Coumesterol (BioDeep_00000002591)

 

Secondary id: BioDeep_00000270035, BioDeep_00000400505, BioDeep_00000870762

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

化学式: C15H8O5 (268.0371718)
中文名称: 拟雌内酯, 考迈斯托醇
谱图信息: 最多检出来源 Homo sapiens(blood) 0.06%

分子结构信息

SMILES: c1(ccc2c(c1)oc(=O)c1c2oc2c1ccc(c2)O)O
InChI: InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H

描述信息

Cumoesterol (or coumestrol), a coumestan isoflavone, has estrogenic properties (phytoestrogens are compounds structurally and functionally similar to 17-estradiol) and is an isoflavonoid phytoalexin produced by soybeans, a low molecular weight antimicrobial compound that is synthesized de novo and accumulates in plants after exposure to microorganisms (i.e.: phytoalexin induction and accumulation in soybean cotyledon tissue is observed with four species of Aspergillus: A. sojae, A. oryzae, A. niger, and A. flavus) (PMID: 10888516). Coumestrol is a naturally occurring plant coumarin that displays high affinity for the hormone-binding site of the human estrogen receptor (hER), for which it serves as a potent non-steroidal agonist. Coumestrol emits intense blue fluorescence when bound to this protein, making it ideally suited for use as a cytological stain to detect ER in fixed and intact cells. Such observations illustrate the potential for using coumestrol to investigate real-time effects of a variety of physiological stimuli on the subcellular distribution of hER in living cells (PMID: 8315272).
Coumestrol is a member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9. It has a role as an anti-inflammatory agent, an antioxidant and a plant metabolite. It is a member of coumestans, a delta-lactone and a polyphenol. It is functionally related to a coumestan.
Coumestrol is a natural product found in Campylotropis hirtella, Melilotus messanensis, and other organisms with data available.
A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.
See also: Medicago sativa whole (part of).
Isolated from Medicago subspecies, Glycine max (soybean), Pisum sativum (pea), Spinacia oleracea (spinach), Brassica oleracea (cabbage), Dolichos biflorus (papadi), Melilotus alba (white melilot), Phaseolus subspecies (inc. lima beans, pinto beans) and Vigna unguiculata (all Leguminosae). Potential nutriceutical
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.
Coumestrol, a phytoestrogen present in soybean products, exhibits activities against cancers, neurological disorders, and autoimmune diseases. It suppresses proliferation of ES2 cells with an IC50 of 50 μM.
Coumestrol, a phytoestrogen present in soybean products, exhibits activities against cancers, neurological disorders, and autoimmune diseases. It suppresses proliferation of ES2 cells with an IC50 of 50 μM.

同义名列表

38 个代谢物同义名

5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one; 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one; 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone; 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, delta-lactone; 3-Benzofurancarboxylic acid,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone; Coumestrol, BioReagent, suitable for fluorescence, >=97.5\\% (HPLC); 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-; 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-; 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihdyroxy-; 3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one; 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one #; 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one; 3,9-dihydroxy-6H-(1)benzofuro(3,2-c)chromen-6-one; 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one; 3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one; 3,9-dihydroxy-6H-benzofuro[3,2-c]chromen-6-one; 5-19-06-00405 (Beilstein Handbook Reference); 3,9-dihydroxybenzofuro[3,2-c]chromen-6-one; 6H-Benzofuro[3, 3,9-dihydroxy-; Coumestrol, >=95.0\\% (HPLC); 7,12-Dihydroxycoumestan; 3,9-Dihydroxycoumestan; Coumestrol (COU); UNII-V7NW98OB34; COUMESTROL [MI]; Oprea1_222511; Tox21_200032; NCI60_001863; SMP2_000163; Cumoesterol; Coumesterol; Chrysanthin; Coumestrol; Cumoestrol; V7NW98OB34; Cumostrol; Cumestrol; A1-00298



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

  • coumestrol biosynthesis: (S)-dihydrodaidzein + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ (3R)-2'-hydroxydihydrodaidzein + H2O + an oxidized [NADPH-hemoprotein reductase]

