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Antioxidant activity of various lignins and lignin-related phenylpropanoid units with high and low molecular weight

  • Jevgenija Ponomarenko , Maris Lauberts , Tatiana Dizhbite , Liga Lauberte , Vilhelmina Jurkjane and Galina Telysheva EMAIL logo
Published/Copyright: April 14, 2015
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Abstract

The antioxidant activities (AoAs) of 50 different technical lignins have been determined. The lignins of various botanical origins (annual plants, coniferous trees, and deciduous trees) were isolated and fractionated by different techniques (delignification by alkali, kraft process, fast pyrolysis, and hydrolysis). The structure and the functionality of lignins were characterized by functional group analyses (phenolic OH, carboxyl, and methoxyl groups), analytical pyrolysis pyrolysis/gas chromatography/mass spectrometry/flame ionization detector (Py-GC/MS/FID), electron paramagnetic resonance, size exclusion chromatography, and titrimetric methods, and the AoAs were evaluated as the capacity to scavenge the DPPH· and ABTS·+ free radicals. The relationship between the lignin structure and the AoA was characterized by pair correlation, partial correlation, and multivariate regression analyses, including correlated components regression. The results were compared with those of lignin model compounds and low molecular weight phenylpropanoids. It has been shown that molecular weight does not influence essentially the AoA of lignins. There is a relationship between the activities of low and high molecular weight polyphenols; their mechanisms of action are also similar. The structure-related AoA of lignins has been quantified for the first time.


Corresponding author: Galina Telysheva, Latvian State Institute of Wood Chemistry, 27 Dzerbenes St., Riga LV-1006, Latvia, e-mail:

Acknowledgments

The financial support from the Latvian budget, grant no. 564/2012 of the Latvian Council of Science and the Government Research Program “Forest and Earth Entrails Resources: Research and Sustainable Utilization – New Products and Technologies” (ResProd) 2014–2017, is gratefully acknowledged.

References

Alves, A., Schwanninger, M., Pereira, H., Rodrigues, J. (2006) Analytical pyrolysis as a direct method to determine the lignin content in wood. Part 1: comparison of pyrolysis lignin with Klason lignin. J. Anal. Appl. Pyrol. 76:209–213.10.1016/j.jaap.2005.11.004Search in Google Scholar

Arshanitsa, A., Ponomarenko, J., Dizhbite, T., Andersone, A., Gosselink, R.J.A., van der Putten, J., Lauberts, M., Telysheva, G. (2013) Fractionation of technical lignins as a tool for improvement of their antioxidant properties. J. Anal. Appl. Pyrol. 103:78–85.10.1016/j.jaap.2012.12.023Search in Google Scholar

Balasundram, N., Sundram, K., Samman, S. (2006) Phenolic compounds in plants and agri-industrial by-products: antioxidant activity, occurrence, and potential uses. Food Chem. 99:191–203.10.1016/j.foodchem.2005.07.042Search in Google Scholar

Baltrusaityte, V., Venskutonis, P., Cheksteryte, V. (2007) Radical scavenging activity of different floral origin honey and beebread phenolic extracts. Food Chem. 101:502–514.10.1016/j.foodchem.2006.02.007Search in Google Scholar

Barclay, L.R.C., Xi, F., Norris, J.Q. (1997) Antioxidant properties of phenolic lignin model compounds. J. Wood Chem. Technol. 17:73–90.10.1080/02773819708003119Search in Google Scholar

Björkman, A. (1956) Studies on finely divided wood. Part 1: extraction of lignin with neutral solvents. Svenk Papperstidn. 59:477–485.Search in Google Scholar

Bracco, P., Brunella, V., Zanetti, M., Luda, M.P., Costa, L. (2007) Stabilisation of ultra-high molecular weight polyethylene with Vitamin E. Polym. Degrad. Stabil. 92:2155–2162.10.1016/j.polymdegradstab.2007.02.023Search in Google Scholar

