Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism

Abstract

Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition. Here, we describe a structure-activity relationship study of ku-76 to determine the essential structural features for the inhibitory activity. A series of ku-76 analogues was synthesized and the key features of ku-76 that are necessary for inhibition of lettuce root gravitropic bending were determined. The (2E,4E)-, (2Z,4Z)- (2E,4Z)- analogues were inactive, and 4,5-saturated and 4,5-alkynyl analogues also did not show inhibitory activity, demonstrating the importance of the (2Z,4E) diene unit. The aromatic ring was also crucial and could not be replaced with an alkyl chain. Derivatives in which the carboxylic acid was replaced with amides, alcohols, or esters were much less potent. These results suggest that the (2Z,4E)-diene, the carboxylic acid moiety, and the aromatic ring are essential for potent inhibitory activity against gravitropic bending.

Keywords: Cis-cinnamic acid; Compositae; Gravitropism; Inhibition; Lactuca sativa; Organic synthesis; Structure-activity relationship study.