480
Views
10
CrossRef citations to date
0
Altmetric
Review Articles

A review of flaxseed lignan and the extraction and refinement of secoisolariciresinol diglucoside

ORCID Icon, ORCID Icon, ORCID Icon, , ORCID Icon, & ORCID Icon show all

References

  • Adlercreutz, H. 2007. Lignans, human health. Critical Reviews in Clinical Laboratory Sciences 44 (5-6):483–525. doi: 10.1080/10408360701612942.
  • Afzal, U., M. S. Butt, F. Ashfaq, A. Bilal, and H. A. R. Suleria. 2020. Bioassessment of flaxseed powder and extract against hyperglycemia and hypercholesterolemia using Sprague Dawley rats. Clinical Phytoscience 6 (1):5. doi: 10.1186/s40816-020-0150-y.
  • Aid, T., M. Kaljurand, and M. Vaher. 2015. Colorimetric determination of total phenolic contents in ionic liquid extracts by paper microzones and digital camera. Analytical Methods 7 (7):3193–9. doi: 10.1039/C5AY00194C.
  • Angeloni, S., L. Navarini, G. Sagratini, E. Torregiani, S. Vittori, and G. Caprioli. 2018. Development of an extraction method for the quantification of lignans in espresso coffee by using HPLC‐MS/MS triple quadrupole. Journal of Mass Spectrometry 53 (9):842–8. doi: 10.1002/jms.4251.
  • Arjmandi, B. H., D. A. Khan, S. Juma, M. L. Drum, S. Venkatesh, E. Sohn, L. Wei, and R. Derman. 1998. Whole flaxseed consumption lowers serum LDL-cholesterol and lipoprotein(a) concentrations in postmenopausal women. Nutrition Research 18 (7):1203–14. doi: 10.1016/S0271-5317(98)00100-6.
  • Asgary, S., A. Rastqar, and M. Keshvari. 2018. Functional food and cardiovascular disease prevention and treatment: A review. Journal of the American College of Nutrition 37 (5):429–55. doi: 10.1080/07315724.2017.1410.
  • Austria, J. A., M. N. Richard, M. N. Chahine, A. L. Edel, L. J. Malcolmson, C. M. C. Dupasquier, and G. N. Pierce. 2008. Bioavailability of alpha-linolenic acid in subjects after ingestion of three different forms of flaxseed. Journal of the American College of Nutrition 27 (2):214–21. doi: 10.1080/07315724.2008.10719693.
  • Axelson, M., J. Sjövall, B. E. Gustafsson, and K. D. Setchell. 1982. Origin of lignans in mammals and identification of a precursor from plants. Nature 298 (5875):659–60. doi: 10.1038/298659a0.
  • Bakke, J. E., and H. J. Klosterman. 1956. A new diglucoside from flaxseed. Proceedings of the North Dakota Academy of Science 10:18–22.
  • Bajpai, M., S. Pandey, and A. K. Vasistha. 1985. Spectrum of variability of characteristics and composition of the oils from different genetic varieties of linseed. Journal of the American Oil Chemists’ Society 62:628.
  • Barthet, V., and R. Bacala. 2010. Development of optimized extraction methodology for cyanogenic glycosides from flaxseed (Linum usitatissimum). Journal of AOAC International 93 (2):478–84.
  • Bechlin, T. R., S. J. Granella, D. Christ, S. R. M. Coelho, and C. A. Viecelli. 2019. Evaluation of grain and oil quality of packaged and ozonized flaxseed. Journal of Stored Products Research 83:311–6. doi: 10.1016/j.jspr.2019.07.014.
  • Bekhit, A. E.-D A., A. Shavandi, T. Jodjaja, J. Birch, S. Teh, I. A. Mohamed Ahmed, F. Y. Al-Juhaimi, P. Saeedi, and A. A. Bekhit. 2018. Flaxseed: Composition, detoxification, utilization, and opportunities. Biocatalysis and Agricultural Biotechnology 13:129–52. doi: 10.1016/j.bcab.2017.11.017.
  • Bhatty, R. S., and P. Cherdkiatgumchai. 1990. Compositional analysis of laboratory–prepared and commercial samples of linseed meal and of hull isolated from flax. Journal of the American Oil Chemists’ Society 67 (2):79–84. doi: 10.1007/BF02540631.
  • Boussetta, N., M. Turk, C. De Taeye, Y. Larondelle, J. L. Lanoisellé, and E. Vorobiev. 2013. Effect of high voltage electrical discharges, heating and ethanol concentration on the extraction of total polyphenols and lignans from flaxseed cake. Industrial Crops and Products 49:690–6. doi: 10.1016/j.indcrop.2013.06.004.
  • Brandão, H. N., H. H. S. Medrado, J. P. David, J. M. David, J. F. B. Pastore, and M. Meira. 2017. Determination of podophyllotoxin and related aryltetralin lignans by HPLC/DAD/MS from Lamiaceae species. Microchemical Journal 130:179–84. doi: 10.1016/j.microc.2016.09.002.
  • Buckner, A. L., C. A. Buckner, S. Montaut, and R. M. Lafrenie. 2019. Treatment with flaxseed oil induces apoptosis in cultured malignant cells. Heliyon 5 (8):e02251. doi: 10.1016/j.heliyon.2019.e02251.
  • Budisa, N., and D. Schulze-Makuch. 2014. Supercritical carbon dioxide and its potential as a life sustaining solvent in a planetary environment. Life (Basel, Switzerland) 4 (3):331–40. doi: 10.3390/life4030331.
  • Cacace, J. E., and G. Mazza. 2006. Pressurized low polarity water extraction of lignans from whole flaxseed. Journal of Food Engineering 77 (4):1087–95. doi: 10.1016/j.jfoodeng.2005.08.039.
  • Calado, A., P. M. Neves, T. Santos, and P. Ravasco. 2018. The effect of flaxseed in breast cancer: A literature review. Frontiers in Nutrition 5:4. doi: 10.3389/fnut.2018.00004.
  • Caligiuri, S. P. B., A. L. Edel, M. Aliani, and G. N. Pierce. 2014. Flaxseed for hypertension: Implications for blood pressure regulation. Pathogenesis of Hypertension 16:499. doi: 10.1007/s11906-014-0499-8.
