Daidzin (BioDeep_00000002593)

 

Secondary id: BioDeep_00000270069

natural product human metabolite PANOMIX_OTCML-2023 Antitumor activity BioNovoGene_Lab2019


代谢物信息卡片


3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

化学式: C21H20O9 (416.110727)
中文名称: 大豆苷, 黄豆甙, 大豆甙, 豆苷, 黄豆苷, 大豆苷(大豆黄酮-7-O-葡萄糖苷), 大豆苷、大豆黄酮-7-O-葡萄糖苷
谱图信息: 最多检出来源 Viridiplantae(plant) 0.05%

分子结构信息

SMILES: c1(ccc2c(c1)occ(c2=O)c1ccc(cc1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
InChI: InChI=1/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1

描述信息

Daidzein 7-O-beta-D-glucoside is a glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic). It has a role as a plant metabolite. It is a hydroxyisoflavone, a monosaccharide derivative and a 7-hydroxyisoflavones 7-O-beta-D-glucoside. It is functionally related to a daidzein.
Daidzin is a natural product found in Thermopsis lanceolata, Thermopsis macrophylla, and other organisms with data available.
See also: Astragalus propinquus root (part of).
Daidzin is found in miso. Daidzin is isolated from soya bean (Glycine max) and soya bean meal, kudzu root (Pueraria lobata), alfalfa (Medicago sativa) and other Leguminosae.Daidzin is a cancer preventive and an alcohol dependency treatment (antidipsotropic) in animal models. Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant Kudzu (Pueraria lobata, Fabaceae) and from soybean leaves
A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).
Isolated from soya bean (Glycine max) and soya bean meal, kudzu root (Pueraria lobata), alfalfa (Medicago sativa) and other Leguminosae
D002491 - Central Nervous System Agents > D000427 - Alcohol Deterrents
D004791 - Enzyme Inhibitors
Acquisition and generation of the data is financially supported in part by CREST/JST.
Daidzin is an isoflavone with antioxidant, anticancer, and antiatherosclerotic activities.
Daidzin is an isoflavone with antioxidant, anticancer, and antiatherosclerotic activities. Daidzin is a potent and selective inhibitor of mitochondrial ALDH-2. Daidzin reduces ethanol consumption[1].
Daidzin is an isoflavone with antioxidant, anticancer, and antiatherosclerotic activities.

同义名列表

50 个代谢物同义名

3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one; 3-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one; 3-(4-hydroxyphenyl)-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one; 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one; 3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; 7-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranoside; 7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one; 3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside; Daidzin, United States Pharmacopeia (USP) Reference Standard; Daidzin, primary pharmaceutical reference standard; 4,7-DIHYDROXYISOFLAVONE; 7-O-B-D-GLUCOPYRANOSIDE; 4,7-Dihydroxyisoflavone 7-O-b-D-glucopyranoside; DAIDZIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]; 4-18-00-01808 (Beilstein Handbook Reference); DAIDZIN (CONSTITUENT OF ASTRAGALUS) [DSC]; DAIDZIN (CONSTITUENT OF SOY ISOFLAVONES); 7,4-Dihydroxyisoflavone 7-glucoside; DAIDZIN (CONSTITUENT OF ASTRAGALUS); Daidzein 7-O-beta-D-glucopyranoside; Daidzein 7-O-|A-D-glucopyranoside; 7-O-glucosyl-4-hydroxyisoflavone; DAIDZEIN 7-O-.BETA.-D-GLUCOSIDE; daidzein 7-O-beta-D-glucoside; Daidzin, analytical standard; KYQZWONCHDNPDP-QNDFHXLGSA-N; 7-O-beta-D-glucopyranoside; Daidzein 7-O-β-D-glucoside; Daidzein 7-O-b-D-glucoside; Daidzin, >=95.0\\% (HPLC); daidzein-7-o-glucoside; Daidzein 7-O-glucoside; DAIDZEIN DAIDZIN [MI]; Daidzein 7-glucoside; Daidzein-7-glucoside; DAIDZEIN DAIDZIN; DAIDZIN [USP-RS]; DAIDZIN (USP-RS); UNII-4R2X91A5M5; MEGxp0_000530; ACon1_002092; Daidzoside; 4R2X91A5M5; Daidzin; Dadzin; 2vle; DZN; Daidzein-7-O-β-D-glucopyranoside; Daidzein O-hexoside; NPI-031D



