RI 6279 Materials In Coal Inhibitory To The Growth Of Microorganisms

The presence of antibiotic materials extractable with polar organic solvents was demonstrated in coals of various ranks. Since these antibiotics occur in low concentrations, 200 pounds of a high-volatile C coal was extracted with acetone at room temperature to obtain sufficient material for detailed study. The biologically active materials in the extract were concentrated by extracting with aqueous sodium hydroxide. The fractions soluble in sodium hydroxide inhibited bacterial cultures when present in concentrations comparable to those at which other antibiotics are active (5 µg/ml). Steam distillation of the extracts did not yield highly active materials, contrary to the finds of other investigators. Mass spectrometry of the extract indicated, mainly, the presence of 6-ring compounds in the region of mass 324 to 392. The predominance of 3-ring aromatic systems found by ultraviolet analysis suggests compounds such as biphenanthryl or similar structures. The activity of the hydroxide- soluble material decreased markedly when the phenolic hydroxyl groups were transformed into trimethylsilyl ethers. Hydrolysis of the ethers yielded a product having the same activity as the original material, which indicates that phenolic compounds are largely responsible for the antibiotic activity observed.