Design and synthesis of conformationally constrained analogues of cis-cinnamic acid and evaluation of their plant growth inhibitory activity

Keisuke Nishikawa, Hiroshi Fukuda, Masato Abe, Kazunari Nakanishi, Yuta Tazawa, Chihiro Yamaguchi, Syuntaro Hiradate, Yoshiharu Fujii, Katsuhiro Okuda, Mitsuru Shindo

研究成果: Contribution to journalArticle査読

9 被引用数 (Scopus)

抄録

1-O-cis-Cinnamoyl-β-d-glucopyranose is known to be one of the most potent allelochemical candidates and was isolated from Spiraea thunbergii Sieb by Hiradate et al. (2004), who suggested that it derived its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. In this study, key structural features and substituent effects of cis-cinnamic acid (cis-CA) on lettuce root growth inhibition was investigated. These structure-activity relationship studies indicated the importance of the spatial relationship of the aromatic ring and carboxylic acid moieties. In this context, conformationally constrained cis-CA analogues, in which the aromatic ring and cis-olefin were connected by a carbon bridge, were designed, synthesized, and evaluated as plant growth inhibitors. The results of the present study demonstrated that the inhibitory activities of the five-membered and six-membered bridged compounds were enhanced, up to 0.27 μM, and were ten times higher than cis-CA, while the potency of the other compounds was reduced.

本文言語英語
ページ(範囲)223-234
ページ数12
ジャーナルPhytochemistry
96
DOI
出版ステータス出版済み - 2013

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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