TY - JOUR
T1 - Design and synthesis of conformationally constrained analogues of cis-cinnamic acid and evaluation of their plant growth inhibitory activity
AU - Nishikawa, Keisuke
AU - Fukuda, Hiroshi
AU - Abe, Masato
AU - Nakanishi, Kazunari
AU - Tazawa, Yuta
AU - Yamaguchi, Chihiro
AU - Hiradate, Syuntaro
AU - Fujii, Yoshiharu
AU - Okuda, Katsuhiro
AU - Shindo, Mitsuru
N1 - Funding Information:
This work is supported by the Program for Promotion of Basic and Applied Research for Innovations in the Bio-oriented Industry (BRAIN) and “Innovations Inspired by Nature Research Support Program (Sekisui Chemical).”
PY - 2013
Y1 - 2013
N2 - 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.
AB - 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.
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U2 - 10.1016/j.phytochem.2013.10.001
DO - 10.1016/j.phytochem.2013.10.001
M3 - Article
C2 - 24176527
AN - SCOPUS:84888359015
SN - 0031-9422
VL - 96
SP - 223
EP - 234
JO - Phytochemistry
JF - Phytochemistry
ER -