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Chromatographic Determination of Lignans (Antioxidants) in Food Products

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Abstract

Interest in lignans is continually growing in recent years because of their strong antioxidant properties and other biological characteristics, positively affecting human health. Methods for the extraction, identification, and determination of lignans are developed; lignan species and their quantity in food products are determined, and databases of lignans in food products have been created in several countries (Finland, Netherlands, United States, Canada, United Kingdom, Japan, and Spain). In this review, we consider chromatographic methods (gas, liquid, supercritical fluid, and thin-layer chromatography) used to identify and determine natural lignans and isolate them in an individual state. Most natural lignans are found in flax and sesame seeds, cereals, some vegetables, fruits, and berries.

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References

  1. Moss, G.P., Pure Appl. Chem., 2000, vol. 72, p. 1493.

    Article  CAS  Google Scholar 

  2. Holmbom, B., Eckerman, C., Eklund, P., Hemming, J., Nisula, L., Reunanen, M., Sjöholm, R., Sundberg, A., Sundberg, K., and Willför, S., Phytochem. Rev., 2003, vol. 2, p.331.

    Article  CAS  Google Scholar 

  3. Holmbom, B., Willfoer, S., Hemming, J., Pietarinen, S., Nisula, L., Eklund, P., and Sjoeholm, R., Knots in trees: A rich source of bioactive polyphenols, in Materials, Chemicals and Energy from Forest Biomass, Argyropoulos, D.S., Ed., ACS Symp. Ser., 2007, vol. 954, p.350.

    Article  CAS  Google Scholar 

  4. Yashunskii, D.V., Men’shov, V.M., Tsvetkov, D.E., Tsvetkov, Yu.E., Bel’ko, A.A., Vasiyarov, G.G., Titova, E.V., Pimenov, A.V., Onuchin, A.A., Dokichev, V.A., Tomilov, Yu.V., and Nifantiev, N.E., Russ. Chem. Bull., 2014, vol. 63, no. 11, p. 2571.

    Article  Google Scholar 

  5. Aehle, E., Müller, U., Eklund, P.C., Willför, S.M., Sippl, W., and Dräger, B., Phytochemistry, 2011, vol. 72, p. 2396.

    Article  CAS  Google Scholar 

  6. Pan, J.Y., Chen, S.L., Yang, M.H., Wu, J., Sinkkonen, J., and Zou, K., Nat. Prod. Rep., 2009, vol. 26, p. 1251.

    Article  CAS  Google Scholar 

  7. Vanholme, R., Demedts, B., Morreel, K., Ralph, J., and Boerjan, W., Plant Physiol., 2010, vol. 153, p.895.

    Article  CAS  Google Scholar 

  8. Umezawa, T., Wood Res. (Kyoto, Jpn.), 2003, vol. 90, p.27.

    CAS  Google Scholar 

  9. Yashin, Y.A., Yashunsky, D.V., Vedenin, A.N., Nifantiev, N.E., Yashin, Ya.I., and Nemzer, B.V., Nutr. Food Sci., 2017, vol. 47, p.297.

    Article  Google Scholar 

  10. Adams, N.R., J. Anim. Sci., 1995, vol. 73, p. 1509.

    Article  CAS  Google Scholar 

  11. Adlercreutz, H., Mousavi, Y., Clark, J., Hockerstedt, K., Hamalainen, E., Wähälä, K., Makela, T., and Hase, T., J. Steroid Biochem. Mol. Biol., 1992, vol. 41, p.331.

    Article  CAS  Google Scholar 

  12. Maslov, M.Y., Plotnikova, T.M., Anishchenko, A.M., Aliev, O.I., Nifantiev, N.E., and Plotnikov, M.B., Biorheology, 2016, vol. 53, p.27.

    Article  Google Scholar 

  13. Phytoestrogens and Health, UK Committee on Toxicity of Chemicals in Food, Consumer Products and the Environment, London, 2003.

  14. Kurzer, M.S. and Xu, X., Ann. Rev. Nutr., 1997, vol. 17, p.353.

    Article  CAS  Google Scholar 

  15. Zhukova, O.S., Kiselevskii, M.V., Shcherbakov, A.M., Fetisova, L.V., Yashunskii, D.V., Tsvetkov, D.E., Men’shov, V.M., and Nifant’ev, N.E., Klet. Tekhnol. Biol. Med., 2010, vol. 1, p.78.

    Google Scholar 

  16. Webb, A.L. and McCullough, M.L., Nutr. Cancer, 2005, vol. 51, p.117.

    Article  CAS  Google Scholar 

  17. Adlercreutz, H., Crit. Rev. Clin. Lab. Sci., 2007, vol. 44, p.483.

    Article  CAS  Google Scholar 

  18. Peterson, J., Dwyer, J., Adlercreutz, H., Scalbert, A., Jacques, P., and McCullough, M.L., Nutr. Rev., 2010, vol. 68, p.571.