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

31 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

  • Magdalena Wójciak, Piotr Drozdowski, Aleksandra Ziemlewska, Martyna Zagórska-Dziok, Zofia Nizioł-Łukaszewska, Tomasz Kubrak, Ireneusz Sowa. ROS Scavenging Effect of Selected Isoflavones in Provoked Oxidative Stress Conditions in Human Skin Fibroblasts and Keratinocytes. Molecules (Basel, Switzerland). 2024 Feb; 29(5):. doi: 10.3390/molecules29050955. [PMID: 38474467]
  • Wiktor Bzdęga, Hubert Żywno, Adrian Kołakowski, Piotr Franciszek Kurzyna, Ewa Harasim-Symbor, Adrian Chabowski, Karolina Konstantynowicz-Nowicka. Coumestrol as a new substance that may diminish lipid precursors of the inflammation in steatotic primary rat hepatocytes. Biochimie. 2023 Jan; 204(?):78-91. doi: 10.1016/j.biochi.2022.09.002. [PMID: 36084910]
  • Bret Cooper, Kimberly B Campbell, Wesley M Garrett. Salicylic Acid and Phytoalexin Induction by a Bacterium that Causes Halo Blight in Beans. Phytopathology. 2022 Aug; 112(8):1766-1775. doi: 10.1094/phyto-12-21-0496-r. [PMID: 35147446]
  • Raquel Cano, José L Pérez, Lissé Angarita Dávila, Ángel Ortega, Yosselin Gómez, Nereida Josefina Valero-Cedeño, Heliana Parra, Alexander Manzano, Teresa Isabel Véliz Castro, María P Díaz Albornoz, Gabriel Cano, Joselyn Rojas-Quintero, Maricarmen Chacín, Valmore Bermúdez. Role of Endocrine-Disrupting Chemicals in the Pathogenesis of Non-Alcoholic Fatty Liver Disease: A Comprehensive Review. International journal of molecular sciences. 2021 May; 22(9):. doi: 10.3390/ijms22094807. [PMID: 34062716]
  • Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach. European journal of medicinal chemistry. 2021 Mar; 213(?):113037. doi: 10.1016/j.ejmech.2020.113037. [PMID: 33257172]
  • Hoda A S El-Garhy, Ahmed A Elsisi, Shereen A Mohamed, Osama M Morsy, Gamal Osman, Fayz A Abdel-Rahman. Transcriptomic changes in green bean pods against grey mould and white rot diseases via field application of chemical elicitor nanoparticles. IET nanobiotechnology. 2020 Sep; 14(7):574-583. doi: 10.1049/iet-nbt.2020.0004. [PMID: 33010132]
  • Masyitah Hasan, Endang Kumolosasi, Malina Jasamai, Jamia Azdina Jamal, Norazrina Azmi, Nor Fadilah Rajab. Evaluation of phytoestrogens in inducing cell death mediated by decreasing Annexin A1 in Annexin A1-knockdown leukemia cells. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2020 Jun; 28(1):97-108. doi: 10.1007/s40199-019-00320-0. [PMID: 31912375]
  • Janine Beatriz Ramos Anastacio, Eduardo Farias Sanches, Fabrício Nicola, Felipe Odorcyk, Rafael Bandeira Fabres, Carlos Alexandre Netto. Phytoestrogen coumestrol attenuates brain mitochondrial dysfunction and long-term cognitive deficits following neonatal hypoxia-ischemia. International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience. 2019 Dec; 79(?):86-95. doi: 10.1016/j.ijdevneu.2019.10.009. [PMID: 31693927]
  • Guillermo Montero, Francisco Arriagada, Germán Günther, Soledad Bollo, Francisco Mura, Eduardo Berríos, Javier Morales. Phytoestrogen coumestrol: Antioxidant capacity and its loading in albumin nanoparticles. International journal of pharmaceutics. 2019 May; 562(?):86-95. doi: 10.1016/j.ijpharm.2019.03.029. [PMID: 30885651]
