Discovery of Natural Rosin Derivatives Containing Oxime Ester Moieties as Potential Antifungal Agents to Control Tomato Gray Mold Caused by Botrytis cinerea
Discovery of Natural Rosin Derivatives Containing Oxime Ester Moieties as Potential Antifungal Agents to Control Tomato Gray Mold Caused by Botrytis cinerea
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发现含有肟酯部分的天然松香衍生物作为潜在的抗真菌剂来控制灰霉病引起的番茄灰霉病
DOI：
10.1021/acs.jafc.2c01532
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发表时间：
2022-05-11
影响因子：
6.1
通讯作者：
Song, Jie
中科院分区：
文献类型：
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作者：
Gao, Yanqing;Xu, Renle;Song, Jie
受天然产物抗病原真菌应用的启发，以松香为原料，合成了两个系列的脱氢松油酮酯类化合物。通过对番茄灰霉病菌、菌核病菌、苹果腐烂病菌、水稻纹枯病菌、尖孢镰刀菌和链格孢菌的体外抑菌活性的评价和筛选，发现化合物4f对番茄灰霉病菌的抑菌活性最强，其EC50值为0.798 mg/L，低于阳性对照的1.112 mg/L。体内抗真菌活性结果表明，4F对番茄有较好的保护和治疗作用。生理生化研究表明，化合物4f对灰霉菌的作用机制是改变菌丝体的形态和超微结构，增加细胞膜的通透性，导致细胞核和线粒体功能障碍，从而导致细胞凋亡。此外，定性和定量的构效关系研究表明，化合物4f与目标受体之间的诱导和接合作用形成电子转移过程，从而达到抗真菌作用。这些结果表明，从天然产物松香中提取的化合物4f是一种新的潜在的抗灰霉病菌候选化合物。
Inspired by the application of natural products against pathogenic fungi, two series of dehydroabietyl oxime ester derivatives were synthesized using rosin as a raw material. Based on the evaluation and screening of in vitro antifungal activities against Botrytis cinerea (B. cinerea), Sclerotinia sclerotiorum, Valsa mali, Rhizoctonia solani, Fusarium oxysporum, and Alternaria alternata, compound 4f exhibited the best antifungal activity against B. cinerea, and its EC50 was 0.798 mg/L, which was lower than that of the positive control trifloxystrobin (1.112 mg/L). The in vivo antifungal activity results showed that 4f had satisfactory protective and curative effects on tomato. Physiological and biochemical studies showed that the action mechanism of compound 4f against B. cinerea is to change the morphology and the ultrastructure of the mycelium, increase the permeability of the cell membrane, and cause nucleus and mitochondrial dysfunction, thus leading to apoptosis. In addition, qualitative and quantitative structure-activity relationship studies showed that the inductive and conjugative interactions between compound 4f and the target receptor form an electron transfer process, thereby achieving an antifungal effect. These results indicated that compound 4f, which was derived from the natural product rosin, is a novel potential fungicidal candidate against B. cinerea.