Enterolactone (BioDeep_00000406298)

Main id: BioDeep_00000004004

 

natural product


代谢物信息卡片


3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone

化学式: C18H18O4 (298.1205028)
中文名称: 肠内酯
谱图信息: 最多检出来源 Homo sapiens(urine) 0.37%

分子结构信息

SMILES: C1C(C(C(=O)O1)CC2=CC(=CC=C2)O)CC3=CC(=CC=C3)O
InChI: InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3951; ORIGINAL_PRECURSOR_SCAN_NO 3949
CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3959; ORIGINAL_PRECURSOR_SCAN_NO 3958
CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3921; ORIGINAL_PRECURSOR_SCAN_NO 3919
CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3952; ORIGINAL_PRECURSOR_SCAN_NO 3950
CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3939; ORIGINAL_PRECURSOR_SCAN_NO 3935
CONFIDENCE standard compound; INTERNAL_ID 483; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3939; ORIGINAL_PRECURSOR_SCAN_NO 3937
Annotation level-1

同义名列表

6 个代谢物同义名

Enterolactone; 3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone; Dihydro-3,4-bis((3-hydroxyphenyl)methyl)-2(3H)-Furanone; 2,3-Bis(3-hydroxybenzyl)butyrolactone; (3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one; Enterolactone



数据库引用编号

51 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)

