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.
| Original language | English |
|---|---|
| Pages (from-to) | 56-67 |
| Number of pages | 12 |
| Journal | Phytochemistry |
| Volume | 84 |
| DOIs | |
| Publication status | Published - Dec 1 2012 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Molecular Biology
- Plant Science
- Horticulture
Cite this
Key structural features of cis-cinnamic acid as an allelochemical. / Abe, Masato; Nishikawa, Keisuke; Fukuda, Hiroshi; Nakanishi, Kazunari; Tazawa, Yuta; Taniguchi, Tomoya; Park, So Young; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru.
In: Phytochemistry, Vol. 84, 01.12.2012, p. 56-67.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Key structural features of cis-cinnamic acid as an allelochemical
AU - Abe, Masato
AU - Nishikawa, Keisuke
AU - Fukuda, Hiroshi
AU - Nakanishi, Kazunari
AU - Tazawa, Yuta
AU - Taniguchi, Tomoya
AU - Park, So Young
AU - Hiradate, Syuntaro
AU - Fujii, Yoshiharu
AU - Okuda, Katsuhiro
AU - Shindo, Mitsuru
PY - 2012/12/1
Y1 - 2012/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84868096014&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84868096014&partnerID=8YFLogxK
U2 - 10.1016/j.phytochem.2012.08.001
DO - 10.1016/j.phytochem.2012.08.001
M3 - Article
C2 - 22959226
AN - SCOPUS:84868096014
VL - 84
SP - 56
EP - 67
JO - Phytochemistry
JF - Phytochemistry
SN - 0031-9422
ER -