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Official Journal of the Japan Wood Research Society

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Biosynthesis of a syringyl 8-O-4′ neolignan in Eucommia ulmoides: formation of syringylglycerol-8-O-4′-(sinapyl alcohol) ether from sinapyl alcohol

Journal of Wood Science volume 51, pages 379–386 (2005)Cite this article

Abstract

To investigate the biosynthesis and stereochemistry of syringylglycerol-8-O-4′-(sinapyl alcohol) ether (SGSE), a syringyl 8-O-4′ neolignan, feeding experiments and enzyme assays using Eucommia ulmoides were carried out. Diastereoselective formation of erythro-SGSE was found. When [8-14C]sinapyl alcohol was administered to excised shoots of E. ulmoides, 14C was incorporated into free SGSE and SGSE glucosides. In stems, incorporation into (+)-erythro-[14C]SGSE (0.037%) with 9.1% enantiomeric excess (% e.e.) was found; incorporation into the threo isomer was not detectable. Erythro-[14C]SGSE glucosides (0.047%) dominated over threo forms (0.007%) with 74.0% diastereomeric excess (% d.e.); both diastereomers were levorotatory with 32.0% e.e. and 18.3% e.e., respectively. In leaves, higher incorporation into (−)-erythro-[14C]SGSE (0.500%, 15.9% e.e.) than into the threo isomer (0.206%, 7.4% e.e.) was observed (41.6% d.e.). (−)-Erythro-[14C]SGSE glucosides (1.692%, 25.0% e.e.) were produced at higher rates than threo isomers (0.177%, 16.4% e.e.) with 81.0% d.e. In incubations of a mixture of [8-14C]sinapyl and [8-14C]coniferyl alcohols with an insoluble enzyme preparation from stems of E. ulmoides, erythro-SGSE was preferentially produced. The highest % d.e. (82.8) was observed at 60 min with the (+)-erythro isomer (21.4% e.e.) and the (−)-threo form (4.3% e.e.).

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Authors and Affiliations

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

    Nattaya Lourith, Takeshi Katayama, Kimiko Ishikawa & Toshisada Suzuki

Authors
  1. Nattaya Lourith
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  2. Takeshi Katayama
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  3. Kimiko Ishikawa
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  4. Toshisada Suzuki
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Correspondence to Takeshi Katayama.

Additional information

Part of this report was presented at the 52nd Annual Meeting of the Japan Wood Research Society, Gifu, April 2002, and the 47th Lignin Symposium, Fukuoka, October 2002

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Lourith, N., Katayama, T., Ishikawa, K. et al. Biosynthesis of a syringyl 8-O-4′ neolignan in Eucommia ulmoides: formation of syringylglycerol-8-O-4′-(sinapyl alcohol) ether from sinapyl alcohol. J Wood Sci 51, 379–386 (2005). https://doi.org/10.1007/s10086-004-0669-4

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  • DOI: https://doi.org/10.1007/s10086-004-0669-4

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