16 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]
  • Juana Hatwik, Hrishikesh Nitin Patil, Anil Mukund Limaye. Proliferative response of ERα-positive breast cancer cells to 10 μM enterolactone, and the associated alteration in the transcriptomic landscape. Gene. 2023 Jul; ?(?):147640. doi: 10.1016/j.gene.2023.147640. [PMID: 37453722]
  • Yanping Li, Fenglei Wang, Jun Li, Kerry L Ivey, Jeremy E Wilkinson, Dong D Wang, Ruifeng Li, Gang Liu, Heather A Eliassen, Andrew T Chan, Clary B Clish, Curtis Huttenhower, Frank B Hu, Qi Sun, Eric B Rimm. Dietary lignans, plasma enterolactone levels, and metabolic risk in men: exploring the role of the gut microbiome. BMC microbiology. 2022 03; 22(1):82. doi: 10.1186/s12866-022-02495-0. [PMID: 35350985]
  • Juyeon Lee, Ju-Young Kang, Kwang-Pil Ko, Sue-Kyung Park. The Association between Plasma Concentration of Phytoestrogens and Hypertension within the Korean Multicenter Cancer Cohort. Nutrients. 2021 Dec; 13(12):. doi: 10.3390/nu13124366. [PMID: 34959918]
  • Gang Liu, Jun Li, Yanping Li, Yang Hu, Adrian A Franke, Liming Liang, Frank B Hu, Andrew T Chan, Kenneth J Mukamal, Eric B Rimm, Qi Sun. Gut microbiota-derived metabolites and risk of coronary artery disease: a prospective study among US men and women. The American journal of clinical nutrition. 2021 07; 114(1):238-247. doi: 10.1093/ajcn/nqab053. [PMID: 33829245]
  • 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]
  • 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]
  • Agnieszka Micek, Justyna Godos, Tomasz Brzostek, Agnieszka Gniadek, Claudia Favari, Pedro Mena, Massimo Libra, Daniele Del Rio, Fabio Galvano, Giuseppe Grosso. Dietary phytoestrogens and biomarkers of their intake in relation to cancer survival and recurrence: a comprehensive systematic review with meta-analysis. Nutrition reviews. 2021 01; 79(1):42-65. doi: 10.1093/nutrit/nuaa043. [PMID: 32632445]
  • 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]
  • Cecilie Kyrø, Kirsten Frederiksen, Marianne Holm, Natalja P Nørskov, Knud E B Knudsen, Kim Overvad, Anne Tjønneland, Anja Olsen. Prediagnosis plasma concentrations of enterolactone and survival after colorectal cancer: the Danish Diet, Cancer and Health cohort. The British journal of nutrition. 2019 09; 122(5):552-563. doi: 10.1017/s0007114518002143. [PMID: 30173678]
  • 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]
  • Anne Tuomisto, Natalja P Nørskov, Päivi Sirniö, Juha P Väyrynen, Shivaprakash J Mutt, Kai Klintrup, Jyrki Mäkelä, Knud Erik Bach Knudsen, Markus J Mäkinen, Karl-Heinz Herzig. Serum enterolactone concentrations are low in colon but not in rectal cancer patients. Scientific reports. 2019 08; 9(1):11209. doi: 10.1038/s41598-019-47622-6. [PMID: 31371751]
  • Anne K Eriksen, Cecilie Kyrø, Natalja P Nørskov, Kirsten Frederiksen, Knud-Erik Bach Knudsen, Kim Overvad, Rikard Landberg, Anne Tjønneland, Anja Olsen. Pre-diagnostic plasma enterolactone concentrations are associated with lower mortality among individuals with type 2 diabetes: a case-cohort study in the Danish Diet, Cancer and Health cohort. Diabetologia. 2019 06; 62(6):959-969. doi: 10.1007/s00125-019-4854-9. [PMID: 30963187]
  • Klaudia Berk, Krzysztof Drygalski, Ewa Harasim-Symbor, Tomasz Charytoniuk, Nicoletta Iłowska, Bartłomiej Łukaszuk, Adrian Chabowski, Karolina Konstantynowicz-Nowicka. The effect of enterolactone on liver lipid precursors of inflammation. Life sciences. 2019 Mar; 221(?):341-347. doi: 10.1016/j.lfs.2019.02.044. [PMID: 30802511]
  • Laura W Bowers, Claire G Lineberger, Nikki A Ford, Emily L Rossi, Arunima Punjala, Kristina K Camp, Bruce K Kimler, Carol J Fabian, Stephen D Hursting. The flaxseed lignan secoisolariciresinol diglucoside decreases local inflammation, suppresses NFκB signaling, and inhibits mammary tumor growth. Breast cancer research and treatment. 2019 Feb; 173(3):545-557. doi: 10.1007/s10549-018-5021-6. [PMID: 30367332]
