Secoisolariciresinol_diglucoside (BioDeep_00000230567)

 

Secondary id: BioDeep_00000019014, BioDeep_00000409319

PANOMIX_OTCML-2023


代谢物信息卡片


(2R,3R,4S,5S,6R)-2-[(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

化学式: C32H46O16 (686.2785716)
中文名称: 开环异落叶松树脂酚二葡萄糖苷, (R,R)-亚麻木酚素, 亚麻木酚素
谱图信息: 最多检出来源 Viridiplantae(plant) 80.63%

分子结构信息

SMILES: COC(C=C1C[C@@H](CO[C@@H]2O[C@@H]([C@H]([C@@H]([C@H]2O)O)O)CO)[C@H](CO[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO)CC4=CC(OC)=C(C=C4)O)=C(C=C1)O
InChI: InChI=1S/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3/t17-,18-,23+,24+,25+,26+,27-,28-,29+,30+,31+,32+/m0/s1

描述信息

Secoisolariciresinol diglucoside is a natural product found in Linum usitatissimum with data available.
See also: Flax seed (part of); Sesame Seed (part of); Sunflower Seed (part of) ... View More ...
(R,R)-Secoisolariciresinol diglucoside ((R,R)-SDG) is the minor isomer of Secoisolariciresinol diglucoside in flaxseed. (R,R)-Secoisolariciresinol diglucoside ((R,R)-SDG) possesses antioxidant and free radical scavenging activities and DNA-radioprotective properties. (R,R)-Secoisolariciresinol diglucoside ((R,R)-SDG) inhibits myeloperoxidase (MPO) activity by suppressing both the peroxidase and chlorination cyclesin inflammatory cells[1][2][3].
Secoisolariciresinol diglucoside ((S,S)-SDG), the main lignan in wholegrain flaxseed, is known for its beneficial effects including anti-inflammatory, antioxidant, anti-mutagenic, anti-microbial, anti-obesity, hypolipidemic, and neuroprotective effects[1][2].

同义名列表

22 个代谢物同义名

(2R,3R,4S,5S,6R)-2-[(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol; (2R,2R,3S,3S,4S,4S,5R,5R,6R,6R)-6,6-(((2R,3R)-2,3-Bis(4-hydroxy-3-methoxybenzyl)butane-1,4-diyl)bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol); .BETA.-D-GLUCOPYRANOSIDE, (2R,3R)-2,3-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-1,4-BUTANEDIYL BIS-; (2R,3R)-2,3-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-1,4-BUTANEDIYL BIS-.BETA.-D-GLUCOPYRANOSIDE; beta-D-GLUCOPYRANOSIDE, (2R,3R)-2,3-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-1,4-BUTANEDIYL BIS-; (2R,3R)-2,3-Bis((4-hydroxy-3-methoxyphenyl)methyl)-1,4-butanediyl bis-beta-D-glucopyranoside; 2,3-bis(3-methoxy-4-hydroxybenzyl)butane-1,4-diol 1,4-diglucoside; (R,R)-Secoisolariciresinol diglucoside; Secoisolarisiresinol diglucoside; Secoisolariciresinol-Diglucoside; Secoisolariciresinol diglycoside; Secoisolariciresinol diglucoside; SecoisolariciresinolDiglucoside; FlaxseedLigans(SDG); Bmhb-diglc; (R,R)-SDG; SDG; Secoisolariciresinol; Seco-isolariciresinol diglucoside; (R,R)-LGM2605; (S,S)-SDG; (S,S)-LGM2605



数据库引用编号

10 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)

