Discovery of Natural Sesquiterpene Lactone 1-O-Acetylbritannilactone Analogues Bearing Oxadiazole, Triazole, or Imidazole Scaffolds for the Development of New Fungicidal Candidates

文献类型： 外文期刊

第一作者： Zhi, Xiao-yan

作者： Zhi, Xiao-yan;Zhang, Yuan;Li, Yang-fan;Liu, Ying;Niu, Wen-peng;Li, Yang;Zhang, Cheng-ran;Cao, Hui;Hao, Xiao-juan;Yang, Chun;Zhi, Xiao-yan;Yang, Chun

作者机构：

关键词： Inula britannica; 1-O-acetylbritannilactone; structural modification; antifungal activity; natural-product-based fungicides; structure-activityrelationship

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：6.1； 五年影响因子：6.3 ）

ISSN： 0021-8561

年卷期： 2023 年 71 卷 30 期

页码：

收录情况： SCI

摘要： Inrecent decades, natural products have been considered importantresources for developing of new agrochemicals because of their novelarchitectures and multibioactivities. Consequently, herein, 1-O-acetylbritannilactone (ABL), a natural sesquiterpene lactonefrom Inula britannica L., was usedas a lead for further modification to discover fungicidal candidates.Six series of ABL-based derivatives containing an oxadiazole, triazole,or imidazole moiety were designed and synthesized, and their antifungalactivities were also evaluated in vitro and in vivo. Bioassay results revealed that compounds 8d, 8h, and 8j (EC50 =61.4, 30.9, and 12.4 & mu;g/mL, respectively) exhibited more pronouncedinhibitory activity against Fusarium oxysporum than their precursor ABL (EC50 > 500 & mu;g/mL)andpositive control hymexazol (EC50 = 77.2 & mu;g/mL). Derivatives 8d and 11j (EC50 = 19.6 and 41.5 & mu;g/mL,respectively) exhibited more potent antifungal activity toward Cytospora mandshurica than ABL (EC50 =68.3 & mu;g/mL). Compound 10 exhibited excellent andbroad-spectrum antifungal activity against seven phytopathogenic fungalmycelia. Particularly, the inhibitory activity of compound 10 against the mycelium of Botrytis cinerea was more than 10.8- and 2.3-fold those of ABL and hymexazol, respectively.Meanwhile, derivative 10 (IC50 = 47.7 & mu;g/mL)displayed more pronounced inhibitory activity against the spore of B. cinerea than ABL (IC50 > 500 & mu;g/mL)and difenoconazole (IC50 = 80.8 & mu;g/mL). Additionally,the in vivo control efficacy of compound 10 against B. cinerea was further studiedusing infected tomatoes (protective effect = 58.4%; therapeutic effect= 48.7%). The preliminary structure-activity relationship analysissuggested that the introduction of the 1,3,4-oxadiazole moiety (especiallythe 1,3,4-oxadiazole heterocycle containing the 4-chlorophenyl, 2-furyl,or 2-pyridinyl group) on the skeleton of ABL was more likely to producepotential antifungal compounds. These findings pave the way for furtherdesign and development of ABL-based derivatives as potential antifungalagents.

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