Matairesinol (BioDeep_00000002786)

Main id: BioDeep_00000398761

 

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


(3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone; (-)-Matairesinol; (8R,8R)-(-)-Matairesinol

化学式: C20H22O6 (358.1416312)
中文名称: 罗汉松树脂酚
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=C(C=CC(=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)O
InChI: InChI=1S/C20H34O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h12-19,21-22H,3-11H2,1-2H3

描述信息

Matairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, matairesinol is found, on average, in the highest concentration in a few different foods such as sesame, burdocks, and flaxseeds, and in a lower concentration in oats, asparagus, and poppies. Matairesinol has also been detected, but not quantified in, several different foods, such as silver lindens, tamarinds, cherry tomato, skunk currants, and fireweeds. This could make matairesinol a potential biomarker for the consumption of these foods. Matairesinol is composed of gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).
(-)-matairesinol is a lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). It has a role as a phytoestrogen, a plant metabolite, an angiogenesis inhibitor and an anti-asthmatic agent. It is a polyphenol, a lignan and a gamma-lactone.
Matairesinol is a natural product found in Crossosoma bigelovii, Brassica oleracea var. sabauda, and other organisms with data available.
See also: Arctium lappa fruit (part of); Pumpkin Seed (part of).
Matairesinol is a plant lignan. It occurs with secoisolariciresinol in numerous foods such as oil seeds, whole grains, vegetables, and fruits. (-)-Matairesinol is found in many foods, some of which are caraway, pecan nut, cereals and cereal products, and longan.
A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).
Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1].
Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1].

同义名列表

35 个代谢物同义名

(3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone; (-)-Matairesinol; (8R,8R)-(-)-Matairesinol; 2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R-trans)-; 2(3H)-Furanone, dihydro-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-, (3R-trans)-; 2(3H)-FURANONE, DIHYDRO-3,4-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-, (3R,4R)-; 2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-,(3R,4R)-; Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-Furanone; (3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone; Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-Furanone; (3R,4R)-3,4-bis[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-2-one; 2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-; 3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanone; Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone; (3R,4R)-3,4-Bis-(4-hydroxy-3-methoxy-benzyl)-dihydro-furan-2-one; (3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one; (3R,4R)-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)oxolan-2-one; (3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one; 3,4-Bis(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanone #; (2R,3R)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-4-butanolide; ARTIGENIN CONGENER; DIBENZYLBUTYROLACTONE LIGNANOLIDE; 2(3H)-Furanone, dihydro-3,4-divanillyl-; Dihydro-3,4-divanillyl-2(3H)-furanone; Matairesinol, analytical standard; Matairesinol, >=85\\% (HPLC); (8R,8’R)-(-)-matairesinol; (8R,8R)-(-)-Matairesinol; Artigenin congener; rac Matairesinol; (-)-Matairesinol; UNII-XLW63P8WUA; matai-resinol; MEGxp0_001689; ACon1_001075; Matairesinol; XLW63P8WUA; MAX



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

132 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(7)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(125)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

