caa a22 4500 463247884 CHVBK 20180405153331.0 cr unu---uuuuu 170326e20070401xx s 000 0 eng 10.1007/s10086-006-0832-1 doi (NATIONALLICENCE)springer-10.1007/s10086-006-0832-1 Stereochemistry and biosynthesis of (+)-lyoniresinol, a syringyl tetrahydronaphthalene lignan in Lyonia ovalifolia var. elliptica I: isolation and stereochemistry of syringyl lignans and predicted precursors to (+)-lyoniresinol from wood [Elektronische Daten] [MD. Rahman, Takeshi Katayama, Toshisada Suzuki, Takashi Nakagawa] Steps leading to the biosynthesis of syringyl lignans and tetrahydronaphthalene and naphthalene lignans, especially the formation of the C2-C7′ linkage, have not been elucidated. Lyoniresinol is a typical syringyl lignan, as well as a tetrahydronaphthalene lignan found in Lyonia ovalifolia var. elliptica. To demonstrate the biosynthetic pathway for (+)-lyoniresinol, three putative biosynthetic intermediates of lyoniresinol, syringaresinol, 5,5′-dimethoxylariciresinol, and 5,5′-dimethoxysecoisolariciresinol, were isolated from wood. The identity of the putative intermediates was confirmed by spectroscopic analyses, as well as by comparison of spectral and chromatographic data with those of authentic samples previously synthesized. The stereochemistry (enantiomeric composition and absolute configuration) of the isolated lignans were determined as (±)-syringaresinol, (8S,8′S)-(−)-5,5′-dimethoxylariciresinol [46% enantiomeric excess (e.e.)], (8S,8′S)-(+)-5,5′-dimethoxysecoisolariciresinol (91% e.e.), and (8R,8′R)-(+)-lyoniresinol (42% e.e.). The absolute configurations of (+)-and (-)-5,5′-dimethoxylariciresinols, and (+)-and (-)-5,5′-dimethoxysecoisolariciresinols were determined by their synthesis (catalytic reduction) from (8R,8′R)-(+)-and (8S,8′S)-(-)-syringaresinols and by subsequent chiral high-performance liquid chromatography analysis. The Japan Wood Research Society, 2007 Lignan nationallicence Lyonia ovalifolia var. elliptica nationallicence 5,5′-Dimethoxylariciresinol nationallicence 5,5′-Dimethoxysecoisolariciresinol nationallicence Lyoniresinol nationallicence Rahman MD Faculty of Agriculture, Kagawa University, 2393 Ikenobe, 761-0795, Miki-cho, Kagawa, Japan aut Katayama Takeshi Faculty of Agriculture, Kagawa University, 2393 Ikenobe, 761-0795, Miki-cho, Kagawa, Japan aut Suzuki Toshisada Faculty of Agriculture, Kagawa University, 2393 Ikenobe, 761-0795, Miki-cho, Kagawa, Japan aut Nakagawa Takashi Faculty of Agriculture, Kagawa University, 2393 Ikenobe, 761-0795, Miki-cho, Kagawa, Japan aut Journal of Wood Science Springer-Verlag 53/2(2007-04-01), 161-167 1435-0211 53:2<161 2007 53 10086 https://doi.org/10.1007/s10086-006-0832-1 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10086-006-0832-1 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Rahman MD Faculty of Agriculture, Kagawa University, 2393 Ikenobe, 761-0795, Miki-cho, Kagawa, Japan aut NATIONALLICENCE 700 1- Katayama Takeshi Faculty of Agriculture, Kagawa University, 2393 Ikenobe, 761-0795, Miki-cho, Kagawa, Japan aut NATIONALLICENCE 700 1- Suzuki Toshisada Faculty of Agriculture, Kagawa University, 2393 Ikenobe, 761-0795, Miki-cho, Kagawa, Japan aut NATIONALLICENCE 700 1- Nakagawa Takashi Faculty of Agriculture, Kagawa University, 2393 Ikenobe, 761-0795, Miki-cho, Kagawa, Japan aut NATIONALLICENCE 773 0- Journal of Wood Science Springer-Verlag 53/2(2007-04-01), 161-167 1435-0211 53:2<161 2007 53 10086 Metadata rights reserved Springer special CC-BY-NC licence nationallicence SWISSBIB 463247884 BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer