Selective recovery of polyphenols from MDF process waters by adsorption on a macroporous, cross-linked pyrrolidone-based resin
Abstract
A scalable, fixed-bed adsorption system for the removal and selective recovery of polyphenols (lignans and stilbenes) from medium-density fiberboard (MDF) process waters was developed. Before adsorption, fibers and non-colloidal substances were removed from process water by centrifugation, while colloidal fatty and resin acids were removed by filtration through a 30-kDa cut-off membrane. Polyphenols were then isothermally adsorbed on a medium-pressure liquid chromatography (MPLC) column packed with Divergan® RS, a regenerable macroporous, cross-linked pyrrolidone-based [polyvinylpolypyrrolidone (PVPP)] resin. Loading at acidic pH and subsequent gradient elution of polyphenols with methanol were monitored at 280 nm, and elution conditions for selective polyphenol recovery were optimized based on gas chromatography/mass spectrometry (GC/MS) analyses of the obtained fractions. Lignans were eluted in successive fractions containing the individual lignans in different proportions, followed by pinosylvin in a separate fraction. The capacity of the PVPP for hydroxymatairesinol (HMR) as a model lignan was determined to be 37.4 mg g−1 at 1% breakthrough. Highly polar substances such as sugars and sugar alcohols, however, were not retained on the column and remained in the flow-through. The results revealed the benefits of PVPP for the recovery of potentially valuable polyphenols from MDF process waters while reducing carbon load and toxicity for subsequent biological treatment.
Acknowledgments
The scanning electron microscopy image acquisition of PVPP was carried out using the facilities at the University Service Center for Transmission Electron Microscopy (USTEM), TU Wien, Austria.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: We thank the Austrian government and the federal governments of Upper Austria, Lower Austria and Carinthia for funding the Competence Center of Wood Composites and Wood Chemistry.
Employment or leadership: None declared.
Honorarium: None declared.
References
Adlercreutz, H., Mousavi, Y., Clark, J., Höckerstedt, K., Hämäläinen,E., Wähälä, K., Mäkelä, T., Hase, T. (1992) Dietary phytoestrogens and cancer: in vitro and in vivo studies.J. Steroid Biochem. Mol. Biol. 41:331–337.10.1016/0960-0760(92)90359-QSuche in Google Scholar
Al Manasrah, M., Kallioinen, M., Ilvesniemi, H., Mänttäri, M. (2012) Recovery of galactoglucomannan from wood hydrolysate using regenerated cellulose ultrafiltration membranes. Bioresour. Technol. 114:375–381.10.1016/j.biortech.2012.02.014Suche in Google Scholar
Asano, K., Shinagawa, K., Hashimoto, N. (1982) Characterization of haze-forming proteins of beer and their roles in chill haze formation. J. Am. Soc. Brew. Chem. 40:147–154.10.1094/ASBCJ-40-0147Suche in Google Scholar
Bridi, R., Troncoso, M., Folch-Cano, C., Fuentes, J., Speisky, H., Lopez-Alarcon, C. (2014) A polyvinylpolypyrrolidone (PVPP)-assisted folin–ciocalteu assay to assess total phenol content of commercial beverages. Food Anal. Method. 7:2075–2083.10.1007/s12161-014-9856-0Suche in Google Scholar
Buck, K., Zaineddin, A.K., Vrieling, A., Linseisen, J., Chang-Claude, J. (2010) Meta-analyses of lignans and enterolignans in relation to breast cancer risk. Am. J. Clin. Nutr. 92:141–153.10.3945/ajcn.2009.28573Suche in Google Scholar
