Our study of the mechanism(s) by which sorgoleone (1) acts as a photos
ystem II (PS II) inhibitor led to the isolation of a new benzoquinone
derivative, (Z,Z)-8',11',14'-pentadecatriene]-rho-benzoquinone (2), fr
om the root exudate of sorghum. The structure of 2, which is being giv
en the name 5-ethoxy-sorgoleone, was determined by spectroscopic means
. A methoxy derivative (3) of 1 was also prepared. Both 2 and 3 caused
a reduction in oxygen evolution by thylakoid membranes and induced va
riable chlorophyll fluorescence. These compounds, however, were less a
ctive inhibitors of PS II than 1.