Secoisolariciresinol (BioDeep_00000000962)

 

Secondary id: BioDeep_00000398758, BioDeep_00000860995

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds natural product


代谢物信息卡片


1,4-Butanediol, 2,3-bis((4-hydroxy-3-methoxyphenyl)methyl)-, (R-(R*,R*))-

化学式: C20H26O6 (362.17292960000003)
中文名称: 开环异落叶松树脂酚, 异豆香脂素
谱图信息: 最多检出来源 Homo sapiens(feces) 0.15%

分子结构信息

SMILES: COC1=C(C=CC(=C1)CC(CO)C(CC2=CC(=C(C=C2)O)OC)CO)O
InChI: InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1

描述信息

Secoisolariciresinol, also known as knotolan or secoisolariciresinol, (r*,s*)-isomer, is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as grape, saskatoon berry, asparagus, and sweet potato, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol can be found primarily in urine. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 \\\\% .
(-)-secoisolariciresinol is an enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration. It has a role as an antidepressant, a plant metabolite and a phytoestrogen. It is an enantiomer of a (+)-secoisolariciresinol.
Secoisolariciresinol has been used in trials studying the prevention of Breast Cancer.
Secoisolariciresinol is a natural product found in Fitzroya cupressoides, Crossosoma bigelovii, and other organisms with data available.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
Secoisolariciresinol is a lignan, a type of phenylpropanoids.
Secoisolariciresinol is a lignan, a type of phenylpropanoids.
Secoisolariciresinol is a lignan, a type of phenylpropanoids.

同义名列表

36 个代谢物同义名

1,4-Butanediol, 2,3-bis((4-hydroxy-3-methoxyphenyl)methyl)-, (R-(R*,R*))-; (R-(R*,R*))-2,3-Bis((4-hydroxy-3-methoxyphenyl)methyl)butane-1,4-diol; 1,4-Butanediol, 2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (2R,3R)-; 1,4-Butanediol,2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (2R,3R)-; (2R,3R)-2,3-bis[(3-methoxy-4-oxidanyl-phenyl)methyl]butane-1,4-diol; (2R,3R)-2,3-bis[(4-hydroxy-3-methoxy-phenyl)methyl]butane-1,4-diol; (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol; (2R*,3R*)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol; 2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol; 2,3-bis((4-hydroxy-3-methoxyphenyl)methyl)-1,4-butanediol; (2R,3R)-2,3-bis(4-hydroxy-3-methoxybenzyl)butane-1,4-diol; 2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol, (-); Secoisolariciresinol, >=95.0\\% (HPLC); 1,4-BUTANEDIOL, 2,3-DIVANILLYL-, (-)-; secoisolariciresinol, (R*,S*)-isomer; (8R,8’R)-(-)-Secoisolariciresinol; (8R,8R)-(-)-SECOISOLARICIRESINOL; 2,3-Divanillyl-1,4-butanediol; (8R,8R)-Secoisolariciresinol; PUETUDUXMCLALY-HOTGVXAUSA-N; 8R,8R-secoisolariciresinol; (+/-)-Secoisolariciresinol; SECOISOLARICIRESINOL, (-)-; secoisolariciresinol-(-); (-)-Secoisolariciresinol; (-) secoisolariciresinol; RR-secoisolariciresinol; seco-Isolariciresinol; Secoisolariciresinol; UNII-M8QRJ7JEJH; M8QRJ7JEJH; knotolan; GO6; Flaxseeds extract; Secoisolariciresinol; Secoisolariciresinol



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

116 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(113)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