  • Cardoso Carraro, J. C., M. I. d S. Dantas, A. C. R. Espeschit, H. Martino, and S. M. Ribeiro. 2012. Flaxseed and human health: Reviewing benefits and adverse effects. Food Reviews International 28 (2):203–30. doi: 10.1080/87559129.2011.595025.
  • Centers for Disease Control. 2002. Toxicological profile for cyanide. Retrieved from the Agency for Toxic Substances and Disease Registry: https://wwwn.cdc.gov/TSP/ToxProfiles/ToxProfiles.aspx?id=72&tid=19.
  • Chen, H. 2004. Nutrient components and utilization of flaxseed. China Oils and Fats 29 (6):72–5.
  • Chen, H., and S. Xu. 2004. Rheological property of flax gum. Journal of Wuxi Light Engineering University 23 (1):30–1.
  • Chen, Z., and L. Gao. 2007. Study on microwave-assisted extraction and rapid detection of secoisolariciresinol diglucoside in flaxseed cake. Acta Agriculture Jiangxi 19 (2):73–5.
  • Clark, W. F., A. D. Muir, N. D. Westcott, and A. Parbtani. 2000. A novel treatment for lupus nephritis: Lignan precursor derived from flax. Lupus 9 (6):429–36. doi: 10.1191/096120300678828622.
  • Comin, L. M., F. Temelli, and M. A. Saldaña. 2011. Supercritical CO2 extraction of flax lignans. Journal of the American Oil Chemists’ Society 88 (5):707–15. doi: 10.1007/s11746-010-1704-9.
  • Coşkuner, Y., and E. Karababa. 2007. Some physical properties of flaxseed (Linum usitatissimum L.). Journal of Food Engineering 78 (3):1067–73. doi: 10.1016/j.jfoodeng.2005.12.017.
  • Dai, Z., H. Xin, Q. Fu, H. Hao, Q. Li, Q. Liu, and Y. Jin. 2019. Exploration and optimization of conditions for quantitative analysis of lignans in Schisandra chinensis by an online supercritical fluid extraction with supercritical fluid chromatography system. Journal of Separation Science 42 (14):2444–54. doi: 10.1002/jssc.201900222.
  • De Silva, S. F., and J. Alcorn. 2019. Flaxseed lignans as important dietary polyphenols for cancer prevention and treatment: Chemistry, pharmacokinetics, and molecular targets. Pharmaceuticals 12 (2):68. doi: 10.3390/ph12020068.
  • Degenhardt, A., S. Habben, and P. Winterhalter. 2002. Isolation of the lignan secoisolariciresinol diglucoside from flaxseed (Linum usitatissimum L.) by high-speed counter-current chromatography. Journal of Chromatography. A 943 (2):299–302. doi: 10.1016/S0021-9673(01)01467-4.
  • DeLuca, J. A. A., E. L. Garcia-Villatoro, and C. D. Allred. 2018. Flaxseed bioactive compounds and colorectal cancer prevention. Current Oncology Reports 20 (8):1–8. doi: 10.1007/s11912-018-0704-z.
  • Demark-Wahnefried, W., T. J. Polascik, S. L. George, B. R. Switzer, J. F. Madden, M. T. Ruffin, D. C. Snyder, K. Owzar, V. Hars, D. M. Albala, 4th, et al. 2008. Flaxseed supplementation (not dietary fat restriction) reduces prostate cancer proliferation rates in men presurgery. Cancer Epidemiology, Biomarkers & Prevention 17 (12):3577–87. doi: 10.1158/1055-9965.EPI-08-0008.
  • Deng, Q., X. Yu, F. Ma, J. Xu, F. Huang, Q. Huang, and F. Sheng. 2017. Comparative analysis of the in-vitro antioxidant activity and bioactive compounds of flaxseed in China according to variety and geographical origin. International Journal of Food Properties 20 (sup3):S2708–S2722. doi: 10.1080/10942912.2017.1402029.
  • Dev, D. K., and E. Quensel. 1986. Functional and microstructural characteristics of linseed (Linum usitatissimum L.) flour and a protein isolate. LWT – Food Science and Technology 19 (4):331–7.
  • Dev, D. K., E. Quensel, and R. Hansen. 1986. Nitrogen extractability and buffer capacity of defatted linseed (Linum usitatissimum L.) flour. Journal of the Science of Food and Agriculture 37 (2):199–205. doi: 10.1002/jsfa.2740370215.
  • Ding, H. H., S. W. Cui, H. D. Goff, Q. Wang, J. Chen, and N. F. Han. 2014. Soluble polysaccharides from flaxseed kernel as a new source of dietary fibres: Extraction and physicochemical characterization. Food Research International 56:166–73. doi: 10.1016/j.foodres.2013.12.005.
  • Dorrell, D. G. 1970. Distribution of fatty acids within seed of flax. Canadian Journal of Plant Science 50 (1):71–5. doi: 10.4141/cjps70-011.
  • Esau, K. 1965. Plant anatomy. 2nd ed. New York: John Wiley.
  • FAOSTAT. 2020. Crops. Retrieved from Food and Agriculture Organization of the United Nations. Accessed November 7, 2022. http://www.fao.org/faostat/en/#data/QC/visualize.
  • Fabian, C. J., S. A. Khan, J. E. Garber, W. C. Dooley, L. D. Yee, J. R. Klemp, J. L. Nydegger, K. R. Powers, A. L. Kreutzjans, C. M. Zalles, et al. 2020. Randomized phase IIB trial of the lignan secoisolariciresinol diglucoside in premenopausal women at increased risk for development of breast cancer. Cancer Prevention Research 13 (7):623–34. doi: 10.1158/1940-6207.CAPR-20-0050.
  • Fabian, C. J., and B. F. Kimler. 2005. Selective estrogen-receptor modoulators for primary prevention of breast cancer. Journal of Clinical Oncology 23 (8):1644–55. doi: 10.1200/JCO.2005.11.005.
  • Febian, F. I., S. N. S. Annuar, and M. A. Memon. 2021. Functional food consumption among older consumers in Malaysia: A health belief model perspective. British Food Journal 123 (8):2880–92. doi: 10.1108/BFJ-07-2020-0663.
  • Flower, G., H. Fritz, L. G. Balneaves, S. Verma, B. Skidmore, R. Fernandes, D. Kennedy, K. Cooley, R. Wong, S. Sagar, et al. 2014. Flax and breast cancer: A systematic review. Integrative Cancer Therapies 13 (3):181–92. doi: 10.1177/1534735413502076.