Bylund, A., Zhang, J.X., Bergh, A., Damber, J.E., Widmark, A., Johansson, A., Hallmans, G. (2000) Rye bran and soy protein delay growth and increase apoptosis of human LNCaP prostate adenocarcinoma in nude mice. Prostate 42:304–314.10.1002/(SICI)1097-0045(20000301)42:4<304::AID-PROS8>3.0.CO;2-ZSuche in Google Scholar
Bylund, A., Saarinen, N., Zhang, J.-X., Bergh, A., Widmark, A., Johansson, A., Stattin, P. (2005) Anticancer effects of a plant lignan 7-hydroxymatairesinol on a prostate cancer model in vivo. Exp. Biol. Med. 230:217–223.10.1177/153537020523000308Suche in Google Scholar
Deyama, T., Nishibe, S. (2016) Pharmacological properties of lignans. In: Lignin and Lignans: Advances in Chemistry. Eds. Heitner, C., Dimmel, D., Schmidt, J. CRC Press, Boca Raton, FL. pp. 585–619.Suche in Google Scholar
DIN ISO 3696. Water for Analytical Laboratory Use: Specification and Test Methods. DIN Standards Committee Materials Testing, Berlin, Germany, 1991.Suche in Google Scholar
Doner, L.W., Becard, G., Irwin, P.L. (1993) Binding of flavonoids by polyvinylpolypyrrolidone. J. Agric. Food Chem. 41:753–757.10.1021/jf00029a014Suche in Google Scholar
Dong, Z.-B., Liang, Y.-R., Fan, F.-Y., Ye, J.-H., Zheng, X.-Q., Lu, J.-L. (2011) Adsorption behavior of the catechins and caffeine onto polyvinylpolypyrrolidone. J. Agric. Food Chem. 59:4238–4247.10.1021/jf200089mSuche in Google Scholar
Eckerman, C., Holmbom, B. (2004) Method for recovery of compression wood and/or normal wood from oversize chips. U.S. Pat. No. 6,739,533 B2.Suche in Google Scholar
Eklund, P.C., Sundell, F.J., Smeds, A.I., Sjöholm, R.E. (2004) Reactions of the natural lignan hydroxymatairesinol in basic and acidic nucleophilic media: formation and reactivity of a quinone methide intermediate. Org. Biomol. Chem. 2:2229–2235.10.1039/B402849JSuche in Google Scholar
Fang, J.-G., Lu, M., Chen, Z.-H., Zhu, H.-H., Li, Y., Yang, L., Wu, L.-M., Liu, Z.-L. (2002) Antioxidant effects of resveratrol and its analogues against the free-radical-induced peroxidation of linoleic acid in micelles. Chem. Eur. J. 8:4191–4198.10.1002/1521-3765(20020916)8:18<4191::AID-CHEM4191>3.0.CO;2-SSuche in Google Scholar
Folch-Cano, C., Olea-Azar, C., Speisky, H. (2013) Structural and thermodynamic factors on the adsorption process of phenolic compounds onto polyvinylpolypyrrolidone. Colloid. Surf. A 418:105–111.10.1016/j.colsurfa.2012.11.017Suche in Google Scholar
Holmbom, B., Eckerman, C., Eklund, P., Hemming, J., Nisula, L., Reunanen, M., Sjöholm, R., Sundberg, A., Sundberg, K., Willför, S. (2003) Knots in trees – a new rich source of lignans.Phytochem. Rev. 2:331–340.10.1023/B:PHYT.0000045493.95074.a8Suche in Google Scholar
Hovelstad, H., Leirset, I., Oyaas, K., Fiksdahl, A. (2006) Screening analyses of pinosylvin stilbenes, resin acids and lignans in Norwegian conifers. Molecules 11:103–114.10.3390/11010103Suche in Google Scholar
Knapp, D.R. Handbook of Analytical Derivatization Reactions. John Wiley & Sons, New York, 1979. p. 390.Suche in Google Scholar
Korte, H., Lehtola, V.-M., Unkila, M., Hiilovaara-Teijo, M., Ahotupa, M. (2014) Hydroxymateiresinol topical formulations. European Pat. No. 1 513 514 B1.Suche in Google Scholar
Koskela, A., Reinisalo, M., Hyttinen, J.M., Kaarniranta, K., Karjalainen, R.O. (2014) Pinosylvin-mediated protection against oxidative stress in human retinal pigment epithelial cells. Mol. Vis. 20:760–769.Suche in Google Scholar
Landete, J.M. (2012) Plant and mammalian lignans: a review of source, intake, metabolism, intestinal bacteria and health. Food Res. Int. 46:410–424.10.1016/j.foodres.2011.12.023Suche in Google Scholar