数据库引用编号

47 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

42 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Shuai Yuan, Ibrahim Abdel Aziz Ibrahim, Ruimin Ren. Anti-urolithiatic Activity of Daidzin in Ethylene Glycol-Induced Urolithiasis in Rats. Applied biochemistry and biotechnology. 2023 Feb; 195(2):905-918. doi: 10.1007/s12010-022-04124-y. [PMID: 36227501]
  • Quanli Liu, Yi Liu, Gang Li, Otto Savolainen, Yun Chen, Jens Nielsen. De novo biosynthesis of bioactive isoflavonoids by engineered yeast cell factories. Nature communications. 2021 10; 12(1):6085. doi: 10.1038/s41467-021-26361-1. [PMID: 34667183]
  • Dan Gao, Jin Hyeok Kim, Cheong Taek Kim, Won Seok Jeong, Hyung Min Kim, Jaehoon Sim, Jong Seong Kang. Evaluation of Anti-Melanogenesis Activity of Enriched Pueraria lobata Stem Extracts and Characterization of Its Phytochemical Components Using HPLC-PDA-ESI-MS/MS. International journal of molecular sciences. 2021 Jul; 22(15):. doi: 10.3390/ijms22158105. [PMID: 34360871]
  • Miwako Toyofuku, Fuki Okutani, Masaru Nakayasu, Shoichiro Hamamoto, Hisabumi Takase, Kazufumi Yazaki, Akifumi Sugiyama. Enhancement of developmentally regulated daidzein secretion from soybean roots in field conditions as compared with hydroponic culture. Bioscience, biotechnology, and biochemistry. 2021 Apr; 85(5):1165-1169. doi: 10.1093/bbb/zbab017. [PMID: 33784734]
  • Su-Jin Ahn, Hyung Joo Kim, Ayoung Lee, Seung-Sik Min, Sangwhan In, Eunmi Kim. Determination of 12 herbal compounds for estimating the presence of Angelica Gigas Root, Cornus Fruit, Licorice Root, Pueraria Root, and Schisandra Fruit in foods by LC-MS/MS. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2020 Sep; 37(9):1437-1448. doi: 10.1080/19440049.2020.1778187. [PMID: 32530783]
  • Zartashia Kazmi, Sara Zeeshan, Adnan Khan, Sumra Malik, Adeeb Shehzad, Eun Kyoung Seo, Salman Khan. Anti-epileptic activity of daidzin in PTZ-induced mice model by targeting oxidative stress and BDNF/VEGF signaling. Neurotoxicology. 2020 07; 79(?):150-163. doi: 10.1016/j.neuro.2020.05.005. [PMID: 32450180]
  • You Jin Lim, Ho Young Jeong, Chan Saem Gil, Soon-Jae Kwon, Jong Kuk Na, Chanhui Lee, Seok Hyun Eom. Isoflavone accumulation and the metabolic gene expression in response to persistent UV-B irradiation in soybean sprouts. Food chemistry. 2020 Jan; 303(?):125376. doi: 10.1016/j.foodchem.2019.125376. [PMID: 31442900]
  • Yingjie Sun, Hongmin Zhang, Ming Cheng, Shijie Cao, Miao Qiao, Boli Zhang, Liqin Ding, Feng Qiu. New hepatoprotective isoflavone glucosides from Pueraria lobata (Willd.) Ohwi. Natural product research. 2019 Dec; 33(24):3485-3492. doi: 10.1080/14786419.2018.1484461. [PMID: 29968479]
  • Kung-Chieh Wu, Wei-Yu Lin, Yi-Ting Sung, Wei-Yi Wu, Yu-Hsiuan Cheng, Tung-Sheng Chen, Bing-Juin Chiang, Chiang-Ting Chien. Glycine tomentella hayata extract and its ingredient daidzin ameliorate cyclophosphamide-induced hemorrhagic cystitis and oxidative stress through the action of antioxidation, anti-fibrosis, and anti-inflammation. The Chinese journal of physiology. 2019 Sep; 62(5):188-195. doi: 10.4103/cjp.cjp_60_19. [PMID: 31670282]
  • Juping Zhang, Qianxiang Guo, Meijin Wei, Junqi Bai, Juan Huang, Yuhong Liu, Ziren Su, Xiaohui Qiu. Metabolite Identification and Pharmacokinetic Profiling of Isoflavones from Black Soybean in Rats Using Ultrahigh-Performance Liquid Chromatography with Linear-Ion-Trap-Orbitrap and Triple-Quadrupole Tandem Mass Spectrometry. Journal of agricultural and food chemistry. 2018 Dec; 66(49):12941-12952. doi: 10.1021/acs.jafc.8b04852. [PMID: 30444115]
  • Kung-Chieh Wu, Bing-Juin Chiang, Wen-Hsin Tsai, Shiu-Dong Chung, Chiang-Ting Chien. I-Tiao-Gung extract through its active component daidzin improves cyclophosphamide-induced bladder dysfunction in rat model. Neurourology and urodynamics. 2018 11; 37(8):2560-2570. doi: 10.1002/nau.23815. [PMID: 30252154]
  • Paulo Luiz DA Silva, Gláucia Cordeiro, Carolina R DA Silva, Rafael A Barros, Camila R DA Silva, José C Zanuncio, Wellington G Campos, Maria G A Oliveira. Does mechanical damage on soybean induces the production of flavonoids?. Anais da Academia Brasileira de Ciencias. 2018 Oct; 90(4):3415-3422. doi: 10.1590/0001-3765201820170850. [PMID: 30365711]
  • Feng Qiu, Linyi Shi, Siqi Wang, Sha Wu, Manyuan Wang. Simultaneous high-performance liquid chromatography with diode array detection and time-of-flight mass spectrometric confirmation of the ten bioactive compounds in Semen Sojae Preparatum. Journal of separation science. 2018 Sep; 41(17):3360-3371. doi: 10.1002/jssc.201800504. [PMID: 30016573]
