2,3-Bis(3-hydroxybenzyl)butane-1,4-diol (BioDeep_00000173492)

   

human metabolite blood metabolite natural product


代谢物信息卡片


2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol

化学式: C18H22O4 (302.1518012)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 49.25%

分子结构信息

SMILES: C1=CC(=CC(=C1)O)CC(CO)C(CC2=CC(=CC=C2)O)CO
InChI: InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens

同义名列表

2 个代谢物同义名

2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol; 2,3-Bis(3-hydroxybenzyl)butane-1,4-diol



数据库引用编号

9 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

10 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

  • Matthew E Poynter, Madeleine M Mank, Jennifer L Ather. Obesity-associated inflammatory macrophage polarization is inhibited by capsaicin and phytolignans. American journal of physiology. Regulatory, integrative and comparative physiology. 2024 May; 326(5):R370-R382. doi: 10.1152/ajpregu.00161.2023. [PMID: 38436058]
  • Inés Domínguez-López, Polina Galkina, Isabella Parilli-Moser, Camila Arancibia-Riveros, Miguel Ángel Martínez-González, Jordi Salas-Salvadó, Dolores Corella, Mireia Malcampo, J Alfredo Martínez, Lucas Tojal-Sierra, Julia Wärnberg, Jesús Vioque, Dora Romaguera, José López-Miranda, Ramon Estruch, Francisco J Tinahones, José Manuel Santos-Lozano, Lluís Serra-Majem, Aurora Bueno-Cavanillas, Josep A Tur, María Rubín-García, Xavier Pintó, Fernando Fernández-Aranda, Miguel Delgado-Rodríguez, Ana Barabash-Bustelo, Josep Vidal, Clotilde Vázquez, Lidia Daimiel, Emilio Ros, Estefania Toledo, Alessandro Atzeni, Eva M Asensio, Natàlia Vera, Antonio Garcia-Rios, Laura Torres-Collado, Napoleón Pérez-Farinós, Marian Zulet, Alice Chaplin, Rosa Casas, Sandra Martín-Peláez, Jessica Vaquero-Luna, Ana Maria Gómez-Pérez, Zenaida Vázquez-Ruiz, Sangeetha Shyam, Carolina Ortega-Azorín, Natàlia Talens, Patricia J Peña-Orihuela, Alejandro Oncina-Canovas, Javier Diez-Espino, Nancy Babio, Montserrat Fitó, Rosa M Lamuela-Raventós. Microbial Phenolic Metabolites Are Associated with Improved Cognitive Health. Molecular nutrition & food research. 2024 Jan; 68(2):e2300183. doi: 10.1002/mnfr.202300183. [PMID: 38062915]
  • Xiaolei Yang, Yajia Guo, Timothy J Tse, Sarah K Purdy, Rana Mustafa, Jianheng Shen, Jane Alcorn, Martin J T Reaney. Oral Pharmacokinetics of Enriched Secoisolariciresinol Diglucoside and Its Polymer in Rats. Journal of natural products. 2021 06; 84(6):1816-1822. doi: 10.1021/acs.jnatprod.1c00335. [PMID: 34043363]
  • Liliana Maribel Perez-Perez, José Ángel Huerta-Ocampo, Saúl Ruiz-Cruz, Francisco Javier Cinco-Moroyoqui, Francisco Javier Wong-Corral, Luisa Alondra Rascón-Valenzuela, Miguel Angel Robles-García, Ricardo Iván González-Vega, Ema Carina Rosas-Burgos, María Alba Guadalupe Corella-Madueño, Carmen Lizette Del-Toro-Sánchez. Evaluation of Quality, Antioxidant Capacity, and Digestibility of Chickpea (Cicer arietinum L. cv Blanoro) Stored under N2 and CO2 Atmospheres. Molecules (Basel, Switzerland). 2021 May; 26(9):. doi: 10.3390/molecules26092773. [PMID: 34066776]
  • Cong-Cong Zhuang, Xu Feng, Hai-Yan Xu, Li Zhang, Ling Liu, Gong Zhang, Zhong Zheng, Chao-Mei Ma. Technical note: Quantification of lignans in the urine, milk, and plasma of flaxseed cake-fed dairy sheep. Journal of dairy science. 2021 Jan; 104(1):391-396. doi: 10.3168/jds.2020-18470. [PMID: 33189295]
  • Stephanie Tannous, Tony Haykal, Jana Dhaini, Mohammad Hassan Hodroj, Sandra Rizk. The anti-cancer effect of flaxseed lignan derivatives on different acute myeloid leukemia cancer cells. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Dec; 132(?):110884. doi: 10.1016/j.biopha.2020.110884. [PMID: 33080470]