  • Huiru Chang, Song Yao, David Tritchler, Meredith A Hullar, Johanna W Lampe, Lilian U Thompson, Susan E McCann. Genetic Variation in Steroid and Xenobiotic Metabolizing Pathways and Enterolactone Excretion Before and After Flaxseed Intervention in African American and European American Women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2019 02; 28(2):265-274. doi: 10.1158/1055-9965.epi-18-0826. [PMID: 30709839]
  • 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]
  • Tomasz Charytoniuk, Nicoletta Iłowska, Klaudia Berk, Krzysztof Drygalski, Adrian Chabowski, Karolina Konstantynowicz-Nowicka. The effect of enterolactone on sphingolipid pathway and hepatic insulin resistance development in HepG2 cells. Life sciences. 2019 Jan; 217(?):1-7. doi: 10.1016/j.lfs.2018.11.044. [PMID: 30468835]
  • Cecilie Kyrø, Louise Hansen, Kirsten Frederiksen, Natalja P Nørskov, Knud Erik Bach Knudsen, Anne Kirstine Eriksen, Marianne Holm, Anne Tjønneland, Anja Olsen. Pre-diagnostic plasma enterolactone concentrations and breast cancer prognosis among postmenopausal women - The Danish Diet, Cancer and Health cohort. Clinical nutrition (Edinburgh, Scotland). 2018 12; 37(6 Pt A):2217-2225. doi: 10.1016/j.clnu.2017.10.023. [PMID: 29154112]
  • Stefanie Jaskulski, Audrey Y Jung, Sabine Behrens, Theron Johnson, Rudolf Kaaks, Kathrin Thöne, Dieter Flesch-Janys, Disorn Sookthai, Jenny Chang-Claude. Circulating enterolactone concentrations and prognosis of postmenopausal breast cancer: assessment of mediation by inflammatory markers. International journal of cancer. 2018 12; 143(11):2698-2708. doi: 10.1002/ijc.31647. [PMID: 29974464]
  • Ahmed A Almousa, François Meurens, Ed S Krol, Jane Alcorn. Linoorbitides and enterolactone mitigate inflammation-induced oxidative stress and loss of intestinal epithelial barrier integrity. International immunopharmacology. 2018 Nov; 64(?):42-51. doi: 10.1016/j.intimp.2018.08.012. [PMID: 30145469]
  • 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]
  • Kwang-Pil Ko, Yohwan Yeo, Ji-Hye Yoon, Cheong-Sik Kim, Shinkan Tokudome, Le Tran Ngoan, Chihaya Koriyama, Young-Khi Lim, Soung-Hoon Chang, Hai-Rim Shin, Daehee Kang, Sue K Park, Chul Hwan Kang, Keun-Young Yoo. Plasma phytoestrogens concentration and risk of colorectal cancer in two different Asian populations. Clinical nutrition (Edinburgh, Scotland). 2018 10; 37(5):1675-1682. doi: 10.1016/j.clnu.2017.07.014. [PMID: 28778370]
  • Peter Wallström, Isabel Drake, Emily Sonestedt, Bo Gullberg, Anders Bjartell, Håkan Olsson, Herman Adlercreutz, Matti J Tikkanen, Elisabet Wirfält. Plasma enterolactone and risk of prostate cancer in middle-aged Swedish men. European journal of nutrition. 2018 Oct; 57(7):2595-2606. doi: 10.1007/s00394-017-1530-z. [PMID: 28884432]
  • Pilar Gaya, Abel Sánchez-Jiménez, Ángela Peirotén, Margarita Medina, José Maria Landete. Incomplete metabolism of phytoestrogens by gut microbiota from children under the age of three. International journal of food sciences and nutrition. 2018 May; 69(3):334-343. doi: 10.1080/09637486.2017.1353955. [PMID: 28728453]
  • C P Ghedini, D C Moura, R A V Santana, A S Oliveira, A F Brito. Replacing ground corn with incremental amounts of liquid molasses does not change milk enterolactone but decreases production in dairy cows fed flaxseed meal. Journal of dairy science. 2018 Mar; 101(3):2096-2109. doi: 10.3168/jds.2017-13689. [PMID: 29274976]
  • 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]
  • A K Eriksen, C Kyrø, N Nørskov, A K Bolvig, J Christensen, A Tjønneland, K Overvad, R Landberg, A Olsen. Prediagnostic enterolactone concentrations and mortality among Danish men diagnosed with prostate cancer. European journal of clinical nutrition. 2017 10; 71(10):1235-1240. doi: 10.1038/ejcn.2017.42. [PMID: 28378849]
  • 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]
  • Fayth L Miles, Sandi L Navarro, Yvonne Schwarz, Haiwei Gu, Danijel Djukovic, Timothy W Randolph, Ali Shojaie, Mario Kratz, Meredith A J Hullar, Paul D Lampe, Marian L Neuhouser, Daniel Raftery, Johanna W Lampe. Plasma metabolite abundances are associated with urinary enterolactone excretion in healthy participants on controlled diets. Food & function. 2017 Sep; 8(9):3209-3218. doi: 10.1039/c7fo00684e. [PMID: 28808723]
