(+)-lariciresinol (BioDeep_00000004010)

 

Secondary id: BioDeep_00000396578

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol

化学式: C20H24O6 (360.1572804)
中文名称: 落叶松树脂醇
谱图信息: 最多检出来源 Viridiplantae(plant) 0.04%

分子结构信息

SMILES: COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)O)OC)O
InChI: InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3

描述信息

(+)-Lariciresinol belongs to the class of organic compounds known as 7,9-epoxylignans. These are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at positons 2, 3 and 4, respectively. (+)-Lariciresinol has been detected in several different foods, such as parsnips, white mustards, narrowleaf cattails, turnips, and common sages. This could make (+)-Lariciresinol a potential biomarker for the consumption of these foods. Lariciresinol is also found in sesame seeds, Brassica vegetables, in the bark and wood of white fir (Abies alba).
(+)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (+)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-lariciresinol can be found in a number of food items such as pili nut, lemon balm, root vegetables, and parsley, which makes (+)-lariciresinol a potential biomarker for the consumption of these food products.

同义名列表

6 个代谢物同义名

4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol; tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanmethanol; Lariciresinol, (+)-; (+)-lariciresinol; larici-resinol; Lariciresinol



数据库引用编号

18 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)

20 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

  • Morteza Yousefzadi, Mozafar Sharifi, Mehrdad Behmanesh, Alireza Ghasempour, Elisabeth Moyano, Javier Palazon. The effect of light on gene expression and podophyllotoxin biosynthesis in Linum album cell culture. Plant physiology and biochemistry : PPB. 2012 Jul; 56(?):41-6. doi: 10.1016/j.plaphy.2012.04.010. [PMID: 22579943]
  • Liang Chen, Lei Wang, Qingwen Zhang, Shengyuan Zhang, Wencai Ye. [Non-alkaloid chemical constituents from Coptis chinensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 May; 37(9):1241-4. doi: 10.4268/cjcmm20120915. [PMID: 22803368]
  • Sedigheh Esmaeilzadeh Bahabadi, Mozafar Sharifi, Mehrdad Behmanesh, Naser Safaie, Jun Murata, Ryoichi Araki, Tohru Yamagaki, Honoo Satake. Time-course changes in fungal elicitor-induced lignan synthesis and expression of the relevant genes in cell cultures of Linum album. Journal of plant physiology. 2012 Mar; 169(5):487-91. doi: 10.1016/j.jplph.2011.12.006. [PMID: 22218086]
  • Sullivan Renouard, Cyrielle Corbin, Tatiana Lopez, Josiane Montguillon, Laurent Gutierrez, Frédéric Lamblin, Eric Lainé, Christophe Hano. Abscisic acid regulates pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol accumulation in developing flax (Linum usitatissimum L.) seeds. Planta. 2012 Jan; 235(1):85-98. doi: 10.1007/s00425-011-1492-y. [PMID: 21837520]
  • Hisashi Nishiwaki, Mitsuko Kumamoto, Yoshihiro Shuto, Satoshi Yamauchi. Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities. Journal of agricultural and food chemistry. 2011 Dec; 59(24):13089-95. doi: 10.1021/jf203222w. [PMID: 22066904]