Brand-Williams, W., Cuvelier, M.E., Reset, C. (1995) Use of a free radical method to evaluate antioxidant activity. Food Sci. Technol. 28:25–30.10.1016/S0023-6438(95)80008-5Search in Google Scholar

Brunow, G., Lundquist, K., Gellerstedt, G. (1999) Lignin. In: Analytical Methods in Wood Chemistry Pulping and Papermaking. Eds. Sjöström, E., Alén, R. Springer-Verlag, Berlin. pp. 77–124.10.1007/978-3-662-03898-7_4Search in Google Scholar

Crestini, C., Melone, F., Sette, M., Saladino, R. (2011) Milled wood lignin: a linear oligomer. Biomacromolecules 12:3928–3935.10.1021/bm200948rSearch in Google Scholar PubMed

Davison, B.H., Parks, J., Davis, M.F., Donohoe, B.S. (2013) Plant cell walls: basics of structure, chemistry, accessibility and the influence on conversion. In: Aqueous Pretreatment of Plant Biomass for Biological and Chemical Conversion to Fuels and Chemicals. Ed. Wyman, C.E. John Wiley & Sons, Ltd. pp. 23–38.10.1002/9780470975831.ch3Search in Google Scholar

Di Meo, F., Lemaur, V., Cornil, J., Lazzaroni, R., Duroux, J.L., Olivier, Y., Trouillas, P. (2013) Free radical scavenging by natural polyphenols: atom versus electron transfer. J. Phys. Chem. A 117:2082–2092.10.1021/jp3116319Search in Google Scholar

Dizhbite, T., Telysheva, G., Jurkjane, V., Viesturs, U. (2004) Characterization of the radical scavenging activity of lignins – natural antioxidants. Bioresource Technol. 95:309–317.10.1016/j.biortech.2004.02.024Search in Google Scholar PubMed

Dizhbite, T., Telysheva, G., Dobele, G., Arshanitsa, A., Bikovens, O., Andersone, A., Kampars, V. (2011) Py-GC/MS for characterization of non-hydrolyzed residues from bioethanol production from softwood. J. Anal. Appl. Pyrol. 90:126–132.10.1016/j.jaap.2010.11.004Search in Google Scholar

Dizhbite, T., Ponomarenko, J., Andersone, A., Dobele, G., Lauberts, M., Krasilnikova, J., Mironova-Ulmane, N., Telysheva, G. (2012) Role of paramagnetic polyconjugated clusters in lignin antioxidant activity (in vitro). IOP Conf. Ser. Mater. Sci. Eng. 38:012033 (doi:10.1088/1757-899X/38/1/012033).10.1088/1757-899X/38/1/012033Search in Google Scholar

Dobele, G., Dizhbite, T., Urbanovich, I., Andersone, A., Ponomarenko, J., Telysheva, G. (2009) Pyrolytic oil on the basis of wood and the antioxidant properties of its water-soluble and -insoluble fraction. J. Anal. Appl. Pyrol. 85:81–85.10.1016/j.jaap.2008.12.006Search in Google Scholar

Domenek, S., Louaifi, A., Guinault, A., Baumberger, S. (2013) Potential of lignins as antioxidant additive in active biodegradable packaging materials. J. Polym. Environ. 21:692–701.10.1007/s10924-013-0570-6Search in Google Scholar

Gorinstein, S., Cvirkova, M., Machackova, I., Haruenkit, R., Park, Y.S., Jung, S.T., Yamamoto, K., Martinez, A.L., Katrich, E., Trakhtenberg, S. (2002) Characterization of antioxidant compounds in Jaffa sweeties and white grapefruits. Food Chem. 84:503–510.10.1016/S0308-8146(03)00127-4Search in Google Scholar

Kozlowski, D., Trouillas, P., Calliste, C., Marsal, P., Lazzaroni, R., Duroux, J.L. (2007a) Density functional theory study of the conformational, electronic, and antioxidant properties of natural chalcones. J. Phys. Chem. A 111:1138–1145.10.1021/jp066496+Search in Google Scholar