  • Anne K Bolvig, Natalja P Nørskov, Mette S Hedemann, Leslie Foldager, Brendan McCarthy-Sinclair, Maria L Marco, Helle N Lærke, Knud E Bach Knudsen. Effect of Antibiotics and Diet on Enterolactone Concentration and Metabolome Studied by Targeted and Nontargeted LC-MS Metabolomics. Journal of proteome research. 2017 06; 16(6):2135-2150. doi: 10.1021/acs.jproteome.6b00942. [PMID: 28294620]
  • Shireen Chikara, Kaitlin Lindsey, Harsharan Dhillon, Sujan Mamidi, Jeffrey Kittilson, Melpo Christofidou-Solomidou, Katie M Reindl. Enterolactone Induces G1-phase Cell Cycle Arrest in Nonsmall Cell Lung Cancer Cells by Downregulating Cyclins and Cyclin-dependent Kinases. Nutrition and cancer. 2017 May; 69(4):652-662. doi: 10.1080/01635581.2017.1296169. [PMID: 28323486]
  • Émilie Fortin, Richard Blouin, Jérôme Lapointe, Hélène V Petit, Marie-France Palin. Linoleic acid, α-linolenic acid and enterolactone affect lipid oxidation and expression of lipid metabolism and antioxidant-related genes in hepatic tissue of dairy cows. The British journal of nutrition. 2017 May; 117(9):1199-1211. doi: 10.1017/s0007114517000976. [PMID: 28643621]
  • 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]
  • Shireen Chikara, Kaitlin Lindsey, Pawel Borowicz, Melpo Christofidou-Solomidou, Katie M Reindl. Enterolactone alters FAK-Src signaling and suppresses migration and invasion of lung cancer cell lines. BMC complementary and alternative medicine. 2017 Jan; 17(1):30. doi: 10.1186/s12906-016-1512-3. [PMID: 28068967]
  • 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]
  • Anne K Bolvig, Cecilie Kyrø, Natalja P Nørskov, Anne K Eriksen, Jane Christensen, Anne Tjønneland, Knud E Bach Knudsen, Anja Olsen. Use of antibiotics is associated with lower enterolactone plasma concentration. Molecular nutrition & food research. 2016 12; 60(12):2712-2721. doi: 10.1002/mnfr.201600566. [PMID: 27500753]
  • 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]
  • 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]
  • 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]
  • Michael K Reger, Terrell W Zollinger, Ziyue Liu, Josette Jones, Jianjun Zhang. Urinary phytoestrogens and cancer, cardiovascular, and all-cause mortality in the continuous National Health and Nutrition Examination Survey. European journal of nutrition. 2016 Apr; 55(3):1029-40. doi: 10.1007/s00394-015-0917-y. [PMID: 25943648]
  • Natalja P Nørskov, Cecilie Kyrø, Anja Olsen, Anne Tjønneland, Knud Erik Bach Knudsen. High-Throughput LC-MS/MS Method for Direct Quantification of Glucuronidated, Sulfated, and Free Enterolactone in Human Plasma. Journal of proteome research. 2016 Mar; 15(3):1051-8. doi: 10.1021/acs.jproteome.5b01117. [PMID: 26809233]
  • 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]
  • J A Otero, V Miguel, L González-Lobato, R García-Villalba, J C Espín, J G Prieto, G Merino, A I Álvarez. Effect of bovine ABCG2 polymorphism Y581S SNP on secretion into milk of enterolactone, riboflavin and uric acid. Animal : an international journal of animal bioscience. 2016 Feb; 10(2):238-47. doi: 10.1017/s1751731115002141. [PMID: 26510964]
  • Maya Zachut. Short communication: Concentrations of the mammalian lignan enterolactone in preovulatory follicles and the correlation with intrafollicular estradiol in dairy cows fed extruded flaxseed. Journal of dairy science. 2015 Dec; 98(12):8814-7. doi: 10.3168/jds.2015-9699. [PMID: 26454291]
  • Mingyue Zhang, Zhenghua Duan, Yinghong Wu, Zhen Liu, Ke Li, Lei Wang. Occurrence and Profiles of the Artificial Endocrine Disruptor Bisphenol A and Natural Endocrine Disruptor Phytoestrogens in Urine from Children in China. International journal of environmental research and public health. 2015 Nov; 12(12):15110-7. doi: 10.3390/ijerph121214964. [PMID: 26633438]
