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Symbiotic microorganisms associated with insects can produce a wide array of metabolic products, which provide an opportunity for the discovery of useful natural products. Selective isolation of bacterial strains associated with the dung beetle,  Onthophagus lenzii , identified two strains, of which the antibiotic-producing  Brevibacillus  sp. PTH23 inhibited the growth of  Bacillus  sp. CCARM 9248, which is most closely related to the well-known entomopathogen,  Bacillus thuringiensis . A comprehensive chemical investigation based on antibiotic activity discovered two new antibiotics, named lenzimycins A and B ( 1 - 2 ), which inhibited growth of  Bacillus  sp. CCARM 9248. The  1 H and  13 C NMR, MS, MS/MS, and IR analyses elucidated the structures of  1  and  2 , which comprised a novel combination of fatty acid (12-methyltetradecanoic acid), glycerol, sulfate, and  N -methyl ethanolamine. Furthermore, the acid hydrolysis of  1  revealed the absolute configuration of 12-methyltetradecanoic acid as 12 S  by comparing its optical rotation value with authentic ( R )- and ( S )-12-methyltetradecanoic acid. In addition to inhibition of  Bacillus  sp. CCARM 9248, lenzimycins A and B were found to inhibit the growth of some human pathogenic bacteria, including  Enterococcus faecium  and certain strains of  Enterococcus faecalis.  Furthermore, the present study elucidated that lenzimycins A and B activated a reporter system designed to detect the bacterial cell envelope stress, thereby indicating an activity against the integrity of the bacterial cell wall.

Lenzimycins A and B, Metabolites With Antibacterial Properties From Brevibacillus sp. Associated With the Dung Beetle Onthophagus lenzii