- Isoflavonoid glycosides from Dalbergia sissoo
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Two isoflavone glycosides, biochanin A 7-O-[β-D-apiofuranosyl-(1 → 5)-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside] and tectorigenin 7-O-[β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside], were isolated from Dalbergia sissoo. Their structures were elucidate
- Farag, Salwa F.,Ahmed, Amany S.,Terashima, Kenji,Takaya, Yoshiaki,Niwa, Masatake
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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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- Synthesis method of biochanin A
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The invention discloses a synthesis method of biochanin A. The synthesis method comprises the following steps: (1) carrying out condensation reaction on p-methoxyacetophenone and N-bromosuccinimide in the presence of absolute ethyl alcohol to obtain Alpha-bromo-4-methoxyacetophenone; and (2) by taking absolute ethyl alcohol as a reaction solvent, carrying out condensation reaction on 2, 4, 6-trihydroxy benzaldehyde and Alpha-bromo-4-methoxyacetophenone in the presence of a catalyst, evaporating reaction liquid, and separating and purifying a solid product by using column chromatography to obtain the biochanin A. The novel catalyst is adopted for catalysis, the product yield is high, reaction conditions are mild, and raw materials of the catalyst are easy to obtain and low in price. The synthesis method disclosed by the invention is simple in process, low in cost, time-saving, high in yield, low in equipment corrosion degree and suitable for industrial production.
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Paragraph 0012; 0016; 0017; 0018
(2021/08/14)
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- Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids
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Methylation of free hydroxyl groups is an important modification for flavonoids. It not only greatly increases absorption and oral bioavailability of flavonoids, but also brings new biological activities. Flavonoid methylation is usually achieved by a specific group of plant O-methyltransferases (OMTs) which typically exhibit high substrate specificity. Here we investigated the effect of several residues in the binding pocket of the Clarkia breweri isoeugenol OMT on the substrate scope and regioselectivity against flavonoids. The mutation T133M, identified as reported in our previous publication, increased the activity of the enzyme against several flavonoids, namely eriodictyol, naringenin, luteolin, quercetin and even the isoflavonoid genistein, while a reduced set of amino acids at positions 322 and 326 affected both, the activity and the regioselectivity of the methyltranferase. On the basis of this work, methylated flavonoids that are rare in nature were produced in high purity.
- Tang, Qingyun,Vianney, Yoanes M.,Weisz, Klaus,Grathwol, Christoph W.,Link, Andreas,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.
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p. 3721 - 3727
(2020/06/02)
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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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- Synthesis method of biochanin A
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The invention provides a synthesis method of biochanin A. The synthesis method includes: under room temperature, adding phosphorus oxychloride into phloroglucinol, 4-Methoxybenzyl cyanide and isopropyl ether, performing hydrolysis after reaction is completed, and decoloring with activated carbon to obtain an intermediate; allowing the obtained intermediate and methylsufonyl chloride to generate crude products of the biochanin A in DMF (dimethyl formamide) in a ring-closing manner; performing recrystallization on the obtained crude products of the biochanin A by adopting ethyl alcohol and decoloring with the activated carbon to obtain the biochanin A. The synthesis method is simple in process, low in cost, timesaving, high in yield, low in equipment corrosiveness and suitable for industrialized production.
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Paragraph 0037; 0038; 0039; 0040
(2017/08/23)
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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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- 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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p. 149 - 152
(2014/07/21)
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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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- Synthesis and aminomethylation of 7-hydroxy-5-methoxyisoflavones
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A synthetic method for 7-hydroxy-5-methoxyisoflavones starting from 5,7-dihydroxyisoflavones was developed. Dimethylcarbamoylchloride was proposed for protection of the 7-hydroxy group. Aminomethylation of the synthesized 7-hydroxy-5-methoxyisoflavones by formaldehyde aminals was studied.
- Mrug,Bondarenko,Khilya,Frasinyuk
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p. 235 - 241
(2013/07/26)
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- Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: Application to the preparation of natural flavones and isoflavones
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A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl2, a C(3) zincation is observed, whereas in the presence of MgCl2 or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.