717 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

  • Jing Chen, Hui Chen, Chengcheng Feng, Qiong Chen, Xiang Fang, Yong Wang, Ning Zhang. Anti-inflammatory effect of lignans from flaxseed after fermentation by lactiplantibacillus plantarum SCB0151 in vitro. World journal of microbiology & biotechnology. 2024 Mar; 40(4):134. doi: 10.1007/s11274-024-03945-9. [PMID: 38480613]
  • Zhiqiang Li, Haonan Zhang, Wanting Li, Min Yao, Huimin Yu, Mingzhen He, Yulin Feng, Zhifeng Li. Potential antioxidative components from Syringa oblata Lindl stems revealed by affinity ultrafiltration with multiple drug targets. Bioorganic chemistry. 2023 May; 138(?):106604. doi: 10.1016/j.bioorg.2023.106604. [PMID: 37178648]
  • U K Hussain Zaki, C Fryganas, L Trijsburg, E J M Feskens, E Capuano. Influence of different processing method on lignan content of selected Malaysian plant-based foods. Food chemistry. 2023 Mar; 404(Pt A):134607. doi: 10.1016/j.foodchem.2022.134607. [PMID: 36272303]
  • Xiumei Han, Leonid Akhov, Paula Ashe, Courteney Lewis, Leah Deibert, L Irina Zaharia, Lily Forseille, Daoquan Xiang, Raju Datla, Matthew Nosworthy, Carol Henry, Jitao Zou, Bianyun Yu, Nii Patterson. Comprehensive compositional assessment of bioactive compounds in diverse pea accessions. Food research international (Ottawa, Ont.). 2023 03; 165(?):112455. doi: 10.1016/j.foodres.2022.112455. [PMID: 36869474]
  • Joanda P R E Silva, Laiane C O Pereira, Lucas S Abreu, Francisca S V Lins, Thalisson A de Souza, Renan F do Espírito-Santo, Renata P C Barros, Cristiane F Villarreal, José I M de Melo, Marcus T Scotti, Vicente C de O Costa, Lucas H Martorano, Fernando M Dos Santos, Raimundo Braz Filho, Marcelo S da Silva, Josean F Tavares. Targeted Isolation of Anti-inflammatory Lignans from Justicia aequilabris by Molecular Networking Approach. Journal of natural products. 2022 09; 85(9):2184-2191. doi: 10.1021/acs.jnatprod.2c00478. [PMID: 35998343]
  • Xixian Feng, Fanjia Peng, Zujun Yin, Junjuan Wang, Yuexin Zhang, Hong Zhang, Yapeng Fan, Nan Xu, Hui Huang, Kesong Ni, Xiaoyu Liu, Yuqian Lei, Tiantian Jiang, Jing Wang, Cun Rui, Chao Chen, Shuai Wang, Xiugui Chen, Xuke Lu, Delong Wang, Lixue Guo, Lanjie Zhao, Yujun Li, Yongbo Wang, Wuwei Ye. Secondary metabolite pathway of SDG (secoisolariciresinol) was observed to trigger ROS scavenging system in response to Ca2+ stress in cotton. Genomics. 2022 07; 114(4):110398. doi: 10.1016/j.ygeno.2022.110398. [PMID: 35675878]
  • Sameh S Elhady, Elsayed A Ibrahim, Marwa S Goda, Mohamed S Nafie, Hanan Samir, Reem M Diri, Abdulrahman M Alahdal, Ama Kyeraa Thomford, Alaa El Gindy, Ghada M Hadad, Jihan M Badr, Reda F A Abdelhameed. GC-MS/MS Quantification of EGFR Inhibitors, β-Sitosterol, Betulinic Acid, (+) Eriodictyol, (+) Epipinoresinol, and Secoisolariciresinol, in Crude Extract and Ethyl Acetate Fraction of Thonningia sanguinea. Molecules (Basel, Switzerland). 2022 Jun; 27(13):. doi: 10.3390/molecules27134109. [PMID: 35807354]
  • Leyla Polat Kose, İlhami Gulcin. Evaluation of the Antioxidant and Antiradical Properties of Some Phyto and Mammalian Lignans. Molecules (Basel, Switzerland). 2021 Nov; 26(23):. doi: 10.3390/molecules26237099. [PMID: 34885681]
  • Bushra Asad, Taimoor Khan, Faiza Zareen Gul, Muhammad Asad Ullah, Samantha Drouet, Sara Mikac, Laurine Garros, Manon Ferrier, Shankhamala Bose, Thibaut Munsch, Duangjai Tungmunnithum, Arnaud Lanoue, Nathalie Giglioli-Guivarc'h, Christophe Hano, Bilal Haider Abbasi. Scarlet Flax Linum grandiflorum (L.) In Vitro Cultures as a New Source of Antioxidant and Anti-Inflammatory Lignans. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154511. [PMID: 34361665]
