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  • Title: Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities.
    Author: Nishiwaki H, Kumamoto M, Shuto Y, Yamauchi S.
    Journal: J Agric Food Chem; 2011 Dec 28; 59(24):13089-95. PubMed ID: 22066904.
    Abstract:
    All stereoisomers of lariciresinol were synthesized to examine the effect of stereochemistry on plant growth. Configuration of benzylic 7-positions was constructed through S(N)1 or S(N)2 intramolecular etherification. 8- and 8'-position configurations were established from the starting material except for all cis stereoisomers, the 8-position configurations of which were achieved by employing stereoselective hydroboration. (-)-Lariciresinol and its 7S,8S,8'R stereoisomer inhibited the root growth of Italian ryegrass to 51-55% relative to the negative control, whereas other stereoisomers had less effect. These results demonstrate that the stereochemistry of lignans is one of the important factors influencing their inhibitory activity.
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