Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors.
1-O-cis-Cinnamoyl-β-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA.
Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan.
Keisuke
K
Nishikawa
Hiroshi
H
Fukuda
Masato
M
Abe
Kazunari
K
Nakanishi
Tomoya
T
Taniguchi
Takashi
T
Nomura
Chihiro
C
Yamaguchi
Syuntaro
S
Hiradate
Yoshiharu
Y
Fujii
Katsuhiro
K
Okuda
Mitsuru
M
Shindo
D000179:Acrylates / Q000737:chemistry / Q000302:isolation & purification; D002934:Cinnamates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018545:Lactuca / Q000187:drug effects* / Q000254:growth & development; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010937:Plant Growth Regulators / Q000378:metabolism*; D018517:Plant Roots / Q000254:growth & development; D031992:Spiraea / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C000588947:1-O-cis-cinnamoyl-beta-D-glucopyranose; D000179:Acrylates; D002934:Cinnamates; D005960:Glucosides; D010937:Plant Growth Regulators; C029010:cinnamic acid; C036658:acrylic acid
Allelochemicals; Asteraceae; Lactuca sativa; Lettuice; Plant growth inhibitors; SAR; Substituent effects; cis-Cinnamic acid