2 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]
  • Markéta Jarošová, František Lorenc, Jan Bedrníček, Eva Petrášková, Marie Bjelková, Veronika Bártová, Eva Jarošová, Zbyněk Zdráhal, Jan Kyselka, Pavel Smetana, Jaromír Kadlec, Adéla Stupková, Jan Bárta. Comparison of Yield Characteristics, Chemical Composition, Lignans Content and Antioxidant Potential of Experimentally Grown Six Linseed (Linum usitatissimum L.) Cultivars. Plant foods for human nutrition (Dordrecht, Netherlands). 2024 Jan; ?(?):. doi: 10.1007/s11130-023-01136-9. [PMID: 38236453]
  • Yingxue Hu, Timothy J Tse, Youn Young Shim, Sarah K Purdy, Young Jun Kim, Venkatesh Meda, Martin J T Reaney. A review of flaxseed lignan and the extraction and refinement of secoisolariciresinol diglucoside. Critical reviews in food science and nutrition. 2024; 64(15):5057-5072. doi: 10.1080/10408398.2022.2148627. [PMID: 36448088]
  • Fatemeh Hajibabaie, Navid Abedpoor, Kamran Safavi, Farzaneh Taghian. Natural remedies medicine derived from flaxseed (secoisolariciresinol diglucoside, lignans, and α-linolenic acid) improve network targeting efficiency of diabetic heart conditions based on computational chemistry techniques and pharmacophore modeling. Journal of food biochemistry. 2022 12; 46(12):e14480. doi: 10.1111/jfbc.14480. [PMID: 36239429]
  • Timothy J Tse, Yajia Guo, Youn Young Shim, Sarah K Purdy, Ji Hye Kim, Jae Youl Cho, Jane Alcorn, Martin J T Reaney. Availability of bioactive flax lignan from foods and supplements. Critical reviews in food science and nutrition. 2022 May; ?(?):1-16. doi: 10.1080/10408398.2022.2072807. [PMID: 35532015]
  • Junlin Ge, Rili Hao, Xue Rong, Q Ping Dou, Xintong Tan, Guannan Li, Feng Li, Dapeng Li. Secoisolariciresinol diglucoside mitigates benzo[a]pyrene-induced liver and kidney toxicity in mice via miR-101a/MKP-1-mediated p38 and ERK pathway. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Jan; 159(?):112733. doi: 10.1016/j.fct.2021.112733. [PMID: 34856318]
  • Amel Taibi, Michelle Ku, Zhen Lin, Giorgio Gargari, Alla Kubant, Dion Lepp, Krista A Power, Simone Guglielmetti, Lilian U Thompson, Elena M Comelli. Discriminatory and cooperative effects within the mouse gut microbiota in response to flaxseed and its oil and lignan components. The Journal of nutritional biochemistry. 2021 12; 98(?):108818. doi: 10.1016/j.jnutbio.2021.108818. [PMID: 34271098]
  • Yajia Guo, Xiaolei Yang, Timothy J Tse, Sarah K Purdy, Rana Mustafa, Jianheng Shen, Jane Alcorn, Martin J T Reaney. Hypocholesterolemic Efficacy of Secoisolariciresinol Diglucoside and Its Polymer in Rat. Journal of natural products. 2021 11; 84(11):2845-2850. doi: 10.1021/acs.jnatprod.1c00549. [PMID: 34699206]
  • 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]
  • Anuradha Dhingra, Rachel C Sharp, Taewan Kim, Anatoliy V Popov, Gui-Shuang Ying, Ralph A Pietrofesa, Kyewon Park, Melpo Christofidou-Solomidou, Kathleen Boesze-Battaglia. Assessment of a Small Molecule Synthetic Lignan in Enhancing Oxidative Balance and Decreasing Lipid Accumulation in Human Retinal Pigment Epithelia. International journal of molecular sciences. 2021 May; 22(11):. doi: 10.3390/ijms22115764. [PMID: 34071220]
  • 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]
  • Liping Wei, Caicai Zhao, Shan Dong, Shundi Yao, Bing Ji, Beita Zhao, Zhigang Liu, Xuebo Liu, Yutang Wang. Secoisolariciresinol diglucoside alleviates hepatic lipid metabolic misalignment involving the endoplasmic reticulum-mitochondrial axis. Food & function. 2020 May; 11(5):3952-3963. doi: 10.1039/d0fo00124d. [PMID: 32426795]
  • Shaoyang Zhang, Meili Cheng, Zhen Wang, Yuzhi Liu, Yuhua Ren, Shikuo Rong, Xue Wang. Secoisolariciresinol Diglucoside Exerts Anti-Inflammatory and Antiapoptotic Effects through Inhibiting the Akt/IκB/NF-κB Pathway on Human Umbilical Vein Endothelial Cells. Mediators of inflammation. 2020; 2020(?):3621261. doi: 10.1155/2020/3621261. [PMID: 32684834]
