Skip to main content

Official Journal of the Japan Wood Research Society

Journal of Wood Science Cover Image

Effective combinations of functional groups in chemically modified kraft lignins for reduction of aluminum toxicity

Abstract

Plant growth tests were performed with radish (Raphanus sativa var. radicula Pers.) in culture solutions containing low molecular weight compounds in the presence of aluminum to determine the types of functional groups in kraft lignin (KL) modified with ozone and alkali that contributed to reducing aluminum toxicity. The low molecular weight compounds used in this study contained carboxyl, formyl, methoxyl, alcohol hydroxyl, and phenolic hydroxyl groups. The compounds that had adjacent two carboxyl groups (oxalic acid), carboxyl/alcohol hydroxyl groups (glycolic acid), or carboxyl/formyl groups (glyoxylic acid) were effective in reducing aluminum toxicity. Malonic acid, having two carboxyl groups, also reduced aluminum toxicity. The ability of ozone-treated KLs to reduce aluminum toxicity was considered to be partly due to these chemical structures. Protocatechuic acid, having two adjacent phenolic hydroxyl groups, was also effective in reducing aluminum toxicity. This indicated that the effectiveness of the alkaline-treated KL was partly due to its catechol structure.

References

  1. 1.

    Matsumoto H (2000) Cell biology of aluminum toxicity and tolerance in higher plants. Int Rev Cytol 200:1–46

    CAS  Article  PubMed  Google Scholar 

  2. 2.

    Aimi R, Murakami T (1964) Cell-physiological studies on the effect of aluminum on the growth of crop plants (in Japanese). Bull Nat Inst Agr Sci 11:31–396

    Google Scholar 

  3. 3.

    Ma JF (2000) Role of organic acids in detoxification of aluminum in higher plants. Plant Cell Physiol 41:83–390

    Google Scholar 

  4. 4.

    Ma JF, Ryan PR, Delhaize E (2001) Aluminum tolerance in plants and the complexing role of organic acids. Trends Plant Sci 6:73–278

    Article  Google Scholar 

  5. 5.

    Ma JF, Furukawa J (2003) Recent progress in the research of external Al detoxification in higher plant: a minireview. J Inorg Biochem 97:6–51

    Article  Google Scholar 

  6. 6.

    Kochian LV (1995) Cellular mechanisms of aluminum toxicity and resistance in plants. Annu Rev Plant Physiol Plant Mol Biol 46:237–260

    CAS  Article  Google Scholar 

  7. 7.

    Kochian LV, Hoekenga OA, Piñeros MA (2004) How do crop plants tolerate acid soil? Mechanisms of aluminum tolerance and phosphorous effi ciency. Annu Rev Plant Biol 55:459–493

    CAS  Article  PubMed  Google Scholar 

  8. 8.

    Bartlett RJ, Riego DC (1972) Effect of chelation on the toxicity of aluminum. Plant Soil 37:419–423

    CAS  Article  Google Scholar 

  9. 9.

    Ma JF, Hiradate S, Nomoto K, Iwashita T, Matsumoto H (1997) Internal detoxification mechanism of Al in hydrangea. Plant Physiol 113:1033–1039

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  10. 10.

    Ma JF, Zheng SJ, Matsumoto H (1997) Detoxifying aluminium with buckwheat. Nature 390:569–570

    Article  Google Scholar 

  11. 11.

    Zheng SJ, Ma JF, Matsumoto H (1998) High aluminum resistance in buckwheat. I. Al-induced specific secretion of oxalic acid from root tip. Plant Physiol 117:745–751

    Article  PubMed Central  Google Scholar 

  12. 12.

    Shen R, Ma JF, Kyo M, Iwashita T (2002) Compartmentation of aluminum in leaves of an Al-accumulator, Fagopyrum esculentum Moench. Planta 215:394–398

    CAS  Article  PubMed  Google Scholar 

  13. 13.

    Vance GF, Stevenson FJ, Sikora FJ (1996) Environmental chemistry of aluminum-organic complexes. In: Sposito G (ed) The environmental chemistry of aluminum, 2nd. edn. Lewis, Boca Raton, pp 169–220

    Google Scholar 

  14. 14.

    Hue NV, Graddock GR, Adams F (1986) Effect of organic acids on aluminum toxicity in subsoils. Soil Sci Soc Am J 50:28–34

    CAS  Article  Google Scholar 

  15. 15.

    Schnitzer M, Skinner SIM (1965) Organo-metallic interactions in soils: 4. Carboxyl and hydroxyl groups in organic matter and metal retention. Soil Sci 99:278–284

    CAS  Article  Google Scholar 

  16. 16.

    Tam SC, McColl JG (1990) Aluminum- and calcium-binding affinities of some organic ligands in acidic conditions. J Environ Qual 19:514–520

    CAS  Article  Google Scholar 

  17. 17.

    Ofei-Manu P, Wagatsuma T, Ishikawa S, Tawaraya K (2001) The plasma membrane strength of the root-tip cells and root phenolic compounds are correlated with Al tolerance in several common woody plants. Soil Sci Plant Nutr 47:359–375

    CAS  Article  Google Scholar 

  18. 18.