  • 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]
  • Ying Xiao, Kai Shao, Jingwen Zhou, Lian Wang, Xueqi Ma, Di Wu, Yingbo Yang, Junfeng Chen, Jingxian Feng, Shi Qiu, Zongyou Lv, Lei Zhang, Peng Zhang, Wansheng Chen. Structure-based engineering of substrate specificity for pinoresinol-lariciresinol reductases. Nature communications. 2021 05; 12(1):2828. doi: 10.1038/s41467-021-23095-y. [PMID: 33990581]
  • Karolina Dobrowolska, Bożena Regulska-Ilow. The legitimacy of using dietary supplement diglycoside secoisolariciresinol (SDG) from flaxseed in cancer. Roczniki Panstwowego Zakladu Higieny. 2021; 72(1):9-20. doi: 10.32394/rpzh.2021.0144. [PMID: 33882661]
  • 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]
  • Bouchentouf Salim, Ghalem Said, Nadia Kambouche, Soumaya Kress. Identification of Phenolic Compounds from Nettle as New Candidate Inhibitors of Main Enzymes Responsible on Type-II Diabetes. Current drug discovery technologies. 2020; 17(2):197-202. doi: 10.2174/1570163815666180829094831. [PMID: 30156162]
  • Chen Cheng, Xiao Yu, David Julian McClements, Qingde Huang, Hu Tang, Kun Yu, Xia Xiang, Peng Chen, Xintian Wang, Qianchun Deng. Effect of flaxseed polyphenols on physical stability and oxidative stability of flaxseed oil-in-water nanoemulsions. Food chemistry. 2019 Dec; 301(?):125207. doi: 10.1016/j.foodchem.2019.125207. [PMID: 31377621]
  • Lucija Markulin, Cyrielle Corbin, Sullivan Renouard, Samantha Drouet, Laurent Gutierrez, Ivan Mateljak, Daniel Auguin, Christophe Hano, Elisabeth Fuss, Eric Lainé. Pinoresinol-lariciresinol reductases, key to the lignan synthesis in plants. Planta. 2019 Jun; 249(6):1695-1714. doi: 10.1007/s00425-019-03137-y. [PMID: 30895445]
  • Yingling Wu, Dawei Xing, Guoliang Ma, Xinlong Dai, Liping Gao, Tao Xia. A variable loop involved in the substrate selectivity of pinoresinol/lariciresinol reductase from Camellia sinensis. Phytochemistry. 2019 Jun; 162(?):1-9. doi: 10.1016/j.phytochem.2019.02.003. [PMID: 30844490]
  • Lucija Markulin, Samantha Drouet, Cyrielle Corbin, Cédric Decourtil, Laurine Garros, Sullivan Renouard, Tatiana Lopez, Gaëlle Mongelard, Laurent Gutierrez, Daniel Auguin, Eric Lainé, Christophe Hano. The control exerted by ABA on lignan biosynthesis in flax (Linum usitatissimum L.) is modulated by a Ca2+ signal transduction involving the calmodulin-like LuCML15b. Journal of plant physiology. 2019 May; 236(?):74-87. doi: 10.1016/j.jplph.2019.03.005. [PMID: 30928768]
  • Ahmed M M Gabr, Hoda B Mabrok, Emam A Abdel-Rahim, Mohamed K El-Bahr, Iryna Smetanska. Determination of lignans, phenolic acids and antioxidant capacity in transformed hairy root culture of Linum usitatissimum. Natural product research. 2018 Aug; 32(15):1867-1871. doi: 10.1080/14786419.2017.1405405. [PMID: 29156979]
  • Cyrielle Corbin, Samantha Drouet, Lucija Markulin, Daniel Auguin, Éric Lainé, Laurence B Davin, John R Cort, Norman G Lewis, Christophe Hano. A genome-wide analysis of the flax (Linum usitatissimum L.) dirigent protein family: from gene identification and evolution to differential regulation. Plant molecular biology. 2018 May; 97(1-2):73-101. doi: 10.1007/s11103-018-0725-x. [PMID: 29713868]
  • 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]
