Natural Sesquiterpene Lactone as Source of Discovery of Novel Fungicidal Candidates: Structural Modification and Antifungal Activity Evaluation of Xanthatin Derived from Xanthium strumarium L

文献类型： 外文期刊

第一作者： Yang, Chun

作者： Yang, Chun;Li, Yang;Zhang, Yuan;Hu, Qiang;Liu, Ying;Li, Yang-fan;Shi, Hong-cheng;Song, Li-li;Cao, Hui;Hao, Xiao-juan;Zhi, Xiao-yan;Yang, Chun;Zhi, Xiao-yan

作者机构：

关键词： Xanthium strumarium L; sesquiterpene lactone; xanthatin; structural modification; antifungalactivity; natural-product-based fungicide; SAR

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 29 期

页码：

收录情况： SCI

摘要： Aspart of our ongoing efforts to discover novel agriculturalfungicidalcandidates from natural sesquiterpene lactones, in the present work,sixty-three xanthatin-based derivatives containing a arylpyrazole,arylimine, thio-acylamino, oxime, oxime ether, or oxime ester moietywere synthesized. Their structures were well characterized by H-1 and C-13 nuclear magnetic resonance and high-resolutionmass spectrometry, while the absolute configurations of compounds 5 & PRIME; and 6a were further determined by single-crystalX-ray diffraction. Meanwhile, the antifungal activities of the preparedcompounds against several phytopathogenic fungi were investigatedusing the spore germination method and the mycelium growth rate method in vitro. The bioassay results illustrated that compounds 5, 5 & PRIME;, and 15 exhibited excellentinhibitory activity against the tested fungal spores and displayedremarkable inhibitory effects on fungal mycelia. Compounds 5 and 5 & PRIME; exhibited more potent inhibitory activity(IC50 = 1.1 and 24.8 & mu;g/mL, respectively) againstthe spore of Botrytis cinerea thantheir precursor xanthatin (IC50 = 37.6 & mu;g/mL), whereinthe antifungal activity of compound 5 was 34-fold higherthan that of xanthatin and 71-fold higher than that of the positivecontrol, difenoconazole (IC50 = 78.5 & mu;g/mL). Notably,compound 6 & PRIME;a also demonstrated broad-spectruminhibitory activity against the four tested fungal spores. Meanwhile,compounds 2, 5, 8, and 15 showed prominent inhibitory activity against the myceliaof Cytospora mandshurica with the EC50 values of 2.3, 11.7, 11.1, and 3.0 & mu;g/mL, respectively,whereas the EC50 value of xanthatin was 14.8 & mu;g/mL.Additionally, compounds 5 & PRIME; and 15 exhibited good in vivo therapeutic and protectiveeffects against B. cinerea with valuesof 55.4 and 62.8%, respectively. The preliminary structure-activityrelationship analysis revealed that the introduction of oxime, oximeether, or oxime ester structural fragment at the C-4 position of xanthatinor the introduction of a chlorine atom at the C-3 position of xanthatinmight be significantly beneficial to antifungal activity. In conclusion,the comprehensive investigation indicated that partial xanthatin-basedderivatives from this study could be considered for further explorationas potential lead structures toward developing novel fungicidal candidatesfor crop protection.

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