  • Kristina Duwensee, Stefan Schwaiger, Ivan Tancevski, Kathrin Eller, Miranda van Eck, Patrick Markt, Tobias Linder, Ursula Stanzl, Andreas Ritsch, Josef R Patsch, Daniela Schuster, Hermann Stuppner, David Bernhard, Philipp Eller. Leoligin, the major lignan from Edelweiss, activates cholesteryl ester transfer protein. Atherosclerosis. 2011 Nov; 219(1):109-15. doi: 10.1016/j.atherosclerosis.2011.07.023. [PMID: 21820657]
  • Bomi Hwang, Jaeyong Cho, In-sok Hwang, Hong-Guang Jin, Eun-Rhan Woo, Dong Gun Lee. Antifungal activity of lariciresinol derived from Sambucus williamsii and their membrane-active mechanisms in Candida albicans. Biochemical and biophysical research communications. 2011 Jul; 410(3):489-93. doi: 10.1016/j.bbrc.2011.06.004. [PMID: 21679690]
  • Anne-Marie Nam, Mathieu Paoli, Vincent Castola, Joseph Casanova, Ange Bighelli. Identification and quantitative determination of lignans in Cedrus atlantica resins using 13C NMR spectroscopy. Natural product communications. 2011 Mar; 6(3):379-85. doi: . [PMID: 21485279]
  • A R Gohari, S Saeidnia, M Bayati-Moghadam, Gh Amin. Lignans and neolignans from Stelleropsis antoninae. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2011; 19(1):74-9. doi: . [PMID: 22615643]
  • 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]
  • 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]
  • Kris Morreel, Oana Dima, Hoon Kim, Fachuang Lu, Claudiu Niculaes, Ruben Vanholme, Rebecca Dauwe, Geert Goeminne, Dirk Inzé, Eric Messens, John Ralph, Wout Boerjan. Mass spectrometry-based sequencing of lignin oligomers. Plant physiology. 2010 Aug; 153(4):1464-78. doi: 10.1104/pp.110.156489. [PMID: 20554692]
  • Qing-Huang Wang, Ke Peng, Le-He Tan, Hao-Fu Dai. Aquilarin A, a new benzenoid derivative from the fresh stem of Aquilaria sinensis. Molecules (Basel, Switzerland). 2010 Jun; 15(6):4011-6. doi: 10.3390/molecules15064011. [PMID: 20657422]
  • 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]
  • Tarja Nurmi, Jaakko Mursu, José L Peñalvo, Henrik E Poulsen, Sari Voutilainen. Dietary intake and urinary excretion of lignans in Finnish men. The British journal of nutrition. 2010 Mar; 103(5):677-85. doi: 10.1017/s0007114509992261. [PMID: 19811696]
  • Niina M Saarinen, Juhani Tuominen, Liisa Pylkkänen, Risto Santti. Assessment of information to substantiate a health claim on the prevention of prostate cancer by lignans. Nutrients. 2010 02; 2(2):99-115. doi: 10.3390/nu2020099. [PMID: 22254011]
  • N Pellegrini, S Valtueña, D Ardigò, F Brighenti, L Franzini, D Del Rio, F Scazzina, P M Piatti, I Zavaroni. Intake of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, and lariciresinol in relation to vascular inflammation and endothelial dysfunction in middle age-elderly men and post-menopausal women living in Northern Italy. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2010 Jan; 20(1):64-71. doi: 10.1016/j.numecd.2009.02.003. [PMID: 19361969]
  • Izabela Redzynia, Natasza E Ziółkowska, Wiesław R Majzner, Stefan Willför, Rainer Sjöholm, Patrik Eklund, Grzegorz D Bujacz. Structural investigation of biologically active phenolic compounds isolated from European tree species. Molecules (Basel, Switzerland). 2009 Oct; 14(10):4147-58. doi: 10.3390/molecules14104147. [PMID: 19924053]
  • Helle N Laerke, Marianne A Mortensen, Mette S Hedemann, Knud E Bach Knudsen, José L Penalvo, Herman Adlercreutz. Quantitative aspects of the metabolism of lignans in pigs fed fibre-enriched rye and wheat bread. The British journal of nutrition. 2009 Oct; 102(7):985-94. doi: 10.1017/s0007114509344098. [PMID: 19393112]