  • Zhen Wang, Tuo Chen, Chunrong Yang, Ting Bao, Xiaoli Yang, Fang He, Yanting Zhang, Lili Zhu, Hongbo Chen, Shikuo Rong, Shaoqi Yang. Secoisolariciresinol diglucoside suppresses Dextran sulfate sodium salt-induced colitis through inhibiting NLRP1 inflammasome. International immunopharmacology. 2020 Jan; 78(?):105931. doi: 10.1016/j.intimp.2019.105931. [PMID: 31812068]
  • 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]
  • Tareq Aqeel, Sunil Chikkalakshmipura Gurumallu, Saeed Mujahid Hashimi, Naif AlQurashi, Rajesh Javaraiah. Evaluation of protective efficacy of flaxseed lignan-Secoisolariciresinol diglucoside against mercuric chloride-induced nephrotoxicity in rats. Molecular biology reports. 2019 Dec; 46(6):6171-6179. doi: 10.1007/s11033-019-05052-7. [PMID: 31493285]
  • Mihir Parikh, Pema Raj, J Alejandro Austria, Liping Yu, Bhavana Garg, Thomas Netticadan, Grant N Pierce. Dietary flaxseed protects against ventricular arrhythmias and left ventricular dilation after a myocardial infarction. The Journal of nutritional biochemistry. 2019 09; 71(?):63-71. doi: 10.1016/j.jnutbio.2019.06.004. [PMID: 31284167]
  • Mihir Parikh, Thane G Maddaford, J Alejandro Austria, Michel Aliani, Thomas Netticadan, Grant N Pierce. Dietary Flaxseed as a Strategy for Improving Human Health. Nutrients. 2019 May; 11(5):. doi: 10.3390/nu11051171. [PMID: 31130604]
  • 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]
  • Adnan Zahir, Waqar Ahmad, Muhammad Nadeem, Nathalie Giglioli-Guivarc'h, Christophe Hano, Bilal Haider Abbasi. In vitro cultures of Linum usitatissimum L.: Synergistic effects of mineral nutrients and photoperiod regimes on growth and biosynthesis of lignans and neolignans. Journal of photochemistry and photobiology. B, Biology. 2018 Oct; 187(?):141-150. doi: 10.1016/j.jphotobiol.2018.08.009. [PMID: 30145465]
  • 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]
  • Guiqiong Huang, Xiaofang Huang, Min Liu, Yue Hua, Bo Deng, Wen Jin, Wen Yan, Zhangbin Tan, Yifen Wu, Bin Liu, Yingchun Zhou. Secoisolariciresinol diglucoside prevents the oxidative stress-induced apoptosis of myocardial cells through activation of the JAK2/STAT3 signaling pathway. International journal of molecular medicine. 2018 Jun; 41(6):3570-3576. doi: 10.3892/ijmm.2018.3560. [PMID: 29568942]
  • JongWook Kang, Jinbong Park, Hye-Lin Kim, Yunu Jung, Dong-Hyun Youn, Seona Lim, Gahee Song, Hyewon Park, Jong Sik Jin, Hyun Jeong Kwak, Jae-Young Um. Secoisolariciresinol diglucoside inhibits adipogenesis through the AMPK pathway. European journal of pharmacology. 2018 Feb; 820(?):235-244. doi: 10.1016/j.ejphar.2017.12.038. [PMID: 29269018]
  • Manoj Shah, Bridget Eklund, Luiz Gustavo Conde Lima, Teresa Bergholz, Clifford Hall. Microbial and Chemical Shelf-Life of Vacuum Steam-Pasteurized Whole Flaxseed and Milled Flaxseed. Journal of food science. 2018 Feb; 83(2):300-308. doi: 10.1111/1750-3841.14050. [PMID: 29350755]
  • 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]
  • Stephanie Puukila, Rafael Oliveira Fernandes, Patrick Türck, Cristina Campos Carraro, Jéssica Hellen Poletto Bonetto, Bruna Gazzi de Lima-Seolin, Alex Sander da Rosa Araujo, Adriane Belló-Klein, Douglas Boreham, Neelam Khaper. Secoisolariciresinol diglucoside attenuates cardiac hypertrophy and oxidative stress in monocrotaline-induced right heart dysfunction. Molecular and cellular biochemistry. 2017 Aug; 432(1-2):33-39. doi: 10.1007/s11010-017-2995-z. [PMID: 28321539]
  • 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]
  • Youn Young Shim, Clara M Olivia, Jun Liu, Rineke Boonen, Jianheng Shen, Martin J T Reaney. Secoisolariciresinol Diglucoside and Cyanogenic Glycosides in Gluten-free Bread Fortified with Flaxseed Meal. Journal of agricultural and food chemistry. 2016 Dec; 64(50):9551-9558. doi: 10.1021/acs.jafc.6b03962. [PMID: 27998066]
