Wood Science and Technology

, Volume 52, Issue 3, pp 855–871 | Cite as

Wood photostabilization roles of the condensed tannins and flavonoids from the EtOAc fraction in the heartwood extract of Acacia confusa

  • Tzu-Cheng Chang
  • Shang-Tzen Chang


Lignin, one of the three major components in wood, can absorb UV light and react with 1O2, leading to wood photodegradation. Previous studies demonstrated the ethyl acetate (EtOAc) fraction of the heartwood extract in Acacia confusa (AcHW) has good photostabilities to prevent photodegradation of the wood. However, these effective constituents have different structural characteristics and may affect their photostabilities and protection efficacies on wood which need to be clarified. This study analyzed the polyphenolic contents, chemical constituents and photostabilities of the six subfractions (EA1–EA6) which successively fractioned from the EtOAc fraction in AcHW by the colorimetric methods, UV/Vis spectrophotometry and high-performance liquid chromatography and evaluated the wood photoprotection abilities of these treatments. The results showed the more flavones and flavonols contained in the subfractions, the better the UVA absorptivity was. Besides, the catecholic-condensed tannins and flavonoids in these subfractions also provide good 1O2 quenching abilities and phenoxyl radical scavenging abilities. Advanced results also established in these subfractions, melanoxetin, transilitin, 7,3′,4′-trihydroxy-3-methoxyflavone, 7,8,3′-trihydroxy-3,4′-dimethoxyflavone (flavonols), 7,8,3′,4′-tetrahydroxyflavone, 7,3′,4′-trihydroxyflavone, 7,3′,4′-trihydroxy-5-methoxyflavone (flavones) and okanin (chalcone) can absorb the energy of UVA light; the condensed tannins, 3,4-dihydroxybenzoic acid (phenolic acid), melacacidin-based oligomers, melacacidin, 4-O-methylmelacacidin, 4′-O-methylmelacacidin (melacacidin-based flavanols), 3,7,8,3′,4′-pentahydroxyflavanone (flavanonol), 7,8,3′,4′-tetrahydroxyflavanone (flavanone), the flavones, flavonols and chalcone can suppress the phenoxyl radicals; the condensed tannins, melacacidin-based oligomers and the flavonoids can quench 1O2. Hence, the photostability of extract-free wood slices treated with these effective constituents was consequently enhanced. In summary, these results clearly demonstrated the multiple wood photoprotection actions of these effective constituents and their potential as natural wood photostabilizers.



We appreciate the financial support (NSC 102-2313-B-002-023-MY3) from the Ministry of Science and Technology Taiwan. We also acknowledge the supports of materials from Assistant Research Fellow Min-Jay Chung (the Experimental Forest, National Taiwan University), the assistance of wood processing by Professor Rank Specialist Chun-Chieh Huang (Department of Wood Science and Design, National Pingtung University of Science and Technology), the assistance of Mass analysis from Associate Professor Ting-Feng Yeh (School of Forestry and Resource Conservation, National Taiwan University) and the NMR spectral analyses by Ms. Shou-Ling Huang (Department of Chemistry, National Taiwan University).