  • Qin-Long Zhu, Tie-Ying Guo, Shun-Zhao Sui, Guang-De Liu, Xing-Hua Lei, Li-Li Luo, Ming-Yang Li. Molecular cloning and characterization of a novel isoflavone reductase-like gene (FcIRL) from high flavonoids-producing callus of Fagopyrum cymosum. Yao xue xue bao = Acta pharmaceutica Sinica. 2009 Jul; 44(7):809-19. doi: . [PMID: 19806925]
  • L S Velentzis, M M Cantwell, C Cardwell, M R Keshtgar, A J Leathem, J V Woodside. Lignans and breast cancer risk in pre- and post-menopausal women: meta-analyses of observational studies. British journal of cancer. 2009 May; 100(9):1492-8. doi: 10.1038/sj.bjc.6605003. [PMID: 19337250]
  • Cui-Ying Ma, Sebisubi Fred Musoke, Ghee Teng Tan, Kongmany Sydara, Somsanith Bouamanivong, Bounhoong Southavong, D Doel Soejarto, Harry H S Fong, Hong-Jie Zhang. Study of antimalarial activity of chemical constituents from Diospyros quaesita. Chemistry & biodiversity. 2008 Nov; 5(11):2442-8. doi: 10.1002/cbdv.200890209. [PMID: 19035573]
  • Tomoyuki Nakatsubo, Masaharu Mizutani, Shiro Suzuki, Takefumi Hattori, Toshiaki Umezawa. Characterization of Arabidopsis thaliana pinoresinol reductase, a new type of enzyme involved in lignan biosynthesis. The Journal of biological chemistry. 2008 Jun; 283(23):15550-7. doi: 10.1074/jbc.m801131200. [PMID: 18347017]
  • Ahmad Saufi, Cosima B I von Heimendahl, A Wilhelm Alfermann, Elisabeth Fuss. Stereochemistry of lignans in Phaleria macrocarpa (Scheff.) Boerl. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Jan; 63(1-2):13-6. doi: 10.1515/znc-2008-1-203. [PMID: 18386481]
  • Heather Ward, Gaelle Chapelais, Gunter G C Kuhnle, Robert Luben, Kay-Tee Khaw, Sheila Bingham. Breast cancer risk in relation to urinary and serum biomarkers of phytoestrogen exposure in the European Prospective into Cancer-Norfolk cohort study. Breast cancer research : BCR. 2008; 10(2):R32. doi: 10.1186/bcr1995. [PMID: 18419813]
  • Allan K Ayella, Harold N Trick, Weiqun Wang. Enhancing lignan biosynthesis by over-expressing pinoresinol lariciresinol reductase in transgenic wheat. Molecular nutrition & food research. 2007 Dec; 51(12):1518-26. doi: 10.1002/mnfr.200700233. [PMID: 18030664]
  • Liu-Yi Tang, Ming-Hua Luo, Ning Jiang, Hong-Hui Lin. [Studies on chemical constituents of Sambucus adnata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 May; 30(5):549-51. doi: ". [PMID: 17727059]
  • Li Zuo, Jian-bei Li, Jing Xu, Jing-zhi Yang, Dong-ming Zhang, Yong-ling Tong. [Studies on chemical constituents in root of Isatis indigotica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Apr; 32(8):688-91. doi: . [PMID: 17608220]
  • Marina S Touillaud, Anne C M Thiébaut, Agnès Fournier, Maryvonne Niravong, Marie-Christine Boutron-Ruault, Françoise Clavel-Chapelon. Dietary lignan intake and postmenopausal breast cancer risk by estrogen and progesterone receptor status. Journal of the National Cancer Institute. 2007 Mar; 99(6):475-86. doi: 10.1093/jnci/djk096. [PMID: 17374837]
  • Ji-feng Liu, Xue-mei Zhang, Duo-qing Xue, Zhi-yong Jiang, Qiong Gu, Ji-jun Chen. [Studies on chemical constituents from leaves of Isatis indigotica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Dec; 31(23):1961-5. doi: . [PMID: 17348190]
