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Official Journal of the Japan Wood Research Society

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Stereochemistry and biosynthesis of (+)-lyoniresinol, a syringyl tetrahydronaphthalene lignan in Lyonia ovalifolia var. elliptica II: feeding experiments with 14C labeled precursors

Journal of Wood Science volume 53, pages 114–120 (2007)Cite this article

Abstract

To clarify the biosynthetic pathway for syringyl lignans, especially syringyl tetrahydronaphthalene lignans and formation of the C2–C7′ linkage, production of (+)-lyoniresinol (LYR) and its predicted intermediates [syringaresinol (SYR), 5,5′-dimethoxylariciresinol (DMLR), and 5,5′-dimethoxysecoisolariciresinol (DMSLR)] in Lyonia ovalifolia var. elliptica was investigated by means of feeding experiments with radiolabeled precursors. Following individual administration of l-[U-14C]phenylalanine (Phe), [8-14C]sinapyl alcohol (SA), and [8,8′-14C]SYR to excised young shoots of L. ovalifolia and their subsequent metabolism, free [14C]lignans and [14C]lignan glycosides were extracted with methanol from stems and leaves and were divided into ethyl acetate-soluble fractions (lignans) and aqueous fractions (lignan glycosides), respectively. Using a combination of xylanase, cellulase, and β-glucosidase, the glycosides were hydrolyzed to liberate [14C]lignans as aglycones. l-[U-14C]Phe was incorporated into (+)-[14C]SYR [stem 0.38%, 8% enantiomeric excess (e.e.)], (−)-[14C]SYR (leaves 2.75%, 72% e.e.), (+)-[14C]DMLR (stem 0.07%, 18% e.e. and leaves 0.009%, 58% e.e.), (−)-[14C]DMSLR (stem 0.03%, 46% e.e. and leaves 0.05%, 20% e.e.), (+)-[14C]LYR (leaves 0.013%, 22% e.e.) and glycosides of (+)-[14C]LYR (stem 0.036%, 50% e.e.) in 24h. Based on the percent incorporation and enantiomeric composition of the lignans, the biosynthetic pathway of (8R,8′R)-(+)-LYR was proposed as follows: a nonselective dehydrogenative dimerization of sinapyl alcohol yields (±)-SYR, which is reduced with low specificity to give (8R,8′R)-(+)-DMLR. This is cyclized to directly give (+)-LYR as well as reduced again to (8R,8′R)-(−)-DMSLR. Although further transformation of (−)-DMSLR also leads to the formation of (+)-LYR, cyclization could be a main pathway for (+)-LYR biosynthesis.

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Authors and Affiliations

  1. Faculty of Agriculture, Kagawa University, 2393 Ikenobe, Miki-cho, Kagawa, 761-0795, Japan

    MD. Atiar Rahman, Takeshi Katayama, Toshisada Suzuki, Yuka Yoshihara & Takashi Nakagawa

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  1. MD. Atiar Rahman
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  2. Takeshi Katayama
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  3. Toshisada Suzuki
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  4. Yuka Yoshihara
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  5. Takashi Nakagawa
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Correspondence to Takeshi Katayama.

Additional information

This report was presented at the IAWPS 2005 International Symposium on Wood Science and Technology, Yokohama, November 2005

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Rahman, M.A., Katayama, T., Suzuki, T. et al. Stereochemistry and biosynthesis of (+)-lyoniresinol, a syringyl tetrahydronaphthalene lignan in Lyonia ovalifolia var. elliptica II: feeding experiments with 14C labeled precursors. J Wood Sci 53, 114–120 (2007). https://doi.org/10.1007/s10086-006-0833-0

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  • DOI: https://doi.org/10.1007/s10086-006-0833-0

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