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Exploring Brominated Aromatic Butenolides from Aspergillus terreus EGF7-0-1 with Their Antifungal Activities
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-01 , DOI: 10.1021/acs.jafc.4c04728 Hao Fan 1 , Xue-Hua Shao 2 , Ping-Ping Wu 1 , Ao-Lin Hao 1 , Zheng-Wu Luo 1 , Meng-Dan Zhang 1 , Jing Xie 1 , Bo Peng 3 , Cui-Xian Zhang 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-01 , DOI: 10.1021/acs.jafc.4c04728 Hao Fan 1 , Xue-Hua Shao 2 , Ping-Ping Wu 1 , Ao-Lin Hao 1 , Zheng-Wu Luo 1 , Meng-Dan Zhang 1 , Jing Xie 1 , Bo Peng 3 , Cui-Xian Zhang 1
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Fungal diseases could severely harm agricultural productions. To develop new antifungal agents, based on the Global Natural Products Social Molecular Networking, typical bromine isotope peak ratios, and ultraviolet absorptions, cultivation of the soft coral-derived endophytic fungi Aspergillus terreus EGF7-0-1 with NaBr led to the targeted isolation of 14 new brominated aromatic butenolides (1–14) and six known analogues (15–20). Their structures were elucidated by extensive spectroscopic analysis and quantum chemical calculations. Compounds 1–14 exhibited wildly antifungal activities (against Colletotrichum gloeosporioides, Pestalotiopsis microspora, Fusarium oxysporum f. sp. cubense, Botrytis cinerea, and Diaporthe phoenicicola). The bioassay results showed that compounds 1–14 exhibited excellent antifungal activities against C. gloeosporioides, with concentration for 50% of maximal effect (EC50) values from 2.72 to 130.41 nM. The mechanistic study suggests that compound 1 may disrupt nutrient signaling pathways by reducing the levels of metabolites, such as carbohydrates, lipids, and amino acids, leading to an increase in low-density granules and a decrease in high-density granules in the cytoplasm, accompanied by numerous vacuoles, thereby inhibiting the growth of C. gloeosporioides. Monobrominated γ-butenolide 1 may be expected to exploit a novel agriculturally antifungal leading drug. Meanwhile, compound M1 has conformed antifugual activities against C. gloeosporioides by papayas in vivo.
中文翻译：
探索土曲霉 EGF7-0-1 中的溴化芳香族丁烯内酯及其抗真菌活性
真菌病害严重危害农业生产。为了开发新的抗真菌剂，基于全球天然产品社会分子网络、典型的溴同位素峰比和紫外线吸收，用NaBr培养软珊瑚源内生真菌土曲霉EGF7-0-1，从而有针对性地分离出14 种新的溴化芳香族丁烯内酯 ( 1 – 14 ) 和六种已知类似物 ( 15 – 20 )。通过广泛的光谱分析和量子化学计算阐明了它们的结构。化合物1 – 14表现出广泛的抗真菌活性（针对胶孢炭疽菌、小孢多盘拟盘菌、古巴尖镰孢、灰葡萄孢和菲尼克斯土霉）。生物测定结果表明，化合物1 ~ 14对胶孢梭菌表现出优异的抗真菌活性，最大作用浓度50%（EC 50 ）值在2.72~130.41 nM之间。机理研究表明，化合物1可能通过降低碳水化合物、脂质和氨基酸等代谢物的水平来破坏营养信号传导途径，导致细胞质中低密度颗粒的增加和高密度颗粒的减少，伴随着大量空泡，从而抑制C. gloeosporioides的生长。一溴化γ-丁烯内酯1有望开发出一种新型农用抗真菌先导药物。同时，化合物M1对念珠菌具有抗真菌活性。 木瓜体内的胶孢子虫。
更新日期：2024-09-01
中文翻译：
探索土曲霉 EGF7-0-1 中的溴化芳香族丁烯内酯及其抗真菌活性
真菌病害严重危害农业生产。为了开发新的抗真菌剂，基于全球天然产品社会分子网络、典型的溴同位素峰比和紫外线吸收，用NaBr培养软珊瑚源内生真菌土曲霉EGF7-0-1，从而有针对性地分离出14 种新的溴化芳香族丁烯内酯 ( 1 – 14 ) 和六种已知类似物 ( 15 – 20 )。通过广泛的光谱分析和量子化学计算阐明了它们的结构。化合物1 – 14表现出广泛的抗真菌活性（针对胶孢炭疽菌、小孢多盘拟盘菌、古巴尖镰孢、灰葡萄孢和菲尼克斯土霉）。生物测定结果表明，化合物1 ~ 14对胶孢梭菌表现出优异的抗真菌活性，最大作用浓度50%（EC 50 ）值在2.72~130.41 nM之间。机理研究表明，化合物1可能通过降低碳水化合物、脂质和氨基酸等代谢物的水平来破坏营养信号传导途径，导致细胞质中低密度颗粒的增加和高密度颗粒的减少，伴随着大量空泡，从而抑制C. gloeosporioides的生长。一溴化γ-丁烯内酯1有望开发出一种新型农用抗真菌先导药物。同时，化合物M1对念珠菌具有抗真菌活性。 木瓜体内的胶孢子虫。
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