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Isolation and enzymatic formation of lignans ofDaphne genkwa andDaphne odora


Four lignans — pinoresinol, lariciresinol, secoisolariciresinol, matairesinol — were isolated from each ofDaphne odora andDaphne genkwa (Thymelaeaceae). Matairesinol isolated from both plants was optically pure (>99% e.e.) and dextrorotatory. Pinoresinol and lariciresinol isolated from the plants were not optically pure, and their enantiomeric compositions ranged from 88% to 95% e.e. in favor of (−)-enantiomers. As for secoisolariciresinol, the one fromD. odora was optically pure [(+)-enantiomer, >99% e.e.], and that fromD. genkwa was 97% e.e. in favor of the (+)-enantiomer. Lignan-synthesizing enzyme activity was detected from a Thymelaeaceae plant for the first time; cell-free extracts fromD. genkwa catalyzed the formation of (−)-lariciresinol (23% e.e.) from racemic (±)-pinoresinols. The stereochemistry of the enzymatic reaction is discussed in relation to the stereochemical features of the isolated lignans.


  1. 1.

    Umezawa T (1997) Lignans. In: Higuchi T (ed) Springer series in wood science, Biochemistry and molecular biology of wood. Springer-Verlag, Berlin, pp 181–194

    Google Scholar 

  2. 2.

    Umezawa T, Davin LB, Lewis NG (1990) Formation of the lignan, (−)-secoisolariciresinol, by cell free extracts ofForsythia intermedia. Biochem Biophys Res Commun 171:1008–1014

    Article  CAS  PubMed  Google Scholar 

  3. 3.

    Umezawa T, Davin LB, Yamamoto E, Kingston DGI, Lewis NG (1990) Lignan biosynthesis in Forsythia species. J Chem Soc Chem Commun 1405–1408

  4. 4.

    Umezawa T, Davin LB, Lewis NG (1991) Formation of lignans (−)-secoisolariciresinol and (−)-matairesinol withForsythia intermedia cell-free extracts. J Biol Chem 266:10210–10217

    CAS  PubMed  Google Scholar 

  5. 5.

    Davin LB, Bedgar DL, Katayama T, Lewis NG (1992) On the stereoselective synthesis of (+)-pinoresinol inForsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry 31:3869–3874

    Article  CAS  PubMed  Google Scholar 

  6. 6.

    Katayama T, Davin LB, Lewis NG (1992) An extraordinary accumulation of (−)-pinoresinol in cell-free extracts ofForsythia intermedia: evidence for enantiospecific reduction of (+)-pinoresinol. Phytochemistry 31:3875–3881

    Article  CAS  PubMed  Google Scholar 

  7. 7.

    Katayama T, Davin LB, Chu A, Lewis NG (1993) Novel benzylic ether reductions in lignan biogenesis inForsythia intermedia. Phytochemistry 33:581–591

    Article  CAS  Google Scholar 

  8. 8.

    Chu A, Dinkova A, Davin LB, Bedgar DL, Lewis NG (1993) Stereospecificity of (+)-pinoresinol and (+)-lariciresinol reductases fromForsythia intermedia. J Biol Chem 268:27026–27033

    CAS  PubMed  Google Scholar 

  9. 9.

    Ozawa S, Davin LB, Lewis NG (1993) Formation of (−)-arctigenin inForsythia intermedia. Phytochemistry 32:643–652

    Article  CAS  Google Scholar 

  10. 10.

    Umezawa T, Kuroda H, Isohata T, Higuchi T, Shimada M (1994) Enantioselective lignan synthesis by cell-free extracts ofForsythia koreana. Biosci Biotech Biochem 58:230–234

    Article  CAS  Google Scholar 

  11. 11.

    Paré PW, Wang H-B, Davin LB, Lewis NG (1994) (+)-Pinoresinol synthesis: a stereoselective oxidase catalysing 8,8′-lignan formation inForsythia intermedia. Tetrahedron Lett 35:4731–1734

    Article  Google Scholar 

  12. 12.

    Dinkova-Kostova AT, Gang DR, Davin LB, Bedgar DL, Chu A, Lewis NG (1996) (+)-Pinoresinol/(+)-lariciresinol reductase fromForsythia intermedia. J Biol Chem 271:29473–29482

    Article  CAS  PubMed  Google Scholar 

  13. 13.

