Dibetanide, a new benzofuran derivative with the rare conjugated triene side chain from a sponge-associated fungus Aspergillus

Benzofuran-containing compounds are found to be promising scaffold with a wide range of pharmacolog-ical properties for drug development. A new benzofuran derivative, dibetanide ( 1 ), along with a known analogue, vermistatin ( 2 ), were discovered successfully from the culture extract of the sponge-associated fungus Aspergillus sp. LS57. Structurally, the new compound dibetanide featured the unusual conjugated triene side chain, which was isolated here for the first time in benzofuran derivatives. Their structures were deduced from HRESIMS, 1D and 2D NMR spectroscopy, and the absolute configurations were further determined by computational electronic circular dichroism (ECD) and comparison of experimental ECD spectra. Compounds 1 and 2 were evaluated for antifungal, antiviral and antibacterial activities, while only 1 exhibited inhibitory activity against Botrytis cinerea in vitro .(c) 2022 Elsevier B.V. All rights reserved.

Automated summary

Benzofuran-containing compounds are a promising scaffold with a wide range of pharmacological properties for drug development. A new benzofuran derivative, dibetanide, was discovered and characterized, featuring an unusual conjugated triene side chain. The structure and absolute configuration of the compound were determined using experimental and computational methods. The compound exhibited inhibitory activity against Botrytis cinerea, suggesting potential antibacterial properties.