  • Charles C Lee, Stéphanie Dudonné, Jong Hun Kim, Ji Seung Kim, Pascal Dubé, Jong-Eun Kim, Yves Desjardins, Jung Han Yoon Park, Ki Won Lee, Chang Yong Lee. A major daidzin metabolite 7,8,4'-trihydroxyisoflavone found in the plasma of soybean extract-fed rats attenuates monocyte-endothelial cell adhesion. Food chemistry. 2018 Feb; 240(?):607-614. doi: 10.1016/j.foodchem.2017.08.002. [PMID: 28946319]
  • Mei-Yan Yang, Ya-Bin Wang, Bo Han, Bo Yang, Yu-Wei Qiang, Yan Zhang, Zhao Wang, Xu Huang, Jie Liu, Yun-Dai Chen, Jun Ren, Feng Cao, Yong Xu. Activation of aldehyde dehydrogenase 2 slows down the progression of atherosclerosis via attenuation of ER stress and apoptosis in smooth muscle cells. Acta pharmacologica Sinica. 2018 Jan; 39(1):48-58. doi: 10.1038/aps.2017.81. [PMID: 28858301]
  • Yunjeong Kim, Ji-Young Jeon, Eun-Young Kim, Cheol-Hee Lim, Hwan Bong Jang, Min-Gul Kim. Pharmacokinetics and Safety of DW1029M, a Botanical Drug for the Treatment of Diabetic Nephropathy, Following Single Doses in Healthy Subjects. Clinical pharmacology in drug development. 2017 Sep; 6(5):499-507. doi: 10.1002/cpdd.343. [PMID: 28301092]
  • Xiao-Ling Wang, Fu-Rong Jiao, Meng Yu, Li-Bin Lin, Jian Xiao, Qiang Zhang, Le Wang, Dong-Zhu Duan, Gang Xie. Constituents with potent α-glucosidase inhibitory activity from Pueraria lobata (Willd.) ohwi. Bioorganic & medicinal chemistry letters. 2017 05; 27(9):1993-1998. doi: 10.1016/j.bmcl.2017.03.013. [PMID: 28343876]
  • Alírica I Suárez, Zaw Min Thu, Jorge Ramírez, Diana León, Luis Cartuche, Chabaco Armijos, Geovanni Vidari. Main Constituents and Antidiabetic Properties of Otholobium mexicanum. Natural product communications. 2017 Apr; 12(4):533-535. doi: . [PMID: 30520590]
  • Hee Rae Kang, Dahae Lee, René Benndorf, Won Hee Jung, Christine Beemelmanns, Ki Sung Kang, Ki Hyun Kim. Termisoflavones A-C, Isoflavonoid Glycosides from Termite-Associated Streptomyces sp. RB1. Journal of natural products. 2016 Dec; 79(12):3072-3078. doi: 10.1021/acs.jnatprod.6b00738. [PMID: 28006913]
  • José P da Graça, Tatiana E Ueda, Tatiani Janegitz, Simone S Vieira, Mariana C Salvador, Maria C N de Oliveira, Sonia M Zingaretti, Stephen J Powers, John A Pickett, Michael A Birkett, Clara B Hoffmann-Campo. The natural plant stress elicitor cis-jasmone causes cultivar-dependent reduction in growth of the stink bug, Euschistus heros and associated changes in flavonoid concentrations in soybean, Glycine max. Phytochemistry. 2016 Nov; 131(?):84-91. doi: 10.1016/j.phytochem.2016.08.013. [PMID: 27659594]
  • Heung Joo Yuk, Yeong Hun Song, Marcus J Curtis-Long, Dae Wook Kim, Su Gyeong Woo, Yong Bok Lee, Zia Uddin, Cha Young Kim, Ki Hun Park. Ethylene Induced a High Accumulation of Dietary Isoflavones and Expression of Isoflavonoid Biosynthetic Genes in Soybean (Glycine max) Leaves. Journal of agricultural and food chemistry. 2016 Oct; 64(39):7315-7324. doi: 10.1021/acs.jafc.6b02543. [PMID: 27626287]
  • Mohd Zaheer, Vudem Dashavantha Reddy, Charu Chandra Giri. Enhanced daidzin production from jasmonic and acetyl salicylic acid elicited hairy root cultures of Psoralea corylifolia L. (Fabaceae). Natural product research. 2016 Jul; 30(13):1542-7. doi: 10.1080/14786419.2015.1054823. [PMID: 26156378]
  • Bili Su, Yongjun Kan, Jianwei Xie, Juan Hu, Wensheng Pang. Relevance of the Pharmacokinetic and Pharmacodynamic Profiles of Puerariae lobatae Radix to Aggregation of Multi-Component Molecules in Aqueous Decoctions. Molecules (Basel, Switzerland). 2016 Jun; 21(7):. doi: 10.3390/molecules21070845. [PMID: 27367654]
  • Naim Stiti, Balakumaran Chandrasekar, Laura Strubl, Shabaz Mohammed, Dorothea Bartels, Renier A L van der Hoorn. Nicotinamide Cofactors Suppress Active-Site Labeling of Aldehyde Dehydrogenases. ACS chemical biology. 2016 06; 11(6):1578-86. doi: 10.1021/acschembio.5b00784. [PMID: 26990764]
  • Kailee A Johnson, Sravan Vemuri, Sameerh Alsahafi, Rudy Castillo, Venugopalan Cheriyath. Glycone-rich Soy Isoflavone Extracts Promote Estrogen Receptor Positive Breast Cancer Cell Growth. Nutrition and cancer. 2016 May; 68(4):622-33. doi: 10.1080/01635581.2016.1154578. [PMID: 27043076]
  • Yan Zhang, Sam K C Chang. Isoflavone Profiles and Kinetic Changes during Ultra-High Temperature Processing of Soymilk. Journal of food science. 2016 Mar; 81(3):C593-9. doi: 10.1111/1750-3841.13236. [PMID: 26814612]