  • C Hano, I Martin, O Fliniaux, B Legrand, L Gutierrez, R R J Arroo, F Mesnard, F Lamblin, E Lainé. Pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol diglucoside accumulation in developing flax (Linum usitatissimum) seeds. Planta. 2006 Nov; 224(6):1291-301. doi: 10.1007/s00425-006-0308-y. [PMID: 16794840]
  • Francesca Cutillo, Marina DellaGreca, Melania Gionti, Lucio Previtera, Armando Zarrelli. Phenols and lignans from Chenopodium album. Phytochemical analysis : PCA. 2006 Sep; 17(5):344-9. doi: 10.1002/pca.924. [PMID: 17019936]
  • Heidi Schwartz, Gerhard Sontag. Determination of secoisolariciresinol, lariciresinol and isolariciresinol in plant foods by high performance liquid chromatography coupled with coulometric electrode array detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jul; 838(2):78-85. doi: 10.1016/j.jchromb.2006.03.058. [PMID: 16750660]
  • Johanna W Lampe, Charlotte Atkinson, Meredith A J Hullar. Assessing exposure to lignans and their metabolites in humans. Journal of AOAC International. 2006 Jul; 89(4):1174-81. doi: . [PMID: 16915861]
  • Annika I Smeds, Kristo Hakala, Teija T Hurmerinta, Liisi Kortela, Niina M Saarinen, Sari I Mäkelä. Determination of plant and enterolignans in human serum by high-performance liquid chromatography with tandem mass spectrometric detection. Journal of pharmaceutical and biomedical analysis. 2006 Jun; 41(3):898-905. doi: 10.1016/j.jpba.2005.12.036. [PMID: 16460900]
  • Thomas Clavel, Daniela Borrmann, Annett Braune, Joël Doré, Michael Blaut. Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans. Anaerobe. 2006 Jun; 12(3):140-7. doi: 10.1016/j.anaerobe.2005.11.002. [PMID: 16765860]
  • Carlos L Céspedes, J Guillermo Avila, Ana M García, José Becerra, Cristian Flores, Pedro Aqueveque, Magalis Bittner, Maritza Hoeneisen, Miguel Martinez, Mario Silva. Antifungal and antibacterial activities of Araucaria araucana (Mol.) K. Koch heartwood lignans. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2006 Jan; 61(1-2):35-43. doi: 10.1515/znc-2006-1-207. [PMID: 16610214]
  • Srinivas V Pullela, Satoshi Takamatsu, Shabana I Khan, Ikhlas A Khan. Isolation of lignans and biological activity studies of Ephedra viridis. Planta medica. 2005 Aug; 71(8):789-91. doi: 10.1055/s-2005-871254. [PMID: 16142651]
  • Ivon E J Milder, Ilja C W Arts, Betty van de Putte, Dini P Venema, Peter C H Hollman. Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. The British journal of nutrition. 2005 Mar; 93(3):393-402. doi: 10.1079/bjn20051371. [PMID: 15877880]
  • Annika I Smeds, Niina M Saarinen, Patrik C Eklund, Rainer E Sjöholm, Sari I Mäkelä. New lignan metabolites in rat urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Feb; 816(1-2):87-97. doi: 10.1016/j.jchromb.2004.11.017. [PMID: 15664338]
  • Bao-hua Yang, Wei-dong Zhang, Zheng-bing Gu, Ting-zhao Li, Chuang Zhang, Yun Zhou. [Studies on chemical constituents in bark of Larix olgensis var. koreana]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Feb; 30(4):270-2. doi: . [PMID: 15724403]
  • Annika I Smeds, Niina M Saarinen, Teija T Hurmerinta, Pauliina E Penttinen, Rainer E Sjöholm, Sari I Mäkelä. Urinary excretion of lignans after administration of isolated plant lignans to rats: the effect of single dose and ten-day exposures. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Dec; 813(1-2):303-12. doi: 10.1016/j.jchromb.2004.10.033. [PMID: 15556546]
