Characterization of Pinus nigra var. laricio [Maire] bark extracts at the analytical and pilot scale
-
Sauro Bianchi
,
Florian Zikeli
Abstract
Pinus nigra var. laricio bark and its hot-water extracts (HWE) obtained at an analytical and pilot plant scale have been characterized in terms of phenolic extractives, condensed tannins (CTs), carbohydrates and inorganic compounds. Analytical extractions with aqueous acetone were also performed for comparison with HWE. The bark contains 35.5 g kg−1 CT, and two-thirds of it could be extracted. Analytical HWE at 75°C led to a total yield of 56.4 g kg−1. The extracts are mainly composed of phenolic compounds (50.7%) and pectins (19.7%). CTs amount to 17.9% of the extracts and are procyanidins with a mean degree of polymerization (DP) of about 9. Non-tannin phenolic oligomers also occurred in the extracts, which could be identified by pyrolysis gas chromatography mass spectrometry (Py-GC/MS) as lignin fragments. Matrix-assisted laser desorption/ionization-time-of-flight-mass spectrometry (MALDI-TOF MS) revealed that the CT is a flavanol derivative in methylated form. Further characterization and tailoring of the HWE properties is needed in the context of their specific application.
Acknowledgments
The authors would like to thank the Ambi.Tec.Fil.Legno project (PON03_00024_1: scientific coordination: Prof. Giuseppe Scarascia-Mugnozza) for the financial support of the study and Schilliger Bois SAS (Volgelsheim, France) for the kind support in drying the bark.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: Ambi.Tec.Fil.Legno Project PON03_ 00024_1.
Employment or leadership: None declared.
Honorarium: None declared.
References
Bianchi, S., Kroslakova, I., Janzon, R., Mayer, I., Saake, B., Pichelin, F. (2015) Characterization of condensed tannins and carbohydrates in hot water bark extracts of European softwood species. Phytochemistry 120:53–61.10.1016/j.phytochem.2015.10.006Suche in Google Scholar
Bianchi, S., Koch, G., Janzon, R., Mayer, I., Saake, B., Pichelin, F. (2016) Hot water extraction of Norway spruce (Picea abies [Karst.]) bark: analyses of the influence of bark aging and process parameters on the extract composition. Holzforschung 70:619–631.10.1515/hf-2015-0160Suche in Google Scholar
Dargaville, T.R., Guerzoni, F.N., Looney, M.G., Shipp, D.A., Solomon, D.H., Zhang, X.Q. (1997) Determination of molecular weight distribution of novolac resins by gel permeation chromatography. J. Polym. Sci. A Polym. Chem. 35:1399–1407.10.1002/(SICI)1099-0518(199706)35:8<1399::AID-POLA8>3.0.CO;2-VSuche in Google Scholar
Diouf, P.N., Tibirna, C.M., Gracia-Perez, M.-E., Royer, M., Dubé, P., Stevanovic, T. (2013) Structural elucidation of condensed tannins from Picea mariana bark. J. Biomat. Nanobiotechnol. 4:1–8.10.4236/jbnb.2013.43A001Suche in Google Scholar
Dix, B., Marutzky, R. (1987) Tanninformaldehydharze aus den Rindenextrakten von Fichte (Picea abies) und Kiefer (Pinus sylvestris). Holz Roh. Werkst. 45:457–463.10.1007/BF02606778Suche in Google Scholar
Everette, J.D., Bryant, Q.M., Green, A.M., Abbey, Y.A., Wangila, G.W., Walker, R.B. (2010) Thorough study of reactivity of various compound classes toward the Folin-Ciocalteu reagent. J. Agric. Food Chem. 58:8139–8144.10.1021/jf1005935Suche in Google Scholar
Faix, O., Meier, D., Fortmann, I. (1990a) Thermal degradation products of wood: gas chromatographic separation and mass spectrometric characterization of monomeric lignin derived products. Holz Roh. Werkst. 48:281–285.10.1007/BF02626519Suche in Google Scholar
Faix, O., Meier, D., Fortmann, I. (1990b) Thermal degradation products of wood: a collection of electron-impact (EI) mass spectra of monomeric lignin derived products. Holz Roh. Werks. 48:351–354.10.1007/BF02639897Suche in Google Scholar
Faix, O., Fortmann, I., Bremer, J., Meier, D. (1991a) Thermal degradation products of wood: gas chromatographic separation and mass spectrometric characterization of polysaccharide derived products. Holz Roh. Werkst. 49:213–219.10.1007/BF02613278Suche in Google Scholar
