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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Stereochemistry and biosynthesis of 8-O-4′ neolignans in Eucommia ulmoides: diastereoselective formation of guaiacylglycerol-8-O-4′-(sinapyl alcohol) ether

Journal of Wood Science volume 51, pages 370–378 (2005)Cite this article

Abstract

Stereochemistry and biosynthesis of guaiacylglycerol-8-O-4′-(sinapyl alcohol) ether (GGSE), an 8-O-4′ neolignan, which consists of coniferyl and sinapyl alcohol moieties, in Eucommia ulmoides were investigated. Four 8-O-4′ neolignans, GGSE, syringylglycerol-8-O-4′-(coniferyl alcohol) ether (SGCE), guaiacylglycerol-8-O-4′-(coniferyl alcohol) ether (GGCE), and syringylglycerol-8-O-4′-(sinapyl alcohol) ether (SGSE), were synthesized. Their erythro and threo diastereomers were separated through acetonide derivatives, intermediates of the synthesis, and identified by means of nuclear magnetic resonance (NMR) spectroscopy. All of the erythro-acetonide derivatives have larger coupling constants (ca 9 Hz) for the C7-H resonances than those of the threo ones (1.5–2 Hz). In the case of the four 8-O-4′ neolignans, the C7-H coupling constants of the threo-isomers are not smaller than those of the erythro ones. GGSE isolated previously from this plant was identified as the erythro isomer by comparison of the 13C-NMR data with synthetic erythro-GGSE and threo-GGSE and the other 8-O-4′ neolignans mentioned as above. Administration of a mixture of [8-14C]coniferyl alcohol and [8-14C]sinapyl alcohol to excised shoots of E. ulmoides was carried out and the incorporation of 14C into erythro-[14C]GGSE was found to be higher than that in threo-[14C]GGSE. The occurrence of diastereoselective formation of erythro-GGSE by cross coupling of coniferyl and sinapyl alcohols is suggested.

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Authors and Affiliations

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

    Nattaya Lourith, Takeshi Katayama & Toshisada Suzuki

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  1. Nattaya Lourith
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  2. Takeshi Katayama
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  3. Toshisada Suzuki
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Correspondence to Takeshi Katayama.

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Part of this paper was presented at the 47th Lignin Symposium, Fukuoka, October 2002 and the 53rd Annual Meeting of the Japan Wood Research Society, Fukuoka, April 2003

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Lourith, N., Katayama, T. & Suzuki, T. Stereochemistry and biosynthesis of 8-O-4′ neolignans in Eucommia ulmoides: diastereoselective formation of guaiacylglycerol-8-O-4′-(sinapyl alcohol) ether. J Wood Sci 51, 370–378 (2005). https://doi.org/10.1007/s10086-004-0660-0

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