  • Niyati R Shah, Bhoomika M Patel. Secoisolariciresinol diglucoside rich extract of L. usitatissimum prevents diabetic colon cancer through inhibition of CDK4. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2016 Oct; 83(?):733-739. doi: 10.1016/j.biopha.2016.07.041. [PMID: 27470575]
  • Om P Mishra, Anatoliy V Popov, Ralph A Pietrofesa, Melpo Christofidou-Solomidou. Gamma-irradiation produces active chlorine species (ACS) in physiological solutions: Secoisolariciresinol diglucoside (SDG) scavenges ACS - A novel mechanism of DNA radioprotection. Biochimica et biophysica acta. 2016 09; 1860(9):1884-97. doi: 10.1016/j.bbagen.2016.05.037. [PMID: 27261092]
  • 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]
  • Ralph A Pietrofesa, Anastasia Velalopoulou, Steven M Albelda, Melpo Christofidou-Solomidou. Asbestos Induces Oxidative Stress and Activation of Nrf2 Signaling in Murine Macrophages: Chemopreventive Role of the Synthetic Lignan Secoisolariciresinol Diglucoside (LGM2605). International journal of molecular sciences. 2016 Mar; 17(3):322. doi: 10.3390/ijms17030322. [PMID: 26938529]
  • Andrea L Edel, Amanda F Patenaude, Melanie N Richard, Elena Dibrov, J Alejandro Austria, Harold M Aukema, Grant N Pierce, Michel Aliani. The effect of flaxseed dose on circulating concentrations of alpha-linolenic acid and secoisolariciresinol diglucoside derived enterolignans in young, healthy adults. European journal of nutrition. 2016 Mar; 55(2):651-663. doi: 10.1007/s00394-015-0885-2. [PMID: 25808116]
  • Anastasia Velalopoulou, Sonia Tyagi, Ralph A Pietrofesa, Evguenia Arguiri, Melpo Christofidou-Solomidou. The Flaxseed-Derived Lignan Phenolic Secoisolariciresinol Diglucoside (SDG) Protects Non-Malignant Lung Cells from Radiation Damage. International journal of molecular sciences. 2015 Dec; 17(1):. doi: 10.3390/ijms17010007. [PMID: 26703588]
  • Zhi-Jian Tan, Chao-Yun Wang, Zi-Zhen Yang, Yong-Jian Yi, Hong-Ying Wang, Wan-Lai Zhou, Fen-Fang Li. Ionic Liquid-Based Ultrasonic-Assisted Extraction of Secoisolariciresinol Diglucoside from Flaxseed (Linum usitatissimum L.) with Further Purification by an Aqueous Two-Phase System. Molecules (Basel, Switzerland). 2015 Sep; 20(10):17929-43. doi: 10.3390/molecules201017929. [PMID: 26437389]
  • Muhammad Imran, Nazir Ahmad, Faqir Muhammad Anjum, Muhammad Kamran Khan, Zarina Mushtaq, Muhammad Nadeem, Shahzad Hussain. Potential protective properties of flax lignan secoisolariciresinol diglucoside. Nutrition journal. 2015 Jul; 14(?):71. doi: 10.1186/s12937-015-0059-3. [PMID: 26215288]
  • 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]
  • Hao Tian, Wan-Yi Li, Dan Xiao, Zhi-Min Li, Jian-Wen Wang. Negative-Pressure Cavitation Extraction of Secoisolariciresinol Diglycoside from Flaxseed Cakes. Molecules (Basel, Switzerland). 2015 Jun; 20(6):11076-89. doi: 10.3390/molecules200611076. [PMID: 26083040]
  • 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]
  • Rudy Simons, Navneet Sonawane, Marian Verbruggen, Jayesh Chaudhary. Efficacy and safety of a flaxseed hull extract in the symptomatic management of benign prostatic hyperplasia: a parallel, randomized, double-blind, placebo-controlled, pilot study. Journal of medicinal food. 2015 Feb; 18(2):233-40. doi: 10.1089/jmf.2013.3129. [PMID: 25546379]
  • Iman O Sherif. Secoisolariciresinol diglucoside in high-fat diet and streptozotocin-induced diabetic nephropathy in rats: a possible renoprotective effect. Journal of physiology and biochemistry. 2014 Dec; 70(4):961-9. doi: 10.1007/s13105-014-0364-x. [PMID: 25316298]