  1. Bonini C, D’Auria M, D’Alessio L, Mauriello G, Tofani D, Viggiano D, Zimbardi F (1998) Singlet oxygen degradation of lignin. J Photochem Photobiol, A 113(2):119–124CrossRefGoogle Scholar
  2. Bridson JH, Kaur J, Zhang Z, Donaldson L, Fernyhough A (2015) Polymeric flavonoids processed with co-polymers as UV and thermal stabilisers for polyethylene films. Polym Degrad Stab 122:18–24CrossRefGoogle Scholar
  3. Chang ST (1985) Effect of light wavelength on the degradation of wood. Forestry Prod Ind 4:118–123 (in Chinese) Google Scholar
  4. Chang HT, Chang ST (2006) Modification of wood with isopropyl glycidyl ether and its effects on decay resistance and light stability. Bioresour Technol 97(11):1265–1271CrossRefPubMedGoogle Scholar
  5. Chang TC, Chang ST (2017) Multiple photostabilization actions of heartwood extract from Acacia confusa. Wood Sci Technol 51(5):1133–1153CrossRefGoogle Scholar
  6. Chang ST, Chou PL (2000) Photodiscoloration inhibition of wood coated with UV-curable acrylic clear coatings and its elucidation. Polym Degrad Stabil 69(3):355–360CrossRefGoogle Scholar
  7. Chang CC, Yang MH, Wen HM, Chern JC (2002) Estimation of total flavonoid content in propolis by two complementary colorimetric methods. J Food Drug Anal 10(3):178–182Google Scholar
  8. Chang HT, Su YC, Chang ST (2006) Studies on photostability of butyrylated milled wood lignin using spectroscopic analyses. Polym Degrad Stabil 91(4):816–822CrossRefGoogle Scholar
  9. Chang TC, Chang HT, Wu CL, Chang ST (2010a) Influences of extractives on the photodegradation of wood. Polym Degrad Stabil 95:516–521CrossRefGoogle Scholar
  10. Chang TC, Chang HT, Wu CL, Lin HY, Chang ST (2010b) Stabilizing effect of extractives on the photo-oxidation of Acacia confusa wood. Polym Degrad Stabil 95:1518–1522CrossRefGoogle Scholar
  11. Chang TC, Lin HY, Wang SY, Chang ST (2014) Study on inhibition mechanisms of light-induced wood radicals by Acacia confusa heartwood extracts. Polym Degrad Stabil 105:42–47CrossRefGoogle Scholar
  12. Chang TC, Hsiao NC, Yu PC, Chang ST (2015) Exploitation of Acacia confusa heartwood extract as natural photostabilizers. Wood Sci Technol 49(4):811–823CrossRefGoogle Scholar
  13. Crestini C, D’Auria M (1997) Singlet oxygen in the photodegradation of lignin models. Tetrahedron 53(23):7877–7888CrossRefGoogle Scholar
  14. de la Caba K, Guerrero P, del Rio M, Mondragon I (2007) Weathering behaviour of wood-faced construction materials. Constr Build Mater 21(6):1288–1294CrossRefGoogle Scholar
  15. El Ghissassi F, Baan R, Straif K, Grosse Y, Secretan B, Bouvard V, Benbrahim-Tallaa L, Guha N, Freeman C, Galichet L, Cogliano V (2009) A review of human carcinogens-part D: radiation. Lancet Oncol 10(8):751–752CrossRefPubMedGoogle Scholar
  16. Evans PD, Wallis AFA, Owen NL (2000) Weathering of chemically modified wood surfaces. Wood Sci Technol 34(2):151–165CrossRefGoogle Scholar
  17. Evans PD, Owen NL, Schmid S, Webster RD (2002) Weathering and photostability of benzoylated wood. Polym Degrad Stabil 76:291–303CrossRefGoogle Scholar
  18. Fischer K, Beyer M (2000) Comparison of light-induced and heat-induced yellowing of pulp. Lenzinger Ber 79:25–31Google Scholar
  19. Grigsby W, Steward D (2017) Applying the protective role of condensed tannins to acrylic-based surface coatings exposed to accelerated weathering. J Polym Environ. Google Scholar