  • Jungmin Ha, Young-Gyu Kang, Taeyoung Lee, Myoyeon Kim, Min Young Yoon, Eunsoo Lee, Xuefei Yang, Donghyun Kim, Yong-Jin Kim, Tae Ryong Lee, Moon Young Kim, Suk-Ha Lee. Comprehensive RNA sequencing and co-expression network analysis to complete the biosynthetic pathway of coumestrol, a phytoestrogen. Scientific reports. 2019 02; 9(1):1934. doi: 10.1038/s41598-018-38219-6. [PMID: 30760815]
  • E C Silva, P L Abhayawardhana, A V Lygin, C L Robertson, M Liu, Z Liu, R W Schneider. Coumestrol Confers Partial Resistance in Soybean Plants Against Cercospora Leaf Blight. Phytopathology. 2018 08; 108(8):935-947. doi: 10.1094/phyto-05-17-0189-r. [PMID: 29451417]
  • Yuankun Zhai, Qingfeng Wang, Yingying Li, Jiawei Cui, Kun Feng, Xijian Kong, Cory J Xian. The higher osteoprotective activity of psoralidin in vivo than coumestrol is attributed by its presence of an isopentenyl group and through activated PI3K/Akt axis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jun; 102(?):1015-1024. doi: 10.1016/j.biopha.2018.03.166. [PMID: 29710518]
  • Débora Fretes Argenta, Juliana Bidone, Letícia Scherer Koester, Valquíria Link Bassani, Cláudia Maria Oliveira Simões, Helder Ferreira Teixeira. Topical Delivery of Coumestrol from Lipid Nanoemulsions Thickened with Hydroxyethylcellulose for Antiherpes Treatment. AAPS PharmSciTech. 2018 Jan; 19(1):192-200. doi: 10.1208/s12249-017-0828-8. [PMID: 28681331]
  • Whasun Lim, Changwon Yang, Muhah Jeong, Fuller W Bazer, Gwonhwa Song. Coumestrol induces mitochondrial dysfunction by stimulating ROS production and calcium ion influx into mitochondria in human placental choriocarcinoma cells. Molecular human reproduction. 2017 11; 23(11):786-802. doi: 10.1093/molehr/gax052. [PMID: 29040664]
  • Elina Karhu, Janne Isojärvi, Pia Vuorela, Leena Hanski, Adyary Fallarero. Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy. Journal of natural products. 2017 10; 80(10):2602-2608. doi: 10.1021/acs.jnatprod.6b01052. [PMID: 29043803]
  • Alessandra Ferramosca, Mariangela Di Giacomo, Vincenzo Zara. Antioxidant dietary approach in treatment of fatty liver: New insights and updates. World journal of gastroenterology. 2017 Jun; 23(23):4146-4157. doi: 10.3748/wjg.v23.i23.4146. [PMID: 28694655]
  • Chelliah Selvam, Brian C Jordan, Sandhya Prakash, Daniel Mutisya, Ramasamy Thilagavathi. Pterocarpan scaffold: A natural lead molecule with diverse pharmacological properties. European journal of medicinal chemistry. 2017 Mar; 128(?):219-236. doi: 10.1016/j.ejmech.2017.01.023. [PMID: 28189086]
  • Jeong Ah Hwang, Nok Hyun Park, Yong Joo Na, Hae Kwang Lee, John Hwan Lee, Yong Jin Kim, Chang Seok Lee. Coumestrol Down-Regulates Melanin Production in Melan-a Murine Melanocytes through Degradation of Tyrosinase. Biological & pharmaceutical bulletin. 2017; 40(4):535-539. doi: 10.1248/bpb.b16-00834. [PMID: 28381809]
  • Roel C Rabara, Prateek Tripathi, Paul J Rushton. Comparative Metabolome Profile between Tobacco and Soybean Grown under Water-Stressed Conditions. BioMed research international. 2017; 2017(?):3065251. doi: 10.1155/2017/3065251. [PMID: 28127554]