  • Jing Sun, Hong Jiang, Weijing Wang, Xue Dong, Dongfeng Zhang. Associations of Urinary Phytoestrogen Concentrations with Sleep Disorders and Sleep Duration among Adults. Nutrients. 2020 Jul; 12(7):. doi: 10.3390/nu12072103. [PMID: 32708566]
  • Elin Hålldin, Anne Kirstine Eriksen, Carl Brunius, Andreia Bento da Silva, Maria Bronze, Kati Hanhineva, Anna-Marja Aura, Rikard Landberg. Factors Explaining Interpersonal Variation in Plasma Enterolactone Concentrations in Humans. Molecular nutrition & food research. 2019 08; 63(16):e1801159. doi: 10.1002/mnfr.201801159. [PMID: 30817848]
  • Ángela Peirotén, Pilar Gaya, Inmaculada Álvarez, Daniel Bravo, José Mª Landete. Influence of different lignan compounds on enterolignan production by Bifidobacterium and Lactobacillus strains. International journal of food microbiology. 2019 Jan; 289(?):17-23. doi: 10.1016/j.ijfoodmicro.2018.08.028. [PMID: 30193121]
  • Giorgio Biasiotto, Isabella Zanella, Federica Predolini, Ivonne Archetti, Moris Cadei, Eugenio Monti, Marcello Luzzani, Barbara Pacchetti, Paola Mozzoni, Roberta Andreoli, Giuseppe De Palma, Federico Serana, Annika Smeds, Diego Di Lorenzo. 7-Hydroxymatairesinol improves body weight, fat and sugar metabolism in C57BJ/6 mice on a high-fat diet. The British journal of nutrition. 2018 10; 120(7):751-762. doi: 10.1017/s0007114518001824. [PMID: 30105962]
  • Alejandro de Athayde Moncorvo Collado, Paula B Salazar, Carlos Minahk. Enterodiol is Actively Transported by Rat Liver Cell Membranes. The Journal of membrane biology. 2018 08; 251(4):593-600. doi: 10.1007/s00232-018-0035-x. [PMID: 29728709]
  • Madhura Shettigar, Sahil Balotra, David Cahill, Andrew C Warden, Michael J Lacey, Hans-Peter E Kohler, Daniel Rentsch, John G Oakeshott, Gunjan Pandey. Isolation of the (+)-Pinoresinol-Mineralizing Pseudomonas sp. Strain SG-MS2 and Elucidation of Its Catabolic Pathway. Applied and environmental microbiology. 2018 02; 84(4):. doi: 10.1128/aem.02531-17. [PMID: 29222099]
  • Jon Andoni Otero, Dafne García-Mateos, Indira Alvarez-Fernández, Rocío García-Villalba, Juan Carlos Espín, Ana Isabel Álvarez, Gracia Merino. Flaxseed-enriched diets change milk concentration of the antimicrobial danofloxacin in sheep. BMC veterinary research. 2018 Jan; 14(1):14. doi: 10.1186/s12917-018-1341-3. [PMID: 29334949]
  • C P Ghedini, N L Whitehouse, D C Moura, A S Oliveira, A F Brito. Short communication: The mammalian lignan enterolactone is absorbed by newborn dairy calves fed enterolactone-enriched milk. Journal of dairy science. 2017 Oct; 100(10):8170-8175. doi: 10.3168/jds.2017-13093. [PMID: 28780087]
  • Mark E Obrenovich, MaryAnn Tima, Alex Polinkovsky, Renliang Zhang, Steven N Emancipator, Curtis J Donskey. Targeted Metabolomics Analysis Identifies Intestinal Microbiota-Derived Urinary Biomarkers of Colonization Resistance in Antibiotic-Treated Mice. Antimicrobial agents and chemotherapy. 2017 08; 61(8):. doi: 10.1128/aac.00477-17. [PMID: 28584146]
  • S Mattioli, S Ruggeri, B Sebastiani, G Brecchia, A Dal Bosco, A Cartoni Mancinelli, C Castellini. Performance and egg quality of laying hens fed flaxseed: highlights on n-3 fatty acids, cholesterol, lignans and isoflavones. Animal : an international journal of animal bioscience. 2017 Apr; 11(4):705-712. doi: 10.1017/s175173111600207x. [PMID: 27819218]
