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Phytochemistry

Title:		Key structural features of cis-cinnamic acid as an allelochemical
Author(s):		Abe M; Nishikawa K; Fukuda H; Nakanishi K; Tazawa Y; Taniguchi T; Park SY; Hiradate S; Fujii Y; Okuda K; Shindo M;
Address:		"Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan"
Journal Title:		Phytochemistry
Year:		2012
Volume:		20120905
Issue:
Page Number:		56 - 67
DOI:		10.1016/j.phytochem.2012.08.001
ISSN/ISBN:		1873-3700 (Electronic) 0031-9422 (Linking)
Abstract:		"1-O-cis-cinnamoyl-beta-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"
Keywords:		Cinnamates/*chemistry/isolation & purification/pharmacology Lettuce/drug effects/growth & development Molecular Structure Pheromones/*chemistry/isolation & purification/pharmacology Spiraea/*chemistry Stereoisomerism;
Notes:		"MedlineAbe, Masato Nishikawa, Keisuke Fukuda, Hiroshi Nakanishi, Kazunari Tazawa, Yuta Taniguchi, Tomoya Park, So-Young Hiradate, Syuntaro Fujii, Yoshiharu Okuda, Katsuhiro Shindo, Mitsuru eng Research Support, Non-U.S. Gov't England 2012/09/11 Phytochemistry. 2012 Dec; 84:56-67. doi: 10.1016/j.phytochem.2012.08.001. Epub 2012 Sep 5"