162 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

  • Shenshen Wu, Jiajia Wang, Zan Fu, Giuseppe Familiari, Michela Relucenti, Michael Aschner, Xiaobo Li, Hanqing Chen, Rui Chen. Matairesinol Nanoparticles Restore Chemosensitivity and Suppress Colorectal Cancer Progression in Preclinical Models: Role of Lipid Metabolism Reprogramming. Nano letters. 2023 Feb; ?(?):. doi: 10.1021/acs.nanolett.3c00035. [PMID: 36802650]
  • Peter Kiplangʼat Koech, Gergely Jócsák, Imre Boldizsár, Kinga Moldován, Sándor Borbély, Ildikó Világi, Arpád Dobolyi, Petra Varró. Anti-glutamatergic Effects of Three Lignan Compounds: Arctigenin, Matairesinol and Trachelogenin - An ex vivo Study on Rat Brain Slices. Planta medica. 2023 Feb; ?(?):. doi: 10.1055/a-2005-5497. [PMID: 36592636]
  • D C C Brito, I P Silva, A C A Ferreira, N A R Sá, M I F Guedes, A P R Rodrigues, R R Santos, J R Figueiredo. Effects of in vitro exposure of sheep ovarian tissue to zearalenone and matairesinol on preantral follicles. Zygote (Cambridge, England). 2022 Jun; 30(3):419-422. doi: 10.1017/s0967199421000794. [PMID: 34689852]
  • Davide Decembrino, Marco Girhard, Vlada B Urlacher. Use of Copper as a Trigger for the in Vivo Activity of E. coli Laccase CueO: A Simple Tool for Biosynthetic Purposes. Chembiochem : a European journal of chemical biology. 2021 04; 22(8):1470-1479. doi: 10.1002/cbic.202000775. [PMID: 33332702]
  • Davide Decembrino, Esther Ricklefs, Stefan Wohlgemuth, Marco Girhard, Katrin Schullehner, Guido Jach, Vlada B Urlacher. Assembly of Plant Enzymes in E. coli for the Production of the Valuable (-)-Podophyllotoxin Precursor (-)-Pluviatolide. ACS synthetic biology. 2020 11; 9(11):3091-3103. doi: 10.1021/acssynbio.0c00354. [PMID: 33095000]
  • Eman Al-Sayed, Tzu-Yi Ke, Tsong-Long Hwang, Shu-Rong Chen, Michal Korinek, Shu-Li Chen, Yuan-Bin Cheng. Cytotoxic and anti-inflammatory effects of lignans and diterpenes from Cupressus macrocarpa. Bioorganic & medicinal chemistry letters. 2020 05; 30(10):127127. doi: 10.1016/j.bmcl.2020.127127. [PMID: 32223924]
  • Yilin Qiao, Nathan K Sunada, Alyssa E Hatada, Ingo Lange, Manana Khutsishvili, Valida Alizade, Daniel Atha, Dana-Lynn Ko'omoa-Lange, Robert P Borris. Potential anti-neuroblastoma agents from Juniperus oblonga. Biochemical and biophysical research communications. 2019 08; 516(3):733-738. doi: 10.1016/j.bbrc.2019.06.123. [PMID: 31255282]
  • Jungmoo Huh, Jae Hyoung Song, Seong Ryeol Kim, Hyo Moon Cho, Hyun-Jeong Ko, Heejung Yang, Sang Hyun Sung. Lignan Dimers from Forsythia viridissima Roots and Their Antiviral Effects. Journal of natural products. 2019 02; 82(2):232-238. doi: 10.1021/acs.jnatprod.8b00590. [PMID: 30676026]
  • 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]
  • Guo Feng, Yun-Long Chen, Wei Li, Lai-Lai Li, Zeng-Guang Wu, Zi-Jun Wu, Yue Hai, Si-Chao Zhang, Chuan-Qi Zheng, Chang-Xiao Liu, Xin He. Exploring the Q-marker of "sweat soaking method" processed radix Wikstroemia indica: Based on the "effect-toxicity-chemicals" study. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Jun; 45(?):49-58. doi: 10.1016/j.phymed.2018.03.063. [PMID: 29691116]
