Design, Synthesis, and Structure–Activity Relationship Studies of Magnolol Derivatives as Antifungal Agents

灰葡萄孢菌 茄丝核菌 EC50型 菌丝体 菌核病 杀菌剂 体内 天然产物 厚朴酚 嘧霉胺 化学 结构-活动关系 生物 生物化学 立体化学 体外 植物 生物技术
作者
Hu Li,Ying‐Hui He,Yongmei Hu,Qing-Ru Chu,Yong-Jia Chen,Zhenrong Wu,Zhijun Zhang,Ying‐Qian Liu,Cheng‐Jie Yang,Hongjie Liang,Yin-Fang Yan
出处
期刊:Journal of Agricultural and Food Chemistry [American Chemical Society]
卷期号:69 (40): 11781-11793 被引量:34
标识
DOI:10.1021/acs.jafc.1c01838
摘要

Plant pathogenic fungi seriously affect agricultural production and are difficult to control. The discovery of new leads based on natural products is an important way to innovate fungicides. In this study, 30 natural-product-based magnolol derivatives were synthesized and characterized on the basis of NMR and mass spectroscopy. Bioactivity tests on phytopathogenic fungi (Rhizoctonia solani, Fusarium graminearum, Botrytis cinerea, and Sclerotinia sclerotiorum) in vitro of these compounds were performed systematically. The results showed that 11 compounds were active against four kinds of phytopathogenic fungi with EC50 values in the range of 1.40-20.00 μg/mL, especially compound L5 that exhibited excellent antifungal properties against B. cinerea with an EC50 value of 2.86 μg/mL, approximately 2.8-fold more potent than magnolol (EC50 = 8.13 μg/mL). Moreover, compound L6 showed the highest antifungal activity against F. graminearum and Rhophitulus solani with EC50 values of 4.39 and 1.40 μg/mL, respectively, and compound L7 showed good antifungal activity against S. sclerotiorum. Then, an in vivo experiment of compound L5 against B. cinerea was further investigated in vivo using infected tomatoes (curative effect, 50/200 and 36%/100 μg/mL). The physiological and biochemical studies illustrated that the primary action mechanism of compound L5 on B. cinerea might change the mycelium morphology, increase cell membrane permeability, and destroy the function of mitochondria. Furthermore, structure-activity relationship (SAR) studies revealed that hydroxyl groups play a key role in antifungal activity. To sum up, this study provides a reference for understanding the application of magnolol-based antifungal agents in crop protection.
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