  • Ford, J. D., K. S. Huang, H. B. Wang, L. B. Davin, and N. G. Lewis. 2001. Biosynthetic pathway to the cancer chemo-preventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed. Journal of Natural Products 64 (11):1388–97. doi: 10.1021/np010367x.
  • Fuentealba, C., F. Figuerola, A. M. Estévez, A. González-Muñoz, and O. Muñoz. 2015. Optimization of secoisolariciresinol diglucoside extraction from flaxseed (Linum usitatissimum L.) and isolation by a simple HPLC-UV method. CyTA – Journal of Food 13 (2):273–81. doi: 10.1080/19476337.2014.953209.
  • Fukumitsu, S., K. Aida, H. Shimizu, and K. Toyoda. 2010. Flaxseed lignan lowers blood cholesterol and decreases liver disease risk factors in moderately hypercholesterolemic men. Nutrition Research 30 (7):441–6. doi: 10.1016/j.nutres.2010.06.004.
  • Ganorkar, P. M., and R. K. Jain. 2013. Flaxseed – a nutritional punch. International Food Research Journal 20 (2):519–25.
  • Gorshkova, O., T. Chernova, N. Mokshina, N. Gogoleva, D. Suslov, A. Tkachenko, and T. Gorshkova. 2019. Intrusive growth of phloem fibers in flax stem: Integrated analysis of miRNA and mRNA expression profiles. Plants 8 (2):47. doi: 10.3390/plants8020047.
  • Gorshkova, T., N. Brutch, B. Chabbert, M. Deyholos, T. Hayashi, S. Lev-Yadun, E. J. Mellerowicz, C. Morvan, G. Neutelings, G. Pilate, et al. 2012. Plant fiber formation: State of the art, recent and expected progress and open questions. Critical Reviews in Plant Sciences 31 (3):201–28. doi: 10.1080/07352689.2011.616096.
  • Guo, K., C. Tong, Q. Fu, J. Xu, S. Shi, and Y. Xiao. 2019. Identification of minor lignans, alkaloids, and phenylpropanoid glycosides in Magnolia officinalis by HPLC–DAD–QTOF-MS/MS. Journal of Pharmaceutical and Biomedical Analysis 170:153–60. doi: 10.1016/j.jpba.2019.03.044.
  • Guo, L., and L. Wang. 2006. Study on parameters and applications of commonly used macroporous adsorption resin. Modern Chinese Medicine 8:26–32.
  • Guo, Y., T. J. Tse, Y. Y. Shim, S. K. Purdy, J. H. Kim, J. Y. Cho, J. Alcorn, and M. J. T. Reaney. 2021. Availability of bioactive flax lignan from foods and supplements. Critical Reviews in Food Science and Nutrition 1–16.
  • Guo, Y., X. Yang, T. J. Tse, S. K. Purdy, R. Mustafa, J. Shen, J. Alcorn, and M. J. T. Reaney. 2021. Hypocholesterolemic efficacy of secoisolariciresinol diglucoside and its polymer in rats. Journal of Natural Products 84 (11):2845–50. doi: 10.1021/acs.jnatprod.1c00549.
  • Haliga, R., V. Mocanu, and M. Badescu. 2013. Flaxseeds have beneficial effects on endothelial dysfunction and oxidative stress in experimental atherosclerosis. Annals of the Romanian Society for Cell Biology 18 (2):91–7.
  • Han, H., F. Qiu, H. Zhao, H. Tang, X. Li, and D. Shi. 2018. Dietary flaxseed oil improved western-type diet-induced atherosclerosis in apolipoprotein-E knockout mice. Journal of Functional Foods 40:417–25. doi: 10.1016/j.jff.2017.11.031.
  • Hano, C., I. Martin, O. Fliniaux, B. Legrand, L. Gutierrez, R. R. J. Arroo, F. Mesnard, F. Lamblin, and E. Lainé. 2006. Pinoresinol-lariciresinol reductase gene expression and sexoisolariciresinol diglucoside accumulation in developing flax (Linum usitatissimum) seeds. Planta 224 (6):1291–301. doi: 10.1007/s00425-006-0308-y.
  • Hasaniani, N., M. Rahimlou, A. R. Ahmadi, A. M. Khalifani, and M. Alizadeh. 2019. The effect of flaxseed enriched yogurt on the glycemic status and cardiovascular risk factors in patients with type 2 diabetes mellitus: Randomized, open-labeled, controlled study. Clinical Nutrition Research 8 (4):284–95. doi: 10.7762/cnr.2019.8.4.284.
  • Health Canada. 2014. Summary of Health Canada’s assessment of a health claim about ground whole flaxseed and blood cholesterol lowering. Accessed November 4, 2022. https://www.canada.ca/content/dam/hc–sc/migration/hc–sc/fn–an/alt_formats/pdf/label–etiquet/claims–reclam/assess–evalu/flaxseed–graines–de–lin–eng.pdf.
  • Ho, C. H., L. J. E. Cacace, and G. Mazza. 2007. Extraction of lignans, proteins and carbohydrates from flaxseed meal with pressurized low polarity water. LWT – Food Science and Technology 40 (9):1637–47. doi: 10.1016/j.lwt.2006.12.003.
  • Hosseinian, F. S., and T. Beta. 2009. Patented techniques for the extraction and isolation of secoisolariciresinol diglucoside from flaxseed. Recent Patents on Food, Nutrition & Agriculture 1 (1):25–31. doi: 10.2174/2212798410901010025.
  • Hu, X. 2005. The nutritional and health care effects of flaxseed lignan. Food and Nutrition in China 8:36–7.
  • Huang, C., T. J. Tse, S. K. Purdy, F. Chicilo, J. Shen, V. Meda, and M. J. T. Reaney. 2023. Depletion of cyanogenic glycosides in whole flaxseed via Lactobacillaceae fermentation. Food Chemistry 403 (1):134441. doi: 10.1016/j.foodchem.2022.134441.
  • Huang, L., and J. Yan. 2008. Determination of secoisolariciresinol diglucoside in flax seed extract by HPLC. The Chinese Journal of Modern Applied Pharmacy 25:512–4.
  • Imran, M., F. M. Anjum, M. S. Butt, M. Siddiq, and M. A. Sheikh. 2013. Reduction of cyanogenic compounds in flaxseed (Linum usitatissimum L.) meal using thermal treatment. International Journal of Food Properties 16 (8):1809–18. doi: 10.1080/10942912.2011.608914.