  • Young Jin Jang, Hyo Jeong Son, Jiyun Ahn, Chang Hwa Jung, Taeyoul Ha. Coumestrol modulates Akt and Wnt/β-catenin signaling during the attenuation of adipogenesis. Food & function. 2016 Dec; 7(12):4984-4991. doi: 10.1039/c6fo01127f. [PMID: 27868125]
  • Shuangqing Zhang, Mengjie He, Zhenwu Huang. [UPLC-MS / MS for the pharmacokinetics of icariin in rats]. Wei sheng yan jiu = Journal of hygiene research. 2016 Sep; 45(5):807-810. doi: NULL. [PMID: 29903136]
  • Xiaojing Jin, Shujun Wang, Xuemin Zhao, Qian Jin, Chenling Fan, Jing Li, Zhongyan Shan, Weiping Teng. Coumestrol inhibits autoantibody production through modulating Th1 response in experimental autoimmune thyroiditis. Oncotarget. 2016 Aug; 7(33):52797-52809. doi: 10.18632/oncotarget.10353. [PMID: 27384679]
  • Atif Zafar, Swarnendra Singh, Imrana Naseem. Cu(II)-coumestrol interaction leads to ROS-mediated DNA damage and cell death: a putative mechanism for anticancer activity. The Journal of nutritional biochemistry. 2016 07; 33(?):15-27. doi: 10.1016/j.jnutbio.2016.03.003. [PMID: 27260464]
  • Prateek Tripathi, Roel C Rabara, R Neil Reese, Marissa A Miller, Jai S Rohila, Senthil Subramanian, Qingxi J Shen, Dominique Morandi, Heike Bücking, Vladimir Shulaev, Paul J Rushton. A toolbox of genes, proteins, metabolites and promoters for improving drought tolerance in soybean includes the metabolite coumestrol and stomatal development genes. BMC genomics. 2016 Feb; 17(?):102. doi: 10.1186/s12864-016-2420-0. [PMID: 26861168]
  • Magdalena Wójciak-Kosior, Ireneusz Sowa, Tomasz Blicharski, Maciej Strzemski, Sławomir Dresler, Grażyna Szymczak, Artur Wnorowski, Ryszard Kocjan, Ryszard Świeboda. The Stimulatory Effect of Strontium Ions on Phytoestrogens Content in Glycine max (L.) Merr. Molecules (Basel, Switzerland). 2016 Jan; 21(1):90. doi: 10.3390/molecules21010090. [PMID: 26784151]
  • Yi-Cheng Hu, Chien-Tung Wu, Jung-Nien Lai, Yueh-Ting Tsai. Detection of a negative correlation between prescription of Chinese herbal products containing coumestrol, genistein or daidzein and risk of subsequent endometrial cancer among tamoxifen-treated female breast cancer survivors in Taiwan between 1998 and 2008: A population-based study. Journal of ethnopharmacology. 2015 Jul; 169(?):356-62. doi: 10.1016/j.jep.2015.04.028. [PMID: 25934515]
  • Huixiao Hong, William S Branham, Hui Wen Ng, Carrie L Moland, Stacey L Dial, Hong Fang, Roger Perkins, Daniel Sheehan, Weida Tong. Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. Toxicological sciences : an official journal of the Society of Toxicology. 2015 Feb; 143(2):333-48. doi: 10.1093/toxsci/kfu231. [PMID: 25349334]
  • Shuangqing Zhang, Zhenwu Huang. [UPLC-MS/MS method for the determination of icaritin in rat plasma]. Wei sheng yan jiu = Journal of hygiene research. 2014 Nov; 43(6):986-9, 997. doi: NULL. [PMID: 25603612]
  • 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]
  • Sergio A Arispe, Betty Adams, Thomas E Adams. Effect of phytoestrogens on basal and GnRH-induced gonadotropin secretion. The Journal of endocrinology. 2013 Dec; 219(3):243-50. doi: 10.1530/joe-13-0158. [PMID: 24050980]
