Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
J Agric Food Chem. 2011 Dec 28;59(24):13089-95. doi: 10.1021/jf203222w. Epub 2011 Nov 22.
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.
所有枞脂素对映异构体均被合成以研究立体化学对植物生长的影响。苄位 7-位的构型通过 S(N)1 或 S(N)2 分子内醚化构建。8-和 8'-位的构型除了所有顺式对映异构体外，均由起始原料确定，其中 8-位的构型通过立体选择性硼氢化反应实现。(-)-枞脂素及其 7S,8S,8'R 对映异构体对黑麦草根生长的抑制率相对于阴性对照为 51-55%，而其他对映异构体的抑制作用较小。这些结果表明，木脂素的立体化学是影响其抑制活性的重要因素之一。