  • Janiak, M., A. Slavova-Kazakova, V. Kancheva, and R. Amarowicz. 2014. Sephadex LH-20 column chromatography of the hydrolysed lignan macromolecule of flaxseed. Bulgarian Chemical Communications 46:640–4.
  • Johnsson, P., A. Kamal-Eldin, L. N. Lundgren, and P. Aman. 2000. HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds. Journal of Agricultural and Food Chemistry 48 (11):5216–9. doi: 10.1021/jf0005871.
  • Kajla, P., A. Sharma, and D. R. Sood. 2015. Flaxseed–a potential functional food source. Journal of Food Science and Technology 52 (4):1857–71. doi: 10.1007/s13197-014-1293-y.
  • Kamal-Eldin, A., N. Peerlkamp, P. Johnsson, R. Andersson, R. E. Andersson, L. N. Lundgren, and P. Åman. 2001. An oligomer from flaxseed composed of secoisolariciresinol diglucoside and 3-hydroxy-3-methyl glutaric acid residues. Phytochemistry 58 (4):587–90. doi: 10.1016/S0031-9422(01)00279-5.
  • Kaur, P., R. Waghmare, V. Kumar, P. Rasane, S. Kaur, and Y. Gat. 2018. Recent advances in utilization of flaxseed as potential source for value addition. OCL 25 (3):A304. doi: 10.1051/ocl/2018018.
  • Kaushik, P., K. Dowling, S. McKnight, C. J. Barrow, B. Wang, and B. Adhikari. 2016. Preparation, characterization and functional properties of flax seed protein isolate. Food Chemistry 197 (Pt A):212–20. doi: 10.1016/j.foodchem.2015.09.106.
  • Kezimana, P., A. A. Dmitriev, A. V. Kudryavtseva, E. V. Romanova, and N. V. Melnikova. 2018. Secoisolariciresinol diglucoside of flaxseed and its metabolites: Biosynthesis and potential for nutraceuticals. Frontiers in Genetics 9:641. doi: 10.3389/fgene.2018.00641.
  • Kheira, H. S., S. A. E.-S. El-Sayed, G. R. Elsayed, and M. A. Rizk. 2019. Dietary flaxseed oil inhibits kidney NF-kappa B activation and pro-inflammatory cytokine expression in cisplatin-treated rats. Comparative Clinical Pathology 28 (2):349–57. doi: 10.1007/s00580-018-2871-6.
  • Kraushofer, T., and G. Sontag. 2002. Determination of matairesinol in flax seed by HPLC with coulometric electrode array detection. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 777 (1-2):61–6. doi: 10.1016/S1570-0232(01)00577-3.
  • Kurzer, M. S., and X. Xu. 1997. Dietary phytoestrogens. Annual Review of Nutrition 17:353–81. doi: 10.1146/annurev.nutr.17.1.353.
  • Lei, V., W. K. A. Amoa-Awua, and L. Brimer. 1999. Degradation of cyanogenic glycosides by Lactobacillus plantarum strains from spontaneous cassava fermentation and other microorganisms. International Journal of Food Microbiology 53 (2-3):169–84. doi: 10.1016/S0168-1605(99)00156-7.
  • Li, G., and X. Ding. 2005. Analysis of fatty acids of flaxseed oil with GC-MS. Food and Machinery 21 (5):30–2.
  • Li, L., Z. Kou, Y. Wang, and J. Zhu. 2008. Separation and purification of secoisolariciresinol diglucoside by AB-8 macroporous adsorption resin. Journal of the Chinese Cereals and Oils Association 23 (2):95–105.
  • Li, L., Z. Kou, J. Zhu, and Y. Wang. 2007. Isolation of secoisolariciresinol diglucoside from flaxseed with macro-porous adsorption resin. China Oils and Fats 32:52–5.
  • Li, M. 2007. Review and prospect of the evolution study of Linum sp. Plant Fiber Sciences in China 29 (3):113–7.
  • Liao, C., and Z. Huang. 2004. Supercritical CO2 fluid extraction technology-development and application. Beijing, China: Chemical Industry Press.
  • Lindemann, M., C. Rieder-Gradinger, T. Kuncinger, and E. Srebotnik. 2020. Selective recovery of polyphenols from MDF process waters by adsorption on a macroporous, cross-linked pyrrolidone-based resin. Holzforschung 74 (2):217–25. doi: 10.1515/hf-2018-0229.
  • Liu, J., J. Shen, Y. Y. Shim, and M. J. T. Reaney. 2016a. Carboxymethyl derivatives of flaxseed (Linum usitatissimum L.) gum: Characterisation and solution rheology. International Journal of Food Science & Technology 51 (2):530–41. doi: 10.1111/ijfs.12985.
  • Liu, J., Y. Y. Shim, A. G. Poth, and M. J. T. Reaney. 2016b. Conlinin in flaxseed (Linum usitatissimum L.) gum and its contribution to emulsification properties. Food Hydrocolloids. 52:963–71. doi: 10.1016/j.foodhyd.2015.09.001.
  • Liu, J., Y. Y. Shim, J. Shen, Y. Wang, S. Ghosh, and M. J. T. Reaney. 2016c. Variation of composition and functional properties of gum from six Canadian flaxseed (Linum usitatissimum L.) cultivars. International Journal of Food Science & Technology 51 (10):2313–26. doi: 10.1111/ijfs.13200.
  • Liu, J., Y. Y. Shim, T. J. Tse, Y. Wang, and M. J. T. Reaney. 2018. Flaxseed gum a versatile natural hydrocolloid for food and non-food applications. Trends in Food Science & Technology 75:146–57. doi: 10.1016/j.tifs.2018.01.011.
  • Lu, B., J. Yang, and T. Liu. 2007. Study on extraction technique of flaxseed gum from flaxseed. Heilongjiang Agricultural Sciences 3:95–6.
  • Macrae, W. D., and G. N. Towers. 1984. Biological activities of lignans. Phytochemistry 23 (6):1207–20. doi: 10.1016/S0031-9422(00)80428-8.
  • Madhusudhan, B., D. Wiesenborn, J. Schwarz, K. Tostenson, and J. Gillespie. 2000. A dry mechanical method for concentrating the lignan secoisolariciresinol diglucoside in flaxseed. LWT – Food Science and Technology 33 (4):268–75. doi: 10.1006/fstl.2000.0652.
