Abstract
An EtOH extract of the polypore mushroom Fomitopsis officinalis afforded two new naturally occurring chlorinated coumarins, which were identified as the previously synthesized compounds 6-chloro-4-phenyl-2H-chromen-2-one (1) and ethyl 6-chloro-2-oxo-4-phenyl-2H-chromen-3-carboxylate (2). The structures of the two isolates were deduced by ab initio spectroscopic methods and confirmed by chemical synthesis. In addition, an analogue of each was synthesized as 7-chloro-4-phenyl-2H-chromen-2-one (3) and ethyl 7-chloro-2-oxo-4-phenyl-2H-chromen-3-carboxylate (4). All four compounds were characterized physicochemically, and their antimicrobial activity profiles revealed a narrow spectrum of activity with lowest MICs against the Mycobacterium tuberculosis complex.
MeSH terms
-
Agaricales / chemistry*
-
Animals
-
Antitubercular Agents / chemistry
-
Antitubercular Agents / isolation & purification*
-
Antitubercular Agents / pharmacology*
-
Chlorocebus aethiops
-
Coumarins / chemistry
-
Coumarins / isolation & purification*
-
Coumarins / pharmacology*
-
Cytotoxins / chemistry
-
Cytotoxins / isolation & purification*
-
Cytotoxins / pharmacology*
-
Hydrocarbons, Chlorinated / chemistry
-
Hydrocarbons, Chlorinated / isolation & purification*
-
Hydrocarbons, Chlorinated / pharmacology*
-
Microbial Sensitivity Tests
-
Molecular Structure
-
Mycobacterium tuberculosis / drug effects*
-
Nuclear Magnetic Resonance, Biomolecular
-
Vero Cells
Substances
-
6-chloro-4-phenyl-2H-chromen-2-one
-
Antitubercular Agents
-
Coumarins
-
Cytotoxins
-
Hydrocarbons, Chlorinated
-
ethyl 6-chloro-2-oxo-4-phenyl-2H-chromen-3-carboxylate