Triquinane sesquiterpene octanoates from Antrodiella zonata with their cytotoxicity and antimalarial activities

By modifying fermentation conditions, ten octanoate-containing triquinane sesquiterpenoids, including six previously undescribed ones, namely antrodizonatins M‒R, were isolated from the fungus Antrodiella zonata. Their structures and absolute configurations have been established by extensive spectroscopic methods, single crystal X-ray diffraction, ECD and ¹³C NMR calculations. Notably, antrodizonatin Q features of an unusual adenine substituent. Antrodizonatins M‒O, and R demonstrated cytotoxic activity against the human tumor cell line MCF-7, with IC₅₀ values ranging from 2.2 to 17.6 μM. Antrodizonatins N-P, Antrodizonatin R, dihydrocoriolin C, and chloriolin C exhibited in vitro antimalarial activity against Plasmodium falciparum, with IC₅₀ values ranging from 21.4 to 33.7 μM.