  • Madhusudhan, K. T., and N. Singh. 1983. Studies on linseed proteins [Linum usitatissimum, India]. Journal of Agricultural and Food Chemistry 31 (5):959–63. doi: 10.1021/jf00119a010.
  • Malcolmson, L. J., R. Przybylski, and J. K. Daun. 2000. Storage stability of milled flaxseed. Journal of the American Oil Chemists’ Society 77 (3):235–8. doi: 10.1007/s11746-000-0038-0.
  • Martinchik, A. N., A. K. Baturin, V. V. Zubtsov, and V. Molofeev. 2012. Nutritional value and functional properties of flaxseed. Voprosy Pitaniia 81 (3):4–10.
  • Masuda, T., J. Akiyama, A. Fujimoto, S. Yamauchi, T. Maekawa, and Y. Sone. 2010. Antioxidation reaction mechanism studies of phenolic lignans, identification of antioxidation products of secoisolariciresinol from lipid oxidation. Food Chemistry 123 (2):442–50. doi: 10.1016/j.foodchem.2010.04.065.
  • Mayo Clinic. 2015. Flaxseed is nutritionally powerful. Retrieved from Mayo Clinic Health System. Accessed November 4, 2022. https://www.mayoclinichealthsystem.org/hometown-health/speaking-of-health/flaxseed-is-nutritionally-powerful#:∼:text=While%20there%20are%20no%20specific,2%20grams%20of%20dietary%20fiber.
  • Mazur, W. 1998. 11 Phytoestrogen content in foods. Baillière’s Clinical Endocrinology and Metabolism 12 (4):729–42. doi: 10.1016/S0950-351X(98)80013-X.
  • Mazur, W., T. Fotsis, K. Wähälä, S. Ojala, A. Salakka, and H. Adlercreutz. 1996. Isotope dilution gas chromatographic-mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples. Analytical Biochemistry 233 (2):169–80. doi: 10.1006/abio.1996.0025.
  • Morita, H., A. Shishido, T. Matsumoto, H. Itokawa, K. Takeya, H. Itokawa, T. Hirano, and K. Oka. 1997. A new immunosuppressive cyclic nonapeptide, cyclolinopeptide B from Linum usitatissimum. Bioorganic & Medicinal Chemistry Letters 7 (10):1269–72. doi: 10.1016/S0960-894X(97)00206-0.
  • Mosavat, S. H., N. Masoudi, H. Hajimehdipoor, M. K. Emami Meybodi, Z. Niktabe, M. Tabarrai, F. Ghorat, and M. Khodadoost. 2018. Efficacy of topical Linum usitatissimum L. (flaxseed) oil in knee osteoarthritis: A double-blind, randomized, placebo-controlled clinical trial. Complementary Therapies in Clinical Practice 31:302–7. doi: 10.1016/j.ctcp.2018.03.003.
  • Moss, G. 2000. Nomenclature of lignans and neolignans (IUPAC Recommendations 2000). Pure and Applied Chemistry 72 (8):1493–523. doi: 10.1351/pac200072081493.
  • Mottaghipisheh, J., and M. Iriti. 2020. Sephadex® LH-20, isolation, and purification of flavonoids from plant species: A comprehensive review. Molecules (Basel, Switzerland) 25 (18):4146. doi: 10.3390/molecules25184146.
  • Nuez, L., A. Magueresse, P. Lu, A. Day, T. Boursat, P. D’Arras, P. Perré, A. Bourmaud, and C. Baley. 2021. Flax xylem as composite material reinforcement: Microstructure and mechanical properties. Composites Part A Applied Science and Manufacturing. 149:106550. doi: 10.1016/j.compositesa.2021.106550.
  • Oomah, B. D., and G. Mazza. 1993. Flaxseed proteins – A review. Food Chemistry 48 (2):109–14. doi: 10.1016/0308-8146(93)90043-F.
  • Oomah, B. D., and G. Mazza. 1997. Effect of dehulling on chemical composition and physical properties of flaxseed. LWT – Food Science and Technology 30 (2):135–40. doi: 10.1006/fstl.1996.0141.
  • Oomah, B. D., and G. Mazza. 1998. Fractionation of flaxseed with a batch dehuller. Industrial Crops and Products 9 (1):19–27. doi: 10.1016/S0926-6690(98)00009-0.
  • Oomah, B. D., and G. Mazza. 2001. Optimization of a spray drying process for flaxseed gum. International Journal of Food Science & Technology 36 (2):135–43. doi: 10.1046/j.1365-2621.2001.00442.x.
  • Oomah, B. D., G. Mazza, and E. O. Kenaschuk. 1992. Cyanogenic compounds in flaxseed. Journal of Agricultural and Food Chemistry 40 (8):1346–8. doi: 10.1021/jf00020a010.
  • Oomah, B. D., G. Mazza, and E. O. Kenaschuk. 1996. Dehulling characteristics of flaxseed. LWT – Food Science and Technology 29 (3):245–50. doi: 10.1006/fstl.1996.0036.
  • Oregon State University. 2021. Lignans. Retrieved from Oregon State University Linus Pauling Institute. Accessed November 4, 2022. https://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/lignans#:∼:text=Secoisolariciresinol%20and%20matairesinol%20were%20among,grains%2C%20fruit%2C%20and%20vegetables.
  • Özkal, S. G. 2009. Response surface analysis and modeling of flaxseed oil yield in supercritical carbon dioxide. Journal of the American Oil Chemists’ Society 86 (11):1129–35. doi: 10.1007/s11746-009-1448-6.
  • Özkaynak Kanmaz, E., and G. Ova. 2013. The effective parameters for subcritical water extraction of SDG lignan from flaxseed (Linum usitatissimum L.) using accelerated solvent extractor. European Food Research and Technology 237 (2):159–66. doi: 10.1007/s00217-013-1974-1.
  • Pan, A., J. Sun, Y. Chen, X. Ye, H. Li, Z. Yu, Y. Wang, W. Gu, X. Zhang, X. Chen, et al. 2007. Effects of a flaxseed-derived lignan supplement in type-2 diabetic patients: A randomized, double-blind, cross-over trial. PLoS One 2 (11):e1148. doi: 10.1371/journal.pone.0001148.
