Abstract
The extraction conditions have been evaluated concerning the recovery of specific polyphenols from Scots pine (Pinus sylvestris) knots by means of an accelerated solvent extractor. The composition of the extracts was determined by gas chromatography, gas chromatography-mass spectrometry, and high-performance size-exclusion chromatography. The main phenolic compounds are the stilbenes pinosylvin and its monomethyl ether and the lignan nortrachelogenin (NTG), and their amounts vary a lot from sample to sample. The sequential extraction with a nonpolar solvent as a first step for removing the lipophilic compounds was the most efficient approach for the recovery of both pinosylvins and NTG. For food applications, hot water and 85% aqueous ethanol were good solvents for the production of the substances in focus. An industrial knotwood sample from a pulp mill was sequentially extracted with cyclohexane and ethanol/water (95:5) in a large-scale Soxhlet equipment. The results show that the industrial production of pinosylvins and NTG from knots is feasible.
The research leading to these results has received funding from the WoodWisdom-Net Research Programme, which is a transnational R&D program jointly funded by national funding organizations within the framework of the ERA-NET WoodWisdom-Net 2. This work was also part of the activities at the Process Chemistry Centre at Åbo Akademi University. Metsä Fibre Oy is acknowledged for providing the industrial pine wood samples.
References
Allen, L.H. (1980) Mechanisms and control of pitch deposition in newsprint mills. Tappi J. 63:81–87.Search in Google Scholar
Bhattacharya, A., Sood, P., Citovsky, V. (2010) The roles of plant phenolics in defence and communication during Agrobacterium and Rhizobium infection. Mol. Plant Pathol. 11:705–719.Search in Google Scholar
Binbuga, N., Ruhs, C., Hasty, J.K., Henry, W.P., Schultz, T.P. (2008) Developing environmentally benign and effective organic wood preservatives by understanding the biocidal and non-biocidal properties of extractives in naturally durable heartwood. Holzforschung 62:264–269.10.1515/HF.2008.038Search in Google Scholar
Donoso-Fierro, C., Becerra, J., Bustos-Concha, E., Silva, M. (2009) Chelating and antioxidant activity of lignans from Chilean woods (Cupressaceae). Holzforschung 63:559–563.10.1515/HF.2009.123Search in Google Scholar
Eckerman, C., Holmbom, B. (2001) Method for recovery of compression wood and/or normal wood from oversize chips. Patent application, PCT/FI101/00691. WO 02/09893 A1, Finn. Pat. 112041.Search in Google Scholar
Ekman, R., Holmbom, B. (1989). Analysis by gas chromatography of the wood extractives in pulp and water samples from mechanical pulping of spruce. Nord. Pulp Pap. Res. J. 4:16–24.Search in Google Scholar
Ekman, R., Willför, S., Sjöholm, R., Reunanen, M., Mäki, J., Lehtilä, R., Eckerman, C. (2002) Identification of the lignan nortrachelogenin in knot and branch heartwood of Scots pine (Pinus sylvestris L.). Holzforschung 56:253–256.10.1515/HF.2002.041Search in Google Scholar
Farrell, R.L., Blanchette, R.A., Brush, T.S., Hadar, Y., Iverson, S., Krisa, K., Wendler, P.A., Zimmerman, W. (1993) Cartapip™: a biopulping product for control of pitch and resin acid problems in pulp mills. J. Biotechnol. 30:115–122.10.1016/0168-1656(93)90032-ISearch in Google Scholar
Ford, J.D., Davin, L.B., Lewis, N.G. (1999) Plant lignans and health: cancer chemoprevention and biotechnological opportunities. Basic Life Sci. 66:675–694.10.1007/978-1-4615-4139-4_38Search in Google Scholar
Gharras, H.E. (2009) Polyphenols: food sources, properties and applications—a review. Int. J. Food Sci. Technol. 44:2512–2518.Search in Google Scholar
