title: Key structural features of cis-cinnamic acid as an allelochemical.
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.
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Abe
authors.forename: Keisuke
authors.initials: K
authors.lastname: Nishikawa
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Fukuda
authors.forename: Kazunari
authors.initials: K
authors.lastname: Nakanishi
authors.forename: Yuta
authors.initials: Y
authors.lastname: Tazawa
authors.forename: Tomoya
authors.initials: T
authors.lastname: Taniguchi
authors.forename: So-Young
authors.initials: SY
authors.lastname: Park
authors.forename: Syuntaro
authors.initials: S
authors.lastname: Hiradate
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Fujii
authors.forename: Katsuhiro
authors.initials: K
authors.lastname: Okuda
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Shindo
mesh_terms: D002934:Cinnamates / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018545:Lactuca / Q000187:drug effects / Q000254:growth & development; D015394:Molecular Structure; D010675:Pheromones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D031992:Spiraea / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002934:Cinnamates; D010675:Pheromones; C029010:cinnamic acid