  • Anand A Zanwar, Mahabaleshwar V Hegde, Supada R Rojatkar, Kiran B Sonawane, P R Rajamohanan, Subhash L Bodhankar. Isolation, characterization and antihyperlipidemic activity of secoisolariciresinol diglucoside in poloxamer-407-induced experimental hyperlipidemia. Pharmaceutical biology. 2014 Sep; 52(9):1094-103. doi: 10.3109/13880209.2013.877492. [PMID: 24649910]
  • 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]
  • 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]
  • Ralph Pietrofesa, Jason Turowski, Sonia Tyagi, Floyd Dukes, Evguenia Arguiri, Theresa M Busch, Shannon M Gallagher-Colombo, Charalambos C Solomides, Keith A Cengel, Melpo Christofidou-Solomidou. Radiation mitigating properties of the lignan component in flaxseed. BMC cancer. 2013 Apr; 13(?):179. doi: 10.1186/1471-2407-13-179. [PMID: 23557217]
  • Sadiq S Moree, G B Kavishankar, J Rajesha. Antidiabetic effect of secoisolariciresinol diglucoside in streptozotocin-induced diabetic rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Feb; 20(3-4):237-45. doi: 10.1016/j.phymed.2012.11.011. [PMID: 23271000]
  • Sadiq S Moree, J Rajesha. Investigation of in vitro and in vivo antioxidant potential of secoisolariciresinol diglucoside. Molecular and cellular biochemistry. 2013 Jan; 373(1-2):179-87. doi: 10.1007/s11010-012-1487-4. [PMID: 23108790]
  • Jingjing Fang, Aina Ramsay, Christian Paetz, Evangelos C Tatsis, Sullivan Renouard, Christophe Hano, Eric Grand, Ophélie Fliniaux, Albrecht Roscher, Francois Mesnard, Bernd Schneider. Concentration kinetics of secoisolariciresinol diglucoside and its biosynthetic precursor coniferin in developing flaxseed. Phytochemical analysis : PCA. 2013 Jan; 24(1):41-6. doi: 10.1002/pca.2377. [PMID: 22689568]
  • M-X Li, H-Y Zhu, D-H Yang, X-Q Ma, C-Z Wang, S-Q Cai, G-R Liu, B-S Ku, S-L Liu. Production of secoisolariciresinol from defatted flaxseed by bacterial biotransformation. Journal of applied microbiology. 2012 Dec; 113(6):1352-61. doi: 10.1111/j.1365-2672.2012.05436.x. [PMID: 22924993]
  • 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]
  • Márcia Constantino Colli, Adelar Bracht, Andréa Assunção Soares, Andréa Luisa de Oliveira, Cinthia Gandolfi Bôer, Cristina Giatti Marques de Souza, Rosane Marina Peralta. Evaluation of the efficacy of flaxseed meal and flaxseed extract in reducing menopausal symptoms. Journal of medicinal food. 2012 Sep; 15(9):840-5. doi: 10.1089/jmf.2011.0228. [PMID: 22925074]
  • Jae B Park, Manuel T Velasquez. Potential effects of lignan-enriched flaxseed powder on bodyweight, visceral fat, lipid profile, and blood pressure in rats. Fitoterapia. 2012 Jul; 83(5):941-6. doi: 10.1016/j.fitote.2012.04.010. [PMID: 22542959]
  • 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]
  • Lucia Roncaglia, Alberto Amaretti, Stefano Raimondi, Alan Leonardi, Maddalena Rossi. Role of bifidobacteria in the activation of the lignan secoisolariciresinol diglucoside. Applied microbiology and biotechnology. 2011 Oct; 92(1):159-68. doi: 10.1007/s00253-011-3338-8. [PMID: 21614502]
  • A M Anishchenko, N V Vasil'eva, T M Plotnikova, O I Aliev. [Effects of flaxseed extract on rheological properties of blood in experimental ovariectomy]. Eksperimental'naia i klinicheskaia farmakologiia. 2011; 74(7):19-21. doi: NULL. [PMID: 21894763]
  • Jennifer L Adolphe, Susan J Whiting, Bernhard H J Juurlink, Lilian U Thorpe, Jane Alcorn. Health effects with consumption of the flax lignan secoisolariciresinol diglucoside. The British journal of nutrition. 2010 Apr; 103(7):929-38. doi: 10.1017/s0007114509992753. [PMID: 20003621]
  • Jianmin Chen, Jasdeep K Saggar, Paul Corey, Lilian U Thompson. Flaxseed and pure secoisolariciresinol diglucoside, but not flaxseed hull, reduce human breast tumor growth (MCF-7) in athymic mice. The Journal of nutrition. 2009 Nov; 139(11):2061-6. doi: 10.3945/jn.109.112508. [PMID: 19776177]
