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Official Journal of the Japan Wood Research Society

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Isolation and enzymatic formation of lignans ofDaphne genkwa andDaphne odora

Abstract

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.

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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). https://doi.org/10.1007/BF00766790

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Key words

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