Phenol derivatives from the cold-seep fungus Aspergillus sydowii 10–31

Abstract

Two bisabolane-type sesquiterpenoid phenols inclusive of the known (7 S )-flavilane A ( 1 ) and the new (7 S )− 4-iodo-flavilane A ( 2 ), along with a new tetraphenyl ether, bisviolaceol II ( 3 ), were isolated from the cold-seep fungus Aspergillus sydowii 10–31. Their structures were identified through spectroscopic methods, such as MS, IR, and NMR, and the absolute configurations of 1 and 2 were ascertained by comparison of ECD curves. Compounds 1 and 2 represent rarely encountered sulfur-bearing sesquiterpenes in nature, and the iodination in 2 makes it unique in particular. Additionally, 3 is the first tetraphenyl ether derivative from the fungal species A. sydowii . Compounds 1 - 3 inhibited the growth of several Vibrio bacteria and harmful microalgae. • Two new metabolites from a cold-seep isolate of Aspergillus sydowii are reported. • (7 S )− 4-Iodo-flavilane A is the first natural sulfur- and iodine-containing sesquiterpene. • Biviolaceol II represents the first tetraphenyl ether derivative from Aspergillus sydowii .