  • Jong-Sik Jin, Masao Hattori. Further studies on a human intestinal bacterium Ruminococcus sp. END-1 for transformation of plant lignans to mammalian lignans. Journal of agricultural and food chemistry. 2009 Aug; 57(16):7537-42. doi: 10.1021/jf900902p. [PMID: 19630415]
  • Hélène V Petit, Nathalie Gagnon, Priyadarshini S Mir, Rong Cao, Steve Cui. Milk concentration of the mammalian lignan enterolactone, milk production, milk fatty acid profile, and digestibility in dairy cows fed diets containing whole flaxseed or flaxseed meal. The Journal of dairy research. 2009 Aug; 76(3):257-64. doi: 10.1017/s0022029909003999. [PMID: 19250577]
  • M A Felmlee, G Woo, E Simko, E S Krol, A D Muir, J Alcorn. Effects of the flaxseed lignans secoisolariciresinol diglucoside and its aglycone on serum and hepatic lipids in hyperlipidaemic rats. The British journal of nutrition. 2009 Aug; 102(3):361-9. doi: 10.1017/s0007114508207488. [PMID: 19216812]
  • Farah S Hosseinian, Trust Beta. Patented techniques for the extraction and isolation of secoisolari-ciresinol diglucoside from flaxseed. Recent patents on food, nutrition & agriculture. 2009 Jan; 1(1):25-31. doi: 10.2174/2212798410901010025. [PMID: 20653523]
  • S Fukumitsu, K Aida, N Ueno, S Ozawa, Y Takahashi, M Kobori. Flaxseed lignan attenuates high-fat diet-induced fat accumulation and induces adiponectin expression in mice. The British journal of nutrition. 2008 Sep; 100(3):669-76. doi: 10.1017/s0007114508911570. [PMID: 18252024]
  • Collin W Galbreath, Eric J Scholljegerdes, Gregory P Lardy, Kenneth G Odde, Matthew E Wilson, Jerome W Schroeder, Kimberly A Vonnahme. Effect of feeding flax or linseed meal on progesterone clearance rate in ovariectomized ewes. Domestic animal endocrinology. 2008 Aug; 35(2):164-9. doi: 10.1016/j.domaniend.2008.05.002. [PMID: 18555637]
  • Ellen Eeckhaut, Karin Struijs, Sam Possemiers, Jean-Paul Vincken, Denis De Keukeleire, Willy Verstraete. Metabolism of the lignan macromolecule into enterolignans in the gastrointestinal lumen as determined in the simulator of the human intestinal microbial ecosystem. Journal of agricultural and food chemistry. 2008 Jun; 56(12):4806-12. doi: 10.1021/jf800101s. [PMID: 18494490]
  • Wei Zhang, Xiaobing Wang, Yi Liu, Haimei Tian, Brent Flickinger, Mark W Empie, Sam Z Sun. Effects of dietary flaxseed lignan extract on symptoms of benign prostatic hyperplasia. Journal of medicinal food. 2008 Jun; 11(2):207-14. doi: 10.1089/jmf.2007.602. [PMID: 18358071]
  • Wei Zhang, Xiaobing Wang, Yi Liu, Haimei Tian, Brent Flickinger, Mark W Empie, Sam Z Sun. Dietary flaxseed lignan extract lowers plasma cholesterol and glucose concentrations in hypercholesterolaemic subjects. The British journal of nutrition. 2008 Jun; 99(6):1301-9. doi: 10.1017/s0007114507871649. [PMID: 18053310]
  • Kailash Prasad. Regression of hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed. Atherosclerosis. 2008 Mar; 197(1):34-42. doi: 10.1016/j.atherosclerosis.2007.07.043. [PMID: 17904562]
  • Suresh Varma Penumathsa, Srikanth Koneru, Lijun Zhan, Saji John, Venogopal P Menon, Kailash Prasad, Nilanjana Maulik. Secoisolariciresinol diglucoside induces neovascularization-mediated cardioprotection against ischemia-reperfusion injury in hypercholesterolemic myocardium. Journal of molecular and cellular cardiology. 2008 Jan; 44(1):170-9. doi: 10.1016/j.yjmcc.2007.09.014. [PMID: 18001768]
  • Chun Hu, Yvonne V Yuan, David D Kitts. Antioxidant activities of the flaxseed lignan secoisolariciresinol diglucoside, its aglycone secoisolariciresinol and the mammalian lignans enterodiol and enterolactone in vitro. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2007 Nov; 45(11):2219-27. doi: 10.1016/j.fct.2007.05.017. [PMID: 17624649]
  • Jong-Sik Jin, Yu-Feng Zhao, Norio Nakamura, Teruaki Akao, Nobuko Kakiuchi, Byung-Sun Min, Masao Hattori. Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria. Biological & pharmaceutical bulletin. 2007 Nov; 30(11):2113-9. doi: 10.1248/bpb.30.2113. [PMID: 17978485]