Faix, O., Fortmann, I., Bremer, J., Meier, D. (1991b) Thermal degradation products of wood: a collection of electron-impact (EI) mass spectra of polysaccharide derived products. Holz Roh. Werkst. 49:299–304.10.1007/BF02663795Suche in Google Scholar
Galletti, G.C., Modaferri, V., Poiana, M., Bocchini, P. (1995) Analytical pyrolysis and thermally assisted hydrolysis-methylation of wine-tannin. J. Agric. Food Chem. 43:1859–1863.10.1021/jf00055a020Suche in Google Scholar
Garnier, S., Pizzi, A., Vorster, O.C., Halasz, L. (2001) Comparative rheological characteristics of industrial polyflavonoid tannin extracts. J. Appl. Polym. Sci. 81:1634–1642.10.1002/app.1594Suche in Google Scholar
Kemppainen, K., Siika-aho, M., Pattathil, S., Giovando, S., Kruus, K. (2014) Spruce bark as an industrial source of condensed tannins and non-cellulosic sugars. Ind. Crops Prod. 52, 158–168.10.1016/j.indcrop.2013.10.009Suche in Google Scholar
Le Normand, M., Mélida, H., Holmbom, B., Michaelsen, T.E., Inngjerdingen, M., Bulone, V., Paulsen, B.S., Ek, M., 2014. Hot-water extracts from the inner bark of Norway spruce with immunomodulating activities. Carbohydr. Polym. 101, 699–704.10.1016/j.carbpol.2013.09.067Suche in Google Scholar
Liang, S., Guo, X.Y., Lautner, S., Saake, B. (2014) Removal of hexavalent chromium by different modified spruce bark adsorbents. J. Wood Chem. Techol. 34:273–290.10.1080/02773813.2013.869606Suche in Google Scholar
Martin-Dupont, F., Gloaguen, V., Granet, R., Guilloton, M., Morvan, H., Krausz, P. (2002) Heavy metal adsorption by crude coniferous barks: a modelling study. J. Environ. Sci. Heal. A 37:1063–1073.10.1081/ESE-120004523Suche in Google Scholar
Matthews, S., Mila, I., Scalbert, A., Donnelly, D.M.X. (1997a) Extractable and non-extractable proanthocyanidins in barks. Phytochemistry 45:405–410.10.1016/S0031-9422(96)00873-4Suche in Google Scholar
Obst, J.R. (1983) Analytical pyrolysis of hardwood and softwood lignins and its use in lignin-type determination of hardwood vessel elements. J. Wood Chem. Technol. 3:377–397.10.1080/02773818308085170Suche in Google Scholar
Pizzi, A. (1982) Condensed tannins for adhesives. Ind. Eng. Chem. Prod. Res. Dev. 21:359–369.10.1021/i300007a005Suche in Google Scholar
Pizzi, A. (2006) Recent developments in eco-efficient bio-based adhesives for wood bonding: opportunities and issues. J. Adhesion Sci. Technol. 20:829–846.10.1163/156856106777638635Suche in Google Scholar
Pizzi, A., Stephanou, A. (1994a) A comparative 13C NMR study of polyflavonol tannin adhesive intermediates. I. Noncolloidal performance determining rearrangements. J. Appl. Polym. Sci. 51:2109–2124.10.1002/app.1994.070511302Suche in Google Scholar
Pizzi, A., Stephanou, A. (1994b) Fast vs. slow-reacting non-modified tannin extracts for exterior particleboards adhesives. Holz Roh. Werkst. 52:218–222.10.1007/BF02619095Suche in Google Scholar
Porter, L.J. (1989) Condensed tannins. In: Natural Products of Woody Plants. Ed. Rowe, J.W. Springler Verlag, Berlin, Germany. pp. 651–690.10.1007/978-3-642-74075-6_18Suche in Google Scholar
Porter, L.J., Hemingway, R.W. (1989) Significance of the condensed tannins. In: Natural Products of Woody Plants. Ed. Rowe, J.W. Springler Verlag, Berlin, Germany. pp. 988–1027.10.1007/978-3-642-74075-6_28Suche in Google Scholar
Roffael, E., Dix, B., Okum, J. (2000) Use of spruce tannin as binder in particleboards and medium density fiberboards (MDF). Holz Roh. Werkst. 58:301–305.10.1007/s001070050432Suche in Google Scholar
Seki, K., Saito, N., Aoyama, M. (1997) Removal of heavy metal ions from solutions by coniferous barks. Wood Sci. Technol. 31:441–447.10.1007/BF00702566Suche in Google Scholar
Singelton, V.L., Orthofer, R., Lamuela-Raventos, R.M. (1999) Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Method Enzymol. 299:152–178.10.1016/S0076-6879(99)99017-1Suche in Google Scholar
Stafford, H.A., Cheng, T.Y. (1980) Procyanidins of Douglas-fir seedlings, callus and cell-suspension cultures derived from cotyledons. Phytochemistry 19:131–135.10.1016/0031-9422(80)85029-1Suche in Google Scholar
