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- Title
Biosynthesis of (+)-syringaresinol in Liriodendron tulipifera I: feeding experiments with l-[U-<sup>14</sup>C]phenylalanine and [8-<sup>14</sup>C]sinapyl alcohol.
- Authors
Katayama, Takeshi; Ogaki, Atsushi
- Abstract
To clarify the biosynthesis of syringyl lignans and lignan formation by stereoselective coupling of monolignols, formation of (+)-syringaresinol and (+)-pinoresinol in Liriodendron tulipifera were investigated by means of feeding experiments. Following individual administration of l-[U-14C]phenylalanine and [8-14C]sinapyl alcohol to excised shoots of L. tulipifera and their subsequent metabolism for 3h, free [14C] lignans and [14C] lignan glucosides were extracted from both of the stems and leaves with methanol and divided into an ether fraction and an aqueous one, respectively. The glucosides were hydrolyzed by a combination of cellulase and Β-glucosidase to liberate [14C]lignans as aglycones. l-[U-14C]Phenylalanine was incorporated into free (+)-[14C]syringaresinol and its glucosides; the (+)-[14C]syringaresinols in the stems and leaves had 52% enantiomeric excess (% e.e.) and 42% e.e., respectively; and the (+)-[14C]syringaresinol aglycones from the glucosides in the stems and leaves had 20% e.e. and 22% e.e., respectively. Furthermore, [8-14C]sinapyl alcohol was incorporated into (+)-[14C]syringaresinol and its glucosides in the stems. These results suggest that the (+)-enantiomer of syringaresinol was enantioselectively formed from two molecules of sinapyl alcohol in L. tulipifera followed by transformation into the (+)-syringaresinol glucosides, accompanying the formation of racemic syringaresinol by nonselective coupling and the subsequent transformation of the racemate into their glucosides. l-[U-14C]Phenylalanine was incorporated also into free (+)-[14C]pinoresinol and its glucosides with 12%–42% e.e.
- Publication
Journal of Wood Science, 2001, Vol 47, Issue 1, p41
- ISSN
1435-0211
- Publication type
Article
- DOI
10.1007/BF00776644