  • Yunyun Di, Jennifer Jones, Kerry Mansell, Susan Whiting, Sharyle Fowler, Lilian Thorpe, Jennifer Billinsky, Navita Viveky, Pui Chi Cheng, Ahmed Almousa, Thomas Hadjistavropoulos, Jane Alcorn. Influence of Flaxseed Lignan Supplementation to Older Adults on Biochemical and Functional Outcome Measures of Inflammation. Journal of the American College of Nutrition. 2017 Nov; 36(8):646-653. doi: 10.1080/07315724.2017.1342213. [PMID: 28922068]
  • Xiao Feng, Guozhu Su, Yunyun Ye, Ruifei Zhang, Xinyao Yang, Bingzhao Du, Bing Peng, Pengfei Tu, Xingyun Chai. Alashinols F and G, two lignans from stem bark of Syringa pinnatifolia. Natural product research. 2017 Jul; 31(13):1555-1560. doi: 10.1080/14786419.2017.1283500. [PMID: 28152612]
  • 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]
  • Bourlaye Fofana, Kaushik Ghose, Jason McCallum, Frank M You, Sylvie Cloutier. UGT74S1 is the key player in controlling secoisolariciresinol diglucoside (SDG) formation in flax. BMC plant biology. 2017 02; 17(1):35. doi: 10.1186/s12870-017-0982-x. [PMID: 28152982]
  • Saimi Tokunaga, Bruce R Woodin, John J Stegeman. Plant lignan secoisolariciresinol suppresses pericardial edema caused by dioxin-like compounds in developing zebrafish: Implications for suppression of morphological abnormalities. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2016 Oct; 96(?):160-6. doi: 10.1016/j.fct.2016.07.012. [PMID: 27427306]
  • 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]
  • Yue-ping Jiang, Yu-feng Liu, Qing-lan Guo, Cheng-bo Xu, Sheng Lin, Cheng-gen Zhu, Yong-chun Yang, Jian-gong Shi. [Lignanoids from an aqueous extract of the roots of Codonopsis pilosula]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 04; 51(4):616-25. doi: . [PMID: 29860746]
  • 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]
  • Mikhail Y Maslov, Tatiana M Plotnikova, Anna M Anishchenko, Oleg I Aliev, Nikolay E Nifantiev, Mark B Plotnikov. Hemorheological effects of secoisolariciresinol in ovariectomized rats. Biorheology. 2016 01; 53(1):23-31. doi: 10.3233/bir-15066. [PMID: 26756280]
  • Pei Hu, Qi-Yong Mei, Li Ma, Wu-Geng Cui, Wen-Hua Zhou, Dong-Sheng Zhou, Qing Zhao, Dong-Ying Xu, Xin Zhao, Qin Lu, Zhen-Yu Hu. Secoisolariciresinol diglycoside, a flaxseed lignan, exerts analgesic effects in a mouse model of type 1 diabetes: Engagement of antioxidant mechanism. European journal of pharmacology. 2015 Nov; 767(?):183-92. doi: 10.1016/j.ejphar.2015.10.024. [PMID: 26494631]
  • Doralyn S Dalisay, Kye Won Kim, Choonseok Lee, Hong Yang, Oliver Rübel, Benjamin P Bowen, Laurence B Davin, Norman G Lewis. Dirigent Protein-Mediated Lignan and Cyanogenic Glucoside Formation in Flax Seed: Integrated Omics and MALDI Mass Spectrometry Imaging. Journal of natural products. 2015 Jun; 78(6):1231-42. doi: 10.1021/acs.jnatprod.5b00023. [PMID: 25981198]
  • 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]
  • Kaushik Ghose, Jason McCallum, Marva Sweeney-Nixon, Bourlaye Fofana. Histidine 352 (His352) and tryptophan 355 (Trp355) are essential for flax UGT74S1 glucosylation activity toward secoisolariciresinol. PloS one. 2015; 10(2):e116248. doi: 10.1371/journal.pone.0116248. [PMID: 25714779]
  • Sullivan Renouard, Marie-Aude Tribalatc, Frederic Lamblin, Gaëlle Mongelard, Ophélie Fliniaux, Cyrielle Corbin, Djurdjica Marosevic, Serge Pilard, Hervé Demailly, Laurent Gutierrez, Christophe Hano, François Mesnard, Eric Lainé. RNAi-mediated pinoresinol lariciresinol reductase gene silencing in flax (Linum usitatissimum L.) seed coat: consequences on lignans and neolignans accumulation. Journal of plant physiology. 2014 Sep; 171(15):1372-7. doi: 10.1016/j.jplph.2014.06.005. [PMID: 25046758]
