Survey and enzymatic formation of lignans of Anthriscus sylvestris

Abstract

Gas chromatography - mass spectrometry analysis of the β-glucosidase- treated MeOH extracts of Anthriscus sylvestris showed, based on comparison of the mass spectra and retention times with those of authentic samples, the presence of lignans, yatein, secoisolariciresinol, lariciresinol, matairesinol, hinokinin, and pluviatolide. The existence of small amounts of bursehernin was suggested by mass chromatography. In addition, nemerosin and deoxypodophyllotoxin were tentatively identified by comparing the mass spectra with those reported in the literature. Enzyme preparations from A. sylvestris catalyzed the formation of secoisolariciresinol and lariciresinol from coniferyl alcohol. Furthermore, the enzyme preparation catalyzed the formation of lariciresinol from (±)-pinoresinols and the formation of secoisolariciresinol from (±)-lariciresinols. Thus, pinoresinol/ lariciresinol reductase (PLR) activity was detected. Chiral high-performance liquid chromatography analysis showed selective formation of (+)-lariciresinol and (-)-secoisolariciresinol from (±)-pinoresinols with the A. sylvestris PLR preparation, indicating that the stereochemical property of A. sylvestris PLR-catalyzed reduction was similar to those of Forsythia PLR and Arctium lappa ripening seed PLR.