  • Kailash Prasad, Paul Lee. Suppression of hypercholesterolemic atherosclerosis by pentoxifylline and its mechanism. Atherosclerosis. 2007 Jun; 192(2):313-22. doi: 10.1016/j.atherosclerosis.2006.07.034. [PMID: 16963055]
  • H A Weiler, H Kovacs, E Nitschmann, N Bankovic-Calic, H Aukema, M Ogborn. Feeding flaxseed oil but not secoisolariciresinol diglucoside results in higher bone mass in healthy rats and rats with kidney disease. Prostaglandins, leukotrienes, and essential fatty acids. 2007 May; 76(5):269-75. doi: 10.1016/j.plefa.2007.02.001. [PMID: 17403603]
  • Farah S Hosseinian, Alister D Muir, Neil D Westcott, Ed S Krol. AAPH-mediated antioxidant reactions of secoisolariciresinol and SDG. Organic & biomolecular chemistry. 2007 Feb; 5(4):644-54. doi: 10.1039/b617426d. [PMID: 17285173]
  • Suresh Varma Penumathsa, Srikanth Koneru, Mahesh Thirunavukkarasu, Lijun Zhan, Kailash Prasad, Nilanjana Maulik. Secoisolariciresinol diglucoside: relevance to angiogenesis and cardioprotection against ischemia-reperfusion injury. The Journal of pharmacology and experimental therapeutics. 2007 Feb; 320(2):951-9. doi: 10.1124/jpet.106.114165. [PMID: 17132814]
  • Thomas Clavel, Ramona Lippman, Françoise Gavini, Joël Doré, Michael Blaut. Clostridium saccharogumia sp. nov. and Lactonifactor longoviformis gen. nov., sp. nov., two novel human faecal bacteria involved in the conversion of the dietary phytoestrogen secoisolariciresinol diglucoside. Systematic and applied microbiology. 2007 Jan; 30(1):16-26. doi: 10.1016/j.syapm.2006.02.003. [PMID: 17196483]
  • 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]
  • U Knust, B Spiegelhalder, T Strowitzki, R W Owen. Contribution of linseed intake to urine and serum enterolignan levels in German females: a randomised controlled intervention trial. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2006 Jul; 44(7):1057-64. doi: 10.1016/j.fct.2005.12.009. [PMID: 16494982]
  • 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]
  • Zhen Liu, Niina M Saarinen, Lilian U Thompson. Sesamin is one of the major precursors of mammalian lignans in sesame seed (Sesamum indicum) as observed in vitro and in rats. The Journal of nutrition. 2006 Apr; 136(4):906-12. doi: 10.1093/jn/136.4.906. [PMID: 16549449]
  • Jesper Hallund, Gitte Ravn-Haren, Susanne Bügel, Tine Tholstrup, Inge Tetens. A lignan complex isolated from flaxseed does not affect plasma lipid concentrations or antioxidant capacity in healthy postmenopausal women. The Journal of nutrition. 2006 Jan; 136(1):112-6. doi: 10.1093/jn/136.1.112. [PMID: 16365068]
  • Thomas Clavel, Gemma Henderson, Carl-Alfred Alpert, Catherine Philippe, Lionel Rigottier-Gois, Joël Doré, Michael Blaut. Intestinal bacterial communities that produce active estrogen-like compounds enterodiol and enterolactone in humans. Applied and environmental microbiology. 2005 Oct; 71(10):6077-85. doi: 10.1128/aem.71.10.6077-6085.2005. [PMID: 16204524]
  • Anneleen Kuijsten, Ilja C W Arts, Tom B Vree, Peter C H Hollman. Pharmacokinetics of enterolignans in healthy men and women consuming a single dose of secoisolariciresinol diglucoside. The Journal of nutrition. 2005 Apr; 135(4):795-801. doi: 10.1093/jn/135.4.795. [PMID: 15795437]
  • Jan Frank, Christina Eliasson, Diane Leroy-Nivard, Alicja Budek, Torbjörn Lundh, Bengt Vessby, Per Aman, Afaf Kamal-Eldin. Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats. The British journal of nutrition. 2004 Jul; 92(1):169-76. doi: 10.1079/bjn20041154. [PMID: 15231000]
  • Susan J Hemmings, Neil Westcott, Alister Muir, Dominika Czechowicz. The effects of dietary flaxseed on the Fischer 344 rat: II. Liver gamma-glutamyltranspeptidase activity. Cell biochemistry and function. 2004 Jul; 22(4):225-31. doi: 10.1002/cbf.1092. [PMID: 15248182]
