Phenol derivatives from the cold-seep fungus Aspergillus sydowii 10–31. (December 2022)

• Record Type: Journal Article
• Authors: Liu, Ya-Ping; Fang, Sheng-Tao; Wang, Bin-Gui; Ji, Nai-Yun
• Is Part Of: Phytochemistry letters. Volume 52(2022)
• Page Start: 63
• Page End: 66
• Publication Date: 2022-12
• Subjects: Aspergillus sydowii -- Sesquiterpene -- Bisabolane -- Tetraphenyl ether -- Iodination; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2022.09.007
• Languages: English
• ISSNs: 1874-3900

Abstract

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. Graphical Abstract: ga1 Highlights: 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 .