  • Yun Zhu, Kayoko Kawaguchi, Ryoiti Kiyama. Differential and directional estrogenic signaling pathways induced by enterolignans and their precursors. PloS one. 2017; 12(2):e0171390. doi: 10.1371/journal.pone.0171390. [PMID: 28152041]
  • Lennard Schröder, Dagmar Ulrike Richter, Birgit Piechulla, Mareike Chrobak, Christina Kuhn, Sandra Schulze, Sybille Abarzua, Udo Jeschke, Tobias Weissenbacher. Effects of Phytoestrogen Extracts Isolated from Elder Flower on Hormone Production and Receptor Expression of Trophoblast Tumor Cells JEG-3 and BeWo, as well as MCF7 Breast Cancer Cells. Nutrients. 2016 Oct; 8(10):. doi: 10.3390/nu8100616. [PMID: 27740591]
  • Motoi Tamura, Sachiko Hori, Hiroyuki Nakagawa, Satoshi Yamauchi, Takuya Sugahara. Effects of an equol-producing bacterium isolated from human faeces on isoflavone and lignan metabolism in mice. Journal of the science of food and agriculture. 2016 Jul; 96(9):3126-32. doi: 10.1002/jsfa.7490. [PMID: 26455424]
  • Andrea Quartieri, Rocío García-Villalba, Alberto Amaretti, Stefano Raimondi, Alan Leonardi, Maddalena Rossi, Francisco Tomàs-Barberàn. Detection of novel metabolites of flaxseed lignans in vitro and in vivo. Molecular nutrition & food research. 2016 07; 60(7):1590-601. doi: 10.1002/mnfr.201500773. [PMID: 26873880]
  • Alejandro de Athayde Moncorvo Collado, Fernando G Dupuy, Roberto D Morero, Carlos Minahk. Cholesterol induces surface localization of polyphenols in model membranes thus enhancing vesicle stability against lysozyme, but reduces protection of distant double bonds from reactive-oxygen species. Biochimica et biophysica acta. 2016 Jul; 1858(7 Pt A):1479-87. doi: 10.1016/j.bbamem.2016.04.002. [PMID: 27063609]
  • Marija M Takić, Vesna B Jovanović, Ivan D Pavićević, Tamara N Uzelac, Jelena M Aćimović, Danijela K Ristić-Medić, Ljuba M Mandić. Binding of enterolactone and enterodiol to human serum albumin: increase of cysteine-34 thiol group reactivity. Food & function. 2016 Feb; 7(2):1217-26. doi: 10.1039/c5fo01346a. [PMID: 26838610]
  • Yang Hu, Yan Song, Adrian A Franke, Frank B Hu, Rob M van Dam, Qi Sun. A Prospective Investigation of the Association Between Urinary Excretion of Dietary Lignan Metabolites and Weight Change in US Women. American journal of epidemiology. 2015 Sep; 182(6):503-11. doi: 10.1093/aje/kwv091. [PMID: 26290574]
  • Anushka Dikshit, Manoel Adrião Gomes Filho, Erfan Eilati, Stacey McGee, Carrie Small, Chunqi Gao, Thomas Klug, Dale Buchanan Hales. Flaxseed reduces the pro-carcinogenic micro-environment in the ovaries of normal hens by altering the PG and oestrogen pathways in a dose-dependent manner. The British journal of nutrition. 2015 May; 113(9):1384-95. doi: 10.1017/s000711451500029x. [PMID: 25850566]
  • Jatinder Kaur Mukker, Ravi Shankar Prasad Singh, Alister D Muir, Ed S Krol, Jane Alcorn. Comparative pharmacokinetics of purified flaxseed and associated mammalian lignans in male Wistar rats. The British journal of nutrition. 2015 Mar; 113(5):749-57. doi: 10.1017/s0007114514004371. [PMID: 25716060]
  • Meredith A J Hullar, Samuel M Lancaster, Fei Li, Elizabeth Tseng, Karlyn Beer, Charlotte Atkinson, Kristiina Wähälä, Wade K Copeland, Timothy W Randolph, Katherine M Newton, Johanna W Lampe. Enterolignan-producing phenotypes are associated with increased gut microbial diversity and altered composition in premenopausal women in the United States. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2015 Mar; 24(3):546-54. doi: 10.1158/1055-9965.epi-14-0262. [PMID: 25542830]