  • Rúbia C G Corrêa, Rosane M Peralta, Charles W I Haminiuk, Giselle Maria Maciel, Adelar Bracht, Isabel C F R Ferreira. New phytochemicals as potential human anti-aging compounds: Reality, promise, and challenges. Critical reviews in food science and nutrition. 2018 Apr; 58(6):942-957. doi: 10.1080/10408398.2016.1233860. [PMID: 27623718]
  • Peng Xu, Meng-Wei Huang, Chen-Xi Xiao, Fen Long, Ying Wang, Si-Yu Liu, Wan-Wan Jia, Wei-Jun Wu, Di Yang, Jin-Feng Hu, Xin-Hua Liu, Yi-Zhun Zhu. Matairesinol Suppresses Neuroinflammation and Migration Associated with Src and ERK1/2-NF-κB Pathway in Activating BV2 Microglia. Neurochemical research. 2017 Oct; 42(10):2850-2860. doi: 10.1007/s11064-017-2301-1. [PMID: 28512713]
  • Labib Noman, Feyza Oke-Altuntas, Amar Zellagui, Ayse Sahin Yaglioglu, Ibrahim Demirtas, Susana M Cardoso, Salah Akkal, Noureddine Gherraf, Salah Rhouati. A novel benzimidazole and other constituents with antiproliferative and antioxidant properties from Thymelaea microphylla Coss. et Dur. Natural product research. 2017 Sep; 31(17):2032-2041. doi: 10.1080/14786419.2016.1274888. [PMID: 28105861]
  • Phu H Dang, Hai X Nguyen, Hanh H T Nguyen, Thai D Vo, Tho H Le, Trong H N Phan, Mai T T Nguyen, Nhan T Nguyen. Lignans from the Roots of Taxus wallichiana and Their α-Glucosidase Inhibitory Activities. Journal of natural products. 2017 06; 80(6):1876-1882. doi: 10.1021/acs.jnatprod.7b00171. [PMID: 28581744]
  • Chang-Ling Hu, Juan Xiong, Peng Xu, Ke-Jun Cheng, Guo-Xun Yang, Jin-Feng Hu. Lignans from the shed trunk barks of the critically endangered plant Abies beshanzuensis and their anti-neuroinflammatory activities. Natural product research. 2017 Jun; 31(12):1358-1364. doi: 10.1080/14786419.2016.1247082. [PMID: 27774796]
  • Phu Hoang Dang, Hai Xuan Nguyen, Truc Thanh Thi Duong, Thao Kim Thi Tran, Phuc Thi Nguyen, Trang Kieu Thi Vu, Hung Chi Vuong, Nguyen Huu Trong Phan, Mai Thanh Thi Nguyen, Nhan Trung Nguyen, Suresh Awale. α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana. Journal of natural products. 2017 04; 80(4):1087-1095. doi: 10.1021/acs.jnatprod.7b00006. [PMID: 28240909]
  • 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]
  • Yoon-Young Sung, A Yeong Lee, Ho Kyoung Kim. Forsythia suspensa fruit extracts and the constituent matairesinol confer anti-allergic effects in an allergic dermatitis mouse model. Journal of ethnopharmacology. 2016 Jul; 187(?):49-56. doi: 10.1016/j.jep.2016.04.015. [PMID: 27085937]
  • 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]
  • Liisa Uusitalo, Maija Salmenhaara, Merja Isoniemi, Alicia Garcia-Alvarez, Lluís Serra-Majem, Lourdes Ribas-Barba, Paul Finglas, Jenny Plumb, Pirkko Tuominen, Kirsti Savela. Intake of selected bioactive compounds from plant food supplements containing fennel (Foeniculum vulgare) among Finnish consumers. Food chemistry. 2016 Mar; 194(?):619-25. doi: 10.1016/j.foodchem.2015.08.057. [PMID: 26471600]
  • Shan Su, Michael Wink. Natural lignans from Arctium lappa as antiaging agents in Caenorhabditis elegans. Phytochemistry. 2015 Sep; 117(?):340-350. doi: 10.1016/j.phytochem.2015.06.021. [PMID: 26141518]
  • Shan Su, Xinlai Cheng, Michael Wink. Cytotoxicity of arctigenin and matairesinol against the T-cell lymphoma cell line CCRF-CEM. The Journal of pharmacy and pharmacology. 2015 Sep; 67(9):1316-23. doi: 10.1111/jphp.12426. [PMID: 25922263]
