Key structural features of cis-cinnamic acid as an allelochemical

被引：31

作者：

Abe, Masato ^{[1
]}

Nishikawa, Keisuke ^{[1
]}

Fukuda, Hiroshi ^{[2
]}

Nakanishi, Kazunari ^{[2
]}

Tazawa, Yuta ^{[2
]}

Taniguchi, Tomoya ^{[2
]}

Park, So-young ^{[3
]}

Hiradate, Syuntaro ^{[3
]}

Fujii, Yoshiharu ^{[4
]}

Okuda, Katsuhiro ^{[1
]}

Shindo, Mitsuru ^{[1
]}

机构：

[1] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Kasuga, Fukuoka 8168580, Japan

[3] Natl Inst Agroenvironm Sci, Biodivers Div, Tsukuba, Ibaraki 3058604, Japan

[4] Tokyo Univ Agr & Technol, Fuchu, Tokyo 1838509, Japan

来源：

PHYTOCHEMISTRY | 2012年 / 84卷

关键词：

cis-Cinnamic acid; Allelochemicals; Plant growth inhibitors; Thunberg spirea; Spiraea thunbergii; Rosaceae; Lactuca sativba L; Lettuce; Asteraceae; PLANT-GROWTH; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; COUPLING REACTIONS; ISOMERIZATION; EFFICIENT; ALDEHYDES; KETONES; ESTERS; CYCLOPROPANATION;

D O I：

10.1016/j.phytochem.2012.08.001

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 as-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclo-hexene 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. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：56 / 67

页数：12

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