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Molecules 2018, 23(9), 2224; https://doi.org/10.3390/molecules23092224

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

1
Department of Microbiology, Faculty of Science and Informatics, University of Szeged, Közép fasor 52, H-6726 Szeged, Hungary
2
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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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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