    Davin LB, Wang H-B, Crowell AL, Bedgar DL, Martin DM, Sarkanen S, Lewis NG (1997) Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275:362–366

    Article  CAS  PubMed  Google Scholar 

  14. 14.

    Umezawa T (1996) Biological activity and biosynthesis of lignans. Mokuzai Gakkaishi 42:911–920

    CAS  Google Scholar 

  15. 15.

    Umezawa T, Shimada M (1996) Formation of the lignan (+)-secoisolariciresinol by cell-free extracts ofArctium lappa. Biosci Biotech Biochem 60:736–737

    Article  CAS  Google Scholar 

  16. 16.

    Suzuki S, Umezawa T, Shimada M (1998) Stereochemical difference in secoisolariciresinol formation between cell-free extracts from petioles and from ripening seeds ofArctium lappa L. Biosci Biotech Biochem 62:1468–1470

    Article  CAS  Google Scholar 

  17. 17.

    Mikame K, Umezawa T, Shimada M (1997) Lignan synthesis by cell-free extracts fromLinum flavum. Proceedings of the 42nd Lignin Symposium, Sapporo, pp 65–68

  18. 18.

    Suzuki S, Umezawa T, Shimada M (1998) Lignan biosynthesis inAnthriscus sylvestris Hoffm. Proceedings of the 43rd Lignin Symposium, Tokyo, pp 131–132

  19. 19.

    Katayama T, Masaoka T, Yamada H (1997) Biosynthesis and stereochemistry of lignans inZanthoxylum ailanthoides. I. (+)-Lariciresinol formation by enzymatic reduction of (±) pinoresinols. Mokuzai Gakkaishi 43:580–588

    CAS  Google Scholar 

  20. 20.

    Umezawa T, Okunishi T, Shimada M (1997) Stereochemical diversity in lignan biosynthesis. Wood Res 84:62–75

    CAS  Google Scholar 

  21. 21.

    Tatematsu H, Kurokawa M, Niwa M, Hirata Y (1984) Piscicidal constituents ofStellera chamaejasme L. II. Chem Pharm Bull 32:1612–1613

    Article  CAS  Google Scholar 

  22. 22.

    Umezawa T, Shimada M (1996) Enantiomeric composition of (−)-pinoresinol, (+)-matairesinol and (+)-wikstromol isolated fromWikstroemia sikokiana. Mokuzai Gakkaishi 42:180–185

    CAS  Google Scholar 

  23. 23.

    Okunishi T, Umezawa T, Shimada M (2000) Enantiomeric compositions and biosynthesis ofWikstroemia sikokiana lignans. J Wood Sci 46:234–242

    Article  CAS  Google Scholar 

  24. 24.

    Kogiso S, Wada K, Munakata K (1977) Nematicidal substances fromDaphne odora. Report of the 26th international congress of pure and applied chemistry, Tokyo, p 291

  25. 25.

    Wang W, Zhou B, Wang C (1995) Chemical constituents of Maoruixiang (Daphne odora). Zhongcaoyao 26:566–567

    CAS  Google Scholar 

  26. 26.

    Umezawa T, Shimada M (1994) Syntheses of (±)-lariciresinols. Mokuzai Gakkaishi 40:231–235

    CAS  Google Scholar 

  27. 27.

    Umezawa T, Isohata T, Kuroda H, Higuchi T, Shimada M (1992) Chiral HPLC and LC-MS analysis of several lignans. In: Kuwahara M, Shimada M (eds) Biotechnology in pulp and paper industry, Uni, Tokyo, pp 507–512

    Google Scholar 

  28. 28.

    Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. 29.

    Fujita M, Gang DR, Davin LB, Lewis NG (1999) Recombinant pinoresinol-lariciresinol reductases from western red cedar (Thujaplicata) catalyze opposite enantiospecific conversions. J Biol Chem 274:618–627

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Toshiaki Umezawa.

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Okunishi, T., Umezawa, T. & Shimada, M. Isolation and enzymatic formation of lignans ofDaphne genkwa andDaphne odora . J Wood Sci 47, 383–388 (2001).

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Key words

  • Lignan
  • Daphne odora
  • Daphne genkwa
  • Thymelaeaceae
  • Pinoresinol reductase