- Formation of polyhydroxylated isoflavones from the isoflavones genistein and biochanin a by bacteria isolated from tempe
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Two tempe-derived bacterial strains identified as Micrococcus or Arthrobacter species were shown to transform the 5-hydroxyisoflavones biochanin A and genistein to polyhydroxylated isoflavones by hydroxylation reactions at positions C-6 and C-8. Both strains transformed genistein to 5,6,7,4'-tetrahydroxyisoflavone and 5,7,8,4'-tetrahydroxyisoflavone and biochanin A to 4'-methoxy-5,7,8,-trihydroxyisoflavone, whereas only strain I converted biochanin A to 4'-methoxy-5,6,7-trihydroxyisoflavone. The structures of these transformation products were elucidated by spectroscopic techniques.
- Klus, Klaus,Barz, Wolfgang
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- Synthesis, Characterization, and Antiradical Activity of 6-Hydroxygenistein
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A convergent synthesis route of 6-hydroxygenistein (6-OHG) was reported, starting from cheap and readily available biochanin A, via methylation, bromination, methoxylation, and demethylation. The structure of the products was confirmed by MS, IR, 1/
- Shao, Jin,Zhao, Tong,Ma, Hui-Ping,Jia, Zheng-Ping,Jing, Lin-Lin
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p. 821 - 826
(2020/09/21)
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- α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors
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The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4- trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyl- containing flavonoid analogs were investigat
- Gao, Hong,Kawabata, Jun
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p. 1661 - 1671
(2007/10/03)
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- Studies of the selective O-alkylation and dealkylation of flavonoids. XX. A convenient method for synthesizing 5,6,7-trihydroxyisoflavones and 5,6-dihydroxy-7-methoxyisoflavones
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3′,6′-Bis(benzyloxy)-2′,4′-dimethoxychalcones, which were derived from dibenzyl ether of 3,6-dihydroxy-2,4-dimethoxyacetophenone, were oxidatively rearranged with thallium(III) nitrate (TTN) in methanol to give 2-aryl-1-[3,6-bis(benzyloxy)-2,4-dimethoxyphenyl]-3,3-dimethoxypropan-1-ones; these products were converted into 6-hydroxy-5,7-dimethoxyisoflavones by hydrogenolysis followed by cyclization. The 5-methoxy group in the acetates of the isoflavones was selectively cleaved with 5% (w/v) anhydrous aluminum bromide in acetonitrile to give quantitatively the corresponding 5-hydroxyisoflavones, which were hydrolyzed to 5,6-dihydroxy-7-methoxyisoflavones. The acetates were also demethylated to 5,6,7-trihydroxyisoflavones with 30% (w/v) anhydrous aluminum chloride in acetonitrile at 70 °C for 36-48 h. The spectral properties of these isoflavones were examined and some natural isoflavones were identified.
- Horie, Tokunaru,Sasagawa, Masahiro,Torii, Furaihito,Kawamura, Yasuhiko,Yamashita, Kazuyo
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p. 486 - 491
(2007/10/03)
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- Isoflavones from Podocarpus amarus
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The isoflavone irisolidone is a major constituent of Podocarpus amarus hearthwood.Its structure has been securely established by 13C n.m.r. studies upon a range of derivatives.The isoflavones biochanin A, genistein and daidzein are also present in the tre
- Carman, Raymond M.,Russel-Maynard, John K. L.,Schumann, Russell C.
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p. 485 - 496
(2007/10/02)
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