Amide-Containing Diphenyl Ethers and Depsidones from Talaromyces pinophilus ZS32

Four new amide-containing diphenyl ethers, talaroacylamides A−D (1−4), and two new depsidones, talarodepsidones A−B (5−6), together with seven previously reported analogues 7−13 were isolated from the marine-derived fungus Talaromyces pinophilus ZS32. Their structures were elucidated by analysis of spectroscopic data, including NMR and HRESIMS, in combination with the modified Mosher’s method, NMR and ECD calculations and DP4+ probability analysis. Compounds 1−4 represent the first naturally occurring diphenyl ethers featuring an amide group at C-6 position. Compounds 1−3, 5, 6, 9, 11, and 13 exhibit weak antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), Staphylococcus epidermidis, Bacillusparanthracis and Bacillus subtilis. Compound 11 showed weak antifungal activity against Rhizoctonia solani, with an EC50 of 57.2 μg/mL. Further evaluation revealed increased membrane permeability, elevated markers of oxidative stress, mitochondrial membrane depolarization, decreased SDH activity in mycelial extracts, and reduced ATP content in R. solani exposed to compound 11.