  • Young-Hoon Lee, Heung Joo Yuk, Ki-Hun Park, Young-Seuk Bae. Coumestrol induces senescence through protein kinase CKII inhibition-mediated reactive oxygen species production in human breast cancer and colon cancer cells. Food chemistry. 2013 Nov; 141(1):381-8. doi: 10.1016/j.foodchem.2013.03.053. [PMID: 23768371]
  • G Ferreira-Dias, M Botelho, A Zagrajczuk, M R Rebordão, A M Galvão, P Pinto Bravo, K Piotrowska-Tomala, A Z Szóstek, W Wiczkowski, M Piskula, M J Fradinho, D J Skarzynski. Coumestrol and its metabolite in mares' plasma after ingestion of phytoestrogen-rich plants: potent endocrine disruptors inducing infertility. Theriogenology. 2013 Oct; 80(6):684-92. doi: 10.1016/j.theriogenology.2013.06.002. [PMID: 23845774]
  • Shu Liu, David Hsieh, Yi-Lin Yang, Zhidong Xu, Csaba Peto, David M Jablons, Liang You. Coumestrol from the national cancer Institute's natural product library is a novel inhibitor of protein kinase CK2. BMC pharmacology & toxicology. 2013 Jul; 14(?):36. doi: 10.1186/2050-6511-14-36. [PMID: 23845105]
  • Mengdong Wang, Miki Sugimoto, Shuntaro Ikeda, Shinichi Kume. Effects of coumestrol administration to maternal mice during pregnancy and lactation on immunoblogulin A-secreting cells in mammary glands. Animal science journal = Nihon chikusan Gakkaiho. 2013 Apr; 84(4):322-7. doi: 10.1111/asj.12007. [PMID: 23590506]
  • Olga Leuner, Jaroslav Havlik, Jana Hummelova, Elena Prokudina, Pavel Novy, Ladislav Kokoska. Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes. Journal of the science of food and agriculture. 2013 Feb; 93(3):575-9. doi: 10.1002/jsfa.5835. [PMID: 22926873]
  • Huixiao Hong, William S Branham, Stacey L Dial, Carrie L Moland, Hong Fang, Jie Shen, Roger Perkins, Daniel Sheehan, Weida Tong. Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. Chemical research in toxicology. 2012 Nov; 25(11):2553-66. doi: 10.1021/tx3003406. [PMID: 23013281]
  • Achref Aloui, Eliane Dumas-Gaudot, Zeina Daher, Diederik van Tuinen, Samira Aschi-Smit, Dominique Morandi. Influence of arbuscular mycorrhizal colonisation on cadmium induced Medicago truncatula root isoflavonoid accumulation. Plant physiology and biochemistry : PPB. 2012 Nov; 60(?):233-9. doi: 10.1016/j.plaphy.2012.08.014. [PMID: 23000816]
  • Cibele Canal Castro, Aline S Pagnussat, Lenir Orlandi, Paulo Worm, Nathalia Moura, Anne M Etgen, Carlos Alexandre Netto. Coumestrol has neuroprotective effects before and after global cerebral ischemia in female rats. Brain research. 2012 Sep; 1474(?):82-90. doi: 10.1016/j.brainres.2012.07.025. [PMID: 22824334]
  • Sarah J Lowry, Brian L Sprague, Erin J Aiello Bowles, Curtis J Hedman, Jocelyn Hemming, John M Hampton, Elizabeth S Burnside, Gale A Sisney, Diana S M Buist, Amy Trentham-Dietz. Mammographic breast density and serum phytoestrogen levels. Nutrition and cancer. 2012 Aug; 64(6):783-9. doi: 10.1080/01635581.2012.707279. [PMID: 22860715]
  • Eliza Gaweł. Chemical composition of lucerne leaf extract (EFL) and its applications as a phytobiotic in human nutrition. Acta scientiarum polonorum. Technologia alimentaria. 2012 Jul; 11(3):303-10. doi: ". [PMID: 22744951]
