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synthesis and antifungal activity of carabrone derivatives合成和抗真菌活性carabrone衍生品
Molecules 2010, 15, 6485-6492; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Communication
Synthesis and Antifungal Activity of Carabrone Derivatives
Jun-Tao Feng 1,* Zhi-Qing Ma 1, Jiang-Hua Li 1, Jun He 1, Hui Xu 1,2,* and Xing Zhang 1
,
1 Research and Development Center of Biorational Pesticide, College of Plant Protection, Northwest
AF University, Yangling 712100, China
2 Laboratory of Pharmaceutical Design Synthesis, College of Sciences, Northwest AF
University,Yangling 712100, China
* Author to whom correspondence should be addressed; E-Mails: fengjt67@ (J.-T.F.);
orgxuhui@ (H.X.)
Received: 6 July 2010; in revised form: 11 August 2010 / Accepted: 23 August 2010 /
Published: 16 September 2010
Abstract: Nine derivatives 6-14 of carabrone (1) were synthesized and tested in vitro
against Colletotrichum lagenarium Ell et Halst using the spore germination method.
Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal
activity than 1. Structure-activity relationships (SAR) demonstrated that the γ-lactone was
necessary for the antifungal activity of 1, and the substituents on the C-4 position of 1
could significantly affect the antifungal activity.
Keywords: carabrone; structural modification; synthesis; antifungal activity
1. Introduction
Carabrone (1, Figure 1), containing cyclopropane and sesquiterpene
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