2,963
Views
11
CrossRef citations to date
0
Altmetric
Articles

Optimization of secoisolariciresinol diglucoside extraction from flaxseed (Linum usitatissimum L.) and isolation by a simple HPLC-UV method

Optimización de la extracción de secoisolariciresinol diglucósido desde linaza (Linum usitatissimum L.) y su purificación a través de un método simple HPLC-UV

, , , &
Pages 273-281 | Received 05 Mar 2014, Accepted 03 Aug 2014, Published online: 25 Sep 2014

References

  • Beejmohun, V., Fliniaux, O., Grand, É., Lamblin, F., Bensaddek, L., Christen, P. … Mesnard, F. (2007). Microwave-assisted extraction of the main phenolic compounds in flaxseed. Phytochemical Analysis, 18(4), 275–282. doi:10.1002/pca.973
  • Bravi, E., Perretti, G., Marconi, O., Patrizi, E., & Fantozzi, P. (2011). Secoisolariciresinol diglucoside determination in flaxseed (Linum usitatissimum L.) oil and application to a shelf life study. Food Chemistry, 126(4), 1553–1558. doi:10.1016/j.foodchem.2010.11.169
  • Chen, J., Liu, X., Shi, Y. P., & Ma, C. Y. (2007). Determination of the lignan secoisolariciresinol diglucoside from flaxseed (Linum usitatissimum L.) by HPLC. Journal of Liquid Chromatography & Related Technologies, 30(4), 533–544. doi:10.1080/10826070601093853
  • Chimichi, S., Bambagiotti-Alberti, M., Coran, S. A., Giannellini, V., & Biddau, B. (1999). Complete assignment of the 1H and 13C NMR spectra of secoisolariciresinol diglucoside, a mammalian lignan precursor isolated from Linum usitatissimum. Magnetic Resonance in Chemistry, 37(11), 860–863. doi:10.1002/(SICI)1097-458X(199911)37:11<860::AID-MRC559>3.0.CO;2-A
  • Clavel, T., Borrmann, D., Braune, A., Dore, J., & Blaut, M. (2006). Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans. Anaerobe, 12(3), 140–147. doi:10.1016/j.anaerobe.2005.11.002
  • Comin, L. M., Temelli, F., & Saldaña, M. A. (2011). Supercritical CO2 extraction of flax lignans. Journal of the American Oil Chemists Society, 88(5), 707–715. doi:10.1007/s11746-010-1704-9
  • Coran, S. A., Giannellini, V., & Bambagiotti-Alberti, M. (2004). High-performance thin-layer chromatographic-densitometric determination of secoisolariciresinol diglucoside in flaxseed. Journal of Chromatography A, 1045(1–2), 217–222. doi:10.1016/j.chroma.2004.06.042
  • Degenhardt, A., Habben, S., & Winterhalter, P. (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
  • Durazzo, A., Turfani, V., Narducci, V., Azzini, E., Maiani, G., & Carcea, M. (2014). Nutritional characterisation and bioactive components of commercial carobs flours. Food Chemistry, 153, 109–113. doi:10.1016/j.foodchem.2013.12.045
  • Eeckhaut, E., Struijs, K., Possemiers, S., Vincken, J. P., De Keukeleire, D., & Verstraete, W. (2008). 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, 56(12), 4806–4812. doi:10.1021/Jf800101s
  • Eliasson, C., Kamal-Eldin, A., Andersson, R., & Åman, P. (2003). High-performance liquid chromatographic analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction. Journal of Chromatography A, 1012(2), 151–159. doi:10.1016/s0021-9673(03)01136-1
  • Fischer, U. A., Jaksch, A. V., Carle, R., & Kammerer, D. R. (2012). Determination of lignans in edible and nonedible parts of pomegranate (Punica granatum L.) and products derived therefrom, particularly focusing on the quantitation of isolariciresinol using HPLC-DAD-ESI/MSn. Journal of Agricultural and Food Chemistry, 60(1), 283–292. doi:10.1021/jf203598m
  • Hano, C., Martin, I., Fliniaux, O., Legrand, B., Gutierrez, L., Arroo, R. R. J. … Lainé, E. (2006). Pinoresinol–lariciresinol reductase gene expression and secoisolariciresinol diglucoside accumulation in developing flax (Linum usitatissimum) seeds. Planta, 224(6), 1291–1301. doi:10.1007/s00425-006-0308-y