  • Michihisa Ueda, Yoshihiro Horiguchi, Miki Sugimoto, Shuntaro Ikeda, Shinichi Kume. Effects of coumestrol administration to maternal mice during pregnancy and lactation on renal Ca metabolism in neonatal mice. Animal science journal = Nihon chikusan Gakkaiho. 2012 Jun; 83(6):469-73. doi: 10.1111/j.1740-0929.2011.00977.x. [PMID: 22694330]
  • Seong Eun Jin, You Kyung Son, Byung-Sun Min, Hyun Ah Jung, Jae Sue Choi. Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots. Archives of pharmacal research. 2012 May; 35(5):823-37. doi: 10.1007/s12272-012-0508-x. [PMID: 22644850]
  • De-Wu Zhang, Yan Yang, Fang Yao, Qun-Ying Yu, Sheng-Jun Dai. Solalyratins A and B, new anti-inflammatory metabolites from Solanum lyratum. Journal of natural medicines. 2012 Apr; 66(2):362-6. doi: 10.1007/s11418-011-0581-3. [PMID: 21898133]
  • Hae-In Lee, Jin-Hwan Lee, Ki-Hun Park, Dipen Sangurdekar, Woo-Suk Chang. Effect of soybean coumestrol on Bradyrhizobium japonicum nodulation ability, biofilm formation, and transcriptional profile. Applied and environmental microbiology. 2012 Apr; 78(8):2896-903. doi: 10.1128/aem.07336-11. [PMID: 22307307]
  • Hee Young Jeon, Dae Bang Seo, Hyun-Jung Shin, Sang-Jun Lee. Effect of Aspergillus oryzae-challenged germination on soybean isoflavone content and antioxidant activity. Journal of agricultural and food chemistry. 2012 Mar; 60(11):2807-14. doi: 10.1021/jf204708n. [PMID: 22409158]
  • Marek Opalka, Barbara Kaminska, Anna Leska, Luiza Dusza. Mechanism of phytoestrogen action in Leydig cells of ganders (Anser anser domesticus): Interaction with estrogen receptors and steroidogenic enzymes. Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering. 2012; 47(9):1335-9. doi: 10.1080/10934529.2012.672146. [PMID: 22540659]
  • Alberto Cassetta, Ivet Krastanova, Katja Kristan, Mojca Brunskole Švegelj, Doriano Lamba, Tea Lanišnik Rižner, Jure Stojan. Insights into subtle conformational differences in the substrate-binding loop of fungal 17β-hydroxysteroid dehydrogenase: a combined structural and kinetic approach. The Biochemical journal. 2012 Jan; 441(1):151-60. doi: 10.1042/bj20110567. [PMID: 21929506]
  • Christiaan J Malherbe, Dalene De Beer, Elizabeth Joubert. Development of on-line high performance liquid chromatography (HPLC)-biochemical detection methods as tools in the identification of bioactives. International journal of molecular sciences. 2012; 13(3):3101-3133. doi: 10.3390/ijms13033101. [PMID: 22489144]
  • Manhai Long, Tanja Krüger, Mandana Ghisari, Eva Cecilie Bonefeld-Jørgensen. Effects of selected phytoestrogens and their mixtures on the function of the thyroid hormone and the aryl hydrocarbon receptor. Nutrition and cancer. 2012; 64(7):1008-19. doi: 10.1080/01635581.2012.711419. [PMID: 22966911]
  • D F Argenta, C Franco, L S Koester, V L Bassani, H F Teixeira. LC analysis of coumestrol incorporated into topical lipid nanoemulsions. Die Pharmazie. 2011 Dec; 66(12):929-32. doi: ". [PMID: 22312696]
  • Wibke S U Roland, Jean-Paul Vincken, Robin J Gouka, Leo van Buren, Harry Gruppen, Gerrit Smit. Soy isoflavones and other isoflavonoids activate the human bitter taste receptors hTAS2R14 and hTAS2R39. Journal of agricultural and food chemistry. 2011 Nov; 59(21):11764-71. doi: 10.1021/jf202816u. [PMID: 21942422]
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