- Isolation and identification of urinary metabolites of tectoridin in rats
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Tectoridin is an active isoflavone from the rhizome of Belamcanda chinensis and flower of Pueraria thomsonii Benth, possessing an anti-inflammation action and the protective effect against ethanol-induced intoxication and hepatic injury. The metabolism of tectoridin was investigated in rats. Nine metabolites were isolated by using repeated chromatographic methods and identified by spectroscopic methods including UV, IR, mass spectrometry, and NMR experiments. A new compound was determined as tectorigenin-7-O-β-D-glucuronide (M-1), together with eight known compounds identified as irisolidone-7-O-β-D- glucuronide (M-2), tectorigenin-7-O-sulfate (M-3), tectorigenin-4′-O- sulfate (M-4), tectorigenin (M-5), irisolidone (M-6), isotectorigenin (M-7), genistein (M-8), and daidzein (M-9), respectively. The metabolic pathway of tectoridin was proposed, which is important to understand its metabolic fate and disposition in humans.
- Bai, Xue,Qu, Jia-Lin,Liu, Jia,Sun, Jia-Hong,Yuan, Dan
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- ISOFLAVONOIDS FROM IRIS CROCEA
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A new 12a-hydroxyrotenoid, 9-methoxyirispurinol, and a new isoflavone glucoside, tectorigenin 4'-glucoside, together with tectoridin, tectorigenin, 5,7-dihydroxy-6,2'-dimethoxyisoflavone and alipinone were isolated from the rhizomes of Iris crocea.The structures of known and new compounds were established by spectroscopic and chemical methods. Key Word Index: Iris crocea; Iridaceae; rhizomes; flavonoids; 9-methoxyirispurinol; tectorigenin 4'-glucoside; tectorigenin; tectoridin; 5,7-dihydroxy-6,2'-dimethoxyisoflavone; alipinone.
- Shawl, Abdul S.,Kumar, Tej
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- Cytoprotective effect of tectorigenin, a metabolite formed by transformation of tectoridin by intestinal microflora, on oxidative stress induced by hydrogen peroxide
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In the present study, the antioxidative properties of tectorigenin, a metabolite formed by transformation of tectoridin by intestinal microflora, were investigated. Tectorigenin was found to scavenge intracellular reactive oxygen species, and 1,1-diphenyl
- Kang, Kyoung Ah,Lee, Kyoung Hwa,Chae, Sungwook,Zhang, Rui,Jung, Myung Sun,Kim, So Young,Kim, Hee Sun,Kim, Dong Hyun,Hyun, Jin Won
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- ISOAURMILLONE, AN ISOFLAVONE FROM THE PODS OF MILLETIA AURICULATA
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The pods of Milletia auriculata have yielded a new substance, 5,7-dihydroxy-6-methoxy-4'-O-prenyloxyisoflavone. - Key Word Index: Milletia auriculata; Leguminosae; pods; isoaurmilone;5,7-dihydroxi-6-methoxy-4'-O-prenyloxyisoflavone.
- Gupta, Bodhendu B.,Bhattacharyya, Anjan,Mitra, Santi R,Adityachaudhury, Narayan
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- Fluorescence spectroscopy and docking study in two flavonoids, isolated tectoridin and its aglycone tectorigenin, interacting with human serum albumin: A comparison study
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Two flavonoids, tectoridin (TD) isolated from rhizomes of Iris tectorum and hydrolyzed aglycone tectorigenin (TG) were prepared and characterized to compare their different interaction ability with human serum albumin (HSA). Based on the results, the affi
- Li, Yuanzhi,Wang, Qing,He, Jiawei,Yan, Jin,Li, Hui
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- Isolation and identification of urinary metabolites of kakkalide in rats
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Kakkalide is a major isoflavonoid from the flowers of Pueraria lobata (Willd.) Ohwi, possessing the protective effect against ethanol-induced intoxication and hepatic injury. The metabolism of kakkalide was investigated in rats. Thirteen metabolites were isolated by using solvent extraction and repeated chromatographic methods and identified by using spectroscopic methods including UV, IR, mass spectrometry, NMR, and circular dichroism experiments. Four new compounds were identified as irisolidone-7-Oglucuronide (M-1), tectorigenin-7-O-sulfate (M-2), tectorigenin-4′-O-sulfate (M-3), and biochanin A-6-O-sulfate (M-4) together with nine known compounds identified as irisolidone (M-5), tectorigenin (M-6), tectoridin (M-7), 5,7-dihydroxy-8, 4′-dimethoxyisoflavone (M-8), isotectorigenin (M-9), biochanin A (M-10), genistein (M-11), daidzein (M-12), and equol (M-13). The metabolic pathway of kakkalide was proposed, which is important to understand its metabolic fate and disposition in humans. Copyright