Gutiérrez, A., Río, J.D., Martínez, J.M., Martínez, A.T. (2001) The biotechnological control of pitch in paper pulp manufacturing. Trends Biotechnol. 19:340–348.10.1016/S0167-7799(01)01705-XSearch in Google Scholar
Hakkila, P. (1998) Structure and properties of wood and woody biomass. In: Forest Resources and Sustainable Management. Eds. Kellomäki, S., Tappi Press, Atlanta. pp. 158–162.Search in Google Scholar
Jayaprakasha, G.K., Singh, R.P., Sakariah, K.K. (2001) Antioxidant activity of grape seed (Vitis vinifera) extracts on peroxidation models in vitro. Food Chem. 73:285–290.10.1016/S0308-8146(00)00298-3Search in Google Scholar
Khokhar, S., Magnusdottir, S. (2002) Total phenol, catechin, and caffeine contents of teas commonly consumed in the United Kingdom. J. Agric. Food Chem. 50:565–570.10.1021/jf010153lSearch in Google Scholar
Kitts, D., Yuan, Y., Wijewickreme, A., Thompson, L. (1999) Antioxidant activity of the flaxseed lignan secoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone. Mol. Cell Biochem. 202:91–100.10.1023/A:1007022329660Search in Google Scholar
Liang, Y., Lu, J., Zhang, L., Wu, S., Wu, Y. (2003) Estimation of black tea quality by analysis of chemical composition and colour difference of tea infusions. Food Chem. 80:283–290.10.1016/S0308-8146(02)00415-6Search in Google Scholar
Mburu, F., Dumarçay, S., Gérardin, P. (2007) Evidence of fungicidal and termicidal properties of Prunus africana heartwood extractives. Holzforschung 61:323–325.10.1515/HF.2007.043Search in Google Scholar
Mukhopadhyay, S., Luthria, D.L., Robbins, R.J. (2006) Optimization of extraction process for phenolic acids from black cohosh (Cimicifuga racemosa) by pressurized liquid extraction. J. Sci. Food Agric. 86:156–162.10.1002/jsfa.2326Search in Google Scholar
Nkhili, E., Tomao, V., Hajji, E.H., Boustani, E.E., Chemat, F., Dangles, O. (2009) Microwave-assisted water extraction of green tea polyphenols. Phytochem. Anal. 20:408–415.Search in Google Scholar
Nishibe, S. (1997) Bioactive phenolic compounds for cancer prevention from herbal medicines. In: Food Factors for Cancer Prevention. Eds. Ohigashi, H., Osawa, T., Terao, J., Watanabe, S., Yoshikawa, T. Springer, Tokyo. pp. 276–279.10.1007/978-4-431-67017-9_55Search in Google Scholar
Pekić, B., Kovač, V., Alonso, E., Revilla, E. (1998) Study of the extraction of proanthocyanidins from grape seeds. Food Chem. 61:201–206.10.1016/S0308-8146(97)00128-3Search in Google Scholar
Pietarinen, S.P., Willför, S.M., Ahotupa, M.O., Hemming, J.E., Holmbom, B.R. (2006) Knotwood and bark extracts: strong antioxidants from waste materials. J. Wood. Sci. 52:436–444.Search in Google Scholar
Rennerfelt, E. (1943) Om vår nuvarande kunskap om törskatesvampen (Peridermium pini) och sättet för dess spridning och tillväxt. Svenska Skogsv. Tidskrift 41:305–324.Search in Google Scholar
Saarinen, N.M., Wärri, A., Airio, M., Smeds, A., Mäkelä, S. (2007) Role of dietary lignans in the reduction of breast cancer risk. Mol. Nutr. Food Res. 51:857–866.Search in Google Scholar
Smeds, A.I., Eklund, P.C., Monogioudi, E., Willför, S.M. (2012) Chemical characterization of polymerized products formed in the reactions of matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl. Holzforschung 66:283–294.10.1515/hf.2011.151Search in Google Scholar
Scheffer, T.C., Cowling, E.B. (1966) Natural resistance of wood to microbial deterioration. Annu. Rev. Phytopathol. 4:147–168.10.1146/annurev.py.04.090166.001051Search in Google Scholar
Sokół-Łętowska, A., Oszmiański, J., Wojdyło, A. (2007) Antioxidant activity of the phenolic compounds of hawthorn, pine and skullcap. Food Chem. 103:853–859.10.1016/j.foodchem.2006.09.036Search in Google Scholar