  • S Persiani, F Sala, C Manzotti, M Colovic, M Zangarini, Y Donazzolo, B Barbetta, C Vitalini, G Giacovelli, C Benvenuti, L C Rovati. Evaluation of Levothyroxine Bioavailability after Oral Administration of a Fixed Combination of Soy Isoflavones in Post-menopausal Female Volunteers. Drug research. 2016 Mar; 66(3):136-40. doi: 10.1055/s-0035-1555784. [PMID: 26125285]
  • Huihua Qu, Baoping Qu, Xueqian Wang, Yue Zhang, Jinjun Cheng, Wenhao Zeng, Shuchen Liu, Qingguo Wang, Yan Zhao. Rapid, sensitive separation of the three main isoflavones in soybean using immunoaffinity chromatography. Journal of separation science. 2016 Mar; 39(6):1195-201. doi: 10.1002/jssc.201501052. [PMID: 26813984]
  • Gorawit Yusakul, Seiichi Sakamoto, Thaweesak Juengwatanatrakul, Waraporn Putalun, Hiroyuki Tanaka, Satoshi Morimoto. Preparation and application of a monoclonal antibody against the isoflavone glycoside daidzin using a mannich reaction-derived hapten conjugate. Phytochemical analysis : PCA. 2016 Jan; 27(1):81-8. doi: 10.1002/pca.2604. [PMID: 26689919]
  • Shuai Wu, Wei Xu, Fu-Rong Wang, Xiu-Wei Yang. Study of the Biotransformation of Tongmai Formula by Human Intestinal Flora and Its Intestinal Permeability across the Caco-2 Cell Monolayer. Molecules (Basel, Switzerland). 2015 Oct; 20(10):18704-16. doi: 10.3390/molecules201018704. [PMID: 26501241]
  • Yeming Chen, Sam K C Chang. Macronutrients, Phytochemicals, and Antioxidant Activity of Soybean Sprout Germinated with or without Light Exposure. Journal of food science. 2015 Jun; 80(6):S1391-8. doi: 10.1111/1750-3841.12868. [PMID: 25916398]
  • Xin Wang, Shutao Li, Jia Li, Changfu Li, Yansheng Zhang. De novo transcriptome sequencing in Pueraria lobata to identify putative genes involved in isoflavones biosynthesis. Plant cell reports. 2015 May; 34(5):733-43. doi: 10.1007/s00299-014-1733-1. [PMID: 25547742]
  • Bingrui Liu, Kenneth T Kongstad, Sun Qinglei, Nils T Nyberg, Anna K Jäger, Dan Staerk. Dual high-resolution α-glucosidase and radical scavenging profiling combined with HPLC-HRMS-SPE-NMR for identification of minor and major constituents directly from the crude extract of Pueraria lobata. Journal of natural products. 2015 Feb; 78(2):294-300. doi: 10.1021/np5009416. [PMID: 25679337]
  • Pei Wang, Hui Zhang, Hailong Yang, Lei Nie, Hengchang Zang. Rapid determination of major bioactive isoflavonoid compounds during the extraction process of kudzu (Pueraria lobata) by near-infrared transmission spectroscopy. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2015 Feb; 137(?):1403-8. doi: 10.1016/j.saa.2014.09.002. [PMID: 25310261]
  • Seiichi Sakamoto, Gorawit Yusakul, Benyakan Pongkitwitoon, Madan Kumar Paudel, Hiroyuki Tanaka, Satoshi Morimoto. Simultaneous determination of soy isoflavone glycosides, daidzin and genistin by monoclonal antibody-based highly sensitive indirect competitive enzyme-linked immunosorbent assay. Food chemistry. 2015 Feb; 169(?):127-33. doi: 10.1016/j.foodchem.2014.08.004. [PMID: 25236207]
  • Yanqing Zang, Kiharu Igarashi, Changqing Yu. Anti-obese and anti-diabetic effects of a mixture of daidzin and glycitin on C57BL/6J mice fed with a high-fat diet. Bioscience, biotechnology, and biochemistry. 2015; 79(1):117-23. doi: 10.1080/09168451.2014.955453. [PMID: 25209298]
  • Vera van der Velpen, Anouk Geelen, Peter C H Hollman, Evert G Schouten, Pieter van 't Veer, Lydia A Afman. Isoflavone supplement composition and equol producer status affect gene expression in adipose tissue: a double-blind, randomized, placebo-controlled crossover trial in postmenopausal women. The American journal of clinical nutrition. 2014 Nov; 100(5):1269-77. doi: 10.3945/ajcn.114.088484. [PMID: 25332325]
  • Kibbeum Song, Sokho Kim, Ji-Young Na, Jong-Heum Park, Jae-Kyung Kim, Jae-Hun Kim, Jungkee Kwon. Rutin attenuates ethanol-induced neurotoxicity in hippocampal neuronal cells by increasing aldehyde dehydrogenase 2. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Oct; 72(?):228-33. doi: 10.1016/j.fct.2014.07.028. [PMID: 25084483]
  • Amy L Strong, Jason F Ohlstein, Quan Jiang, Qiang Zhang, Shilong Zheng, Stephen M Boue, Steven Elliott, Jeffrey M Gimble, Matthew E Burow, Guangdi Wang, Bruce A Bunnell. Novel daidzein analogs enhance osteogenic activity of bone marrow-derived mesenchymal stem cells and adipose-derived stromal/stem cells through estrogen receptor dependent and independent mechanisms. Stem cell research & therapy. 2014 Aug; 5(4):105. doi: 10.1186/scrt493. [PMID: 25168698]
