Skip to main content
Top
Published in: Wood Science and Technology 3/2013

01-05-2013 | Original

MALDI-TOF, HPLC-ESI-TOF and 13C-NMR characterization of chestnut (Castanea sativa) shell tannins for wood adhesives

Authors: Gonzalo Vázquez, Antonio Pizzi, M. Sonia Freire, Jorge Santos, Gervasio Antorrena, Julia González-Álvarez

Published in: Wood Science and Technology | Issue 3/2013

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

MALDI-TOF, HPLC-ESI-TOF and 13C-NMR techniques were used to analyse the structure of non-purified aqueous chestnut shell tannin extracts. In addition, the influence of the extraction agent (water or aqueous solutions of Na2SO3 and/or NaOH) on tannin structure was analysed by MALDI-TOF in order to select the extract with the best properties for wood adhesives. Using HPLC-ESI-TOF, catechin/epicatechin, gallocatechin/epigallocatechin, dicatechin structures, dicatechin structures without a hydroxyl group, galloyl-glucoses and ellagic acid were identified as the main monomeric components in the aqueous extract. 13C-NMR and MALDI-TOF spectra revealed that extracts are mostly composed of procyanidin and prodelphinidin structures although prorobinetidins might be also present. MALDI-TOF spectrometry was used to identify the extract oligomeric components. Extractions with Na2SO3 and/or NaOH produced changes in the predominant structures in the extracts and on the amount of sugar units linked to the flavonoid structures, which decreased in the presence of Na2SO3. Extract obtained using low Na2SO3 and NaOH concentrations (1.5 and 0.75 %, respectively) was selected as more suitable for wood adhesive preparation.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Appendix
Available only for authorised users
Literature
go back to reference Garro-Gálvez JM, Riedl B, Conner AH (1997) Analytical studies on tara tannins. Holzforschung 51:235–243CrossRef Garro-Gálvez JM, Riedl B, Conner AH (1997) Analytical studies on tara tannins. Holzforschung 51:235–243CrossRef
go back to reference Hemingway RW, McGraw GW (1978) Formaldehyde condensation products of model phenols for conifer bark tannins. J Liq Chromatogr 1:163–179CrossRef Hemingway RW, McGraw GW (1978) Formaldehyde condensation products of model phenols for conifer bark tannins. J Liq Chromatogr 1:163–179CrossRef
go back to reference Hillis WE, Urbach G (1959) Reactions of polyphenols with formaldehyde. J Appl Chem 9:665–673CrossRef Hillis WE, Urbach G (1959) Reactions of polyphenols with formaldehyde. J Appl Chem 9:665–673CrossRef
go back to reference Hwang JY, Hwang IK, Park JB (2001) Analysis of physicochemical factors related to the automatic pellicle removal in Korean chestnut (Castanea crenata). J Agric Food Chem 49:6045–6049PubMedCrossRef Hwang JY, Hwang IK, Park JB (2001) Analysis of physicochemical factors related to the automatic pellicle removal in Korean chestnut (Castanea crenata). J Agric Food Chem 49:6045–6049PubMedCrossRef
go back to reference Karas M, Bachmann D, Bahr U, Hillenkamp F (1987) Matrix-assisted ultraviolet laser desorption of non-volatile compounds. Int J Mass Spectrom Ion Process 78:53–58CrossRef Karas M, Bachmann D, Bahr U, Hillenkamp F (1987) Matrix-assisted ultraviolet laser desorption of non-volatile compounds. Int J Mass Spectrom Ion Process 78:53–58CrossRef
go back to reference Lorenz K, Preston CM (2002) Characterisation of high-tannin fractions from humus by carbon-13 cross-polarization and magic angle spinning nuclear magnetic resonance. J Environ Qual 31:431–436PubMedCrossRef Lorenz K, Preston CM (2002) Characterisation of high-tannin fractions from humus by carbon-13 cross-polarization and magic angle spinning nuclear magnetic resonance. J Environ Qual 31:431–436PubMedCrossRef
go back to reference McGraw GW, Rials TG, Steynberg JP, Hemingway RW (1992) Chemistry of pecan tannins and analysis of cure of pecan tannin-based cold-setting adhesives with a DMA ‘Micro Beam’ test. In: Hemingway RW, Laks PE (eds) Plant polyphenols: synthesis, properties, significance. Plenum Press, New York, pp 979–990CrossRef McGraw GW, Rials TG, Steynberg JP, Hemingway RW (1992) Chemistry of pecan tannins and analysis of cure of pecan tannin-based cold-setting adhesives with a DMA ‘Micro Beam’ test. In: Hemingway RW, Laks PE (eds) Plant polyphenols: synthesis, properties, significance. Plenum Press, New York, pp 979–990CrossRef
go back to reference Navarrete P, Pizzi A, Pasch H, Rode K, Delmotte L (2010) MALDI-TOF and 13C NMR characterization of maritime pine industrial tannin extract. Ind Crop Prod 32:105–110CrossRef Navarrete P, Pizzi A, Pasch H, Rode K, Delmotte L (2010) MALDI-TOF and 13C NMR characterization of maritime pine industrial tannin extract. Ind Crop Prod 32:105–110CrossRef
go back to reference Newman RH, Porter LJ (1992) Solid state 13C NMR studies on condensed tannins. In: Hemingway WR, Laks PE (eds) Plant polyphenols: synthesis, properties, significance. Plenum Press, New York, pp 339–347CrossRef Newman RH, Porter LJ (1992) Solid state 13C NMR studies on condensed tannins. In: Hemingway WR, Laks PE (eds) Plant polyphenols: synthesis, properties, significance. Plenum Press, New York, pp 339–347CrossRef
