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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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The main fragmentation routes of peak 1 (group 1, linear derivative of surfactin isomer).
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f4-marinedrugs-08-02605: The main fragmentation routes of peak 1 (group 1, linear derivative of surfactin isomer).

Mentions: Peak 1 gave a pseudo-molecular ion at m/z 1040 [M + H]+, which indicated that its molecular weight was 1039. In the MS2 spectrum of [M + H]+ at m/z 1040, product ions at m/z 1022 [M − 18 + H]+, 909 [M − (AA7 + 18) + H]+, and 685 [(H) AA2 − AA7 (OH) + H]+ were observed, which suggested that it was a linear lipopeptide with a fatty acid side chain of 14 carbons, and AA7 was Leu or Ile. In the MS3 spectrum of precursor ion at m/z 685, product ions at m/z 554 [(H) AA2 − AA7 (OH) − 131 + H]+ and m/z 441 [(H) AA2 − AA7 (OH) − 131 − 113 + H]+ further confirmed the deduction mentioned above. The main fragmentation routes of peak 1 are displayed as Figure 4 (Group 1, linear derivative of surfactin isomer). Consequently, peak 2 and peak 4 were deduced to be linear lipopeptides with AA7 of Leu or Ile. The chain length of fatty acid side chains were 14 and 15 carbons, respectively.


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)

The main fragmentation routes of peak 1 (group 1, linear derivative of surfactin isomer).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f4-marinedrugs-08-02605: The main fragmentation routes of peak 1 (group 1, linear derivative of surfactin isomer).
Mentions: Peak 1 gave a pseudo-molecular ion at m/z 1040 [M + H]+, which indicated that its molecular weight was 1039. In the MS2 spectrum of [M + H]+ at m/z 1040, product ions at m/z 1022 [M − 18 + H]+, 909 [M − (AA7 + 18) + H]+, and 685 [(H) AA2 − AA7 (OH) + H]+ were observed, which suggested that it was a linear lipopeptide with a fatty acid side chain of 14 carbons, and AA7 was Leu or Ile. In the MS3 spectrum of precursor ion at m/z 685, product ions at m/z 554 [(H) AA2 − AA7 (OH) − 131 + H]+ and m/z 441 [(H) AA2 − AA7 (OH) − 131 − 113 + H]+ further confirmed the deduction mentioned above. The main fragmentation routes of peak 1 are displayed as Figure 4 (Group 1, linear derivative of surfactin isomer). Consequently, peak 2 and peak 4 were deduced to be linear lipopeptides with AA7 of Leu or Ile. The chain length of fatty acid side chains were 14 and 15 carbons, respectively.

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
Related in: MedlinePlus