  • Shan Su, Xinlai Cheng, Michael Wink. Natural lignans from Arctium lappa modulate P-glycoprotein efflux function in multidrug resistant cancer cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 Feb; 22(2):301-7. doi: 10.1016/j.phymed.2014.12.009. [PMID: 25765837]
  • K M Njåstad, S A Adler, J Hansen-Møller, E Thuen, A-M Gustavsson, H Steinshamn. Gastrointestinal metabolism of phytoestrogens in lactating dairy cows fed silages with different botanical composition. Journal of dairy science. 2014 Dec; 97(12):7735-50. doi: 10.3168/jds.2014-8208. [PMID: 25306275]
  • 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]
  • Xiao-Ting Liu, Zhe-Xing Wang, Yu Yang, Lin Wang, Ruo-Feng Sun, Yi-Min Zhao, Neng-Jiang Yu. Active components with inhibitory activities on IFN-γ/STAT1 and IL-6/STAT3 signaling pathways from Caulis Trachelospermi. Molecules (Basel, Switzerland). 2014 Aug; 19(8):11560-71. doi: 10.3390/molecules190811560. [PMID: 25100250]
  • Sik-Won Choi, Kie-In Park, Jeong-Tae Yeon, Byung Jun Ryu, Kwang-Jin Kim, Seong Hwan Kim. Anti-osteoclastogenic activity of matairesinol via suppression of p38/ERK-NFATc1 signaling axis. BMC complementary and alternative medicine. 2014 Jan; 14(?):35. doi: 10.1186/1472-6882-14-35. [PMID: 24444335]
  • Oue-artorn Rajachan, Somdej Kanokmedhakul, Phitak Nasomjai, Kwanjai Kanokmedhakul. Chemical constituents and biological activities from roots of Enkleia siamensis. Natural product research. 2014; 28(4):268-70. doi: 10.1080/14786419.2013.838241. [PMID: 24047498]
  • Emrah Yatkin, Lauri Polari, Teemu D Laajala, Annika Smeds, Christer Eckerman, Bjarne Holmbom, Niina M Saarinen, Tero Aittokallio, Sari I Mäkelä. Novel Lignan and stilbenoid mixture shows anticarcinogenic efficacy in preclinical PC-3M-luc2 prostate cancer model. PloS one. 2014; 9(4):e93764. doi: 10.1371/journal.pone.0093764. [PMID: 24699425]
  • Sooryun Lee, Inn-Hye Song, Jung-Ho Lee, Woo-Young Yang, Ki-Bong Oh, Jongheon Shin. Sortase A inhibitory metabolites from the roots of Pulsatilla koreana. Bioorganic & medicinal chemistry letters. 2014 Jan; 24(1):44-8. doi: 10.1016/j.bmcl.2013.12.006. [PMID: 24360605]
  • Lei Zhao, Xue-jing Peng, Peng-fei Xia, Wen-da Duan. [Chemical constituents of Tamarix chinensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Jan; 37(1):61-3. doi: ". [PMID: 25090705]
  • Susanne Kuehnl, Sebastian Schroecksnadel, Veronika Temml, Johanna M Gostner, Harald Schennach, Daniela Schuster, Stefan Schwaiger, Judith M Rollinger, Dietmar Fuchs, Hermann Stuppner. Lignans from Carthamus tinctorius suppress tryptophan breakdown via indoleamine 2,3-dioxygenase. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Oct; 20(13):1190-5. doi: 10.1016/j.phymed.2013.06.006. [PMID: 23867649]
  • 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]
  • Lilla Szokol-Borsodi, Anna Sólyomváry, Ibolya Molnár-Perl, Imre Boldizsár. Optimum yields of dibenzylbutyrolactone-type lignans from Cynareae fruits, during their ripening, germination and enzymatic hydrolysis processes, determined by on-line chromatographic methods. Phytochemical analysis : PCA. 2012 Nov; 23(6):598-603. doi: 10.1002/pca.2360. [PMID: 22396124]
