Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

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

研究成果: Contribution to journalArticle査読

抄録

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, and revealed the structure–activity relationship in this inhibitory activity. The conformation of ku-76 is flexible owing to the open-chain structure of pentan-2,4-dienoic acid with freely rotating single bonds, and the (2Z)-alkene moiety may be isomerized by external factors. To develop more potent inhibitors and obtain insight into the target biomolecules, various analogues of ku-76, fixed through conformation and/or configuration, were synthesized and evaluated. Stereochemical fixation was effective in improving the potency of gravitropic bending inhibition. Finally, we found highly potent conformational and/or configurational analogues (ku-257, ku-294 and ku-308), that did not inhibit root growth. The inhibition of root curvature by these analogues was comparable to that of naptalam.

本文言語英語
論文番号112508
ジャーナルPhytochemistry
179
DOI
出版ステータス出版済み - 11 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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