    Article  Google Scholar 

  19. Prasad, K., J. Cardiovasc. Pharmacol., 2009, vol. 54, p.369.

    Article  CAS  Google Scholar 

  20. Loers, G., Yashunsky, D.V., Nifantiev, N.E., and Schachner, M., J. Nat. Prod., 2014, vol. 77, p. 1554.

    Article  CAS  Google Scholar 

  21. Silva, M., Sousa, E., Duarte, B., Marques, F., Cunha-Ribeiro, L.M., and Pinto, M.M., Eur. J. Med. Chem., 2011, vol. 46, p. 2347.

    Article  Google Scholar 

  22. Krylov, V.B., Ustyuzhanina, N.E., Grachev, A.A., and Nifantiev, N.E., Tetrahedron Lett., 2008, vol. 49, p. 5877.

    Article  CAS  Google Scholar 

  23. Schwartz, H. and Sontag, G., Curr. Bioact. Compd., 2011, vol. 7, p.156.

    Article  CAS  Google Scholar 

  24. Maxwell, A., Optimizing lignan extraction from flaxseed, Thermo Ficher Sci., 2014, vol. 1, p.2.

    Google Scholar 

  25. Beejmohun, V., Fliniaux, O., Grand, E., Lamblin, F., Bensaddek, L., Christen, P., Kovensky, J., Fliniaux, M.A., and Mesnard, F., Phytochem. Anal., 2007, vol. 18, p.275.

    Article  CAS  Google Scholar 

  26. Boussetta, N., Soichi, E., Lanoisellé, J.L., and Vorobiev, E., Ind. Crops Prod., 2014, vol. 52, p.347.

    Article  CAS  Google Scholar 

  27. Cacace, J.E. and Mazza, G., J. Food Eng., 2006, vol. 77, p. 1087.

    Article  CAS  Google Scholar 

  28. Comin, L.M., Temelli, F., and Saldaña, M.A., J. Am. Oil Chem. Soc., 2011, vol. 88, p.707.

    Article  CAS  Google Scholar 

  29. Essam, F.A., Ali, O.A., and Esmail, K.S., Asian J. Plant Sci. Res., 2012, vol. 2, p.306.

    Google Scholar 

  30. Kanmaz, E.Ö., Eur. Food Res. Technol., 2014, vol. 238, p.85.

    Article  CAS  Google Scholar 

  31. Perretti, G., Virgili, C., Troilo, A., Marconi, O., Regnicoli, G.F., and Fantozzi, P., J. Supercrit. Fluids, 2013, vol. 75, p.94.

    Article  CAS  Google Scholar 

  32. Sun, W. and Xiao, R., Anal. Methods, 2014, vol. 6, p. 6432.

    Article  CAS  Google Scholar 

  33. Taha, F.S., Mohamed, G.F., Mohamed, S.H., Mohamed, S.S., and Kamil, M.M., Am. J. Food Technol., 2011, vol. 6, p. 1002.

    Article  CAS  Google Scholar 

  34. Zhang, Q., Zhu, W., Guan, H., Liu, H., Yang, W., Wang, H., and Cai, D., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2016, vol. 1011, p.151.

    Article  CAS  Google Scholar 

  35. Zhang, Z.-S., Li, D., Wang, L.-J., Ozkan, N., Chen, X.D., Mao, Z.-H., and Yang, H.-Z., Sep. Purif. Technol., 2007, vol. 57, p.17.

    Article  CAS  Google Scholar 

  36. Zhou, X., Chen, C., Ye, X., Song, F., Fan, G., and Wu, F., J. Sep. Sci., 2016, vol. 39, p. 1266.

    Article  CAS  Google Scholar 

  37. Khoddami, A., Wilkes, M.A., and Roberts, T.H., Molecules, 2013, vol. 18, p. 2328.

    Article  CAS  Google Scholar 

  38. Slanina, J. and Glatz, Z., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2004, vol. 812, p.215.

    Article  CAS  Google Scholar 

  39. Willför, S.M., Smeds, A.I., and Holmbom, B.R., J. Chromatogr. A, 2006, vol. 1112, p.64.

    Article  Google Scholar 

  40. Peñalvo, J.L., Haajanen, K.M., Botting, N., and Adlercreutz, H., J. Agric. Food Chem., 2005, vol. 53, p. 9342.

    Article  Google Scholar 

  41. Nurmi, T., Voutilainen, S., Nyyssonen, K., Adlercreutz, H., and Salonen, J.T., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2003, vol. 798, p.101.

    Article  CAS  Google Scholar 

  42. Penalvo, J.L., Nurmi, T., Haajanen, K., Al-Maharik, N., Botting, N., and Adlercreutz, H., Anal. Biochem., 2004, vol. 332, p.384.

