The isoflavone and flavone 5-glucosides were shown to be hydrolysed more rapidly than the flavanone 5-glucosides, whereas no hydrolysis was observed with the corresponding 7-glucosides under the same conditions.The chalcone 2'-glucoside neosakuranin was transformed at first to the corresponding flavanone 5-glucoside, which was hydrolysed thereafter. Key Word Index - Prunus cerasus; Prunus avium; Rosaceae; bark; pinostrobin 5-glucoside; flavonoid 5-glucosides; hydrolysis.
- Geibel, Martin,Feucht, Walter
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p. 1519 - 1521
(2007/10/02)
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- Ground mixture
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A ground mixture of a poorly soluble crystalline drug and an adsorbent is remarkably improved in the rates of dissolution and adsorption of the drug.
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- Studies on Zoospore-Attracting Activity. I. Synthesis of Isoflavones and Their Attracting Activity to Aphanomyces euteiches Zoospore
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Prunetin (2) and its derivatives were synthesized in order to study the relationship between structure and attracting activity to Aphanomyces euteiches zoospore.All of the derivatives (1, 2, 4 and 6), which had a hydroxyl group at the C-5 position in the isoflavone, showed attracting activity, but the methyl ether derivatives (3, 5, 7 and 8) do not have or have very weak attracting activity.The isoflavones (1, 2, and 4) with strong attracting activity also had estrogenic activity.Keywords - isoflavone; prunetin; genistein; biochanin A; 5-methylgenistein; 5-hydroxy-4',7-dimethoxyisoflavone; Aphanomyces euteiches; zoospore; attracting activity; estrogenic activity
- Sekizaki, Haruo,Yokosawa, Ryozo
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p. 4876 - 4880
(2007/10/02)
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- GENISTEIN 7-(2"-p-COUMAROYLGLUCOSIDE) FROM TRIFOLIUM REPENS
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Key Word Index - Trifolium repens; Leguminosae; genistein 7-O-(2"-p-coumaroyl-β-D-glucopyranoside); isoflavone.A new acetylated isoflavone, genistein 7-(2"-p-coumaroylglucoside), has been characterized from Trifolium repens.
- Saxena, V. K.,Jain, A. K.
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p. 2687 - 2688
(2007/10/02)
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- STRUCTURE D'UN NOUVEL HETEROSIDE D'ISOFLAVONE : LE SAROTHAMNOSIDE
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The structure of sarothamnoside (genistein 7,4'-di-O-4-O-β-D-glucopyranosyl-β-D-apiofuranoside), a new isoflavone glycoside from Sarothamnus scoparius and S. patens, has been established by spectral analysis, mainly 13C NMR.
- Brum-Bousquet, M.,Lallemand, Y.,Tillequin, F.,Delaveau, P.
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p. 1223 - 1226
(2007/10/02)
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- Synthesis of the Pyranoisoflavonoid, Heminitidulan. Isoflavanoid and Rotenoid Glycosides from the Bark of Dalbergia nitidula Welw. ex Bak.
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Synthesis of racemates of the complex pyranoisoflavan, (3S)-heminitidulan, a metabolite from the bark of Dalbergia nitidula, is accomplished.The isoflavone C-glycoside pairs 8-C-β-D-glucopyranosyl- and 6,8-di-C-β-glucopyranosyl-genistein and -orobol and the associated rotenoid glycoside (5'R,6aR,12aR)-8'-O-β-D-glucopyranosyl-12a-hydroxyamorphigenin comprise the predominant isoflavonoids in the same source. 13C N.m.r. spectra of the glycosides are recorded.
- Heerden, Fanie R. van,Brandt, E. Vincent,Roux, David G.
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p. 2463 - 2469
(2007/10/02)
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