Structure–Plant Growth Inhibitory Activity Relationship of Lariciresinol

The syntheses of 55 lariciresinol derivatives containing derivatives on the 9-position and an aryl group at both 7- and 7'-positions were successful to examine the effect of structure of (-)-lariciresinol (1) on plant growth regulatory activity. (-)-(7R,8R,8'S)-9-Dehydroxylariciresinol 9 showed activity 2-fold more potent than that of natural (-)-lariciresinol (1) and -95% growth inhibitory activity to negative control against rye grass root at 1 mM. The derivatives bearing hydrophobic and smaller groups at the 9-position showed higher activity. The importance of 4- and 4'-hydroxy groups and 3- and 3'-small hydrophobic groups on 7- and 7'-phenyl groups for higher activity was also suggested.