  • Pan, A., D. Yu, W. Demark-Wahnefried, O. H. Franco, and X. Lin. 2009. Meta-analysis of the effects of flaxseed interventions on blood lipids. The American Journal of Clinical Nutrition 90 (2):288–97. doi: 10.3945/acjn.2009.27469.
  • Pan, Y. L., L. I. Jing, L. I. Xiang, and J. W. Chen. 2014. Enrichment and purification of lignans from by D101 macroporous resin. Natural Product Research and Development 26 (4):579–82.
  • Parikh, M., T. G. Maddaford, J. A. Austria, M. Aliani, T. Netticadan, and G. N. Pierce. 2019. Dietary flaxseed as a strategy for improving human health. Nutrients 11 (5):1171. doi: 10.3390/nu11051171.
  • Park, H. J., J. S. Park, M. G. Hayek, G. A. Reinhart, and B. P. Chew. 2011. Dietary fish oil and flaxseed oil suppress inflammation and immunity in cats. Veterinary Immunology and Immunopathology 141 (3-4):301–6. doi: 10.1016/j.vetimm.2011.02.024.
  • Payne, T. J. 2000. Promoting better health with flaxseed in bread. Cereal Foods World 45 (3):102–4.
  • Peñalvo, J. L., K. M. Haajanen, N. Botting, and H. Adlercreutz. 2005. Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry. Journal of Agricultural and Food Chemistry 53 (24):9342–7. doi: 10.1021/jf051488w.
  • Pihlava, J.-M., H. Hyvarinen, E.-L. Ryhan, and V. Hietantemi. 2004. Process for isolating and purifying secoisolariciresinol diglucoside (SDG) from flaxseed, US Patent, US 2004030108.
  • Plaza, M., and C. Turner. 2015. Pressurized hot water extraction of bioactives. TrAC Trends in Analytical Chemistry 71:39–54. doi: 10.1016/j.trac.2015.02.022.
  • Pradhan, R. C., V. Meda, S. N. Naik, and L. Tabil. 2010. Physical properties of Canadian grown flaxseed in relation to its processing. International Journal of Food Properties 13 (4):732–43. doi: 10.1080/10942910902818137.
  • Pradhan, R. C., V. Meda, P. K. Rout, S. Naik, and A. K. Dalai. 2010. Supercritical CO2 extraction of fatty oil from flaxseed and comparison with screw press expression and solvent extraction processes. Journal of Food Engineering 98 (4):393–7. doi: 10.1016/j.jfoodeng.2009.11.021.
  • Prasad, K. 1999. Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed. Circulation 99 (10):1355–62. doi: 10.1161/01.CIR.99.10.1355.
  • Prasad, K. 2000. Antioxidant activity of secoisolariciresinol diglucoside-derived metabolites, secoisolariciresinol, enterodiol, and enterolactone. The International Journal of Angiology 9 (4):220–5. doi: 10.1007/BF01623898.
  • Prasad, K. 2001. Secoisolariciresinol diglucoside from flaxseed delays the development of type 2 diabetes in Zucker rat. The Journal of Laboratory and Clinical Medicine 138 (1):32–9. doi: 10.1067/mlc.2001.115717.
  • Prasad, K. 2007. A study on regression of hypercholesterolemic atherosclerosis in rabbits by flax lignan complex. Journal of Cardiovascular Pharmacology and Therapeutics 12 (4):304–13. doi: 10.1177/1074248407307853.
  • Prasad, K. 2011. Suppression of phosphoenolpyruvate carboxykinase gene expression by secoisolariciresinol diglucoside (SDG), a new antidiabetic agent. International Journal of Angiology 11 (02):107–9. doi: 10.1007/BF01616377.
  • Qian, K. Y., S. W. Cui, Y. Wu, and H. D. Goff. 2012. Flaxseed gum from flaxseed hulls: Extraction, fractionation, and characterization. Food Hydrocolloids 28 (2):275–83. doi: 10.1016/j.foodhyd.2011.12.019.
  • Rodriguez-Leyva, D., W. Weighell, A. L. Edel, R. LaVallee, E. Dibrov, R. Pinneker, T. G. Maddaford, B. Ramjiawan, M. Aliani, R. Guzman, et al. 2013. Potent antihypertensive action of dietary flaxseed in hypertensive patients. Hypertension 62 (6):1081–9. doi: 10.1161/HYPERTENSIONAHA.113.02094.
  • Rubilar, M., C. Gutiérrez, M. Verdugo, C. Shene, and J. Sineiro. 2010. Flaxseed as a source of functional ingredients. Journal of Soil Science and Plant Nutrition 10 (3):373–7. doi: 10.4067/S0718-95162010000100010.
  • Rutkowska, M., K. Owczarek, M. de la Guardia, J. Płotka-Wasylka, and J. Namieśnik. 2017. Application of additional factors supporting the microextraction process. TrAC Trends in Analytical Chemistry 97:104–19. doi: 10.1016/j.trac.2017.09.005.
  • Ruxton, C., S. Reed, M. Simpson, and K. Millington. 2004. The health benefits of omega-3 polyunsaturated fatty acids: A review of the evidence. Journal of Human Nutrition and Dietetics 17 (5):449–59. doi: 10.1111/j.1365-277X.2004.00552.x.
  • Salunkhe, D. K., and B. B. Desai. 1986. Linseed, niger and cottonseed. In Postharvest biotechnology of oilseeds, eds. D. K. Salunkhe and B. B. Desai, 171–86. Boca Raton, FL: CRC Press.
  • Schmidt, T. J., S. Hemmati, E. Fuss, and A. W. Alfermann. 2006. A combined HPLC-UV and HPLC-MS method for the identification of lignans and its application to the lignans of Linum usitatissimum L. and L. bienne Mill. Phytochemical Analysis 17 (5):299–311. doi: 10.1002/pca.918.
  • Shim, Y. Y., B. Gui, P. G. Arnison, Y. Wang, and M. J. Reaney. 2014. Flaxseed (Linum usitatissimum L.) bioactive compounds and peptide nomenclature: A review. Trends in Food Science & Technology 38 (1):5–20. doi: 10.1016/j.tifs.2014.03.011.
  • Shim, Y. Y., B. Gui, Y. Wang, and M. J. T. Reaney. 2015. Flaxseed (Linum usitatissimum L.) oil processing and selected products. Trends in Food Science & Technology 43 (2):162–77. doi: 10.1016/j.tifs.2015.03.001.
