Synthesis of beta-hydroxy fatty acids and beta-amino fatty acids by the strains of Bacillus subtilis producing iturinic antibiotics.
The iturinic antibiotics, which contain long chain beta-amino acids, are produced by Bacillus subtilis. Screening these strains for the presence of a possible precursor of the iturinic antibiotics, we isolated a lipopeptide containing beta-hydroxy fatty acids. The structure of this compound was studied and it appears to be identical or structurally very similar to surfactin. The carbon chain of its beta-hydroxy fatty acids was n C16, iso C16, iso C15 or anteiso C15. The percentages of each beta-hydroxy fatty acids varied according to the strain producing iturinic antibiotics and were influenced by addition of branched-chain alpha-amino acids to the culture medium. These results demonstrate for the first time that iso C14 beta-hydroxy fatty acid is a constituent present in such a surfactin like lipopeptide. Besides, the presence of radioactive beta-hydroxy fatty acids in the phospholipids when the strains were grown in the presence of sodium [14C]acetate seems also characterize the different strains producing iturinic antibiotics.
Besson
F
F
Laboratoire de Biochimie Microbienne (C.N.R.S. UMR 24), Université Claude-Bernard, Lyon, France.
Tenoux
I
I
Hourdou
M L
ML
Michel
G
G
D000595:Amino Acid Sequence; D000597:Amino Acids, Branched-Chain / Q000494:pharmacology; D000935:Antifungal Agents / Q000096:biosynthesis* / Q000302:isolation & purification; D001412:Bacillus subtilis / Q000378:metabolism*; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000096:biosynthesis* / Q000302:isolation & purification / Q000378:metabolism; D006461:Hemolysis / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010452:Peptide Biosynthesis; D010455:Peptides / Q000302:isolation & purification; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet
D000597:Amino Acids, Branched-Chain; D000935:Antifungal Agents; D005227:Fatty Acids; D010455:Peptides