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. 2010 Oct 11;8(10):2605-18.
doi: 10.3390/md8102605.

Characterization and online detection of surfactin isomers based on HPLC-MS(n) analyses and their inhibitory effects on the overproduction of nitric oxide and the release of TNF-α and IL-6 in LPS-induced macrophages

Jin-Shan Tang  1 , Feng Zhao, Hao Gao, Yi Dai, Zhi-Hong Yao, Kui Hong, Jia Li, Wen-Cai Ye, Xin-Sheng Yao
Affiliations

Characterization and online detection of surfactin isomers based on HPLC-MS(n) analyses and their inhibitory effects on the overproduction of nitric oxide and the release of TNF-α and IL-6 in LPS-induced macrophages

Jin-Shan Tang et al. Mar Drugs. .

Abstract

A rapid method for characterization and online detection of surfactin isomers was developed based on HPLC-MS(n) (n = 1, 2, 3) analyses, and many surfactin isomers were detected and characterized from the bioactive fraction of the mangrove bacterium Bacillus sp. Inhibitory activities of surfactin isomers on the overproduction of nitric oxide and the release of TNF-α and IL-6 in LPS-induced macrophages were systematically investigated. It was revealed that the surfactin isomers showed strong inhibitory properties on the overproduction of nitric oxide and the release of IL-6 on LPS-induced murine macrophage cell RAW264.7 with IC(50) values ranging from 1.0 to 7.0 μM. Structure-activity relationship (SAR) studies revealed that the existence of the free carboxyl group in the structure of surfactin isomers was crucial. These findings will be very helpful for the development of this novel kind of natural product as new anti-inflammatory agents.

Keywords: Bacillus sp.; LC-MS; anti-inflammatory activity; surfactin isomer.

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Figures

Figure 1
Figure 1
Chemical structures of compounds 1–9 obtained from the bacterium Bacillus sp.
Figure 1
Figure 1
Chemical structures of compounds 1–9 obtained from the bacterium Bacillus sp.
Figure 2
Figure 2
HPLC-UV-ESI-ITMS analysis of the fraction (061341-A9) derived from the mangrove bacterium Bacillus sp. (a): UV chromatogram at 220 nm; (b): total ion chromatogram (TIC) in the positive ion mode.
Figure 2
Figure 2
HPLC-UV-ESI-ITMS analysis of the fraction (061341-A9) derived from the mangrove bacterium Bacillus sp. (a): UV chromatogram at 220 nm; (b): total ion chromatogram (TIC) in the positive ion mode.
Figure 3
Figure 3
(A–G): Extracted ion chromatogram for m/z 1040 (A), 994 (B), 1054 (C), 1008 (D), 1022 (E), 1036 (F), and 1050 (G); (H): TIC for the fraction (061341-9A).
Figure 3
Figure 3
(A–G): Extracted ion chromatogram for m/z 1040 (A), 994 (B), 1054 (C), 1008 (D), 1022 (E), 1036 (F), and 1050 (G); (H): TIC for the fraction (061341-9A).
Figure 4
Figure 4
The main fragmentation routes of peak 1 (group 1, linear derivative of surfactin isomer).
Figure 5
Figure 5
The main fragmentation routes of peak 3 (group 2, surfactin isomer with AA7 of Leu or Ile).
Figure 6
Figure 6
The main fragmentation routes of peaks 7 (Group 3, surfactin isomer with AA7 of Val).
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