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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.

Tang JS, Zhao F, Gao H, Dai Y, Yao ZH, Hong K, Li J, Ye WC, Yao XS - Mar Drugs (2010)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou 510632, Guangdong, China. gztangjinshan@126.com

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.

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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.
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f2-marinedrugs-08-02605: 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.

Mentions: A rapid method for characterizing surfactin isomers from the fraction (061341-A9) of the mangrove bacterium Bacillus sp. was developed based on HPLC-MSn (n = 1, 2, 3) analyses. Initially, when only MeOH-H2O or ACN-H2O solvent systems were used as mobile phase, no peak was observed. To obtain better separation and more peaks, a mobile phase of 90% MeOH/H2O (0.05% CF3COOH) was adopted. 0.05% CF3COOH in the mobile phase could suppress the dissociation of the free carboxyl group in the structure of surfactin isomers. Figure 2 displays the HPLC fingerprint map and total ion chromatogram (TIC) of the fraction 061341-A9. Twenty peaks were detected from it and the corresponding peak numbers, retention times, pseudo-molecular ions, and main product ions of them are displayed in Table 2 (Figure 3). Peaks at 8.22 (peak 6), 10.54 (peak 8), 11.51 (peak 9), 13.39 (peak 13), 15.36 (peak 16), and 18.21 min (peak 20) were unambiguously attributed to compounds 2–6, and 8, respectively, by comparing the retention times and mass spectra with reference standards obtained from the mangrove bacterium Bacillus sp. (No. 061341) [13]. Apart from the six compounds mentioned above (2–6, 8), some trace amounts of surfactin isomers were also detected from the fraction (061341-A9). Based on the rules deduced from the fragmentation behavior of pure surfactin isomers (1–9), eleven surfactin isomers were characterized based on HPLC-MSn (n = 1, 2, 3) analyses, which could be classified into three groups according to their chemical structures.


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.

Tang JS, Zhao F, Gao H, Dai Y, Yao ZH, Hong K, Li J, Ye WC, Yao XS - Mar Drugs (2010)

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.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC2992995&req=5

f2-marinedrugs-08-02605: 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.
Mentions: A rapid method for characterizing surfactin isomers from the fraction (061341-A9) of the mangrove bacterium Bacillus sp. was developed based on HPLC-MSn (n = 1, 2, 3) analyses. Initially, when only MeOH-H2O or ACN-H2O solvent systems were used as mobile phase, no peak was observed. To obtain better separation and more peaks, a mobile phase of 90% MeOH/H2O (0.05% CF3COOH) was adopted. 0.05% CF3COOH in the mobile phase could suppress the dissociation of the free carboxyl group in the structure of surfactin isomers. Figure 2 displays the HPLC fingerprint map and total ion chromatogram (TIC) of the fraction 061341-A9. Twenty peaks were detected from it and the corresponding peak numbers, retention times, pseudo-molecular ions, and main product ions of them are displayed in Table 2 (Figure 3). Peaks at 8.22 (peak 6), 10.54 (peak 8), 11.51 (peak 9), 13.39 (peak 13), 15.36 (peak 16), and 18.21 min (peak 20) were unambiguously attributed to compounds 2–6, and 8, respectively, by comparing the retention times and mass spectra with reference standards obtained from the mangrove bacterium Bacillus sp. (No. 061341) [13]. Apart from the six compounds mentioned above (2–6, 8), some trace amounts of surfactin isomers were also detected from the fraction (061341-A9). Based on the rules deduced from the fragmentation behavior of pure surfactin isomers (1–9), eleven surfactin isomers were characterized based on HPLC-MSn (n = 1, 2, 3) analyses, which could be classified into three groups according to their chemical structures.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Institute of Traditional Chinese Medicine & Natural Products, Jinan University, Guangzhou 510632, Guangdong, China. gztangjinshan@126.com

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.

Show MeSH