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Wood Research and Technology

Holzforschung

Cellulose – Hemicelluloses – Lignin – Wood Extractives

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Volume 69, Issue 6

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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 / Galina Telysheva
Published Online: 2015-04-14 | DOI: https://doi.org/10.1515/hf-2014-0280

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.

Keywords: ABTS•+; correlated components regression; DPPH•; natural antioxidants; quantitative structure-antioxidant activity relationship; structure-antioxidant activity relationship; technical lignins

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.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.CrossrefGoogle 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.CrossrefGoogle 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.CrossrefGoogle 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.CrossrefGoogle Scholar

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

  • Crestini, C., Melone, F., Sette, M., Saladino, R. (2011) Milled wood lignin: a linear oligomer. Biomacromolecules 12:3928–3935.Web of ScienceCrossrefPubMedGoogle Scholar

  • 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.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.CrossrefGoogle 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.CrossrefGoogle Scholar

  • 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.CrossrefWeb of ScienceGoogle 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).CrossrefGoogle 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.Web of ScienceCrossrefGoogle 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.Web of ScienceCrossrefGoogle 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.CrossrefGoogle 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.CrossrefGoogle 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.PubMedCrossrefWeb of ScienceGoogle 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.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.CrossrefGoogle 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.CrossrefWeb of ScienceGoogle 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.Google Scholar

  • Louli, V., Ragoussis, N., Magoulas, K. (2004) Recovery of phenolic antioxidants from wine industry by-products. Bioresource Technol. 92:201–208.CrossrefGoogle Scholar

  • Morikawa, T. (2007) Search for bioactive constituents from several medicinal foods: hepatoprotective, antidiabetic, and antiallergic activities. J. Nat. Med. 61:112–126.Web of ScienceCrossrefGoogle 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.CrossrefGoogle 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.Web of ScienceCrossrefGoogle Scholar

  • Ozsoy, N., Can, A., Yanardag, R., Akev, N. (2008) Antioxidant activity of Smilax excelsa L. leaf extracts. Food Chem. 110: 571–583.CrossrefGoogle 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.CrossrefGoogle Scholar

  • 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.CrossrefGoogle 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.PubMedWeb of ScienceCrossrefGoogle Scholar

  • 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.CrossrefGoogle 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.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.Web of ScienceCrossrefGoogle Scholar

  • Seyoum, A., Asres, K., El-Fiky, F.K. (2006) Structure-radical scavenging activity relationships of flavonoids. Phytochemistry 67:2058–2070.PubMedCrossrefGoogle Scholar

  • 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.Web of ScienceCrossrefGoogle Scholar

  • 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.PubMedCrossrefGoogle 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.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.CrossrefGoogle 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.CrossrefWeb of ScienceGoogle 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.CrossrefGoogle 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.CrossrefWeb of ScienceGoogle 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.CrossrefGoogle 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.CrossrefPubMedGoogle Scholar

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

About the article

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


Received: 2014-10-01

Accepted: 2015-02-17

Published Online: 2015-04-14

Published in Print: 2015-08-01


Citation Information: Holzforschung, Volume 69, Issue 6, Pages 795–805, ISSN (Online) 1437-434X, ISSN (Print) 0018-3830, DOI: https://doi.org/10.1515/hf-2014-0280.

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