Skip to main content
Journal of Wood Science

Official Journal of the Japan Wood Research Society

Download PDF
  • Original Article
  • Published:

Biosynthesis of (+)-syringaresinol inLiriodendron tulipifera I: feeding experiments withl-[U-14C]phenylalanine and [8-14C]sinapyl alcohol

Journal of Wood Science volume 47, pages 41–47 (2001)Cite this article

Abstract

To clarify the biosynthesis of syringyl lignans and lignan formation by stereoselective coupling of monolignols, formation of (+)-syringaresinol and (+)-pinoresinol inLiriodendron tulipifera were investigated by means of feeding experiments. Following individual administration ofl-[U-14C]phenylalanine and [8-14C]sinapyl alcohol to excised shoots ofL. tulipifera and their subsequent metabolism for 3h, free [14C] lignans and [14C] lignan glucosides were extracted from both of the stems and leaves with methanol and divided into an ether fraction and an aqueous one, respectively. The glucosides were hydrolyzed by a combination of cellulase andΒ-glucosidase to liberate [14C]lignans as aglycones.l-[U-14C]Phenylalanine was incorporated into free (+)-[14C]syringaresinol and its glucosides; the (+)-[14C]syringaresinols in the stems and leaves had 52% enantiomeric excess (% e.e.) and 42% e.e., respectively; and the (+)-[14C]syringaresinol aglycones from the glucosides in the stems and leaves had 20% e.e. and 22% e.e., respectively. Furthermore, [8-14C]sinapyl alcohol was incorporated into (+)-[14C]syringaresinol and its glucosides in the stems. These results suggest that the (+)-enantiomer of syringaresinol was enantioselectively formed from two molecules of sinapyl alcohol inL. tulipifera followed by transformation into the (+)-syringaresinol glucosides, accompanying the formation of racemic syringaresinol by nonselective coupling and the subsequent transformation of the racemate into their glucosides.l-[U-14C]Phenylalanine was incorporated also into free (+)-[14C]pinoresinol and its glucosides with 12%–42% e.e.

References

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

    Article  Google Scholar 

  2. 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  Google Scholar 

  3. Paré PW, Wang H-B, Davin LB, Lewis NG (1994) (+)-Pinoresinol synthase: a stereoselective oxidase catalysing 8,8'-lignan formation inForsythia intermedia. Tetrahedron Lett 35:4731–4734

    Article  Google Scholar 

  4. 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  Google Scholar 

  5. 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 

  6. 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  Google Scholar 

  7. Katayama T, Kado Y (1998) Formation of optically active neolignans from achiral coniferyl alcohol by cell-free extracts ofEucommia ulmoides. J Wood Sci 44:244–246

    Article  CAS  Google Scholar 

  8. Kado Y, Katayama T (1997) Enantioselective formation of neolignans/lignans by cell-free extracts ofEucommia ulmoides (in Japanese). In: Proceedings of the 42nd Lignin Symposium, Sapporo, pp 61–64

  9. Fujimoto H, Higuchi T (1977) Lignans from the bark of yellow poplar (Liriodendron tulipifera L.). Mokuzai Gakkaishi 23:405–410

    CAS  Google Scholar 

  10. Yamaguchi H, Nakatsubo F, Katsura Y, Murakami K (1990) Characterization of (+)- and (−)-syringaresinol di-Β-d-glucosides. Holzforschung 44:381–385

    Article  CAS  Google Scholar 

  11. Dickey EE (1958) Liriodendrin, a new lignan diglucoside from the inner bark of yellow poplar (Liriodendron tulipifera L.). J Org Chem 23:179–184

    Article  Google Scholar 

  12. Jolad SD, Huffman JJ, Cole JR, Tempesta MS, Bates RB (1980) Cytotoxic agent fromPenstemon deustus (Scrophulariaceae): Isolation and stereochemistry of liriodendrin, a symmetrically substituted furofuranoid lignan diglucoside. J Org Chem 45:1327–1329

    Article  CAS  Google Scholar 

  13. Nishibe S, Kinoshita H, Takeda H, Okano G (1990) Phenolic compounds from stem bark ofAcanthopanax senticosus and their pharmacological effect in chronic swimming stressed rats. Chem Pharm Bull (Tokyo) 38:1763–1765

    Article  CAS  Google Scholar 

  14. Fujikawa T, Yamaguchi A, Morita I, Takeda H, Nishibe S (1996) Protective effects ofAcanthopanax senticosus Harms from Hokkaido and its components on gastric ulcer in restrained cold water stressed rats. Biol Pharm Bull 19:1227–1230

    Article  CAS  Google Scholar 

  15. Nikaido T, Ohmoto T, Kinoshita T, Sankawa U, Nishibe S, Hisada S (1981) Inhibition of cyclic AMP phosphodiesterase. Chem Pharm Bull (Tokyo) 29:3586–3592

    Article  CAS  Google Scholar 

  16. Fujimoto H, Higuchi T (1977) Biosynthesis of liriodendrin byLiriodendron tulipifera. Wood Res (Kyoto) No.62:1–10

    Google Scholar 

  17. 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 

  18. Katayama Y, Fukuzumi T (1978) Enzymatic synthesis of three lignin-related dimers by an improved peroxidase-hydrogen peroxide system (in Japanese). Mokuzai Gakkaishi 24:664–667

    CAS  Google Scholar 

  19. Kuriyama K, Murui T (1993) Effect of cellulase on hydrolysis of lignan glycosides in sesame seed by Β-glucosidase (in Japanese). Nippon Nogeikagaku Kaishi 67:1701–1705

    Article  CAS  Google Scholar 

  20. Ogaki A, Katayama T (1997) Biosynthesis of furofuran lignans inLiriodendron tulipifera (in Japanese). In: Abstracts of the 47th annual meeting of the Japan Wood Research Society, Kochi, p 390

  21. Rahman MMA, Dewick PM, Jackson DE, Lucas JA (1990) Biosynthesis of lignans inForsythia intermedia. Phytochemistry 29:1841–1846

    Article  CAS  Google Scholar 

  22. Broomhead AJ, Rahman MMA, Dewick PM, Jackson DE, Lucas JA (1991) Matairesinol as precursor ofPodophyllum lignans. Phytochemistry 30:1489–1492

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Agriculture, Kagawa University, Miki-cho, 761-0795, Kagawa, Japan

    Takeshi Katayama & Atsushi Ogaki

Authors
  1. Takeshi Katayama
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Atsushi Ogaki
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Takeshi Katayama.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Katayama, T., Ogaki, A. Biosynthesis of (+)-syringaresinol inLiriodendron tulipifera I: feeding experiments withl-[U-14C]phenylalanine and [8-14C]sinapyl alcohol. J Wood Sci 47, 41–47 (2001). https://doi.org/10.1007/BF00776644

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00776644

Key words