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

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)223-234
Number of pages12
JournalPhytochemistry
Volume96
DOIs
Publication statusPublished - Oct 29 2013

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NSC 153174
cinnamic acid
plant growth
synthesis
Growth
Spiraea
aromatic compounds
Bridged-Ring Compounds
olefin
Lettuce
Growth Inhibitors
Pheromones
allelochemicals
Alkenes
structure-activity relationships
Structure-Activity Relationship
phytotoxicity
carboxylic acids
Carboxylic Acids
lettuce

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Design and synthesis of conformationally constrained analogues of cis-cinnamic acid and evaluation of their plant growth inhibitory activity. / Nishikawa, Keisuke; Fukuda, Hiroshi; Abe, Masato; Nakanishi, Kazunari; Tazawa, Yuta; Yamaguchi, Chihiro; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru.

In: Phytochemistry, Vol. 96, 29.10.2013, p. 223-234.

Research output: Contribution to journalArticle

Nishikawa, Keisuke ; Fukuda, Hiroshi ; Abe, Masato ; Nakanishi, Kazunari ; Tazawa, Yuta ; Yamaguchi, Chihiro ; Hiradate, Syuntaro ; Fujii, Yoshiharu ; Okuda, Katsuhiro ; Shindo, Mitsuru. / Design and synthesis of conformationally constrained analogues of cis-cinnamic acid and evaluation of their plant growth inhibitory activity. In: Phytochemistry. 2013 ; Vol. 96. pp. 223-234.
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