  • Sunni L Mumford, Sungduk Kim, Zhen Chen, Dana Boyd Barr, Germaine M Buck Louis. Urinary Phytoestrogens Are Associated with Subtle Indicators of Semen Quality among Male Partners of Couples Desiring Pregnancy. The Journal of nutrition. 2015 Nov; 145(11):2535-41. doi: 10.3945/jn.115.214973. [PMID: 26423741]
  • Margaret A Adgent, Walter J Rogan. Triclosan and prescription antibiotic exposures and enterolactone production in adults. Environmental research. 2015 Oct; 142(?):66-71. doi: 10.1016/j.envres.2015.06.017. [PMID: 26114916]
  • 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]
  • Cheng Xu, Qian Liu, Qunwei Zhang, Zhao-Yan Jiang, Aihua Gu. Urinary enterolactone associated with liver enzyme levels in US adults: National Health and Nutrition Examination Survey (NHANES). The British journal of nutrition. 2015 Jul; 114(1):91-7. doi: 10.1017/s000711451500149x. [PMID: 25990984]
  • Lisa Y Cho, Jae Jeong Yang, Kwang-Pil Ko, Seung Hyun Ma, Aesun Shin, Bo Youl Choi, Hyun Ja Kim, Dong Soo Han, Kyu Sang Song, Yong Sung Kim, Soung-Hoon Chang, Hai-Rim Shin, Daehee Kang, Keun-Young Yoo, Sue K Park. Gene polymorphisms in the ornithine decarboxylase-polyamine pathway modify gastric cancer risk by interaction with isoflavone concentrations. Gastric cancer : official journal of the International Gastric Cancer Association and the Japanese Gastric Cancer Association. 2015 Jul; 18(3):495-503. doi: 10.1007/s10120-014-0396-5. [PMID: 25079701]
  • 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]
  • Cheng Xu, Qian Liu, Qunwei Zhang, Aihua Gu, Zhao-Yan Jiang. Urinary enterolactone is associated with obesity and metabolic alteration in men in the US National Health and Nutrition Examination Survey 2001-10. The British journal of nutrition. 2015 Feb; 113(4):683-90. doi: 10.1017/s0007114514004115. [PMID: 25634494]
  • 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]
  • Takeshi Yokoyama, Yuto Kosaka, Mineyuki Mizuguchi. Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin. Journal of medicinal chemistry. 2014 Nov; 57(21):8928-35. doi: 10.1021/jm500997m. [PMID: 25314129]
  • 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]
  • 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]
  • Jean-François Bisson, Sophie Hidalgo, Rudy Simons, Marian Verbruggen. Preventive effects of lignan extract from flax hulls on experimentally induced benign prostate hyperplasia. Journal of medicinal food. 2014 Jun; 17(6):650-6. doi: 10.1089/jmf.2013.0046. [PMID: 24460407]
  • Verónica Miguel, Jon Andoni Otero, Rocío García-Villalba, Francisco Tomás-Barberán, Juan Carlos Espín, Gracia Merino, Ana I Álvarez. Role of ABCG2 in transport of the mammalian lignan enterolactone and its secretion into milk in Abcg2 knockout mice. Drug metabolism and disposition: the biological fate of chemicals. 2014 May; 42(5):943-6. doi: 10.1124/dmd.113.055970. [PMID: 24568887]
  • Kenneth D R Setchell, Nadine M Brown, Linda Zimmer-Nechemias, Brian Wolfe, Pinky Jha, James E Heubi. Metabolism of secoisolariciresinol-diglycoside the dietary precursor to the intestinally derived lignan enterolactone in humans. Food & function. 2014 Mar; 5(3):491-501. doi: 10.1039/c3fo60402k. [PMID: 24429845]
  • 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]
  • 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]
  • Svitlana Shinkaruk, Edith Pinot, Valérie Lamothe, Jean-Marie Schmitter, Laurie Baguenard, Bernard Bennetau, Catherine Bennetau-Pelissero. Design and validation of a novel immunological test for enterolactone. Talanta. 2014 Feb; 119(?):116-24. doi: 10.1016/j.talanta.2013.10.034. [PMID: 24401393]
  • Reetta Holma, Riina A Kekkonen, Katja Hatakka, Tuija Poussa, Heikki Vapaatalo, Herman Adlercreutz, Riitta Korpela. Low serum enterolactone concentration is associated with low colonic Lactobacillus-Enterococcus counts in men but is not affected by a synbiotic mixture in a randomised, placebo-controlled, double-blind, cross-over intervention study. The British journal of nutrition. 2014 Jan; 111(2):301-9. doi: 10.1017/s0007114513002420. [PMID: 23919920]