  • Singh, K. K., D. Mridula, J. Rehal, and P. Barnwal. 2011. Flaxseed: A potential source of food, feed and fiber. Critical Reviews in Food Science and Nutrition 51 (3):210–22. doi: 10.1080/10408390903537241.
  • Sosulski, F. W., and A. Bakal. 1969. Isolated proteins from rapeseed, flax and sunflower meals. Canadian Institute of Food Technology Journal 2 (1):28–32. doi: 10.1016/S0008-3860(69)74338-0.
  • Stasevich, O. V., S. G. Mikhalenok, and V. P. Kurchenko. 2009. Selection of optimal conditions for separating lignan-containing extract from oil flax seed by thin-layer chromatography. Pharmaceutical Chemistry Journal 43 (7):415–7. doi: 10.1007/s11094-009-0313-0.
  • Sun, W., H. Yang, Y. Zhong, and J. Li. 2009. Condition optimization for ultrasonic-assistant extraction of lignan in flaxseeds. Journal of the Chinese Cereals and Oils Association 24:124–7.
  • Surh, Y. J. 2003. Cancer chemoprevention with dietary phytochemicals. Nature Reviews. Cancer 3 (10):768–80. doi: 10.1038/nrc1189.
  • Tan, Z.-J., C.-Y. Wang, Z.-Z. Yang, Y.-J. Yi, H.-Y. Wang, W.-L. Zhou, and F.-F. Li. 2015. 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) 20 (10):17929–43. doi: 10.3390/molecules201017929.
  • Tang, Z.-X., L.-E. Shi, X.-M. Wang, G.-W. Dai, L.-A. Cheng, Z.-X. Wan, H. He, Q. Wu, Y.-B. Wang, X.-Y. Jin, et al. 2020. Whole flaxseed-based products and their health benefits. Food Science and Technology Research 26 (5):561–78. doi: 10.3136/fstr.26.561.
  • Thompson, L. U., B. A. Boucher, Z. Liu, M. Cotterchio, and N. Kreiger. 2006. Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan. Nutrition and Cancer 54 (2):184–201. doi: 10.1207/s15327914nc5402_5.
  • Thompson, L. U., P. Robb, M. Serraino, and F. Cheung. 1991. Mammalian lignan production from various foods. Nutrition and Cancer 16 (1):43–52. doi: 10.1080/01635589109514139.
  • Todd, R., and S. Baroutian. 2017. A techno-economic comparison of subcritical water, supercritical CO2 and organic solvent extraction of bioactives from grape marc. Journal of Cleaner Production 158:349–58. doi: 10.1016/j.jclepro.2017.05.043.
  • Tripodo, G., E. Ibáñez, A. Cifuentes, B. Gilbert‐López, and C. Fanali. 2018. Optimization of pressurized liquid extraction by response surface methodology of Goji berry (Lycium barbarum L.) phenolic bioactive compounds. Electrophoresis 39 (13):1673–82. doi: 10.1002/elps.201700448.
  • Tse, T. J., Y. Guo, Y. Y. Shim, S. K. Purdy, J. H. Kim, J. Y. Cho, J. Alcorn, and M. J. T. Reaney. 2022. Availability of bioactive flax lignan from foods and supplements. Critical Reviews in Food Science and Nutrition, 2 (1):1–16. doi: 10.1080/10408398.2022.2072807.
  • Vaisey-Genser, M., and D. H. Morris. 2003. History of the cultivation and uses of flaxseed. In Flax, the genus Linum, ed. A. D. Muir and N. D. Westcott, 1–21. Boca Raton, FL: CRC Press.
  • Venglat, P., D. Xiang, S. Qiu, S. L. Stome, C. Tibiche, and D. Cram. 2011. Gene expression analysis of flax seed development. NMC Plant Biology 11:74.
  • Wanasundara, P. K. J. P. D., R. Amarowicz, M. T. Kara, and F. Shahidi. 1993. Removal of cyanogenic glycosides of flaxseed meal. Food Chemistry 48 (3):263–6. doi: 10.1016/0308-8146(93)90138-6.
  • Wang, H., J. Wang, C. Qiu, Y. Ye, X. Guo, G. Chen, T. Li, Y. Wang, X. Fu, and R. H. Liu. 2017. Comparison of phytochemical profiles and health benefits in fiber and oil flaxseeds (Linum usitatissimum L.). Food Chemistry 214:227–33. doi: 10.1016/j.foodchem.2016.07.075.
  • Wang, J., B. Jiang, Y. Shan, X. Wang, X. Lv, J. Mohamed, H. Li, C. Wang, J. Chen, and J. Sun. 2020. Metabolic mapping of Schisandra chinensis lignans and their metabolites in rats using a metabolomic approach based on HPLC with quadrupole time‐of‐flight MS/MS spectrometry. Journal of Separation Science 43 (2):378–88. doi: 10.1002/jssc.201900860.
  • Wang, P. 2012. Study on the extraction technology and kinetics of flaxseed oil. Master thes., Guangxi University.
  • Wang, X., J. Su, X. Chu, X. Zhang, Q. Kan, R. Liu, and X. Fu. 2021. Adsorption and desorption characteristics of total flavonoids from Acanthopanax senticosus on macroporous adsorption resins. Molecules 26 (14):4162. doi: 10.3390/molecules26144162.
  • Wang, Y., M. Chantreau, R. Sibout, and S. Hawkins. 2013. Plant cell wall lignification and monolignol metabolism. Frontiers in Plant Science 4:220. doi: 10.3389/fpls.2013.00220.
  • Westcott, N. D., and A. D. Muir. 1996. Variation in the concentration of the flaxseed lignan concentration with variety, location, and year. Proceedings of the 56th Flax Institute of the United States Conference, Fargo, ND, USA.
  • Whistler, R. L., and J. N. BeMiller. 1993. Industrial gums: Polysaccharides and their derivatives. New York, NY: Academic Press.
  • Willför, S. M., A. I. Smeds, and B. R. Holmbom. 2006. Chromatographic analysis of lignans. Journal of Chromatography. A 1112 (1-2):64–77. doi: 10.1016/j.chroma.2005.11.054.