  • Liwu Chen, Jian Du, Qiwen Dai, Hongcheng Zhang, Wensheng Pang, Juan Hu. Prediction of anti-tumor chemical probes of a traditional Chinese medicine formula by HPLC fingerprinting combined with molecular docking. European journal of medicinal chemistry. 2014 Aug; 83(?):294-306. doi: 10.1016/j.ejmech.2014.06.037. [PMID: 24974349]
  • Liqin Du, Zilong Wang, Yingli Zhao, Jinqun Huang, Hao Pang, Yutuo Wei, Lihua Lin, Ribo Huang. A β-glucosidase from Novosphingobium sp. GX9 with high catalytic efficiency toward isoflavonoid glycoside hydrolysis and (+)-catechin transglycosylation. Applied microbiology and biotechnology. 2014 Aug; 98(16):7069-79. doi: 10.1007/s00253-014-5661-3. [PMID: 24682446]
  • Abubaker M A Morgan, Hyun Woo Lee, Sang-Hyun Lee, Chi-Hwan Lim, Hae-Dong Jang, Young Ho Kim. Anti-osteoporotic and antioxidant activities of chemical constituents of the aerial parts of Ducrosia ismaelis. Bioorganic & medicinal chemistry letters. 2014 Aug; 24(15):3434-9. doi: 10.1016/j.bmcl.2014.05.077. [PMID: 24953601]
  • Jia Li, Zhaobo Li, Changfu Li, Junbo Gou, Yansheng Zhang. Molecular cloning and characterization of an isoflavone 7-O-glucosyltransferase from Pueraria lobata. Plant cell reports. 2014 Jul; 33(7):1173-85. doi: 10.1007/s00299-014-1606-7. [PMID: 24700248]
  • Yan Yan, Cheng-Zhi Chai, Da-Wei Wang, Jie Wu, Hong-He Xiao, Li-Xia Huo, Dan-Ni Zhu, Bo-Yang Yu. Simultaneous determination of puerarin, daidzin, daidzein, paeoniflorin, albiflorin, liquiritin and liquiritigenin in rat plasma and its application to a pharmacokinetic study of Ge-Gen Decoction by a liquid chromatography-electrospray ionization-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2014 Jul; 95(?):76-84. doi: 10.1016/j.jpba.2014.02.013. [PMID: 24637051]
  • Vamsidhar Yerramsetty, Daniel D Gallaher, Baraem Ismail. Malonylglucoside conjugates of isoflavones are much less bioavailable compared with unconjugated β-glucosidic forms in rats. The Journal of nutrition. 2014 May; 144(5):631-7. doi: 10.3945/jn.114.190801. [PMID: 24647389]
  • Jing Xu, Shixiu Feng, Qi Wang, Min Zhang, Cunli Zhang. A new flavonoid glycoside from the rhizomes and roots of Smilax scobinicaulis. Natural product research. 2014; 28(8):517-21. doi: 10.1080/14786419.2014.880913. [PMID: 24483603]
  • Hyeon-Jeong Oh, Young-Gyu Kang, Tae-Young Na, Hyeon-Ji Kim, Jun Seong Park, Won-Jea Cho, Mi-Ock Lee. Identification of daidzein as a ligand of retinoic acid receptor that suppresses expression of matrix metalloproteinase-9 in HaCaT cells. Molecular and cellular endocrinology. 2013 Aug; 376(1-2):107-13. doi: 10.1016/j.mce.2013.06.015. [PMID: 23791815]
  • Xiaoming Liu, Yunli Zhao, Enze Gao, Xing Zhao, Zheng Liu, Zhiguo Yu. Pharmacokinetic comparisons of puerarin, daidzin and the glucuronide metabolite of puerarin after administration of total flavonoid from Gegen alone and total flavonoid from Gegen combined with total saponin from Sanqi in rats under different physiological states. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Jul; 931(?):127-33. doi: 10.1016/j.jchromb.2013.05.016. [PMID: 23774247]
  • Yun-Hui Cui, Zhi-Ping Wang, Hua Fan, Ke Yang. [Adsorption and isolation of macroporous resin for three isoflavonoids from puerariae lobatae radix]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Apr; 36(4):650-3. doi: . [PMID: 24134015]
  • Xin Dong, Wenqing Xu, Robert A Sikes, Changqing Wu. Apoptotic effects of cooked and in vitro digested soy on human prostate cancer cells. Food chemistry. 2012 Dec; 135(3):1643-52. doi: 10.1016/j.foodchem.2012.06.023. [PMID: 22953905]
  • Rui An, Hua Zhang, Yi-Zhu Zhang, Ran-Chi Xu, Xin-Hong Wang. [Intestinal absorption of different combinations of active compounds from Gegenqinlian decoction by rat single pass intestinal perfusion in situ]. Yao xue xue bao = Acta pharmaceutica Sinica. 2012 Dec; 47(12):1696-702. doi: ". [PMID: 23460978]
  • Huihui Liu, Bin Wu, Guoyu Pan, Lei He, Zhixiong Li, Mingsong Fan, Longhai Jian, Mingcang Chen, Ke Wang, Chenggang Huang. Metabolism and pharmacokinetics of mangiferin in conventional rats, pseudo-germ-free rats, and streptozotocin-induced diabetic rats. Drug metabolism and disposition: the biological fate of chemicals. 2012 Nov; 40(11):2109-18. doi: 10.1124/dmd.112.045849. [PMID: 22859782]
  • Martine Kienzle Hagen, Ana Ludke, Alex Sander Araujo, Roberta Hack Mendes, Tânia Gatelli Fernandes, Jose Marcos Gontijo Mandarino, Susana Llesuy, Erna Vogt de Jong, Adriane Belló-Klein. Antioxidant characterization of soy derived products in vitro and the effect of a soy diet on peripheral markers of oxidative stress in a heart disease model. Canadian journal of physiology and pharmacology. 2012 Aug; 90(8):1095-103. doi: 10.1139/y2012-028. [PMID: 22808939]