  • 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]
  • Pepijn Prinsen, Ana Gutiérrez, José C del Río. Lipophilic extractives from the cortex and pith of elephant grass ( Pennisetum purpureum Schumach.) stems. Journal of agricultural and food chemistry. 2012 Jun; 60(25):6408-17. doi: 10.1021/jf301753w. [PMID: 22646817]
  • Boram Lee, Ki Hyun Kim, Hye Jin Jung, Ho Jeong Kwon. Matairesinol inhibits angiogenesis via suppression of mitochondrial reactive oxygen species. Biochemical and biophysical research communications. 2012 Apr; 421(1):76-80. doi: 10.1016/j.bbrc.2012.03.114. [PMID: 22483751]
  • 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]
  • Mengyue Wang, Ke Li, Yuxiao Nie, Yingfang Wei, Xiaobo Li. Antirheumatoid Arthritis Activities and Chemical Compositions of Phenolic Compounds-Rich Fraction from Urtica atrichocaulis, an Endemic Plant to China. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):818230. doi: 10.1155/2012/818230. [PMID: 21904564]
  • F Saleh, F Afnan, F Ara, S Yasmin, K Nahar, F Khatun, L Ali. Phytoestrogen intake and cardiovascular risk markers in Bangladeshi postmenopausal women. Mymensingh medical journal : MMJ. 2011 Apr; 20(2):219-25. doi: . [PMID: 21522091]
  • Jin Hee Lee, Ji Yun Lee, Tae Doo Kim, Chang Jong Kim. Antiasthmatic action of dibenzylbutyrolactone lignans from fruits of Forsythia viridissima on asthmatic responses to ovalbumin challenge in conscious guinea-pigs. Phytotherapy research : PTR. 2011 Mar; 25(3):387-95. doi: 10.1002/ptr.3273. [PMID: 20734328]
  • Sung-Hee Cho, Jeong-Hee Jang, Ji Young Yoon, Chi-Dong Han, Youngsun Choi, Sang-Won Choi. Effects of a safflower tea supplement on antioxidative status and bone markers in postmenopausal women. Nutrition research and practice. 2011 Feb; 5(1):20-7. doi: 10.4162/nrp.2011.5.1.20. [PMID: 21487492]
  • Manami Yamawaki, Kosuke Nishi, Sogo Nishimoto, Satoshi Yamauchi, Koichi Akiyama, Taro Kishida, Masafumi Maruyama, Hisashi Nishiwaki, Takuya Sugahara. Immunomodulatory effect of (--)-matairesinol in vivo and ex vivo. Bioscience, biotechnology, and biochemistry. 2011; 75(5):859-63. doi: 10.1271/bbb.100781. [PMID: 21597179]
  • Sajida Abdureyim, Nurmuhammat Amat, Anwar Umar, Halmurat Upur, Benedicte Berke, Nicholas Moore. Anti-inflammatory, immunomodulatory, and heme oxygenase-1 inhibitory activities of ravan napas, a formulation of uighur traditional medicine, in a rat model of allergic asthma. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):. doi: 10.1155/2011/725926. [PMID: 20953388]
  • Herman Adlercreutz. Can rye intake decrease risk of human breast cancer?. Food & nutrition research. 2010 Nov; 54(?):. doi: 10.3402/fnr.v54i0.5231. [PMID: 21311613]
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  • Riitta Luoto, Elham Kharazmi, Niina M Saarinen, Annika I Smeds, Sari Mäkelä, Mahdi Fallah, Jani Raitanen, Leena Hilakivi-Clarke. Effect of dietary intervention on serum lignan levels in pregnant women - a controlled trial. Reproductive health. 2010 Oct; 7(?):26. doi: 10.1186/1742-4755-7-26. [PMID: 20932282]
  • 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]
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