Lee, S.K., Lee, H.J., Min, H.Y., Park, E.J., Lee, K.M., Ahn, Y.H., Cho,Y.J., Pyee, J.H. (2005) Antibacterial and antifungal activity of pinosylvin, a constituent of pine. Fitoterapia 76:258–260.10.1016/j.fitote.2004.12.004Suche in Google Scholar
Park, E.-J., Min, H.-Y., Ahn, Y.-H., Bae, C.-M., Pyee, J.-H., Lee, S.K. (2004) Synthesis and inhibitory effects of pinosylvin derivatives on prostaglandin E2 production in lipopolysaccharide-induced mouse macrophage cells. Bioorg. Med. Chem. Lett. 14:5895–5898.10.1016/j.bmcl.2004.09.022Suche in Google Scholar
Park, E.-J., Chung, H-J., Park, H.J., Kim, G.D., Ahn, Y-H., Lee, S.K. (2013) Suppression of Src/ERK and GSK-3/β-catenin signaling by pinosylvin inhibits the growth of human colorectal cancer cells. Food Chem. Toxicol. 55:424–433.10.1016/j.fct.2013.01.007Suche in Google Scholar
Persson, T., Krawczyk, H., Nordin, A.-K., Jönsson, A.-S. (2010) Fractionation of process water in thermomechanical pulp mills. Bioresour. Technol. 101:3884–3892.10.1016/j.biortech.2009.12.142Suche in Google Scholar
Peuhu, E., Paul, P., Remes, M., Holmbom, T., Eklund, P., Sjöholm,R., Eriksson, J.E. (2013) The antitumor lignan Nortrachelogenin sensitizes prostate cancer cells to TRAIL-induced cell death by inhibition of the Akt pathway and growth factor signaling. Biochem. Pharmacol. 86:571–583.10.1016/j.bcp.2013.05.026Suche in Google Scholar
Qu, H., Madl, R.L., Takemoto, D.J., Baybutt, R.C., Wang, W. (2005) Lignans are involved in the antitumor activity of wheat bran in colon cancer SW480 cells. J. Nutr. 135:598–602.10.1093/jn/135.3.598Suche in Google Scholar PubMed
Rajbhar, K., Dawda, H., Mukundan, U. (2015) Polyphenols: methods of extraction. Sci. Revs. Chem. Commun. 5:1–6.Suche in Google Scholar
Rawle, A. (2003) The basic principles of particle-size analysis. Surf. Coat. Int. A 86:58–65.Suche in Google Scholar
Siebert, K.J., Troukhanova, N.V., Lynn, P.Y. (1996) Nature of polyphenol-protein interactions. J. Agric. Food Chem. 44: 80–85.10.1021/jf9502459Suche in Google Scholar
Stojanović, S., Brede, O. (2002) Elementary reactions of the antioxidant action of trans-stilbene derivatives: resveratrol, pinosylvin and 4-hydroxystilbene. Phys. Chem. Chem. Phys. 4:757–764.10.1039/b109063cSuche in Google Scholar
Sundberg, K., Holmbom, B., Eckerman, C., Adams, M. (2002) Method for recovering non-fibrous substances from wood material. WO, 2, 40767.Suche in Google Scholar
Widhalm, B., Rieder-Gradinger, C., Kuncinger, T., Srebotnik, E. (2017) Biodegradation of terpenes for emission-reduced oriented strand boards (OSB). Holzforschung 71:259–264.10.1515/hf-2016-0103Suche in Google Scholar
Widhalm, B., Rieder-Gradinger, C., Kuncinger, T., Srebotnik, E. (2018) Biotechnological approach for α-pinene, β-pinene, and Δ3-carene degradation in pine wood for reduced terpene emissions from Oriented Strand Boards. Int. Biodeterior. Biodegrad. 134:103–109.10.1016/j.ibiod.2018.08.010Suche in Google Scholar
Willför, S., Hemming, J., Reunanen, R., Eckerman, C., Holmbom, B. (2003a) Lignans and lipophilic extractives in Norway spruce knots and stemwood. Holzforschung 57:27–36.10.1515/HF.2003.005Suche in Google Scholar
Willför, S., Hemming, J., Reunanen, R., Holmbom, B. (2003b) Phenolic and lipophilic extractives in Scots pine knots and stemwood. Holzforschung 57:359–372.10.1515/HF.2003.054Suche in Google Scholar
Yoder, S.C., Lancaster, S.M., Hullar, M.A.J., Lampe, J.W. (2014) Gut microbial metabolism of plant lignans: influence on human health. In: Diet-Microbe Interactions in the Gut. Eds. Tuohi, K., Del Rio, D. Academic Press, San Diego, CA. pp. 103–117.Suche in Google Scholar