  • Aiguo Zeng, Jianfeng Xing, Changhe Wang, Jie Song, Cong Li, Xin Yang, Guangde Yang. Simultaneous analysis and retention behavior of major isoflavonoids in Radix Puerariae lobatae and Radix Puerariae thomsonii by high performance liquid chromatography with cyclodextrins as a mobile phase modifier. Analytica chimica acta. 2012 Jan; 712(?):145-51. doi: 10.1016/j.aca.2011.10.061. [PMID: 22177078]
  • John B Sutherland, Brad M Bridges, Thomas M Heinze, Michael R Adams, Patrick J Delio, Charlotte Hotchkiss, Fatemeh Rafii. Comparison of the effects of antimicrobial agents from three different classes on metabolism of isoflavonoids by colonic microflora using Etest strips. Current microbiology. 2012 Jan; 64(1):60-5. doi: 10.1007/s00284-011-0020-4. [PMID: 22006071]
  • MinHee Park, Min Kyu Jeong, MiJa Kim, JaeHwan Lee. Modification of isoflavone profiles in a fermented soy food with almond powder. Journal of food science. 2012 Jan; 77(1):C128-34. doi: 10.1111/j.1750-3841.2011.02504.x. [PMID: 22182181]
  • Chenxi Zhao, Hoi-yan Chan, Dalin Yuan, Yizeng Liang, Tsui-yan Lau, Foo-Tim Chau. Rapid simultaneous determination of major isoflavones of Pueraria lobata and discriminative analysis of its geographical origins by principal component analysis. Phytochemical analysis : PCA. 2011 Nov; 22(6):503-8. doi: 10.1002/pca.1308. [PMID: 21495105]
  • Li Yang, Cong Li, Tianhu Yuan, Tianwei Tan, Liqun Zhang. Preparation of highly pure daidzin on oligo-β-cyclodextrin-Sepharose HP and investigation of chromatographic behavior of isoflavones by molecular docking. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Jun; 879(20):1773-80. doi: 10.1016/j.jchromb.2011.04.022. [PMID: 21602109]
  • Rafael Bolaños, Angélica Del Castillo, José Francia. Soy isoflavones versus placebo in the treatment of climacteric vasomotor symptoms: systematic review and meta-analysis. Menopause (New York, N.Y.). 2010 May; 17(3):660-6. doi: . [PMID: 20464785]
  • Benyakan Pongkitwitoon, Seiichi Sakamoto, Hiroyuki Tanaka, Ryota Tsuchihashi, Junei Kinjo, Satoshi Morimoto, Waraporn Putalun. Enzyme-linked immunosorbent assay for total isoflavonoids in Pueraria candollei using anti-puerarin and anti-daidzin polyclonal antibodies. Planta medica. 2010 May; 76(8):831-6. doi: 10.1055/s-0029-1240725. [PMID: 20033865]
  • Haiyang Zhang, Wei Feng, Cong Li, Tianwei Tan. Investigation of the inclusions of puerarin and daidzin with beta-cyclodextrin by molecular dynamics simulation. The journal of physical chemistry. B. 2010 Apr; 114(14):4876-83. doi: 10.1021/jp907488j. [PMID: 20297792]
  • B G Terigar, S Balasubramanian, D Boldor, Z Xu, M Lima, C M Sabliov. Continuous microwave-assisted isoflavone extraction system: design and performance evaluation. Bioresource technology. 2010 Apr; 101(7):2466-71. doi: 10.1016/j.biortech.2009.11.039. [PMID: 20018507]
  • Dewu Zhang, Yan Ren, Shengjun Dai, Wanhui Liu, Guihai Li. [Isoflavones from vines of Pueraria lobata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Dec; 34(24):3217-20. doi: . [PMID: 20353004]
  • Maria P Arolfo, David H Overstreet, Lina Yao, Peidong Fan, Andrew J Lawrence, Guoxin Tao, Wing-Ming Keung, Bert L Vallee, M Foster Olive, Justin T Gass, Emanuel Rubin, Helen Anni, Clyde W Hodge, Joyce Besheer, Jeff Zablocki, Kwan Leung, Brent K Blackburn, Louis G Lange, Ivan Diamond. Suppression of heavy drinking and alcohol seeking by a selective ALDH-2 inhibitor. Alcoholism, clinical and experimental research. 2009 Nov; 33(11):1935-44. doi: 10.1111/j.1530-0277.2009.01031.x. [PMID: 19673742]
  • Corinna E Rüfer, Sabine E Kulling, Jutta Möseneder, Peter Winterhalter, Achim Bub. Role of plasma lipoproteins in the transport of the soyabean isoflavones daidzein and daidzein-7-O-beta-D-glucoside. The British journal of nutrition. 2009 Sep; 102(6):793-6. doi: 10.1017/s0007114509297224. [PMID: 19335924]
  • Sung-Hwa Kim, Jeong-Haing Heo, Yeong Shik Kim, Sam Sik Kang, Jae Sue Choi, Sun-Mee Lee. Protective effect of daidzin against D-galactosamine and lipopolysaccharide-induced hepatic failure in mice. Phytotherapy research : PTR. 2009 May; 23(5):701-6. doi: 10.1002/ptr.2710. [PMID: 19107740]
  • M V Wenzl, G Wölkart, H Stessel, M Beretta, K Schmidt, B Mayer. Different effects of ascorbate deprivation and classical vascular nitrate tolerance on aldehyde dehydrogenase-catalysed bioactivation of nitroglycerin. British journal of pharmacology. 2009 Apr; 156(8):1248-55. doi: 10.1111/j.1476-5381.2009.00126.x. [PMID: 19254277]