go back to reference Pasch H, Pizzi A (2002) Considerations on the macromolecular structure of chestnut ellagitannins by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry. J Appl Polym Sci 85:429–437CrossRef Pasch H, Pizzi A (2002) Considerations on the macromolecular structure of chestnut ellagitannins by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry. J Appl Polym Sci 85:429–437CrossRef
go back to reference Pasch H, Pizzi A, Rode K (2001) MALDI-TOF mass spectrometry of polyflavonoid tannins. Polymer 42:7531–7539CrossRef Pasch H, Pizzi A, Rode K (2001) MALDI-TOF mass spectrometry of polyflavonoid tannins. Polymer 42:7531–7539CrossRef
go back to reference Pizzi A (1983) Wood adhesives. Chemistry and technology. Marcel Dekker, New York Pizzi A (1983) Wood adhesives. Chemistry and technology. Marcel Dekker, New York
go back to reference Pizzi A (1994) Advanced wood adhesives technology. Dekker, New York Pizzi A (1994) Advanced wood adhesives technology. Dekker, New York
go back to reference Pizzi A (2006) Recent developments in eco-efficient bio-based adhesives for wood bonding: opportunities and issues. J Adhesion Sci Technol 20:829–846CrossRef Pizzi A (2006) Recent developments in eco-efficient bio-based adhesives for wood bonding: opportunities and issues. J Adhesion Sci Technol 20:829–846CrossRef
go back to reference Pizzi A, Stephanou A (1993) A comparative 13C NMR study of polyflavonoid tannin extracts for phenolic polycondensates. J Appl Polym Sci 50:2105–2113CrossRef Pizzi A, Stephanou A (1993) A comparative 13C NMR study of polyflavonoid tannin extracts for phenolic polycondensates. J Appl Polym Sci 50:2105–2113CrossRef
go back to reference Vasconcelos M, Bennett RN, Quideau S, Jacquet R, Rosa E, Ferreira Cardoso JV (2010) Evaluating the potential of chestnut (Castanea sativa Mill.) fruit pericarp and integument as a source of tocopherols, pigments and polyphenols. Ind Crop Prod 31:301–311CrossRef Vasconcelos M, Bennett RN, Quideau S, Jacquet R, Rosa E, Ferreira Cardoso JV (2010) Evaluating the potential of chestnut (Castanea sativa Mill.) fruit pericarp and integument as a source of tocopherols, pigments and polyphenols. Ind Crop Prod 31:301–311CrossRef
go back to reference Vázquez G, López-Suevos F, Villar-Garea A, González-Alvarez J, Antorrena G (2004) 13C-NMR analysis of phenol-urea-formaldehyde prepolymers and phenol-urea-formaldehyde-tannin adhesives. J Adhes Sci Technol 18(13):1529–1543CrossRef Vázquez G, López-Suevos F, Villar-Garea A, González-Alvarez J, Antorrena G (2004) 13C-NMR analysis of phenol-urea-formaldehyde prepolymers and phenol-urea-formaldehyde-tannin adhesives. J Adhes Sci Technol 18(13):1529–1543CrossRef
go back to reference Vázquez G, Fontenla E, Santos J, Freire MS, González-Alvarez J, Antorrena G (2008) Antioxidant activity and phenolic content of chestnut (Castanea sativa) shell and eucalyptus (Eucalyptus globulus) bark extracts. Ind Crop Prod 28:279–285CrossRef Vázquez G, Fontenla E, Santos J, Freire MS, González-Alvarez J, Antorrena G (2008) Antioxidant activity and phenolic content of chestnut (Castanea sativa) shell and eucalyptus (Eucalyptus globulus) bark extracts. Ind Crop Prod 28:279–285CrossRef
go back to reference Vázquez G, Freire MS, Santos J, Antorrena G, González-Álvarez J (2010) Optimisation of polyphenols extraction from chestnut shell by response surface methodology. Waste Biomass Valor 1(2):119–225CrossRef Vázquez G, Freire MS, Santos J, Antorrena G, González-Álvarez J (2010) Optimisation of polyphenols extraction from chestnut shell by response surface methodology. Waste Biomass Valor 1(2):119–225CrossRef
go back to reference Waver I, Wolniak M, Paradowska K (2006) Solid state NMR study of dietary fiber powders from aronia, bilberry, black currant and apple. Solid State Nucl Mag 30:106–113CrossRef Waver I, Wolniak M, Paradowska K (2006) Solid state NMR study of dietary fiber powders from aronia, bilberry, black currant and apple. Solid State Nucl Mag 30:106–113CrossRef
go back to reference Zhang LL, Lin YM (2008) HPLC, NMR and MALDI-TOF MS analysis of condensed tannins from Lithocarpus glaber leaves with potent free radical scavenging activity. Molecules 13:2986–2997PubMedCrossRef Zhang LL, Lin YM (2008) HPLC, NMR and MALDI-TOF MS analysis of condensed tannins from Lithocarpus glaber leaves with potent free radical scavenging activity. Molecules 13:2986–2997PubMedCrossRef
Metadata
Title
MALDI-TOF, HPLC-ESI-TOF and 13C-NMR characterization of chestnut (Castanea sativa) shell tannins for wood adhesives
Authors
Gonzalo Vázquez
Antonio Pizzi
M. Sonia Freire
Jorge Santos
Gervasio Antorrena
Julia González-Álvarez
Publication date
01-05-2013
Publisher
Springer-Verlag
Published in
Wood Science and Technology / Issue 3/2013
Print ISSN: 0043-7719
Electronic ISSN: 1432-5225
DOI
https://doi.org/10.1007/s00226-012-0513-8

Other articles of this Issue 3/2013

Wood Science and Technology 3/2013 Go to the issue