Bacillus subtilis SSE4 produces subtulene A, a new lipopeptide antibiotic possessing an unusual C15 unsaturated beta-amino acid

Abstract

Subtulene A, a new cyclic lipopeptide, was isolated from the culture broth of Bacillus subtilis SSE4. This antibiotic compound contained the seven common alpha-amino acids, L-Asn-1, D-Tyr-2, D-Asn-3, L-Gln-4, L-Pro-5, D-Asn-6, L-Ser-7 and the unique beta-amino acid-8 present in the iturin family. 1D and 2D NMR, as well as MS analyses, identified the beta-amino acid as 3-amino-13-methyltetradec-8-enoic acid, an Iso C15 long chain beta-amino acid. B. subtilis SSE4 was also found to produce iturin A. B. subtilis SSE4 culture filtrate exhibited both antifungal and antibacterial activities.