Kozlowski, D., Marsal, P., Steel, M., Mokrini, R., Duroux, J.L., Lazzaroni, R., Trouillas, P. (2007b) Theoretical investigation of the formation of a new series of antioxidant depsides from the radiolysis of flavonoid compounds. Radiat. Res. 168:243–252.10.1667/RR0824.1Search in Google Scholar

Lapierre, C., Mila, I., Begum, A.N., Fukushima, K., Heinonen, S.M., Adlercreutz, H., Remesy, C., Scalbert, A. (2004) New precusors of mammalian lignans in rats. In: Proceeding of the 8th European Workshop on Lignocellulisics and Pulp, Riga, Latvia, August 22–25. pp. 101–104.Search in Google Scholar

Leopoldini, M., Pitarch, I.P., Russo, N., Toscano, M. (2004) Structure, conformation, and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study. J. Phys. Chem. A 108:92–96.10.1021/jp035901jSearch in Google Scholar

Litwinienko, G., Ingold, K.U. (2007) Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Acc. Chem. Res. 40:222–230.10.1021/ar0682029Search in Google Scholar

Louaifi, A., Guinault, A., Domenek, S., Ducruet, V., Baumberger, S. (2011) Valorisation of industrial lignon as additive with antioxidiant properties in PLA. Ital. J. Food Sci. 23:142–145.Search in Google Scholar

Louli, V., Ragoussis, N., Magoulas, K. (2004) Recovery of phenolic antioxidants from wine industry by-products. Bioresource Technol. 92:201–208.10.1016/j.biortech.2003.06.002Search in Google Scholar

Morikawa, T. (2007) Search for bioactive constituents from several medicinal foods: hepatoprotective, antidiabetic, and antiallergic activities. J. Nat. Med. 61:112–126.10.1007/s11418-006-0105-8Search in Google Scholar

Moure, A., Cruz, J.M., Franco, D., Domõanguez, J.M., Sineiro, J., Domoanguez, H., Josea, M., Parajoa, C. (2001) Review: natural antioxidants from residual sources. Food Chem. 72:145–171.10.1016/S0308-8146(00)00223-5Search in Google Scholar

Ohra-aho, T., Gomes, F.J.B., Colodette, J.L., Tamminen, T. (2013) S/G ratio and lignin structure among Eucalyptus hybrids determined by Py-GC/MS and nitrobenzene oxidation. J. Anal. Appl. Pyrol. 101:166–171.10.1016/j.jaap.2013.01.015Search in Google Scholar

Ozsoy, N., Can, A., Yanardag, R., Akev, N. (2008) Antioxidant activity of Smilax excelsa L. leaf extracts. Food Chem. 110: 571–583.10.1016/j.foodchem.2008.02.037Search in Google Scholar

Pan, X., Kadla, J.F., Ehara, K., Gilkes, N., Saddler, J.N. (2006) Organosolv ethanol lignin from hybrid poplar as a radical scavenger: relationships between lignin structure, extraction conditions, and antioxidant activity. J. Agric. Food Chem. 54:5806–5813.10.1021/jf0605392Search in Google Scholar PubMed

Ponomarenko, J., Dizhbite, T., Lauberts, M., Viksna, A., Dobele, G., Bikovens, O., Telysheva, G. (2014a) Characterization of softwood and hardwood LignoBoost kraft lignins with emphasis on their antioxidant activity. Bioresources 9:2051–2068.10.15376/biores.9.2.2051-2068Search in Google Scholar

Ponomarenko, J., Trouillas, P., Martin, N., Dizhbite, T., Krasilnikova, J., Telysheva, G. (2014b) Elucidation of antioxidant properties of wood bark derived saturated diarylheptanoids: a comprehensive (DFT-supported) understanding. Phytochemistry 103:178–187.10.1016/j.phytochem.2014.03.010Search in Google Scholar PubMed

Pouteau, C., Cathala, B., Dole, P., Kurek, B., Monties, B. (2005) Structural modification of Kraft lignin after acid treatment: characterization of the apolar extracts and the influence on the antioxidant properties in polypropylene. Ind. Crop. Prod. 21:101–108.10.1016/j.indcrop.2004.01.003Search in Google Scholar