- Klier, Lydia,Bresser, Tomke,Nigst, Tobias A.,Karaghiosoff, Konstantin,Knochel, Paul
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p. 13584 - 13587
(2012/10/08)
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- Ester and carbamate ester derivatives of Biochanin A: Synthesis and in vitro evaluation of estrogenic and antiproliferative activities
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Biochanin A (BCA), a major isoflavone in red clover and many other legumes, has been reported to display estrogenic as well as cancer chemopreventive properties. Ingested BCA is known to display low bioavailability due to poor solubility, extensive metabolism and rapid clearance. Esters of bioactive isoflavones are known to increase metabolic stability and bioavailability following local rather than systemic administration. We synthesized BCA from phloroglucinol and p-methoxy-phenylacetic acid by a Friedel-Crafts reaction and cyclization. We also synthesized esters (1, 3) and carbamate esters (2, 4, 5) at position 7 of BCA using short aliphatic chains bearing a chlorine (1, 2) or a bromine atom (3, 4) or long aliphatic chains without such atoms (5). We tested the estrogenic and antiproliferative activities of 1-5 and BCA using human breast and endometrial adenocarcinoma cells. We found that 5 affects MCF-7 and Ishikawa cells in a manner providing for induction of gene expression to a level similar to 17β-estradiol and BCA but, unlike both of the latter, for suppression of cell proliferation as well. In addition, 5 appeared to display higher stability compared to 1-4 and BCA in both MCF-7 and Ishikawa cells. The inference is that 5 may represent a safer than BCA alternative to hormone replacement therapy.
- Fokialakis, Nikolas,Alexi, Xanthippi,Aligiannis, Nektarios,Siriani, Despina,Meligova, Aggeliki K.,Pratsinis, Harris,Mitakou, Sofia,Alexis, Michael N.
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p. 2962 - 2970
(2012/07/16)
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- Syntheses, characterization and antitumor activities of transition metal complexes with isoflavone
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Five new complexes were synthesized by the reaction of 4′-methoxy-5,7-dihydroxy-isoflavone ligand (a) with transition metal ions zinc (Zn2+) (complex b), manganese (Mn2+) (complex c), copper (Cu2+) (complex d), cobalt (Co2+) (complex e) and nickel (Ni2+) (complex f). The composition of the complexes has been characterized by elemental analysis, IR, mass spectrometry (MS) and 1H NMR spectrometric techniques. Their antitumor properties were evaluated against five human cancer cell lines using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and flow cytometry. The results indicated that the complexes possess higher growth inhibitory effects than free isoflavone and corresponding metal ions. Complex c and f showed greater antitumor activity and selectivity than other described complexes, even more effective than the positive control cisplatin against the selected cell lines. In addition, DNA flow cytometric analysis demonstrated that complexes display a significant G2/M phase arrest, which then progressed to early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide (PI).
- Chen, Xiang,Tang, Li-Jun,Sun, Yu-Na,Qiu, Pei-Hong,Liang, Guang
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experimental part
p. 379 - 384
(2011/12/22)
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- Synthesis of isoflavones via base catalysed condensation reaction of deoxybenzoin
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Base catalysed condensation reaction of o-hydroxyl-α- phenylacetophenones with formyl reagents affords various substituted isoflavones. Many bases were tested in the condensation reaction and DMAP was found to be the most effective catalysis.
- Li, Wanmei,Liu, Fangming,Zhang, Pengfei
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experimental part
p. 683 - 685
(2009/09/25)
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- Synthesis and evaluation of derrubone and select analogues
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(Chemical Equation Presented) Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.
- Hastings, Jedidiah M.,Hadden, M. Kyle,Blagg, Brian S. J.
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p. 369 - 373
(2008/09/17)
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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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- Synthesis of analogs of natural isoflavonoids containing phloroglucinol
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Analogs of the natural isoflavonoids biochanin A and orobol were synthesized. Alkylation involving phenolic hydroxyls and the chromone ring was studied.
- Bondarenko,Levenets,Frasinyuk,Khilya
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p. 271 - 275
(2007/10/03)
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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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- 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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- 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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- Mixed Anhydride of Acetic and Formic Acids in the Synthesis of Chromones. 2. Synthesis of 3-Arylchromones
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A study was carried out on the reaction of α-substituted 2-hydroxyacetophenones eith the mixed anhydride of acetic and formic acids in the presence of bases of different strength.Chromones containing a conjugated electron-withdrawing substituent at C(3) are formed in close to quantitative yield in the presence of triethylamine.The preparation of chromones containing an unconjugated substituent under these conditions is recommended only for 5-hydroxychromones.
- Pivovarenko, V. G.,Khilya, V. P.
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p. 497 - 502
(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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- 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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