title: Design and synthesis of conformationally constrained analogues of cis-cinnamic acid and evaluation of their plant growth inhibitory activity.
abstract: 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.
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Nishikawa
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Fukuda
authors.forename: Masato
authors.initials: M
authors.lastname: Abe
authors.forename: Kazunari
authors.initials: K
authors.lastname: Nakanishi
authors.forename: Yuta
authors.initials: Y
authors.lastname: Tazawa
authors.forename: Chihiro
authors.initials: C
authors.lastname: Yamaguchi
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 / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018545:Lactuca / Q000187:drug effects / Q000254:growth & development; D008968:Molecular Conformation; D015394:Molecular Structure; D063245:Plant Development / Q000187:drug effects*; D018517:Plant Roots / Q000254:growth & development; D031992:Spiraea / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D002934:Cinnamates; C029010:cinnamic acid
keywords: Asteraceae; Lactuca sativa; Lettuce; Plant growth inhibitors; SAR; cis-Cinnamic acid