  • Hao, M. L., & Beta, T. (2012). Qualitative and quantitative analysis of the major phenolic compounds as antioxidants in barley and flaxseed hulls using HPLC/MS/MS. Journal of the Science of Food and Agriculture, 92(10), 2062–2068. doi:10.1002/jsfa.5582
  • Herchi, W., Arráez-Román, D., Trabelsi, H., Bouali, I., Boukhchina, S., Kallel, H. … Fernández-Gutierrez, A. (2014). Phenolic compounds in flaxseed: A review of their properties and analytical methods. An overview of the last decade. Journal of Oleo Science, 63(1), 7–14. doi:10.5650/jos.ess13135
  • Hosseinian, F. S., & Mazza, G. (2009). Triticale bran and straw: Potential new sources of phenolic acids, proanthocyanidins, and lignans. Journal of Functional Foods, 1(1), 57–64. doi:10.1016/j.jff.2008.09.009
  • Hu, C., Yuan, Y. V., & Kitts, D. D. (2007). Antioxidant activities of the flaxseed lignan secoisolariciresinol diglucoside, its aglycone secoisolariciresinol and the mammalian lignans enterodiol and enterolactone in vitro. Food and Chemical Toxicology, 45(11), 2219–2227. doi:10.1016/j.fct.2007.05.017
  • Johnsson, P., Kamal-Eldin, A., Lundgren, L. N., & Åman, P. (2000). HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds. Journal of Agricultural and Food Chemistry, 48(11), 5216–5219. doi:10.1021/jf0005871
  • Johnsson, P., Peerlkamp, N., Kamal-Eldin, A., Andersson, R. E., Andersson, R., Lundgren, L. N., & Åman, P. (2002). Polymeric fractions containing phenol glucosides in flaxseed. Food Chemistry, 76(2), 207–212. doi:10.1016/S0308-8146(01)00269-2
  • Kamal-Eldin, A., Peerlkamp, N., Johnsson, P., Andersson, R., Andersson, R. E., Lundgren, L. N., & Åman, P. (2001). An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues. Phytochemistry, 58(4), 587–590. doi:10.1016/S0031-9422(01)00279-5
  • Kanmaz, E. O., & Ova, G. (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), 159–166. doi:10.1007/s00217-013-1974-1
  • Kim, J. H., Seo, W. D., Lee, S. K., Lee, Y. B., Park, C. H., Ryu, H. W., & Lee, J. H. (2014). Comparative assessment of compositional components, antioxidant effects, and lignan extractions from Korean white and black sesame (Sesamum indicum L.) seeds for different crop years. Journal of Functional Foods, 7, 495–505. doi:10.1016/j.jff.2014.01.006
  • Kitts, D. D., Yuan, Y. V., Wijewickreme, A. N., & Thompson, L. U. (1999). Antioxidant activity of the flaxseed lignan secoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone. Molecular and Cellular Biochemistry, 202, 91–100. doi:10.1023/A:1007022329660
  • Konar, N. (2013). Non-isoflavone phytoestrogenic compound contents of various legumes. European Food Research and Technology, 236(3), 523–530. doi:10.1007/s00217-013-1914-0
  • Konar, N., Poyrazoğlu, E. S., Demir, K., & Artik, N. (2012). Effect of different sample preparation methods on isoflavone, lignan, coumestan and flavonoid contents of various vegetables determined by triple quadrupole LC-MS/MS. Journal of Food Composition and Analysis, 26(1–2), 26–35. doi:10.1016/j.jfca.2012.01.002
  • Li, X., Yuan, J.-P., Xu, S.-P., Wang, J.-H., & Liu, X. (2008). Separation and determination of secoisolariciresinol diglucoside oligomers and their hydrolysates in the flaxseed extract by high-performance liquid chromatography. Journal of Chromatography A, 1185(2), 223–232. doi:10.1016/j.chroma.2008.01.066
  • Meagher, L. P., & Beecher, G. R. (2000). Assessment of data on the lignan content of foods. Journal of Food Composition and Analysis, 13(6), 935–947. doi:10.1006/jfca.2000.0932
  • Muir, A. D., & Wescott, N. D. (Eds.). (2003). Flax: The genus linum. Saskatchewan, CA: Taylor & Francis.
  • Myers, R. H., Montgomery, D. C., & Anderson-Cook, C. M. (2009). Response surface methodology: Process and product optimization using designed experiments. New York, NY: Wiley.