Ringena, O., Lebioda, S., Lehnen, R., Saake, B. (2006) Size-exclusion chromatography of technical lignins in dimethyl sulfoxide/water and dimethylacetamide. J. Chromatogr. A 1102:154–163.10.1016/j.chroma.2005.10.037Search in Google Scholar

Setzer, W.N. (2011) Lignin-derived oak phenolics: a theoretical examination of additional potential health benefits of red wine. J. Mol. Model. 17:1841–1845.10.1007/s00894-010-0893-3Search in Google Scholar PubMed

Seyoum, A., Asres, K., El-Fiky, F.K. (2006) Structure-radical scavenging activity relationships of flavonoids. Phytochemistry 67:2058–2070.10.1016/j.phytochem.2006.07.002Search in Google Scholar PubMed

Shen, D.K., Gu, S., Luo, K.H., Wang, S.R., Fang, M.X. (2010) The pyrolytic degradation of wood-derived lignin from pulping process. Bioresource Technol. 101:6136–6146.10.1016/j.biortech.2010.02.078Search in Google Scholar PubMed

Tao, J., Morikawa, T., Toguchida, I., Ando, S., Matsuda, H., Yoshikawa, M. (2002) Inhibitors of nitric oxide production from the bark of Myrica rubra: structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene. Bioorg. Med. Chem. 10:4005–4012.10.1016/S0968-0896(02)00314-0Search in Google Scholar

Torres, R., Urbina, F., Morales, C., Modak, B., Monache F. (2003) Antioxidant properties of lignans and ferulic acid from the resinous exudate of Larrea nitida. J. Chil. Chem. Soc. 48:61–63.10.4067/S0717-97072003000300012Search in Google Scholar

Trouillas, P., Marsal, P., Siri, D., Lazzaroni, R., Duroux, J.L. (2006) A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: the specificity of the 3-OH site. Food Chem. 97:679–688.10.1016/j.foodchem.2005.05.042Search in Google Scholar

Trouillas, P., Marsal, P., Svobodova, A., Vostalova, J., Gazak, R., Hrbac, J., Sedmera, P., Kren, V., Lazzaroni, R., Duroux, J.L., Walterova, D. (2008) Mechanism of the antioxidant action of silybin and 2,3-dehydrosillybin flavonolignans: a joint experimental and theoretical study. J. Phys. Chem. A 112:1054–1063.10.1021/jp075814hSearch in Google Scholar

Volf, I., Ignat, J., Neamtu, M., Popa, I. (2014) Thermal stability, antioxidant activity and photo-oxidation of natural polyphenols. Chem. Pap. 68:121–129.10.2478/s11696-013-0417-6Search in Google Scholar

Wang, S., Melnyk, J.P., Tsao, R., Marcone, M.F. (2011) How natural dietary antioxidants in fruits, vegetables and legumes promote vascular health. Food Res. Int. 44:14–22.10.1016/j.foodres.2010.09.028Search in Google Scholar

Wolf, C., Krivec, T., Blassnig, J., Lederer, K., Schneider, W. (2002) Examination of the suitability of alpha-tocopherol as a stabilizer for ultra-high molecular weight polyethylene used for articulating surfaces in joint endoprostheses. J. Mater. Sci. Mater. Med. 13:185–189.Search in Google Scholar

Yang, Y., Kinoshita, K., Koyama, K., Takahashi, K., Kondo, S., Watanabe, K. (2002) Structure-antiemetic-activity of some diarylheptanoids and their analogues. Phytomedicine 9:146–152.10.1078/0944-7113-00091Search in Google Scholar PubMed

Zakis, G.F. Functional Analysis of Lignins and Their Derivatives. TAPPI Press, Atlanta, 1994.Search in Google Scholar

Received: 2014-10-1
Accepted: 2015-2-17
Published Online: 2015-4-14
Published in Print: 2015-8-1

©2015 by De Gruyter

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