Skip to main content

Advertisement

Official Journal of the Japan Wood Research Society

Journal of Wood Science Cover Image

Generation and alteration of norlignans in a transition zone during the drying of a Cryptomeria japonica log

Article metrics

  • 107 Accesses

  • 6 Citations

Abstract

Sugi (Cryptomeria japonica D. Don) produces secondary metabolite norlignans in xylem. Several norlignans are involved in the coloration of heartwood and defense of sapwood against microbial invasion. Their biosynthetic process should be well understood so that their properties can be exploited to improve the quality and utility of C. japonica wood. Unfortunately, information on the norlignan biosynthesis is limited because norlignans are mainly synthesized in a particular season in the transition zone (TZ) along with the heartwood formation, and is difficult to study. Although the generation of two norlignans of C. japonica, agatharesinol and (E)-hinokiresinol, has been reported, systems for producing other norlignans are not yet known. To establish a novel norlignan generating system, we examined the changes occurring in norlignans in a TZ during the process of drying a C. japonica log. On the day of felling, the TZ contained agatharesinol and (E)-hinokiresinol, which increased until they reached a maximum on day 40 after felling. Sequirin-C appeared on day 40 and increased to day 70. The generation of sequirin-C in the TZ can be used to investigate the biosynthetic process of heartwood norlignans. This study describes for the first time the changes that occur in the composition of norlignan during the drying of the TZ.

References

  1. 1.

    Umezawa T (2000) Chemistry of extractives. In: Hon DN-S, Shiraisi N (eds) Wood and cellulosic chemistry. Marcel Dekker, New York, pp 213–241

  2. 2.

    Takahashi K (1981) Heartwood phenols and their significance to color in Cryptomeria japonica D. Don. Mokuzai Gakkaishi 27:654–657

  3. 3.

    Yamada T, Nakashima T (1998) Phytoalexin accumulation and hyphal spread in Japanese cedar sapwood inoculated with a canker fungus, Guignardia cryptomeriae. 7th International Congress of Plant Pathology Abstracts 1.9.2

  4. 4.

    Begley MJ, Davies RV, Henley-Smith P, Whiting DA (1973) Constitution of sequirin-D (Sequoia sempervirens), a novel dihydronaphthalene norlignan. Chem Commun 649–650

  5. 5.

    Enoki A, Takahama S, Kitao K (1977) The extractives of metasekoia, Metasequoia glyptostroboides Hu et Cheng. I. The isolation of metasequirin-A, athrotaxin and agatharesinol from the heartwood. Mokuzai Gakkaishi 23:579–586

  6. 6.

    Beracierta AP, Whiting DA (1978) Stereoselective total syntheses of the (±)-di-O-methyl ethers of agatharesinol, sequirin-A, and hinokiresinol, and of (±)-tri-O-methyl-sequirin-E, characteristic norlignans of coniferae. J Chem Soc Perkin Trans I 1257-1263

  7. 7.

    Erdtman H, Harmatha J (1979) Phenolic and terpenoid heartwood constituents of Libocedrus yateensis. Phytochemistry 18:1495–1500

  8. 8.

    Suzuki S, Umezawa T, Shimada M (2001) Norlignan biosynthesis in Asparagus officinalis L.: the norlignan originates from two non-identical phenylpropane units. J Chem Soc Perkin Trans I 3252-3257

  9. 9.

    Suzuki S, Nakatsubo T, Umezawa T, Shimada M (2002) First in vitro norlignan formation with Asparagus officinalis enzyme preparation. Chem Commun 1088-1089

  10. 10.

    Suzuki S, Yamamura M, Shimada M, Umezawa T (2004) A heartwood norlignan, (E)-hinokiresinol, is formed from 4-coumaryl 4-coumarate by a Cryptomeria japonica enzyme preparation. Chem Commun 2838-2839

  11. 11.

    Nobuchi T, Kuroda K, Iwata R, Harada H (1982) Cytological study of the seasonal features of heartwood formation of Sugi (Cryptomeria japonica D. Don). Mokuzai Gakkaishi 28:669–676

  12. 12.

    Taylor AM, Gartner BL, Morrell JJ (2002) Heartwood formation and natural durability — a review. Wood Fiber Sci 34:587–611

  13. 13.

    Ohashi H, Goto T, Imai T, Yasue M (1988) Accumulation and distribution of extractives in the living stem of Cryptomeria japonica. Res Bull Fac Agr Gifu Univ 53:301–314

  14. 14.

    Ohashi H, Imai T, Yoshida K, Yasue M (1990) Characterization of physiological functions of sapwood fluctuation of extractives in the withering process of Japanese cedar sapwood. Holzforschung 44:79–86

  15. 15.

    Yoshida K, Hiraide M, Nishiguchi M, Hishiyama S, Kato A (2004) A heartwood norlignan, agatharesinol, was generated in sapwood during withering of a Sugi (Cryptomeria japonica D. Don) log. Bull For For Prod Res Inst 3:25–28

  16. 16.

    Magel EA (2000) Biochemistry and physiology of heartwood formation. In: Savidge RA, Barnett JR, Napier R (eds) Cell and molecular biology of wood formation. BIOS, Oxford, pp 363–376

  17. 17.

    Nagasaki T, Yasuda S, Imai T (2002) Immunohistochemical localization of agatharesinol, a heartwood norlignan, in Cryptomeria japonica. Phytochemistry 60:461–466

  18. 18.

    Nobuchi T, Matsuno H, Harada H (1985) Radial distribution of heartwood phenols and the related cytological structure in the fresh wood of Sugi (Cryptomeria japonica D. Don). Mokuzai Gakkaishi 31:711–718

  19. 19.

    Takahashi K, Ogiyama K (1986) Phenols of discolored Sugi (Cryptomeria japonica D. Don) sapwood IV. Norlignans of Ayasugi (cultivar) in the Kyushu region (in Japanese). Mokuzai Gakkaishi 32:457–461

  20. 20.

    Takahashi K (1998) Relationships between the blacking phenomenon and norlignans of Sugi (Cryptomeria japonica D. Don) heartwood II. On blacking heartwood containing two main norlignans, sugiresinol and hydroxysugiresinol (in Japanese). Mokuzai Gakkaishi 44:125–133

  21. 21.

    Nobuchi T, Harada H (1983) Physiological features of the “white zone” of Sugi (Cryptomeria japonica D. Don) — cytological structure and moisture content. Mokuzai Gakkaishi 29:824–832

  22. 22.

    Thomas P (2000) Trees: their natural history. Cambridge University Press, Cambridge, pp 242–244

Download references

Author information

Correspondence to Kazumasa Yoshida.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Yoshida, K., Nishiguchi, M., Hishiyama, S. et al. Generation and alteration of norlignans in a transition zone during the drying of a Cryptomeria japonica log. J Wood Sci 52, 372–375 (2006) doi:10.1007/s10086-005-0777-9

Download citation

Key words

  • Norlignan
  • Transition zone
  • Drying
  • Cryptomeria japonica
  • Sugi