Key structural features of cis-cinnamic acid as an allelochemical

Masato Abe, Keisuke Nishikawa, Hiroshi Fukuda, Kazunari Nakanishi, Yuta Tazawa, Tomoya Taniguchi, So Young Park, Syuntaro Hiradate, Yoshiharu Fujii, Katsuhiro Okuda, Mitsuru Shindo

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

1-O-cis-cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the cis-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclohexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated.

Original languageEnglish
Pages (from-to)56-67
Number of pages12
JournalPhytochemistry
Volume84
DOIs
Publication statusPublished - Dec 1 2012

Fingerprint

NSC 153174
cinnamic acid
Pheromones
allelochemicals
Spiraea
aromatic compounds
alkynes
Lettuce
Alkynes
photostability
phytotoxicity
Bioactivity
lettuce
growth retardation
Light sources
root growth
chemical derivatives
Derivatives
Light
Geometry

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Abe, M., Nishikawa, K., Fukuda, H., Nakanishi, K., Tazawa, Y., Taniguchi, T., ... Shindo, M. (2012). Key structural features of cis-cinnamic acid as an allelochemical. Phytochemistry, 84, 56-67. https://doi.org/10.1016/j.phytochem.2012.08.001

Key structural features of cis-cinnamic acid as an allelochemical. / Abe, Masato; Nishikawa, Keisuke; Fukuda, Hiroshi; Nakanishi, Kazunari; Tazawa, Yuta; Taniguchi, Tomoya; Park, So Young; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru.

In: Phytochemistry, Vol. 84, 01.12.2012, p. 56-67.

Research output: Contribution to journalArticle

Abe, M, Nishikawa, K, Fukuda, H, Nakanishi, K, Tazawa, Y, Taniguchi, T, Park, SY, Hiradate, S, Fujii, Y, Okuda, K & Shindo, M 2012, 'Key structural features of cis-cinnamic acid as an allelochemical', Phytochemistry, vol. 84, pp. 56-67. https://doi.org/10.1016/j.phytochem.2012.08.001
Abe M, Nishikawa K, Fukuda H, Nakanishi K, Tazawa Y, Taniguchi T et al. Key structural features of cis-cinnamic acid as an allelochemical. Phytochemistry. 2012 Dec 1;84:56-67. https://doi.org/10.1016/j.phytochem.2012.08.001
Abe, Masato ; Nishikawa, Keisuke ; Fukuda, Hiroshi ; Nakanishi, Kazunari ; Tazawa, Yuta ; Taniguchi, Tomoya ; Park, So Young ; Hiradate, Syuntaro ; Fujii, Yoshiharu ; Okuda, Katsuhiro ; Shindo, Mitsuru. / Key structural features of cis-cinnamic acid as an allelochemical. In: Phytochemistry. 2012 ; Vol. 84. pp. 56-67.
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