  • Giorgio Biasiotto, Marialetizia Penza, Isabella Zanella, Moris Cadei, Luigi Caimi, Cristina Rossini, Annika I Smeds, Diego Di Lorenzo. Oilseeds ameliorate metabolic parameters in male mice, while contained lignans inhibit 3T3-L1 adipocyte differentiation in vitro. European journal of nutrition. 2014 Dec; 53(8):1685-97. doi: 10.1007/s00394-014-0675-2. [PMID: 24566767]
  • Kuo-Ching Jan, Binghuei-Barry Yang, Tristan C Liu. Gene expression profiling of sesaminol triglucoside and its tetrahydrofuranoid metabolites in primary rat hepatocytes. International journal of food sciences and nutrition. 2014 Dec; 65(8):981-8. doi: 10.3109/09637486.2014.950204. [PMID: 25156454]
  • Cara L Frankenfeld. Cardiometabolic risk factors are associated with high urinary enterolactone concentration, independent of urinary enterodiol concentration and dietary fiber intake in adults. The Journal of nutrition. 2014 Sep; 144(9):1445-53. doi: 10.3945/jn.114.190512. [PMID: 24966407]
  • A Durazzo, M Carcea, H Adlercreutz, E Azzini, A Polito, L Olivieri, M Zaccaria, C Meneghini, F Maiani, G Bausano, F Martiri, A Samaletdin, A Fumagalli, A Raguzzini, E Venneria, M S Foddai, D Ciarapica, B Mauro, F Volpe, G Maiani. Effects of consumption of whole grain foods rich in lignans in healthy postmenopausal women with moderate serum cholesterol: a pilot study. International journal of food sciences and nutrition. 2014 Aug; 65(5):637-45. doi: 10.3109/09637486.2014.893283. [PMID: 24611636]
  • Claudia Fuentealba, Fernando Figuerola, Ana M Estévez, José M Bastías, Ociel Muñoz. Bioaccessibility of lignans from flaxseed (Linum usitatissimum L.) determined by single-batch in vitro simulation of the digestive process. Journal of the science of food and agriculture. 2014 Jul; 94(9):1729-38. doi: 10.1002/jsfa.6482. [PMID: 24243589]
  • Monika Eichholzer, Aline Richard, Holly L Nicastro, Elizabeth A Platz, Jakob Linseisen, Sabine Rohrmann. Urinary lignans and inflammatory markers in the US National Health and Nutrition Examination Survey (NHANES) 1999-2004 and 2005-2008. Cancer causes & control : CCC. 2014 Mar; 25(3):395-403. doi: 10.1007/s10552-014-0340-3. [PMID: 24463788]
  • Sunni L Mumford, Rajeshwari Sundaram, Enrique F Schisterman, Anne M Sweeney, Dana Boyd Barr, Michael E Rybak, Jose M Maisog, Daniel L Parker, Christine M Pfeiffer, Germaine M Buck Louis. Higher urinary lignan concentrations in women but not men are positively associated with shorter time to pregnancy. The Journal of nutrition. 2014 Mar; 144(3):352-8. doi: 10.3945/jn.113.184820. [PMID: 24401816]
  • Qi Sun, Nicole M Wedick, An Pan, Mary K Townsend, Aedin Cassidy, Adrian A Franke, Eric B Rimm, Frank B Hu, Rob M van Dam. Gut microbiota metabolites of dietary lignans and risk of type 2 diabetes: a prospective investigation in two cohorts of U.S. women. Diabetes care. 2014; 37(5):1287-95. doi: 10.2337/dc13-2513. [PMID: 24550220]
  • C L Frankenfeld. Relationship of obesity and high urinary enterolignan concentrations in 6806 children and adults: analysis of National Health and Nutrition Examination Survey data. European journal of clinical nutrition. 2013 Aug; 67(8):887-9. doi: 10.1038/ejcn.2013.107. [PMID: 23756386]
  • Maria Azrad, Robin T Vollmer, John Madden, Mark Dewhirst, Thomas J Polascik, Denise C Snyder, Mack T Ruffin, Judd W Moul, Dean E Brenner, Wendy Demark-Wahnefried. Flaxseed-derived enterolactone is inversely associated with tumor cell proliferation in men with localized prostate cancer. Journal of medicinal food. 2013 Apr; 16(4):357-60. doi: 10.1089/jmf.2012.0159. [PMID: 23566060]
