Stereochemical Diversity in Lignan Biosynthesis of Arctium lappa L.(Organic Chemistry)

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The stereochemistry of lignan biosynthesis in Arctium lappa L. is regulated organ-specifically. (+)-Secoisolariciresinol [81% enantiomeric excess (e. e.)] was isolated from A. lappa petioles. In sharp contrast, lignans whose predominant enantiomers have the opposite absolute configuration to that of (+)-secoisolariciresinol [i. e., (-)-matairesinol (>99% e. e.), (-)-arctigenin (>99% e. e.), and (-)-secoisolariciresinol (65% e. e.)] were isolated from seeds of the species. The stereochemical diversity of secoisolariciresinol was demonstrated with enzyme preparations from A. lappa petioles and seeds. Thus, a petiole enzyme preparation catalyzed the formation of (+)-pinoresinol (33% e. e.), (+)-lariciresinol (30% e. e.), and (+)-secoisolariciresinol (20% e. e.) from achiral coniferyl alcohol in the presence of NADPH and H_2O_2, whereas that from ripening seeds catalyzed the formation of (-)-pinoresinol (22% e. e.), (-)-lariciresinol (>99% e. e.), and (-)-secoisolariciresinol (38% e. e.) under the same conditions. In addition, the ripening seed enzyme preparation mediated the selective formation of the optically pure (>99% e.e.) (-)-enantiomer of matairesinol from racemic (±)-secoisolariciresinols in the presence of NADP. These results indicate that the stereochemical mechanism for lignan biosynthesis in A. lappa varies with organs, suggesting that multiple lignan-synthesizing isozymes are involved in the stereochemical control of lignan formation in A. lappa.
社団法人日本農芸化学会の論文
2002-06-23

Stereochemical Diversity in Lignan Biosynthesis of Arctium lappa L.(Organic Chemistry)

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