  • Shuichi Yamamoto, Angelika Otto, Bernd R T Simoneit. Lignans in resin of Araucaria angustifolia by gas chromatography/mass spectrometry. Journal of mass spectrometry : JMS. 2004 Nov; 39(11):1337-47. doi: 10.1002/jms.726. [PMID: 15532064]
  • Francisco A Macías, Adriana López, Rosa M Varela, Ascensión Torres, José M G Molinillo. Bioactive lignans from a cultivar of Helianthus annuus. Journal of agricultural and food chemistry. 2004 Oct; 52(21):6443-7. doi: 10.1021/jf048945d. [PMID: 15479004]
  • Ivon E J Milder, Ilja C W Arts, Dini P Venema, Johan J P Lasaroms, Kristina Wähälä, Peter C H Hollman. Optimization of a liquid chromatography-tandem mass spectrometry method for quantification of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in foods. Journal of agricultural and food chemistry. 2004 Jul; 52(15):4643-51. doi: 10.1021/jf0497556. [PMID: 15264894]
  • José L Peñalvo, Satu-M Heinonen, Tarja Nurmi, Takeshi Deyama, Sansey Nishibe, Herman Adlercreutz. Plant lignans in soy-based health supplements. Journal of agricultural and food chemistry. 2004 Jun; 52(13):4133-8. doi: 10.1021/jf0497509. [PMID: 15212459]
  • Yanjun Zhang, Robert H Cichewicz, Muraleedharan G Nair. Lipid peroxidation inhibitory compounds from daylily (Hemerocallis fulva) leaves. Life sciences. 2004 Jun; 75(6):753-63. doi: 10.1016/j.lfs.2004.03.002. [PMID: 15172183]
  • Ilhan Gurbuz, Nurgun Erdemoglu, Erdem Yesilada, Bilge Sener. Anti-ulcerogenic lignans from Taxus baccata L. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Mar; 59(3-4):233-6. doi: 10.1515/znc-2004-3-420. [PMID: 15241933]
  • Tarja Nurmi, Sari Voutilainen, Kristiina Nyyssönen, Herman Adlercreutz, Jukka T Salonen. Liquid chromatography method for plant and mammalian lignans in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Dec; 798(1):101-10. doi: 10.1016/j.jchromb.2003.09.018. [PMID: 14630364]
  • Ting-zhao Li, Wei-dong Zhang, Zheng-bing Gu, Wen-yong Liu, Jing Zhou, Wan-sheng Chen. [Studies on the lignans from Patrinia scabra]. Yao xue xue bao = Acta pharmaceutica Sinica. 2003 Jul; 38(7):520-2. doi: ". [PMID: 14515797]
  • Bin Li, Wang-sheng Chen, Han-ming Zhang, Wei-dong Zhang, Gen-jin Yang, Chuan-zhuo Qiao. [A new alkaloids isolated from tetraploidy banlangen]. Yao xue xue bao = Acta pharmaceutica Sinica. 2003 Jun; 38(6):430-2. doi: ". [PMID: 14513802]
  • Li-Hua Xie, Teruaki Akao, Kenjiro Hamasaki, Takeshi Deyama, Masao Hattori. Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol. Chemical & pharmaceutical bulletin. 2003 May; 51(5):508-15. doi: 10.1248/cpb.51.508. [PMID: 12736449]
  • Tina Sicilia, Heike B Niemeyer, Doris M Honig, Manfred Metzler. Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. Journal of agricultural and food chemistry. 2003 Feb; 51(5):1181-8. doi: 10.1021/jf0207979. [PMID: 12590454]
  • Zhengbing Gu, Xinjian Chen, Genjin Yang, Tingzhao Li, Wenyong Liu, Weidong Zhang. [Studies on immunocompetent constituents of Patrinia scabra Bunge]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2002 Mar; 25(3):178-80. doi: ". [PMID: 12583160]
  • S Heinonen, T Nurmi, K Liukkonen, K Poutanen, K Wähälä, T Deyama, S Nishibe, H Adlercreutz. In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. Journal of agricultural and food chemistry. 2001 Jul; 49(7):3178-86. doi: 10.1021/jf010038a. [PMID: 11453749]
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