  • Alexandrine During, Céline Debouche, Thomas Raas, Yvan Larondelle. Among plant lignans, pinoresinol has the strongest antiinflammatory properties in human intestinal Caco-2 cells. The Journal of nutrition. 2012 Oct; 142(10):1798-805. doi: 10.3945/jn.112.162453. [PMID: 22955517]
  • Sibylle Abarzua, Tatsuo Serikawa, Marlen Szewczyk, Dagmar-Ulrike Richter, Birgit Piechulla, Volker Briese. Antiproliferative activity of lignans against the breast carcinoma cell lines MCF 7 and BT 20. Archives of gynecology and obstetrics. 2012 Apr; 285(4):1145-51. doi: 10.1007/s00404-011-2120-6. [PMID: 22037685]
  • José L Peñalvo, Pedro López-Romero. Urinary enterolignan concentrations are positively associated with serum HDL cholesterol and negatively associated with serum triglycerides in U.S. adults. The Journal of nutrition. 2012 Apr; 142(4):751-6. doi: 10.3945/jn.111.150516. [PMID: 22378329]
  • A N Martinchik, V V Zubtsov. [Phytoestrogenis properties of flaxseed lignans]. Voprosy pitaniia. 2012; 81(6):61-6. doi: . [PMID: 23530438]
  • Aida Karina Zaineddin, Katharina Buck, Alina Vrieling, Judith Heinz, Dieter Flesch-Janys, Jakob Linseisen, Jenny Chang-Claude. The association between dietary lignans, phytoestrogen-rich foods, and fiber intake and postmenopausal breast cancer risk: a German case-control study. Nutrition and cancer. 2012; 64(5):652-65. doi: 10.1080/01635581.2012.683227. [PMID: 22591208]
  • Lucia Roncaglia, Alberto Amaretti, Stefano Raimondi, Alan Leonardi, Maddalena Rossi. Role of bifidobacteria in the activation of the lignan secoisolariciresinol diglucoside. Applied microbiology and biotechnology. 2011 Oct; 92(1):159-68. doi: 10.1007/s00253-011-3338-8. [PMID: 21614502]
  • Anni Woting, Thomas Clavel, Gunnar Loh, Michael Blaut. Bacterial transformation of dietary lignans in gnotobiotic rats. FEMS microbiology ecology. 2010 Jun; 72(3):507-14. doi: 10.1111/j.1574-6941.2010.00863.x. [PMID: 20370826]
  • Cheng-Zhi Wang, Xiao-Qing Ma, Dong-Hui Yang, Zhi-Rong Guo, Gui-Rong Liu, Ge-Xin Zhao, Jie Tang, Ya-Nan Zhang, Miao Ma, Shao-Qing Cai, Bao-Shan Ku, Shu-Lin Liu. Production of enterodiol from defatted flaxseeds through biotransformation by human intestinal bacteria. BMC microbiology. 2010 Apr; 10(?):115. doi: 10.1186/1471-2180-10-115. [PMID: 20398397]
  • Jong-Sik Jin, Masao Hattori. Human intestinal bacterium, strain END-2 is responsible for demethylation as well as lactonization during plant lignan metabolism. Biological & pharmaceutical bulletin. 2010; 33(8):1443-7. doi: 10.1248/bpb.33.1443. [PMID: 20686246]
  • Selin Bolca, Ciska Wyns, Sam Possemiers, Herman Depypere, Denis De Keukeleire, Marc Bracke, Willy Verstraete, Arne Heyerick. Cosupplementation of isoflavones, prenylflavonoids, and lignans alters human exposure to phytoestrogen-derived 17beta-estradiol equivalents. The Journal of nutrition. 2009 Dec; 139(12):2293-300. doi: 10.3945/jn.109.113639. [PMID: 19864398]
  • Hélène V Petit, Nathalie Gagnon, Priyadarshini S Mir, Rong Cao, Steve Cui. Milk concentration of the mammalian lignan enterolactone, milk production, milk fatty acid profile, and digestibility in dairy cows fed diets containing whole flaxseed or flaxseed meal. The Journal of dairy research. 2009 Aug; 76(3):257-64. doi: 10.1017/s0022029909003999. [PMID: 19250577]
  • Anneleen Kuijsten, H Bas Bueno-de-Mesquita, Jolanda M A Boer, Ilja C W Arts, Frans J Kok, Pieter van't Veer, Peter C H Hollman. Plasma enterolignans are not associated with nonfatal myocardial infarction risk. Atherosclerosis. 2009 Mar; 203(1):145-52. doi: 10.1016/j.atherosclerosis.2008.06.005. [PMID: 18687435]