Spigno, G., Tramelli, L., Faveri, D.M.D. (2007) Effects of extraction time, temperature and solvent on concentration and antioxidant activity of grape marc phenolics. J. Food Eng. 81:200–208.10.1016/j.jfoodeng.2006.10.021Search in Google Scholar
Välimaa, A., Honkalampi-Hamalainen, U., Pietarinen, S., Willför, S., Holmbom, B., Vonwright, A. (2007) Antimicrobial and cytotoxic knotwood extracts and related pure compounds and their effects on food-associated microorganisms. Int. J. Food Microbiol. 115:235–243.10.1016/j.ijfoodmicro.2006.10.031Search in Google Scholar PubMed
Venäläinen, M., Harju, A.M., Saranpää, P., Kainulainen, P., Tiitta, M., Velling, P. (2004) The concentration of phenolics in brown-rot decay resistant and susceptible Scots pine heartwood. Wood Sci. Technol. 38:109–118.Search in Google Scholar
Venäläinen, M., Harju, A.M., Terziev, N., Laakso, T., Saranpää, P. (2006) Decay resistance, extractive content, and water sorption capacity of Siberian larch (Larix sibirica Lebed.) heartwood timber. Holzforschung 60:99–103.10.1515/HF.2006.017Search in Google Scholar
Ward, R.S. (1999) Lignans, neolignans and related compounds. Nat. Prod. Rep. 16:75–96.Search in Google Scholar
Willför, S., Hemming, J., Reunanen, M., Eckerman, C., Holmbom, B. (2003a) Lignans and lipophilic extractives in Norway spruce knots and stemwood. Holzforschung 57:27–36.10.1515/HF.2003.005Search in Google Scholar
Willför, S., Hemming, J., Reunanen, M., Holmbom, B. (2003b) Phenolic and lipophilic extractives in Scots pine knots and stemwood. Holzforschung 57:359–372.10.1515/HF.2003.054Search in Google Scholar
Willför, S.M., Ahotupa, M.O., Hemming, J.E., Reunanen, M.H.T., Eklund, P.C., Sjöholm, R.E., Eckerman, C.S.E., Pohjamo, S.P., Holmbom, B.R. (2003c) Antioxidant activity of knotwood extractives and phenolic compounds of selected tree species. J. Agric. Food Chem. 51:7600–7606.10.1021/jf030445hSearch in Google Scholar PubMed
Willför, S., Nisula, L., Hemming, J., Reunanen, M., Holmbom, B. (2004a) Bioactive phenolic substances in industrially important tree species. Part 1: knots and stemwood of different spruce species. Holzforschung 58:335–344.10.1515/HF.2004.052Search in Google Scholar
Willför, S., Nisula, L., Hemming, J., Reunanen, M., Holmbom, B. (2004b) Bioactive phenolic substances in industrially important tree species. Part 2: knots and stemwood of fir species. Holzforschung 58:650–659.10.1515/HF.2004.119Search in Google Scholar
Willför, S., Eklund, P., Sjöholm, R., Reunanen, M., Sillanpää, R., von Schoultz S., Hemming, J., Nisula, L., Holmbom, B. (2005) Bioactive phenolic substances in industrially important tree species. Part 4: Identification of two new 7-hydroxy divanillyl butyrolactol lignans in some spruce, fir, and pine species. Holzforschung 59:413–417.10.1515/HF.2005.067Search in Google Scholar
Willför, S., Hafizoglu, H., Tümen, I., Yazici, H., Arfan, M., Ali, M., Holmbom, B. (2006) Extractives of Turkish and Pakistani tree species. Holz Roh. Werkst. 65:215–221.10.1007/s00107-006-0160-6Search in Google Scholar
Willför, S., Ali, M., Karonen, M., Reunanen, M., Arfan, M., Harlamow, R. (2009) Extractives in bark of different conifer species growing in Pakistan. Holzforschung 63:551–558.10.1515/HF.2009.095Search in Google Scholar
Xu, B.J., Chang, S.K. (2007) A comparative study on phenolic profiles and antioxidant activities of legumes as affected by extraction solvents. J. Food Sci. 72:S159–S166.10.1111/j.1750-3841.2006.00260.xSearch in Google Scholar PubMed
Yilmaz, Y., Toledo, R.T. (2006) Oxygen radical absorbance capacities of grape/wine industry byproducts and effect of solvent type on extraction of grape seed polyphenols. J. Food Compos. Anal. 19:41–48.10.1016/j.jfca.2004.10.009Search in Google Scholar
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