TY - JOUR
T1 - Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism
AU - Shindo, Mitsuru
AU - Makigawa, Saki
AU - Matsumoto, Kenji
AU - Iwata, Takayuki
AU - Wasano, Naoya
AU - Kano, Arihiro
AU - Morita, Miyo Terao
AU - Fujii, Yoshiharu
N1 - Publisher Copyright:
© 2020 Elsevier Ltd
PY - 2020/4
Y1 - 2020/4
N2 - 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.
AB - 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.
KW - Cis-cinnamic acid
KW - Compositae
KW - Gravitropism
KW - Inhibition
KW - Lactuca sativa
KW - Organic synthesis
KW - Structure-activity relationship study
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U2 - 10.1016/j.phytochem.2020.112287
DO - 10.1016/j.phytochem.2020.112287
M3 - Article
C2 - 32018089
AN - SCOPUS:85078664428
SN - 0031-9422
VL - 172
JO - Phytochemistry
JF - Phytochemistry
M1 - 112287
ER -