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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
Phytochemistry 2012 v.84 pp. 56-67
Spiraea, allelochemicals, cinnamic acid, growth retardation, lettuce, photostability, phytotoxicity, root growth
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.