  • Jianmin Chen, Kah Poh Tan, Wendy E Ward, Lilian U Thompson. Exposure to flaxseed or its purified lignan during suckling inhibits chemically induced rat mammary tumorigenesis. Experimental biology and medicine (Maywood, N.J.). 2003 Sep; 228(8):951-8. doi: 10.1177/153537020322800811. [PMID: 12968067]
  • K Prasad. Secoisolariciresinol diglucoside from flaxseed delays the development of type 2 diabetes in Zucker rat. The Journal of laboratory and clinical medicine. 2001 Jul; 138(1):32-9. doi: 10.1067/mlc.2001.115717. [PMID: 11433226]
  • S E Rickard, Y V Yuan, L U Thompson. Plasma insulin-like growth factor I levels in rats are reduced by dietary supplementation of flaxseed or its lignan secoisolariciresinol diglycoside. Cancer letters. 2000 Dec; 161(1):47-55. doi: 10.1016/s0304-3835(00)00592-9. [PMID: 11078912]
  • L Q Wang, M R Meselhy, Y Li, G W Qin, M Hattori. Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone. Chemical & pharmaceutical bulletin. 2000 Nov; 48(11):1606-10. doi: 10.1248/cpb.48.1606. [PMID: 11086885]
  • S E Rickard, L U Thompson. Urinary composition and postprandial blood changes in H-secoisolariciresinol diglycoside (SDG) metabolites in rats do not differ between acute and chronic SDG treatments. The Journal of nutrition. 2000 Sep; 130(9):2299-305. doi: 10.1093/jn/130.9.2299. [PMID: 10958827]
  • K Prasad. Oxidative stress as a mechanism of diabetes in diabetic BB prone rats: effect of secoisolariciresinol diglucoside (SDG). Molecular and cellular biochemistry. 2000 Jun; 209(1-2):89-96. doi: 10.1023/a:1007079802459. [PMID: 10942205]
  • K Prasad, S V Mantha, A D Muir, N D Westcott. Protective effect of secoisolariciresinol diglucoside against streptozotocin-induced diabetes and its mechanism. Molecular and cellular biochemistry. 2000 Mar; 206(1-2):141-9. doi: 10.1023/a:1007018030524. [PMID: 10839204]
  • D D Kitts, Y V Yuan, A N Wijewickreme, L U Thompson. Antioxidant activity of the flaxseed lignan secoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone. Molecular and cellular biochemistry. 1999 Dec; 202(1-2):91-100. doi: 10.1023/a:1007022329660. [PMID: 10705999]
  • K Prasad. Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed. Circulation. 1999 Mar; 99(10):1355-62. doi: 10.1161/01.cir.99.10.1355. [PMID: 10077521]
  • S E Rickard, L U Thompson. Chronic exposure to secoisolariciresinol diglycoside alters lignan disposition in rats. The Journal of nutrition. 1998 Mar; 128(3):615-23. doi: 10.1093/jn/128.3.615. [PMID: 9482772]
  • K Prasad. Hydroxyl radical-scavenging property of secoisolariciresinol diglucoside (SDG) isolated from flax-seed. Molecular and cellular biochemistry. 1997 Mar; 168(1-2):117-23. doi: 10.1023/a:1006847310741. [PMID: 9062900]
  • L U Thompson, S E Rickard, L J Orcheson, M M Seidl. Flaxseed and its lignan and oil components reduce mammary tumor growth at a late stage of carcinogenesis. Carcinogenesis. 1996 Jun; 17(6):1373-6. doi: 10.1093/carcin/17.6.1373. [PMID: 8681458]
  • M Jenab, L U Thompson. The influence of flaxseed and lignans on colon carcinogenesis and beta-glucuronidase activity. Carcinogenesis. 1996 Jun; 17(6):1343-8. doi: 10.1093/carcin/17.6.1343. [PMID: 8681453]
  • M Bambagiotti-Alberti, S A Coron, C Ghiara, G Moreti, A Raffaelli. Investigation of mammalian lignan precursors in flax seed: first evidence of secoisolariciresinol diglucoside in two isomeric forms by liquid chromatograph/mass spectrometry. Rapid communications in mass spectrometry : RCM. 1994 Dec; 8(12):929-32. doi: 10.1002/rcm.1290081204. [PMID: 7696701]
  • M Bambagiotti-Alberti, S A Coran, C Ghiara, V Giannellini, A Raffaelli. Revealing the mammalian lignan precursor secoisolariciresinol diglucoside in flax seed by ionspray mass spectrometry. Rapid communications in mass spectrometry : RCM. 1994 Aug; 8(8):595-8. doi: 10.1002/rcm.1290080805. [PMID: 7949328]