    Katsumata K, Meshitsuka G (2002) Modified kraft lignin and its use for soil preservation. In: Hu TQ (ed) Chemical modification, properties and usage of lignin. Kluwer, New York, pp 151–165

    Google Scholar 

  19. 19.

    Saito K, Nakanishi MT, Matsubayashi M, Meshitsuka G (1997) Development of new lignin derivatives as soil conditioning agents by radical sulfonation and alkaline-oxygen treatment. Mokuzai Gakkaishi 43:669–677

    CAS  Google Scholar 

  20. 20.

    Katsumata SK, Maruyama M, Meshitsuka G (2001) Reduction of aluminum toxicity to radish by alkaline oxygen treated kraft lignin. J Wood Sci 47:129–134

    CAS  Article  Google Scholar 

  21. 21.

    Katsumata SK, Shintani H, Meshitsuka G (2003) Mechanism of detoxification of aluminum ions by kraft lignin treated with alkaline oxygen. J Wood Sci 49:93–99

    CAS  Article  Google Scholar 

  22. 22.

    Wang D, Katsumata SK, Meshitsuka G (2005) Characterization of lignin fragments in alkaline oxygen-stage waste liquor as soil-conditioning agent. J Wood Sci 51:357–362

    CAS  Article  Google Scholar 

  23. 23.

    Wang D, Katsumata SK, Meshitsuka G (2005) Effect of low molecular weight lignin fragments including oxalic acid in alkaline-oxygen stage waste liquor on Al toxicity. J Wood Sci 51:634–639

    CAS  Article  Google Scholar 

  24. 24.

    Aimi H, Ohmura S, Kato T, Nakahara T, Shimizu K (2008) Development of acid soil conditioning agent from lignin by ozone treatment I. J Wood Sci 54:214–219

    CAS  Article  Google Scholar 

  25. 25.

    Aimi H, Ohmura S, Uetake M, Shimizu K (2009) Development of acid soil conditioning agent from lignin by ozone treatment II. J Wood Sci 55:121–125

    CAS  Article  Google Scholar 

  26. 26.

    Eriksson T, Gierer J (1985) Studies on the ozonation of structural elements in residual kraft lignins. J Wood Chem Technol 5:53–84

    CAS  Article  Google Scholar 

  27. 27.

    Miller JN, Miller JC (1988) Statistics and chemometrics for analytical chemistry, 2nd edn. Ellis Horwood, Chichester, UK

    Google Scholar 

  28. 28.

    Kaneko H, Hosoya S, Nakano J (1980) Degradation of lignin with ozone. Mokuzai Gakkaishi 26:752–758

    CAS  Google Scholar 

  29. 29.

    Kratzl K, Claus P, Reichel G (1976) Reactions of lignin and lignin model compounds with ozone. TAPPI 59:86–87

    CAS  Google Scholar 

  30. 30.

    Tsutsumi Y, Islam A, Anderson CD, Sarkanen KV (1990) Acidic permanganate oxidations of lignin and model compounds: comparison with ozonolysis. Holzforschung 44:59–66

    CAS  Article  Google Scholar 

  31. 31.

    Sarkanen KV, Islam A, Anderson CD (1992) Ozonation. In: Lin SY, Dence CW (eds) Methods in lignin chemistry. Springer, Berlin Heidelberg New York, pp 387–406

    Google Scholar 

  32. 32.

    Matsumoto Y, Ishizu A, Nakano J (1986) Studies on chemical structure of lignin by ozonation. Holzforschung 40(Suppl):81–85

    CAS  Google Scholar 

  33. 33.

    Matsumoto Y, Minami K, Ishizu A (1993) Structural study on lignin by ozonation. The erythro and threo ratio of the β-O-4 structure indicates how lignin polymerizes. Mokuzai Gakkaishi 39: 734–736

    CAS  Google Scholar 

  34. 34.

    Akiyama T, Sugimoto T, Matsumoto Y, Meshitsuka G (2002) Erythro/threo ratio of β-O-4 structures as an important structural characteristic of lignin I. Improvement of ozonation method for the quantitative analysis of lignin side-chain structure. J Wood Sci 48:210–215

    CAS  Article  Google Scholar 

  35. 35.

    Gierer J (1970) The reactions of lignin during pulping. A description and comparison of conventional pulping processes. Sven Papperstidn 73:571–596

    CAS  Google Scholar 

  36. 36.

    Barceló J, Poschenrieder C (2002) Fast root growth responses, root exudates, and internal detoxification as clues to the mechanisms of aluminum toxicity and resistance: a review. Environ Exp Bot 48:75–92

    Article  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Hikaru Aimi.

Additional information

This report was presented in part at the 58th Annual Meeting of the Japan Wood Research Society, Tsukuba, Japan, March 2008

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Aimi, H., Uetake, M. & Shimizu, K. Effective combinations of functional groups in chemically modified kraft lignins for reduction of aluminum toxicity. J Wood Sci 55, 220–224 (2009). https://doi.org/10.1007/s10086-008-1025-x

Download citation

Key words

  • Aluminum toxicity
  • Acid soil
  • Combination of functional groups
  • Lignin
  • Soil-conditioning agent