    Article  CAS  Google Scholar 

  43. Nurmi, T., Doctoral (Chem.) Dissertation, Kuopio, 2014.

    Google Scholar 

  44. Schwertner, H.A. and Stankus, J.J., J. Chromatogr. Sci., 2015, vol. 53, p. 1481.

    Article  CAS  Google Scholar 

  45. Hao, M. and Beta, T., J. Sci. Food Agric., 2012, vol. 92, p. 2062.

    Article  CAS  Google Scholar 

  46. Norskov, N.P. and Knudsen, K.E., J. Agric. Food Chem., 2016, vol. 64, p. 8343.

    Article  Google Scholar 

  47. Popova, I.E., Hall, C., and Kubátová, A., J. Chromatogr. A, 2009, vol. 1216, p.217.

    Article  CAS  Google Scholar 

  48. Marconi, O., Calabro, G., and Perretti, G., Food Anal. Methods, 2014, vol. 7, p.783.

    Article  Google Scholar 

  49. Penalvo, J.L. and Nurmi, T., J. Pharm. Biomed. Anal., 2006, vol. 41, p. 1497.

    Article  CAS  Google Scholar 

  50. Schwartz, H. and Sontag, G., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2006, vol. 838, p.78.

    Article  CAS  Google Scholar 

  51. Setchell, K.D., Childress, C., Zimmer-Nechemias, L., and Cai, J., J. Med. Food, 1999, vol. 2, p.193.

    Article  CAS  Google Scholar 

  52. Ganzera, M., J. Pharm. Biomed. Anal., 2015, vol. 107, p.364.

    Article  CAS  Google Scholar 

  53. Sun, M., Liden, G., Sandahl, M., and Turner, C., J. Sep. Sci., 2016, vol. 39, p. 3123.

    Article  CAS  Google Scholar 

  54. Zhu, L., Li, B., Liu, X., Huang, G., and Meng, X., Food Chem., 2015, vol. 186, p.146.

    Article  CAS  Google Scholar 

  55. Fuentealba, C., Figuerola, F., Estévez, A.M., González-Muñoz, A., and Muñoz, O., CyTA–J. Food, 2015, vol. 13, p.273.

    Article  CAS  Google Scholar 

  56. Mukker, J.K., Kotlyarova, V., Singh, R.S., and Alcorn, J., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2010, vol. 878, p. 3076.

    Article  CAS  Google Scholar 

  57. Sukumar, D., Arimboor, R., and Arumughan, C., J. Pharm. Biomed. Anal., 2008, vol. 47, p.795.

    Article  CAS  Google Scholar 

  58. Cecchi, L., Innocenti, M., Melani, F., Migliorini, M., Conte, L., and Mulinacci, N., Food Chem., 2017, vol. 219, p.148.

    Article  CAS  Google Scholar 

  59. Long, H., Zhang, H., Deng, A., Ma, L., Wu, L., Li, Z., Zhang, Z., Wang, W., Jiang, J., and Qin, H., Acta Pharm. Sin. B, 2016, vol. 6, p.229.

    Article  Google Scholar 

  60. Zhang, J., Chen, J., Liang, Z., and Zhao, C., Chem. Biodiversity, 2014, vol. 11, p.1.

    Article  Google Scholar 

  61. Pillow, P.C., Duphorne, C.M., Chang, S., Contois, J.H., Strom, S.S., Spitz, M.R., and Hursting, S.D., Nutr. Cancer, 1999, vol. 33, p.3.

    Article  CAS  Google Scholar 

  62. Horn-Ross, P.L., Barnes, S., Lee, M., Coward, L., Mandel, J.E., Koo, J., John, E.M., and Smith, M., Cancer, Causes Control, 2000, vol. 11, p.289.

    Article  CAS  Google Scholar 

  63. Thompson, L.U., Boucher, B.A., Liu, Z., Cotterchio, M., and Kreiger, N., Nutr. Cancer, 2006, vol. 54, p.184.

    Article  CAS  Google Scholar 

  64. Kilkkinen, A., Valsta, L.M., Virtamo, J., Stumpf, K., Adlercreutz, H., and Pietinen, P., J. Nutr., 2003, vol. 133, p. 1830.

    Article  CAS  Google Scholar 

  65. Moreno-Franco, B., Garcia-Gonzalez, A., Montero-Bravo, A.M., Iglesias-Gutierrez, E., Ubeda, N., Maroto-Nunez, L., Adlercreutz, H., and Penalvo, J.L., J. Agric. Food Chem., 2011, vol. 59, p. 9827.

