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Molecules 2018, 23(9), 2224;

High-Frequency Occurrence of Surfactin Monomethyl Isoforms in the Ferment Broth of a Bacillus subtilis Strain Revealed by Ion Trap Mass Spectrometry

Department of Microbiology, Faculty of Science and Informatics, University of Szeged, Közép fasor 52, H-6726 Szeged, Hungary
Department of Botany and Microbiology, College of Science, King Saud University, Riyadh 11451, Saudi Arabia
Author to whom correspondence should be addressed.
Received: 23 July 2018 / Revised: 17 August 2018 / Accepted: 30 August 2018 / Published: 1 September 2018
(This article belongs to the Section Natural Products Chemistry)
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Surfactins are cyclic lipopeptides consisting of a β-hydroxy fatty acid of various chain length and a peptide ring of seven amino acids linked together by a lactone bridge, forming the cyclic structure of the peptide chain. These compounds are produced mainly by Bacillus species and possess numerous biological effects such as antimicrobial (antiviral, antibacterial, and antifungal) activities. A mixture of surfactins extracted from Bacillus subtilis strain SZMC 6179J was examined by HPLC-ESI-IT-MS technique, enhancing their separation to reveal novel lipopeptide varieties with higher masses and to characterize their structures. During the MS2 spectra analyses of their sodiated molecular ions [M + Na]+, a previously rarely encountered group of surfactins was detected and two novel types of the group were discovered containing methyl esterified aspartic acid residue in their fifth amino acid position. The relative amounts of these monomethyl isoforms exceeded 35% of the produced surfactin in total. In the m/z value of 1114, all the detected isoforms possessed aspartic acid 4-methyl ester residue in their fifth amino acid position (C17-[Lxx4, AME5], C18-[AME5]), offering an opportunity to separate a pure fraction of the compound and to study its biological activities in the future. View Full-Text
Keywords: Bacillus; cyclic lipopeptides; HPLC-ESI-IT-MS; surfactin Bacillus; cyclic lipopeptides; HPLC-ESI-IT-MS; surfactin

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Kecskeméti, A.; Bartal, A.; Bóka, B.; Kredics, L.; Manczinger, L.; Shine, K.; Alharby, N.S.; Khaled, J.M.; Varga, M.; Vágvölgyi, C.; Szekeres, A. High-Frequency Occurrence of Surfactin Monomethyl Isoforms in the Ferment Broth of a Bacillus subtilis Strain Revealed by Ion Trap Mass Spectrometry. Molecules 2018, 23, 2224.

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