  20. Grigsby WJ, Bridson JH, Lomas C, Frey H (2014) Evaluating modified tannin esters as functional additives in polypropylene and biodegradable aliphatic polyester. Macromol Mater Eng 299(10):1251–1258CrossRefGoogle Scholar
  21. Grigsby WJ, Bridson JH, Schrade C (2015) Modifying biodegradable plastics with additives based on condensed tannin esters. J Appl Polym Sci 132(11):41626Google Scholar
  22. Hayoz P, Peter W, Rogez D (2003) A new innovative stabilization method for the protection of natural wood. Prog Org Coat 48:298–309CrossRefGoogle Scholar
  23. Heitner C (1993) Light-induced yellowing of wood-containing papers. In: Heitner C, Scaiano JC (eds) Photochemistry of lignocellulosic materials. American Chemistry Society, Washington, pp 2–22CrossRefGoogle Scholar
  24. Hon NS (1975) Formation of free radicals in photoirradiated cellulose. I. Effect of wavelength. J Polymer Sci Polymer Chem Ed 13(6):1347–1361CrossRefGoogle Scholar
  25. Hon DNS (1979) Photooxidative degradation of cellulose: reactions of the cellulosic free radicals with oxygen. J Polymer Sci Polymer Chem Ed 17(2):441–454CrossRefGoogle Scholar
  26. Hon DNS (1991) Weathering and phytochemistry of wood. In: Hon DNS, Shiraishi N (eds) Wood and Cellulosic Chemistry. Marcel Dekker, New York, pp 513–546Google Scholar
  27. Hon DNS, Feist WC (1992) Hydroperoxidation in photo-irradiated wood surfaces. Wood Fiber Sci 24:448–455Google Scholar
  28. Hon DNS, Chang ST, Feist WC (1982) Participation of singlet oxygen in the photodegradation of wood surfaces. Wood Sci Technol 16(3):193–201CrossRefGoogle Scholar
  29. Hsieh CY, Chang ST (2010) Antioxidant activities and xanthine oxidase inhibitory effects of phenolic phytochemicals from Acacia confusa twigs and branches. J Agric Food Chem 58(3):1578–1583CrossRefPubMedGoogle Scholar
  30. Huvaere K, Skibsted LH (2015) Flavonoids protecting food and beverages against light. J Sci Food Agric 95:20–35CrossRefPubMedGoogle Scholar
  31. Kai D, Tan MJ, Chee PL, Chua YK, Yap YL, Loh XJ (2016) Towards lignin-based functional materials in a sustainable world. Green Chem 18:1175–1200CrossRefGoogle Scholar
  32. Koontz JL, Marcy JE, O’Keefe SF, Duncan SE, Long TE, Moffitt RD (2010) Polymer processing and characterization of LLDPE films loaded with α-tocopherol, quercetin, and their cyclodextrin inclusion complexes. J Appl Polym Sci 117(4):2299–2309CrossRefGoogle Scholar
  33. Kuo ML, Hu N (1991) Ultrastructural changes of photodegradation of wood surface exposed to UV. Holzforschung 45(5):347–353CrossRefGoogle Scholar
  34. Lin HY, Chang ST (2013) Antioxidant potency of phenolic phytochemicals from the root extract of Acacia confusa. Ind Crops Prod 49:871–878CrossRefGoogle Scholar
  35. Makino R, Ohara S, Hashida K (2011) Radical scavenging characteristics of condensed tannins from barks of various tree species compared with quebracho wood tannin. Holzforschung 65(5):651–657CrossRefGoogle Scholar
  36. Masek A (2015) Flavonoids as natural stabilizers and color indicators of ageing for polymeric materials. Polymers 7(6):1125–1144CrossRefGoogle Scholar
  37. McPhail DB, Hartley RC, Gardner PT, Duthie GG (2003) Kinetic and stoichiometric assessment of the antioxidant activity of flavonoids by electron spin resonance spectroscopy. J Agric Food Chem 51(6):1684–1690CrossRefPubMedGoogle Scholar
  38. Min DB, Boff JM (2002) Chemistry and reaction of singlet oxygen in foods. Compr Rev Food Sci F 1(2):58–72CrossRefGoogle Scholar