  • 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]
  • David A Zinniker, Camille A Holmgren, Bernd R T Simoneit. Enterolactone and other lignan metabolites as taxon-specific markers in modern and ancient woodrat middens. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2013 Jul; 68(7-8):327-35. doi: ". [PMID: 24066519]
  • Nancy A Mervish, Eliza W Gardiner, Maida P Galvez, Larry H Kushi, Gayle C Windham, Frank M Biro, Susan M Pinney, Michael E Rybak, Susan L Teitelbaum, Mary S Wolff. Dietary flavonol intake is associated with age of puberty in a longitudinal cohort of girls. Nutrition research (New York, N.Y.). 2013 Jul; 33(7):534-42. doi: 10.1016/j.nutres.2013.04.005. [PMID: 23827127]
  • Julie Aarestrup, Cecilie Kyrø, Knud E B Knudsen, Elisabete Weiderpass, Jane Christensen, Mette Kristensen, Anne M L Würtz, Nina F Johnsen, Kim Overvad, Anne Tjønneland, Anja Olsen. Plasma enterolactone and incidence of endometrial cancer in a case-cohort study of Danish women. The British journal of nutrition. 2013 Jun; 109(12):2269-75. doi: 10.1017/s0007114512004424. [PMID: 23114205]
  • Michael E Rybak, Maya R Sternberg, Christine M Pfeiffer. Sociodemographic and lifestyle variables are compound- and class-specific correlates of urine phytoestrogen concentrations in the U.S. population. The Journal of nutrition. 2013 Jun; 143(6):986S-94S. doi: 10.3945/jn.112.172981. [PMID: 23596167]
  • Jing Xie, Shelley S Tworoger, Adrian A Franke, Kathryn L Terry, Megan S Rice, Bernard A Rosner, Walter C Willett, Susan E Hankinson, A Heather Eliassen. Plasma enterolactone and breast cancer risk in the Nurses' Health Study II. Breast cancer research and treatment. 2013 Jun; 139(3):801-9. doi: 10.1007/s10549-013-2586-y. [PMID: 23760859]
  • Yulan Lin, Alicja Wolk, Niclas Håkansson, Jose Luis Peñalvo, Jesper Lagergren, Herman Adlercreutz, Yunxia Lu. Validation of FFQ-based assessment of dietary lignans compared with serum enterolactone in Swedish women. The British journal of nutrition. 2013 May; 109(10):1873-80. doi: 10.1017/s000711451200387x. [PMID: 23006454]
  • Christophe Hano, Sullivan Renouard, Roland Molinié, Cyrielle Corbin, Esmatullah Barakzoy, Joël Doussot, Frédéric Lamblin, Eric Lainé. Flaxseed (Linum usitatissimum L.) extract as well as (+)-secoisolariciresinol diglucoside and its mammalian derivatives are potent inhibitors of α-amylase activity. Bioorganic & medicinal chemistry letters. 2013 May; 23(10):3007-12. doi: 10.1016/j.bmcl.2013.03.029. [PMID: 23583514]
  • Wei Wang, Qiang Pan, Xue-Ying Han, Jing Wang, Ri-Qiu Tan, Fan He, De-Qiang Dou, Ting-Guo Kang. Simultaneous determination of arctiin and its metabolites in rat urine and feces by HPLC. Fitoterapia. 2013 Apr; 86(?):6-12. doi: 10.1016/j.fitote.2013.01.016. [PMID: 23380537]
  • 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]
  • Isabel Bondia-Pons, Thaer Barri, Kati Hanhineva, Katri Juntunen, Lars O Dragsted, Hannu Mykkänen, Kaisa Poutanen. UPLC-QTOF/MS metabolic profiling unveils urinary changes in humans after a whole grain rye versus refined wheat bread intervention. Molecular nutrition & food research. 2013 Mar; 57(3):412-22. doi: 10.1002/mnfr.201200571. [PMID: 23307617]
  • Cristiano Côrtes, Daniele da Silva-Kazama, Ricardo Kazama, Chaouki Benchaar, Geraldo dos Santos, Lucia M Zeoula, N Gagnon, Hélène V Petit. Effects of abomasal infusion of flaxseed (Linum usitatissimum) oil on microbial β-glucuronidase activity and concentration of the mammalian lignan enterolactone in ruminal fluid, plasma, urine and milk of dairy cows. The British journal of nutrition. 2013 Feb; 109(3):433-40. doi: 10.1017/s0007114512001341. [PMID: 22717302]
  • Jay K Udani, Donald J Brown, Maria Olivia C Tan, Mary Hardy. Pharmacokinetics and bioavailability of plant lignan 7-hydroxymatairesinol and effects on serum enterolactone and clinical symptoms in postmenopausal women: a single-blinded, parallel, dose-comparison study. Journal of the American College of Nutrition. 2013; 32(6):428-35. doi: 10.1080/07315724.2013.849578. [PMID: 24606716]