  • Adam Reppert, Gad G Yousef, Randy B Rogers, Mary Ann Lila. Isolation of radiolabeled isoflavones from kudzu (Pueraria lobata) root cultures. Journal of agricultural and food chemistry. 2008 Sep; 56(17):7860-5. doi: 10.1021/jf801413z. [PMID: 18690681]
  • B Klejdus, J Vacek, L Lojková, L Benesová, V Kubán. Ultrahigh-pressure liquid chromatography of isoflavones and phenolic acids on different stationary phases. Journal of chromatography. A. 2008 Jun; 1195(1-2):52-9. doi: 10.1016/j.chroma.2008.04.069. [PMID: 18501366]
  • Wichai Cherdshewasart, Suttijit Sriwatcharakul. Metabolic activation promotes estrogenic activity of the phytoestrogen-rich plant. Maturitas. 2008 Feb; 59(2):128-36. doi: 10.1016/j.maturitas.2008.01.002. [PMID: 18313242]
  • Wichai Cherdshewasart, Suttijit Sriwatcharakul. Major isoflavonoid contents of the 1-year-cultivated phytoestrogen-rich herb, Pueraria mirifica. Bioscience, biotechnology, and biochemistry. 2007 Oct; 71(10):2527-33. doi: 10.1271/bbb.70316. [PMID: 17928711]
  • Hong-Ying Zhou, Jian-Hua Wang, Feng-Yun Yan. [Separation and determination of puerarin, daidzin and daidzein in stems and leaves of Pueraria thomsonii by RP-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 May; 32(10):937-9. doi: ". [PMID: 17655152]
  • Wichai Cherdshewasart, Subongkoj Subtang, Winai Dahlan. Major isoflavonoid contents of the phytoestrogen rich-herb Pueraria mirifica in comparison with Pueraria lobata. Journal of pharmaceutical and biomedical analysis. 2007 Jan; 43(2):428-34. doi: 10.1016/j.jpba.2006.07.013. [PMID: 16930918]
  • Ara Kirakosyan, Peter B Kaufman, Soo Chul Chang, Sara Warber, Steven Bolling, Hrachik Vardapetyan. Regulation of isoflavone production in hydroponically grown Pueraria montana (kudzu) by cork pieces, XAD-4, and methyl jasmonate. Plant cell reports. 2006 Dec; 25(12):1387-91. doi: 10.1007/s00299-006-0198-2. [PMID: 16841218]
  • Feng Xu, Yue Zhang, Shengyuan Xiao, Xiaowei Lu, Donghui Yang, Xiaoda Yang, Changling Li, Mingying Shang, Pengfei Tu, Shaoqing Cai. Absorption and metabolism of Astragali radix decoction: in silico, in vitro, and a case study in vivo. Drug metabolism and disposition: the biological fate of chemicals. 2006 Jun; 34(6):913-24. doi: 10.1124/dmd.105.008300. [PMID: 16507649]
  • Congbing Fang, Xiaochun Wan, Huarong Tan, Changjun Jiang. Separation and determination of isoflavonoids in several kudzu samples by high-performance capillary electrophoresis (HPCE). Annali di chimica. 2006 Jan; 96(1-2):117-24. doi: 10.1002/adic.200690002. [PMID: 16734027]
  • Tong-Tong Yang, Min-Jian Qin. [Isolation and structure identification of a new isoflavone from Psoralea corylifolias]. Yao xue xue bao = Acta pharmaceutica Sinica. 2006 Jan; 41(1):76-9. doi: . [PMID: 16683532]
  • Roberto Minutolo, Luca De Nicola, Pasquale Zamboli, Paolo Chiodini, Giuseppe Signoriello, Clemente Toderico, Gennaro Arfè, Giuseppe Boschi, Ciro Brancati, Patrizia Iaccarino, Giuseppe Conte. Management of hypertension in patients with CKD: differences between primary and tertiary care settings. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2005 Jul; 46(1):18-25. doi: 10.1053/j.ajkd.2005.03.019. [PMID: 15983953]
  • Ihsan Ergün, M Cenk Akbostanci, Başol Canbakan, Bilge Koçer, Arzu Ensari, Gökhan Nergizoglu, Kenan Keven. Minimal change nephrotic syndrome with stiff-person syndrome: is there a link?. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2005 Jul; 46(1):e11-4. doi: 10.1053/j.ajkd.2005.03.009. [PMID: 15983949]
  • Kara L Britt, Evan R Simpson, Jock K Findlay. Effects of phytoestrogens on the ovarian and pituitary phenotypes of estrogen-deficient female aromatase knockout mice. Menopause (New York, N.Y.). 2005 Mar; 12(2):174-85. doi: 10.1097/00042192-200512020-00012. [PMID: 15772565]
  • Shin Yasuda, Po-Sheng Wu, Emi Hattori, Hirofumi Tachibana, Koji Yamada. Simultaneous determination of isoflavones and bisphenol A in rat serum by high-performance liquid chromatography coupled with coulometric array detection. Bioscience, biotechnology, and biochemistry. 2004 Jan; 68(1):51-8. doi: 10.1271/bbb.68.51. [PMID: 14745163]
  • A Matkowski, D Woźniak, J Oszmiański, E Lamer-Zarawska. Flavonoids of Pueraria lobata: chromatographic analysis of leaves and roots of cultivated plants. Die Pharmazie. 2003 Sep; 58(9):682-3. doi: ". [PMID: 14531473]
  • Wen-shan Jin, Yu-yuan Tan, You-gen Chen, Yan Wang. [Determination of puerarin, daidzin and daidzein in root of Pueraria lobata of different origin by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 Jan; 28(1):49-51. doi: ". [PMID: 15015267]