Sun, B., Leandro, C., da Silva, J.M.R., Spranger, I. (1998) Separation of grape and wine proanthocyanidins according to their degree of polymerization. J. Agric. Food Chem. 46:1390–396.10.1021/jf970753dSuche in Google Scholar
Ucar, M.B., Ucar, G., Pizzi, A., Gonultas, O. (2013) Characterization of Pinus brutia bark tannin by MALDI-TOF MS and 13C NMR. Ind. Crop. Prod. 49:697–704.10.1016/j.indcrop.2013.06.010Suche in Google Scholar
Weissman, G. (1981) Untersuchung der Rinderextrakte von Picea abies Karst. Holz Roh. Werkst. 39:457–461.10.1007/BF02606461Suche in Google Scholar
Weissman, G. (1985) Untersuchung der Rinderextrakte von Lärchen. Holzforsch. Holzwert. 37:67–71.Suche in Google Scholar
Willför, S., Pranovich, A., Tamminen, T., Puls, J., Laine, C., Suurnäkki, A., Saake, B., Uotila, K., Simolin, H., Hemming, J., Holmbom, B. (2009) Carbohydrate analysis of plant materials with uronic acid containing polysaccharides – a comparison between different hydrolysis and subsequent chromatographic analytical techniques. Ind. Crop. Prod. 29:571–581.10.1016/j.indcrop.2008.11.003Suche in Google Scholar
©2019 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Original Articles
- Rapid identification of wood species by near-infrared spatially resolved spectroscopy (NIR-SRS) based on hyperspectral imaging (HSI)
- Comparison of various multivariate models to estimate structural properties by means of non-destructive techniques (NDTs) in Pinus sylvestris L. timber
- Influence of length on acoustic time-of-flight (ToF) measurement in built-in structures of Norway spruce timber
- Characterization of Pinus nigra var. laricio [Maire] bark extracts at the analytical and pilot scale
- Determination of the absolute molar mass of acetylated eucalyptus kraft lignin by two types of size-exclusion chromatography combined with multi-angle laser light-scattering detectors
- Moisture-induced deformation in the neck of a classical guitar
- Prediction of physical and mechanical properties of thermally modified wood based on color change evaluated by means of “group method of data handling” (GMDH) neural network
- A self-cleaning surface based on heat treatment of g-C3N4-coated wood prepared by a rapid and eco-friendly method
- Mechanical, thermo-mechanical and water uptake performance of wood flour filled polyurethane elastomer eco-composites: influence of surface treatment of wood flour
- Investigation of a new formaldehyde-free adhesive consisting of soybean flour and Kymene® 736 for interior plywood
- Negative oxygen ion (NOI) production by enhanced photocatalytic TiO2/GO composites anchored on wooden substrates
Artikel in diesem Heft
- Frontmatter
- Original Articles
- Rapid identification of wood species by near-infrared spatially resolved spectroscopy (NIR-SRS) based on hyperspectral imaging (HSI)
- Comparison of various multivariate models to estimate structural properties by means of non-destructive techniques (NDTs) in Pinus sylvestris L. timber
- Influence of length on acoustic time-of-flight (ToF) measurement in built-in structures of Norway spruce timber
- Characterization of Pinus nigra var. laricio [Maire] bark extracts at the analytical and pilot scale
- Determination of the absolute molar mass of acetylated eucalyptus kraft lignin by two types of size-exclusion chromatography combined with multi-angle laser light-scattering detectors
- Moisture-induced deformation in the neck of a classical guitar
- Prediction of physical and mechanical properties of thermally modified wood based on color change evaluated by means of “group method of data handling” (GMDH) neural network
- A self-cleaning surface based on heat treatment of g-C3N4-coated wood prepared by a rapid and eco-friendly method
- Mechanical, thermo-mechanical and water uptake performance of wood flour filled polyurethane elastomer eco-composites: influence of surface treatment of wood flour
- Investigation of a new formaldehyde-free adhesive consisting of soybean flour and Kymene® 736 for interior plywood
- Negative oxygen ion (NOI) production by enhanced photocatalytic TiO2/GO composites anchored on wooden substrates
