Plant growth inhibitors:: patchoulane-type sesquiterpenes from Cyperus rotundus L.

Two sesquiterpene ketones, cyperotundone and alpha-cyperone, were isolated from dried tubers of purple nutsedge (Cyperus rotundus L.) as major constituents: approximate to 0.26% and 0.1% of dried tuber, respectively. These allelochemicals affect plant growth, but we consider that these terpenoids undergo modification when they are released into the rhizosphere from the donor plant. For the structure-activity relationship study, cyperotundone was oxidized with selenium dioxide in acetic acid to 4-patchoulene-2,3-dione and 4-patchoulene-2,3,6-trione. Subsequent hydrogenation of 4-patchoulene-2,3-dione and 4-patchoulene-2,3,6-trione gave hydroxylated derivatives, cyperotundon-2-ol and 3-hydroxy-4-patchoulene-2,6-dione, respectively. 4-Patchoulene-2,3-dione inhibited the hypocotyl growth of lettuce seedlings but promoted radicle elongation at 0.1-2 mg L-1 concentration without chlorosis. Moreover, this radicle elongation recovered with the addition of galactose and was not antagonized by gibberellin A(3). The effect of 4-patchoulene-2,3,6-trione showed a similar chlorosis, caused by 3,6,9-sugetriol triketone, against lettuce seedlings. These ketones did not show the radicle elongation.