  • Zhao-Ning Ji, Guo-Qing Liu. Daidzin protects PC12 cells from serum deprivation-induced apoptosis. Journal of Asian natural products research. 2002 Dec; 4(4):265-9. doi: 10.1080/1028602021000049050. [PMID: 12450254]
  • Min-Kyung Choo, Eun-Kyung Park, Hae-Kyung Yoon, Dong-Hyun Kim. Antithrombotic and antiallergic activities of daidzein, a metabolite of puerarin and daidzin produced by human intestinal microflora. Biological & pharmaceutical bulletin. 2002 Oct; 25(10):1328-32. doi: 10.1248/bpb.25.1328. [PMID: 12392089]
  • Evelyne Drapier Faure, Philippe Chantre, Pierre Mares. Effects of a standardized soy extract on hot flushes: a multicenter, double-blind, randomized, placebo-controlled study. Menopause (New York, N.Y.). 2002 Sep; 9(5):329-34. doi: 10.1097/00042192-200209000-00005. [PMID: 12218721]
  • Jun Kanno, Hideo Kato, Toshio Iwata, Tohru Inoue. Phytoestrogen-low diet for endocrine disruptor studies. Journal of agricultural and food chemistry. 2002 Jun; 50(13):3883-5. doi: 10.1021/jf020235p. [PMID: 12059176]
  • Feifei Tian, Yongxin Zhu, Hong Long, Meloney Cregor, Fuming Xie, Candice B Kissinger, Peter T Kissinger. Liquid chromatography coupled with multi-channel electrochemical detection for the determination of daidzin in rat blood sampled by an automated blood sampling system. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2002 May; 772(1):173-7. doi: 10.1016/s1570-0232(02)00087-9. [PMID: 12016029]
  • O I Sukmanskiĭ. [Isoflavones and calcified tissues]. Uspekhi fiziologicheskikh nauk. 2002 Apr; 33(2):83-94. doi: ". [PMID: 12004580]
  • A Albert, C Altabre, F Baró, E Buendía, A Cabero, M J Cancelo, C Castelo-Branco, P Chantre, M Duran, J Haya, P Imbert, D Julía, J L Lanchares, P Llaneza, M Manubens, A Miñano, F Quereda, C Ribes, F Vázquez. Efficacy and safety of a phytoestrogen preparation derived from Glycine max (L.) Merr in climacteric symptomatology: a multicentric, open, prospective and non-randomized trial. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2002 Mar; 9(2):85-92. doi: 10.1078/0944-7113-00107. [PMID: 11995954]
  • M J Plewa, M A Berhow, S F Vaughn, E J Woods, M Rundell, K Naschansky, S Bartolini, E D Wagner. Isolating antigenotoxic components and cancer cell growth suppressors from agricultural by-products. Mutation research. 2001 Sep; 480-481(?):109-20. doi: 10.1016/s0027-5107(01)00174-9. [PMID: 11506804]
  • T Uesugi, T Toda, K Tsuji, H Ishida. Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin. Biological & pharmaceutical bulletin. 2001 Apr; 24(4):368-72. doi: 10.1248/bpb.24.368. [PMID: 11305597]
  • H G Hur, J O Lay, R D Beger, J P Freeman, F Rafii. Isolation of human intestinal bacteria metabolizing the natural isoflavone glycosides daidzin and genistin. Archives of microbiology. 2000 Dec; 174(6):422-8. doi: 10.1007/s002030000222. [PMID: 11195098]
  • D H Upmalis, R Lobo, L Bradley, M Warren, F L Cone, C A Lamia. Vasomotor symptom relief by soy isoflavone extract tablets in postmenopausal women: a multicenter, double-blind, randomized, placebo-controlled study. Menopause (New York, N.Y.). 2000 Jul; 7(4):236-42. doi: 10.1097/00042192-200007040-00005. [PMID: 10914616]
  • C Martín-Cordero, M López-Lazaro, J Piñero, T Ortiz, F Cortés, M J Ayuso. Glucosylated isoflavones as DNA topoisomerase II poisons. Journal of enzyme inhibition. 2000; 15(5):455-60. doi: 10.3109/14756360009040701. [PMID: 11030085]
  • M K Piskula, J Yamakoshi, Y Iwai. Daidzein and genistein but not their glucosides are absorbed from the rat stomach. FEBS letters. 1999 Mar; 447(2-3):287-91. doi: 10.1016/s0014-5793(99)00307-5. [PMID: 10214963]
  • N Okamura, H Miki, H Orii, Y Masaoka, S Yamashita, H Kobayashi, A Yagi. Simultaneous high-performance liquid chromatographic determination of puerarin, daidzin, paeoniflorin, liquiritin, cinnamic acid, cinnamaldehyde and glycyrrhizin in Kampo medicines. Journal of pharmaceutical and biomedical analysis. 1999 Mar; 19(3-4):603-12. doi: 10.1016/s0731-7085(98)00262-3. [PMID: 10704126]
  • T Yasuda, K Ohsawa. Urinary metabolites of daidzin orally administered in rats. Biological & pharmaceutical bulletin. 1998 Sep; 21(9):953-7. doi: 10.1248/bpb.21.953. [PMID: 9781846]
  • D H Kim, K U Yu, E A Bae, M J Han. Metabolism of puerarin and daidzin by human intestinal bacteria and their relation to in vitro cytotoxicity. Biological & pharmaceutical bulletin. 1998 Jun; 21(6):628-30. doi: 10.1248/bpb.21.628. [PMID: 9657051]