  • Govindarajan Thangavelu, Marcos Germán Colazo, Masahito Oba, Michael Kane Dyck, Erasmus Kojo Okine, Divakar Justus Ambrose. Fecal and urinary lignans, intrafollicular estradiol, and endometrial receptors in lactating dairy cows fed diets supplemented with hydrogenated animal fat, flaxseed or sunflower seed. The Journal of reproduction and development. 2008 Dec; 54(6):439-46. doi: 10.1262/jrd.20030. [PMID: 18762721]
  • C Côrtes, N Gagnon, C Benchaar, D da Silva, G T D Santos, H V Petit. In vitro metabolism of flax lignans by ruminal and faecal microbiota of dairy cows. Journal of applied microbiology. 2008 Nov; 105(5):1585-94. doi: 10.1111/j.1365-2672.2008.03922.x. [PMID: 19146494]
  • S Fukumitsu, K Aida, N Ueno, S Ozawa, Y Takahashi, M Kobori. Flaxseed lignan attenuates high-fat diet-induced fat accumulation and induces adiponectin expression in mice. The British journal of nutrition. 2008 Sep; 100(3):669-76. doi: 10.1017/s0007114508911570. [PMID: 18252024]
  • Jie Feng, Zhongli Shi, Zhaoming Ye. Effects of metabolites of the lignans enterolactone and enterodiol on osteoblastic differentiation of MG-63 cells. Biological & pharmaceutical bulletin. 2008 Jun; 31(6):1067-70. doi: 10.1248/bpb.31.1067. [PMID: 18520031]
  • Charlotte Carreau, Gilles Flouriot, Catherine Bennetau-Pelissero, Mylène Potier. Enterodiol and enterolactone, two major diet-derived polyphenol metabolites have different impact on ERalpha transcriptional activation in human breast cancer cells. The Journal of steroid biochemistry and molecular biology. 2008 May; 110(1-2):176-85. doi: 10.1016/j.jsbmb.2008.03.032. [PMID: 18457947]
  • Chun Hu, Yvonne V Yuan, David D Kitts. Antioxidant activities of the flaxseed lignan secoisolariciresinol diglucoside, its aglycone secoisolariciresinol and the mammalian lignans enterodiol and enterolactone in vitro. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2007 Nov; 45(11):2219-27. doi: 10.1016/j.fct.2007.05.017. [PMID: 17624649]
  • Jong-Sik Jin, Yu-Feng Zhao, Norio Nakamura, Teruaki Akao, Nobuko Kakiuchi, Byung-Sun Min, Masao Hattori. Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria. Biological & pharmaceutical bulletin. 2007 Nov; 30(11):2113-9. doi: 10.1248/bpb.30.2113. [PMID: 17978485]
  • Ivon E J Milder, Anneleen Kuijsten, Ilja C W Arts, Edith J M Feskens, Ellen Kampman, Peter C H Hollman, Pieter Van 't Veer. Relation between plasma enterodiol and enterolactone and dietary intake of lignans in a Dutch endoscopy-based population. The Journal of nutrition. 2007 May; 137(5):1266-71. doi: 10.1093/jn/137.5.1266. [PMID: 17449591]
  • Ajay Bommareddy, Bhanu L Arasada, Duane P Mathees, Chandradhar Dwivedi. Determination of mammalian lignans in biological samples by modified gas chromatography/mass spectrometry. Journal of AOAC International. 2007 May; 90(3):641-6. doi: 10.1093/jaoac/90.3.641. [PMID: 17580615]
  • Galam Khan, Pauliina Penttinen, Anna Cabanes, Aaron Foxworth, Antonia Chezek, Kristen Mastropole, Bin Yu, Annika Smeds, Teemu Halttunen, Carolyn Good, Sari Mäkelä, Leena Hilakivi-Clarke. Maternal flaxseed diet during pregnancy or lactation increases female rat offspring's susceptibility to carcinogen-induced mammary tumorigenesis. Reproductive toxicology (Elmsford, N.Y.). 2007 Apr; 23(3):397-406. doi: 10.1016/j.reprotox.2007.02.002. [PMID: 17398067]
  • Herman Adlercreutz. Lignans and human health. Critical reviews in clinical laboratory sciences. 2007; 44(5-6):483-525. doi: 10.1080/10408360701612942. [PMID: 17943494]
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