  39. Min D, Smith SW, Chang H, Jameel H (2013) Influence of isolation condition on structure of milled wood lignin characterized by quantitative 13C nuclear magnetic resonance spectroscopy. BioResources 8(2):1790–1800CrossRefGoogle Scholar
  40. Mukai K, Nagai S, Ohara K (2005) Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution. Free Radic Biol Med 39(6):752–761CrossRefPubMedGoogle Scholar
  41. Müller U, Ratzsch M, Schwanninger M, Steiner M, Zobl H (2003) Yellowing and IR-changes of spruce wood as result of UV-irradiation. J Photochem Photobiol, B 69:97–105CrossRefGoogle Scholar
  42. Nagai S, Ohara K, Mukai K (2005) Kinetic study of the quenching reaction of singlet oxygen by flavonoids in ethanol solution. J Phys Chem B 109(9):4234–4240CrossRefPubMedGoogle Scholar
  43. Pandey KK (2005) Study of the effect of photo-irradiation on the surface chemistry of wood. Polym Degrad Stab 90(1):9–20CrossRefGoogle Scholar
  44. Parejo PG, Zayat M, Levy D (2006) Highly efficient UV-absorbing thin-film coatings for protection of organic materials against photodegradation. J Mater Chem 22:2113–2208Google Scholar
  45. Peng Y, Liu R, Cao J, Luo S (2014) Antiweathering effects of vitamin E on wood flour/polypropylene composites. Polym Compos 35(11):2085–2093CrossRefGoogle Scholar
  46. Peng Y, Liu R, Cao J, Guo X (2015) Effects of vitamin E combined with antioxidants on wood flour/polypropylene composites during accelerated weathering. Holzforschung 69(1):113–120Google Scholar
  47. Pospíšil J, Nešpurek S (2000) Photostabilization of coatings. Mechanisms and performance. Prog Polym Sci 25(9):1261–1335CrossRefGoogle Scholar
  48. Pu Y, Ragauskas AJ (2005) Structural analysis of acetylated hardwood lignins and their photoyellowing properties. Can J Chem 83:2132–2139CrossRefGoogle Scholar
  49. Rabek JF (1990) Introduction to the oxidative and photo-stabilization of polymers. In: Rabek JF (ed) Photostabilization of polymers: principles and applications. Elsevier Applied Science, New York, pp 42–79CrossRefGoogle Scholar
  50. Sisa M, Bonne SL, Ferreira D, van der Westhuizen JH (2010) Photochemistry of flavonoids. Molecules 15(8):5196–5245CrossRefPubMedGoogle Scholar
  51. Tondi G, Schnabel T, Wieland S, Petutschnigg A (2013) Surface properties of tannin treated wood during natural and artificial weathering. Int Wood Prod J 4(3):150–157CrossRefGoogle Scholar
  52. Tournaire C, Croux S, Maurette MT (1993) Antioxidant activity of flavonoids: efficiency of singlet oxygen (1Δg) quenching. J Photochem Photobiol, B 19(3):205–215CrossRefGoogle Scholar
  53. Valencia D, Alday E, Robles-Zepeda R, Garibay-Escobar A, Galvez-Ruiz JC, Salas-Reyes M, Jiménez-Estrada M, Velazquez-Contreras E, Hernandez J, Velazquez C (2012) Seasonal effect on chemical composition and biological activities of Sonoran propolis. Food Chem 131(2):645–651CrossRefGoogle Scholar
  54. Watkins D, Nuruddin M, Hosur M, Tcherbi-Narteh A, Jeelani S (2015) Extraction and characterization of lignin from different biomass resources. J Mater Res Technol 4(1):26–32CrossRefGoogle Scholar
  55. Williams RS (2005) Weathering of wood. In: Rowell RM (ed) Handbook of wood chemistry and wood composites. CRC Press, Florida, pp 139–185Google Scholar
  56. Wu JH, Tung YT, Wang SY, Shyur LF, Kuo YH, Chang ST (2005) Phenolic antioxidants from the heartwood of Acacia confusa. J Agric Food Chem 53:5917–5921CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Forestry and Resource ConservationNational Taiwan UniversityTaipeiTaiwan

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