    Article  CAS  Google Scholar 

  66. Penalvo, J.L., Adlercreutz, H., Uehara, M., Ristimaki, A., and Watanabe, S., J. Agric. Food Chem., 2008, vol. 56, p.401.

    Article  CAS  Google Scholar 

  67. Kuhnle, G.G., Dell’aquila, C., Aspinall, S.M., Runswick, S.A., Mulligan, A.A., and Bingham, S.A., Nutr. Cancer, 2009, vol. 61, p.302.

    Article  CAS  Google Scholar 

  68. Smeds, A.I., Eklund, P.C., Sjöholm, R.E., Willför, S.M., Nishibe, S., Deyama, T., and Holmbom, B.R., J. Agric. Food Chem., 2007, vol. 55, p. 1337.

    Article  CAS  Google Scholar 

  69. Smeds, A.I., Jauhiainen, L., Tuomola, E., and Peltonen-Sainio, P., J. Agric. Food Chem., 2009, vol. 57, p. 5837.

    Article  CAS  Google Scholar 

  70. Nurmi, T., Heinonen, S., Mazur, W., Deyama, T., Nishibe, S., and Adlercreutz, H., Food Chem., 2003, vol. 83, p.303.

    Article  CAS  Google Scholar 

  71. Mazur, W.M., Wähälä, K., Rasku, S., Salakka, A., Hase, T., and Adlercreutz, H., Br. J. Nutr., 1998, vol. 79, p.37.

    Article  CAS  Google Scholar 

  72. Mazur, W.M., Duke, J.A., Wähälä, K., Rasku, S., and Adlercreutz, H., J. Nutr. Biochem., 1998, vol. 9, p.193.

    Article  CAS  Google Scholar 

  73. Smeds, A.I., Eklund, P.C., and Willför, S.M., Food Chem., 2012, vol. 134, p. 1991.

    Article  CAS  Google Scholar 

  74. Blitz, C.L., Murphy, S.P., and Au, D.L.M., J. Food Comp. Anal., 2007, vol. 20, p.99.

    Article  CAS  Google Scholar 

  75. Muir, A.D., Flax lignans: New opportunities for functional foods, in Food Science & Technology Bulletin: Functional Foods, 2009, vol. 6, no. 6, p.61.

    Google Scholar 

  76. Meija, L., Soderholm, P., Samaletdin, A., Ignace, G., Siksna, I., Joffe, R., Lejnieks, A., Lietuvietis, V., Krams, I., and Adlercreutz, H., Int. J. Food Sci. Nutr., 2013, vol. 64, p.535.

    Article  CAS  Google Scholar 

  77. Milder, I.E., Arts, I.C., van de Putte, B., Venema, D.P., and Hollman, P.C., Br. J. Nutr., 2005, vol. 93, p.393.

    Article  CAS  Google Scholar 

  78. Oomah, B.D., J. Sci. Food Agric., 2001, vol. 81, p.889.

    Article  CAS  Google Scholar 

  79. Tetens, I., Turrini, A., Tapanainen, H., Christensen, T., Lampe, J.W., Fagt, S., Hakansson, N., Lundquist, A., Hallund, J., Valsta, L.M., and Phytohealth WP1 working group, Food Nutr. Res., 2013, vol. 57, no. 1. https://doi.org/10.3402/fnr.v57i0.19805

    Google Scholar 

  80. Milder, I.E., Arts, I.C., Venema, D.P., Lasaroms, J.J., Wähälä, K., and Hollman, P.C., J. Agric. Food Chem., 2004, vol. 52, p. 4643.

    Article  CAS  Google Scholar 

  81. Jana, K., Pavel, H., Josef, B., Jan, T., Nadežda, V., and Milan, H., Slovak J. Food Sci., 2016, vol. 10, p.649.

    Google Scholar 

  82. Josef, B., Pavel, H., Jana, K., Pavla, N., Jan, T., Nadežda, V., Jan, S., and Milan, H., Czech. J. Food Sci., 2016, vol. 34, p.439.

    Article  Google Scholar 

  83. Novotná, P., Tríska, J., Híc, P., Balík, J., Vrchotová, N., Strohalm, J., and Houška, M., Czech. J. Food Sci., 2017, vol. 34, p. 318.

    Article  Google Scholar 

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Correspondence to N. E. Nifant’ev.

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Original Russian Text © A.Ya. Yashin, D.B. Yashunskii, A.N. Vedenin, N.E. Nifant’ev, B.V. Nemzer, Ya.I. Yashin, 2018, published in Zhurnal Analiticheskoi Khimii, 2018, Vol. 73, No. 5, pp. 323–332.

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Yashin, A.Y., Yashunskii, D.B., Vedenin, A.N. et al. Chromatographic Determination of Lignans (Antioxidants) in Food Products. J Anal Chem 73, 399–406 (2018). https://doi.org/10.1134/S106193481805012X

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