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

Mitsuru Shindo, Saki Makigawa, Kenji Matsumoto, Takayuki Iwata, Naoya Wasano, Arihiro Kano, Miyo Terao Morita, Yoshiharu Fujii

研究成果: Contribution to journalArticle

抜粋

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.

元の言語英語
記事番号112287
ジャーナルPhytochemistry
172
DOI
出版物ステータス出版済み - 4 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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