- Bai, Xue,Xie, Yuanyuan,Liu, Jia,Qu, Jialin,Kano, Yoshihiro,Yuan, Dan
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experimental part
p. 281 - 286
(2010/11/17)
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- Efficient method for the synthesis of tectorigenin
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Tectorigenin, isolated from the rhizomes of Belamcanda chinensis, shows a wide variety of biological activities. The interest in its biological activities has been matched by a corresponding interest in its synthesis. We herein reported a convenient synth
- Xiao, Zhu-Ping,Li, Huan-Qiu,Xue, Jia-Yu,Shi, Lei,Zhu, Hai-Liang
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p. 525 - 529
(2008/04/12)
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- Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease
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Twenty polyphenols were synthesized and evaluated for their effect on Helicobacter pylori urease. Among these compounds, 4-(p-hydroxyphenethyl)pyrogallol (15) (IC50 = 0.03 mM) and 7,8,4′-trihydroxyisoflavone (19) (IC50 = 0.14 mM) showed potent inhibitory activities, and inhibited Helicobacter pylori urease in a time-dependent manner. The structure-activity relationship of these polyphenols revealed: the two ortho hydroxyl groups were essential for inhibitory activity of polyphenol. When the C-ring of isoflavone was broken, the inhibitory activity markedly decreased. As for deoxybenzoin, the carboxyl group was clearly detrimental.
- Xiao, Zhu-Ping,Shi, Da-Hua,Li, Huan-Qiu,Zhang, Li-Na,Xu, Chen,Zhu, Hai-Liang
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p. 3703 - 3710
(2008/02/07)
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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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- 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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p. 1263 - 1268
(2007/10/03)
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- Studies of the selective O-Alkylation and dealkylation of flavonoids. XXIV. A convenient method for synthesizing 6- and 8-methoxylated 5,7- dihydroxyisoflavones
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2',4'-Bis(benzyloxy)-3',6'-dimethoxychalcones (5), which were obtained from the dibenzyl ether of 2,4-dihydroxy-3,6-dimethoxyacetophenone (3), were oxidatively rearranged with thallium (III) nitrate in methanol and the resultant products were converted into 7-hydroxy-5,8-dimethoxyisoflavones (8) by hydrogenolysis, followed by cyclization. The isoflavones were quantitatively demethylated to 5,7-dihydroxy-8-methoxyisoflavones (2) via their acetates. The isomeric 5,7-dihydroxy-6-methoxyisoflavones (1) were also synthesized from the chalcones, obtained from 2,3-dimethoxy- (16) or 2- isopropoxy-3-methoxy-4,6-bis(benzyloxy)acetophenones (21), by a similar method. On the other hand, the isoflavones with two hydroxy groups at the 2'- and 4'-positions were easily synthesized by the following method. Treatment of the rearranged product from 2,2',4,4'-tetrakis(benzyloxy)-3'6'- dimethoxychalcone (5f) with hydrochloric acid (HCl) in acetic acid afforded 2',4',7-tris(benzyloxy)-5,8-dimethoxyisoflavone (10f). The 5-methoxy group in the isoflavone was quantitatively cleaved to give the corresponding 5- hydroxyisoflavone (11f), which was isomerized to 2',4',7-tris(benzyloxy)-5- hydroxy-6-methoxyisoflavone (25f) in the presence of anhydrous potassium carbonate. Hydrogenolysis of the two 5-hydroxyisoflavones proceeded smoothly to give 2',4',5,7-tetrahydroxy-8-(2f) and 6-methoxyisoflavones (1f), respectively. The 13C-NMR spectra of these isoflavones supported the proposed structures of polyhydroxyisoflavones. The proposed structures of two natural isoflavones were revised.
- Horie, Tokunaru,Shibata, Kenichi,Yamashita, Kazuyo,Fujii, Kenichi,Tsukayama, Masao,Ohtsuru, Yoshizumi
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p. 222 - 230
(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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