  • Williams, D., M. Verghese, L. T. Walker, J. Boateng, L. Shackelford, and C. B. Chawan. 2007. Flax seed oil and flax seed meal reduce the formation of aberrant crypt foci (ACF) in azoxymethane-induced colon cancer in Fisher 344 male rats. Food and Chemical Toxicology 45 (1):153–9. doi: 10.1016/j.fct.2006.08.014.
  • Wong, H., N. Chahal, C. Manlhiot, E. Niedra, and B. W. McCrindle. 2013. Flaxseed in pediatric hyperlipidemia: A placebo-controlled, blinded, randomized clinical trial of dietary flaxseed supplementation for children and adolescents with hypercholesterolemia. JAMA Pediatrics 167 (8):708–13. doi: 10.1001/jamapediatrics.2013.1442.
  • Wu, C. F., X. M. Xu, S. H. Huang, M. C. Deng, A. J. Feng, J. Peng, J. P. Yuan, and J. H. Wang. 2012. An efficient fermentation method for the degradation of cyanogenic glycosides in flaxseed. Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment 29 (7):1085–91. doi: 10.1080/19440049.2012.680202.
  • Xu, H., T. He, Z. Zhao, X. Chang, F. Wang, and X. Wang. 2015. Equilibrium and kinetic studies on the adsorption of lignans from Schisandra chinensis by commercial macroporous resins. Separation Science and Technology 50 (9):1321–30. doi: 10.1080/01496395.2014.968263.
  • Xu, H., and L. Sun. 2007. Research progress on flaxseed lignan. Academic Periodical of Farm Products Processing 112:17–20.
  • Xu, L., and C. Huang. 1998. Pandaceae. In C. A. Flora Republicae Popularis Sinicae Editorial Board, Flora Republicae Popularis Sinicae, eds. Z. Wu, P. H. Raven, and D. Hong, 43: 102–3. Beijing, China: Science Press.
  • Yamashita, T., T. Sano, T. Hashimoto, and K. Kanazawa. 2007. Development of a method to remove cyanogen glycosides from flaxseed meal. International Journal of Food Science & Technology 42 (1):70–5. doi: 10.1111/j.1365-2621.2006.01212.x.
  • Yang, H. 2005. Study on detoxification and lignans-extraction techniques of flaxseed. Master thes., China Agricultural University.
  • Yang, H., Z. Mao, and T. Hequn. 2004. Determination and removal methods for cyanogenic glucoside in flaxseed. ASAE Annual International Meeting 2004. doi: 10.13031/2013.16947.
  • Yang, H. Z. 2012. Establishment of dynamic model for flaxseed lignans extraction with solvent method. Advanced Materials Research 550-553:1671–6. doi: 10.4028/www.scientific.net/AMR.550-553.1671.
  • Yang, L., and C. Tian. 2011. The role of flaxseed lignans in health care. Chinese Community Doctors 13:35–6.
  • Yang, X. 2016. Comprehensive utilization of flaxseed. Master thes., Beijing University of Chemical Technology.
  • Yang, X., Y. Guo, T. J. Tse, S. K. Purdy, R. Mustafa, J. Shen, J. Alcorn, and M. J. T. Reaney. 2021. Oral pharmacokinetics of enriched secoisolariciresinol diglucoside and its polymer in rats. Journal of Natural Products 84 (6):1816–22. doi: 10.1021/acs.jnatprod.1c00335.
  • Yu, X., S. Huang, C. Cheng, F. Huang, Q. Deng, and Q. Huang. 2018. Composition and antioxidant characteristics of different flaxseed cultivars. Chinese Journal of Oil Crop Sciences 40 (6):879–88.
  • Zhang, H., and F. Liu. 2000. Review on function, resource and production of alpha-linolenic acid. China Oils and Fats 25 (6):192–4.
  • Zhang, W., and S. Xu. 2006a. Study on demucilage process of flaxseed. Journal of Food Science and Biotechnology 25:93–7.
  • Zhang, W., and S. Xu. 2006b. Study on microwave-assisted extraction of flaxseed lignan. Natural Product Research and Development 18 (2):286–90.
  • Zhang, W., and S. Xu. 2007. Purification of secoisolariciresinol diglucoside with column chromatography on a Sephadex LH-20. Journal of Chromatographic Science 45 (4):177–82. doi: 10.1093/chromsci/45.4.177.
  • Zhang, W., X. Wang, Y. Liu, H. Tian, B. Flickinger, M. W. Empie, and S. Z. Sun. 2008. Dietary flaxseed lignan extract lowers plasma cholesterol and glucose concentrations in hypercholesterolemic subjects. The British Journal of Nutrition 99 (6):1301–9. doi: 10.1017/S0007114507871649.
  • Zhang, X., S. Heinonen, and E. Levanen. 2014. Applications of supercritical carbon dioxide in materials processing and synthesis. RSC Advances 4 (105):61137–52. doi: 10.1039/C4RA10662H.
  • Zhang, X., P. Yin, L. Yang, F. Huang, L. Sun, and Y. Liu. 2017. Oil contents in flaxseeds from different origins and fatty acid compositions of flaxseed oils. China Oils and Fats 42 (11):142–6.
  • Zhang, Z., Y. Zhang, Y. Wu, Y. Xu, Y. Jiang, Y. Zhang, L. Wang, and L. Zhang. 2022. Ultrasonic-assisted aqueous two-phase extraction combined with macroporous resin enrichment of lignans from flaxseed meal and their antioxidant activities. Journal of AOAC International 105 (4):1183–92. doi: 10.1093/jaoacint/qsab124.
  • Zhou, Y., and M. Li. 2010. Review and prospection for linseed production in the world. Chinese Agricultural Science Bulletin 26 (9):151–5.
  • Zhu, L., L. Sha, K. Li, Z. Wang, T. Wang, Y. Li, P. Liu, X. Dong, Y. Dong, X. Zhang, et al. 2020. Dietary flaxseed oil rich in omega-3 suppresses severity of type 2 diabetes mellitus via anti-inflammation and modulating gut microbiota in rats. Lipids in Health and Disease 19 (1):20. doi: 10.1186/s12944-019-1167-4.
  • Zhuang, C.-C., C.-R. Liu, C.-B. Shan, Z. Liu, L. Liu, and C.-M. Ma. 2021. High-yield production of secoisolariciresinol diglucoside from flaxseed hull by extraction with alcoholic ammonium hydroxide and chromatography on microporous resin. Food Production, Processing and Nutrition 3 (1):1–10. doi: 10.1186/s43014-021-00079-5.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.