Zikeli, F., Ters, T., Fackler, K., Srebotnik, E., Li, J. (2014) Successive and quantitative fractionation and extensive structural characterization of lignin from wheat straw. Ind. Crop. Prod. 61:249–257.10.1016/j.indcrop.2014.07.013Suche in Google Scholar
©2020 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Editorial
- The 15th European Workshop on Lignocellulosics and Pulp (EWLP) in Aveiro, Portugal (June 26–29, 2018)
- Review
- Extractives and biological activities of Lamiaceae species growing in Uzbekistan
- Original Articles
- New drum-chipping technology for a more uniform size distribution of wood chips
- Characterization of enzyme-resistant xylooligosaccharides extracted from hardwood chips by pre-hydrolysis and further depolymerized by enzymatic treatment
- Stabilising mannose using sodium dithionite at alkaline conditions
- Xylan accessibility of bleached eucalypt pulp in alkaline solutions
- Investigation of eucalypt and pine wood acid-soluble lignin by Py-GC-MS
- The reaction of lignin model compounds during enzymatic bleaching with a Curvularia verruculosa haloperoxidase: impact on chlorination
- Molecular weight-based fractionation of lignin oils by membrane separation technology
- Phenol-formaldehyde resins with suitable bonding strength synthesized from “less-reactive” hardwood lignin fractions
- Impact of birch xylan composition and structure on film formation and properties
- Gram-scale economical synthesis of trans-coniferyl alcohol and its corresponding thiol
- Lignosulfonate-based polyurethane materials via cyclic carbonates: preparation and characterization
- Bioconversion of pine stumps to ethanol: pretreatment and simultaneous saccharification and fermentation
- Selective recovery of polyphenols from MDF process waters by adsorption on a macroporous, cross-linked pyrrolidone-based resin
- Short Note
- Lignin analysis with benchtop NMR spectroscopy
Artikel in diesem Heft
- Frontmatter
- Editorial
- The 15th European Workshop on Lignocellulosics and Pulp (EWLP) in Aveiro, Portugal (June 26–29, 2018)
- Review
- Extractives and biological activities of Lamiaceae species growing in Uzbekistan
- Original Articles
- New drum-chipping technology for a more uniform size distribution of wood chips
- Characterization of enzyme-resistant xylooligosaccharides extracted from hardwood chips by pre-hydrolysis and further depolymerized by enzymatic treatment
- Stabilising mannose using sodium dithionite at alkaline conditions
- Xylan accessibility of bleached eucalypt pulp in alkaline solutions
- Investigation of eucalypt and pine wood acid-soluble lignin by Py-GC-MS
- The reaction of lignin model compounds during enzymatic bleaching with a Curvularia verruculosa haloperoxidase: impact on chlorination
- Molecular weight-based fractionation of lignin oils by membrane separation technology
- Phenol-formaldehyde resins with suitable bonding strength synthesized from “less-reactive” hardwood lignin fractions
- Impact of birch xylan composition and structure on film formation and properties
- Gram-scale economical synthesis of trans-coniferyl alcohol and its corresponding thiol
- Lignosulfonate-based polyurethane materials via cyclic carbonates: preparation and characterization
- Bioconversion of pine stumps to ethanol: pretreatment and simultaneous saccharification and fermentation
- Selective recovery of polyphenols from MDF process waters by adsorption on a macroporous, cross-linked pyrrolidone-based resin
- Short Note
- Lignin analysis with benchtop NMR spectroscopy