  • Pihlava, J. M., Hyvarinen, H., Ryhanen, E. L., & Hietantemi, V. (2004). Process for isolating and purifying secoisolariciresinol diglucoside (SDG) from flaxseed. U.S. Patent No. 2004/0030108. United States Patent Application.
  • Prasad, K. (2000). Antioxidant activity of secoisolariciresinol diglucoside-derived metabolites, secoisolariciresinol, enterodiol, and enterolactone. International Journal of Angiology, 9(4), 220–225. doi:10.1007/bf01623898
  • Renouard, S., Hano, C., Corbin, C., Fliniaux, O., Lopez, T., Montguillon, J. … Lainé, E. (2010). Cellulase-assisted release of secoisolariciresinol from extracts of flax (Linum usitatissimum) hulls and whole seeds. Food Chemistry, 122(3), 679–687. doi:10.1016/j.foodchem.2010.03.036
  • Smeds, A. I., Eklund, P. C., Sjöholm, R. E., Willför, S. M., Nishibe, S., Deyama, T., & Holmbom, B. R. (2007). Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts. Journal of Agricultural and Food Chemistry, 55(4), 1337–1346. doi:10.1021/jf0629134
  • Smeds, A. I., Jauhiainen, L., Tuomola, E., & Peltonen-Sainio, P. (2009). Characterization of variation in the lignan content and composition of winter rye, spring wheat, and spring oat. Journal of Agricultural and Food Chemistry, 57(13), 5837–5842. doi:10.1021/jf9004274
  • Stasevich, O. V., Mikhalenok, S. G., & Kurchenko, V. P. (2009). Isolation of secoisolariciresinol diglucoside from lignan-containing extract of Linum usitatissimum seeds. Chemistry of Natural Compounds, 45(1), 21–23. doi:10.1007/s10600-009-9217-1
  • Struijs, K., Vincken, J. P., Doeswijk, T. G., Voragen, A. G. J., & Gruppen, H. (2009). The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid glucosides and ferulic acid glucosides. Phytochemistry, 70(2), 262–269. doi:10.1016/j.phytochem.2008.12.015
  • Thompson, L. U., Boucher, B. A., Liu, Z., Cotterchio, M., & Kreiger, N. (2006). Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan. Nutrition and Cancer-an International Journal, 54(2), 184–201. doi:10.1207/s15327914nc5402_5
  • Thompson, L. U., Robb, P., Serraino, M., & Cheung, F. (1991). Mammalian lignan production from various foods. Nutrition and Cancer-an International Journal, 16(1), 43–52. doi:10.1080/01635589109514139
  • Touillaud, M. S., Thiebaut, A. C. M., Fournier, A., Niravong, M., Boutron-Ruault, M.-C., & Clavel-Chapelon, F. (2007). Dietary lignan intake and postmenopausal breast cancer risk by estrogen and progesterone receptor status. JNCI Journal of the National Cancer Institute, 99(6), 475–486. doi:10.1093/jnci/djk096
  • Wang, L. Q., Meselhy, M. R., Li, Y., Qin, G. W., & Hattori, M. (2000). Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone. Chemical & Pharmaceutical Bulletin, 48(11), 1606–1610. doi:10.1248/cpb.48.1606
  • Westcott, N. D., & Muir, A. D. (1998). Process for extracting lignans from flaxseed. U.S. Patent No. 5, 705,618.
  • Yuan, J. P., Li, X., Xu, S. P., Wang, J. H., & Liu, X. (2008). Hydrolysis kinetics of secoisolariciresinol diglucoside oligomers from flaxseed. Journal of Agricultural and Food Chemistry, 56(21), 10041–10047. doi:10.1021/jf8020656
  • Zhang, W., Wang, X., Liu, Y., Tian, H., Flickinger, B., Empie, M. W., & Sung, S. Z. (2008). Dietary flaxseed lignan extract lowers plasma cholesterol and glucose concentrations in hypercholesterolaemic subjects. British Journal of Nutrition, 99(6), 1301–1309. doi:10.1017/S0007114507871649
  • Zhang, W. B., & Xu, S. Y. (2007). Microwave-assisted extraction of secoisolariciresinol diglucoside from flaxseed hull. Journal of the Science of Food and Agriculture, 87(8), 1455–1462. doi:10.1002/jsfa.2793
  • Zhang, Z. S., Li, D., Wang, L. J., Ozkan, N., Chen, X. D., Mao, Z. H., & Yang, H. Z. (2007). Optimization of ethanol-water extraction of lignans from flaxseed. Separation and Purification Technology, 57(1), 17–24. doi:10.1016/j.seppur.2007.03.006

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.