  • C K M Ho, L Halley, J Wei, F K Habib. Analysis of prostate cancer association with four single-nucleotide polymorphisms from genome-wide studies and serum phyto-estrogen concentrations. Prostate cancer and prostatic diseases. 2012 Dec; 15(4):365-8. doi: 10.1038/pcan.2012.24. [PMID: 22733159]
  • Kirstine S Krogholm, Anette Bysted, Anne Lise Brantsæter, Jette Jakobsen, Salka E Rasmussen, Lis Kristoffersen, Ulla Toft. Evaluation of flavonoids and enterolactone in overnight urine as intake biomarkers of fruits, vegetables and beverages in the Inter99 cohort study using the method of triads. The British journal of nutrition. 2012 Nov; 108(10):1904-12. doi: 10.1017/s0007114512000104. [PMID: 22453033]
  • Cristiano Côrtes, Marie-France Palin, Nathalie Gagnon, Chaouki Benchaar, Pierre Lacasse, Hélène V Petit. Mammary gene expression and activity of antioxidant enzymes and concentration of the mammalian lignan enterolactone in milk and plasma of dairy cows fed flax lignans and infused with flax oil in the abomasum. The British journal of nutrition. 2012 Oct; 108(8):1390-8. doi: 10.1017/s0007114511006829. [PMID: 22214882]
  • 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]
  • Kuo-Ching Jan, Yi-Wei Chang, Lucy Sun Hwang, Chi-Tang Ho. Tissue distribution and cytochrome P450 inhibition of sesaminol and its tetrahydrofuranoid metabolites. Journal of agricultural and food chemistry. 2012 Sep; 60(35):8616-23. doi: 10.1021/jf302699f. [PMID: 22894606]
  • Pamela Guglielmini, Alessandra Rubagotti, Francesco Boccardo. Serum enterolactone levels and mortality outcome in women with early breast cancer: a retrospective cohort study. Breast cancer research and treatment. 2012 Apr; 132(2):661-8. doi: 10.1007/s10549-011-1881-8. [PMID: 22094938]
  • 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]
  • Aida Karina Zaineddin, Alina Vrieling, Katharina Buck, Susen Becker, Jakob Linseisen, Dieter Flesch-Janys, Rudolf Kaaks, Jenny Chang-Claude. Serum enterolactone and postmenopausal breast cancer risk by estrogen, progesterone and herceptin 2 receptor status. International journal of cancer. 2012 Mar; 130(6):1401-10. doi: 10.1002/ijc.26157. [PMID: 21544804]
  • E Ginter, V Simko. Plant polyphenols in prevention of heart disease. Bratislavske lekarske listy. 2012; 113(8):476-80. doi: 10.4149/bll_2012_105. [PMID: 22897371]
  • Daniel L Parker, Michael E Rybak, Christine M Pfeiffer. Phytoestrogen biomonitoring: an extractionless LC-MS/MS method for measuring urinary isoflavones and lignans by use of atmospheric pressure photoionization (APPI). Analytical and bioanalytical chemistry. 2012 Jan; 402(3):1123-36. doi: 10.1007/s00216-011-5550-x. [PMID: 22124753]
  • Jae Jeong Yang, Lisa Y Cho, Kwang-Pil Ko, Aesun Shin, Seung Hyun Ma, Bo Youl Choi, Dong Soo Han, Kyu Sang Song, Yong Sung Kim, Jong-Young Lee, Bok Ghee Han, Soung-Hoon Chang, Hai-Rim Shin, Daehee Kang, Keun-Young Yoo, Sue K Park. Genetic susceptibility on CagA-interacting molecules and gene-environment interaction with phytoestrogens: a putative risk factor for gastric cancer. PloS one. 2012; 7(2):e31020. doi: 10.1371/journal.pone.0031020. [PMID: 22383989]
  • A N Martinchik, V V Zubtsov. [Phytoestrogenis properties of flaxseed lignans]. Voprosy pitaniia. 2012; 81(6):61-6. doi: . [PMID: 23530438]
  • Hoda B Mabrok, Robert Klopfleisch, Kadry Z Ghanem, Thomas Clavel, Michael Blaut, Gunnar Loh. Lignan transformation by gut bacteria lowers tumor burden in a gnotobiotic rat model of breast cancer. Carcinogenesis. 2012 Jan; 33(1):203-8. doi: 10.1093/carcin/bgr256. [PMID: 22080573]
  • Jennifer S Truan, Jian-Min Chen, Lilian U Thompson. Comparative effects of sesame seed lignan and flaxseed lignan in reducing the growth of human breast tumors (MCF-7) at high levels of circulating estrogen in athymic mice. Nutrition and cancer. 2012; 64(1):65-71. doi: 10.1080/01635581.2012.630165. [PMID: 22136581]