Biotransformation of Thiochroman Derivatives Using Marine-Derived Fungi: Isolation, Characterization, and Antimicrobial Activity

Abstract

Thiochroman derivatives are highly versatile molecules widely used for the synthesis of novel heterocycles and bioactive compounds. In our study, we conducted the biotransformation of thiochroman-4-ol (1) and 6-chlorothiochroman-4-ol (1a) using the marine-derived fungal strains Emericellopsis maritima BC17 and Purpureocillium lilacinum BC17-2. Biotransformations yielded ten known thiochroman derivatives along with the compound 1-(5-chloro-2-(methylthio)phenyl)propane-1,3-diol (6a), which was described for the first time. Moreover, we successfully characterized the stereoisomers of sulfoxides 3 and 3a. Their structures and absolute configurations were established though comprehensive analyses of NMR, HR ESI-MS, and ECD spectra, as well as by using Mosher’s method. Antimicrobial activity of the isolated metabolites was evaluated against bacterial and fungal human pathogens, specifically Staphylococcus aureus ATCC 29213, Escherichia coli ATCC25922, and Candida albicans HPM-1922816.