  • Yufeng Qin, Guizhen Du, Minjian Chen, Weiyue Hu, Chuncheng Lu, Wei Wu, Bo Hang, Zuomin Zhou, Xinru Wang, Yankai Xia. Combined effects of urinary phytoestrogens metabolites and polymorphisms in metabolic enzyme gene on idiopathic male infertility. Archives of toxicology. 2014 Aug; 88(8):1527-36. doi: 10.1007/s00204-014-1205-y. [PMID: 24488272]
  • T Kulik, M Buśko, A Pszczółkowska, J Perkowski, A Okorski. Plant lignans inhibit growth and trichothecene biosynthesis in Fusarium graminearum. Letters in applied microbiology. 2014 Jul; 59(1):99-107. doi: 10.1111/lam.12250. [PMID: 24635164]
  • Eliana Spilioti, Bjarne Holmbom, Athanasios G Papavassiliou, Paraskevi Moutsatsou. Lignans 7-hydroxymatairesinol and 7-hydroxymatairesinol 2 exhibit anti-inflammatory activity in human aortic endothelial cells. Molecular nutrition & food research. 2014 Apr; 58(4):749-59. doi: 10.1002/mnfr.201300318. [PMID: 24311533]
  • Kaushik Ghose, Kumarakurubaran Selvaraj, Jason McCallum, Chris W Kirby, Marva Sweeney-Nixon, Sylvie J Cloutier, Michael Deyholos, Raju Datla, Bourlaye Fofana. Identification and functional characterization of a flax UDP-glycosyltransferase glucosylating secoisolariciresinol (SECO) into secoisolariciresinol monoglucoside (SMG) and diglucoside (SDG). BMC plant biology. 2014 Mar; 14(?):82. doi: 10.1186/1471-2229-14-82. [PMID: 24678929]
  • 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]
  • Yankai Xia, Minjian Chen, Pengfei Zhu, Chuncheng Lu, Guangbo Fu, Xiaojin Zhou, Daozhen Chen, Honghua Wang, Bo Hang, Shoulin Wang, Zuomin Zhou, Jiahao Sha, Xinru Wang. Urinary phytoestrogen levels related to idiopathic male infertility in Chinese men. Environment international. 2013 Sep; 59(?):161-7. doi: 10.1016/j.envint.2013.06.009. [PMID: 23820060]
  • Julie Boberg, Karen Riiber Mandrup, Pernille Rosenskjold Jacobsen, Louise Krag Isling, Niels Hadrup, Line Berthelsen, Anders Elleby, Maria Kiersgaard, Anne Marie Vinggaard, Ulla Hass, Christine Nellemann. Endocrine disrupting effects in rats perinatally exposed to a dietary relevant mixture of phytoestrogens. Reproductive toxicology (Elmsford, N.Y.). 2013 Sep; 40(?):41-51. doi: 10.1016/j.reprotox.2013.05.014. [PMID: 23770295]
  • Laila Meija, Paivi Söderholm, Adile Samaletdin, Gita Ignace, Inese Siksna, Rafaels Joffe, Aivars Lejnieks, Vilnis Lietuvietis, Indrikis Krams, Herman Adlercreutz. Dietary intake and major sources of plant lignans in Latvian men and women. International journal of food sciences and nutrition. 2013 Aug; 64(5):535-43. doi: 10.3109/09637486.2013.765835. [PMID: 23373826]
  • 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]
  • Cyrielle Corbin, Sullivan Renouard, Tatiana Lopez, Frédéric Lamblin, Eric Lainé, Christophe Hano. Identification and characterization of cis-acting elements involved in the regulation of ABA- and/or GA-mediated LuPLR1 gene expression and lignan biosynthesis in flax (Linum usitatissimum L.) cell cultures. Journal of plant physiology. 2013 Mar; 170(5):516-22. doi: 10.1016/j.jplph.2012.11.003. [PMID: 23273926]
  • Xing Ma, Rui Wang, Xin Zhao, Chong Zhang, Jiao Sun, Jianxin Li, Lu Zhang, Tuo Shao, Lina Ruan, Liang Chen, Ying Xu, Jianchun Pan. Antidepressant-like effect of flaxseed secoisolariciresinol diglycoside in ovariectomized mice subjected to unpredictable chronic stress. Metabolic brain disease. 2013 Mar; 28(1):77-84. doi: 10.1007/s11011-012-9371-1. [PMID: 23263992]
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