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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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Chemical structures of compounds 1–9 obtained from the bacterium Bacillus sp.
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f1-marinedrugs-08-02605: Chemical structures of compounds 1–9 obtained from the bacterium Bacillus sp.

Mentions: Surfactin isomers are cyclic lipopeptide biosurfactants consisting of seven amino acid units and one β-hydroxyl fatty acid side chain with diverse chain lengths of 13–15 carbons which are characteristic metabolites of the genus Bacillus. Surfactin isomers have received much attention during the last two decades since they exhibit numerous pharmaceutical activities including anticoagulation [1], anti-tumor [2], antiviral [3], anti-inflammatory, and immunosuppressive activities [4–7]. Surfactin isomers are best known for their multifaceted interactions with biological systems that result in a number of physiological and biochemical activities [8], and can incorporate into the phospholipid bilayer and induce permeabilization and perturbation of target cell owing to their amphipathic nature. These characteristics make them promising for the treatment of a number of global public health issues. High performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MSn) is one of the most powerful techniques for online analysis of complex components in a crude extract. A variety of natural products, such as flavonoids, alkaloids, saponins, and steroids [9–12], have been analyzed by HPLC-MSn. During our search for bioactive metabolites from marine microorganisms, a series of surfactin isomers was obtained from the bacterium Bacillus sp. (Figure 1) [13]. In this paper, we developed a fast and reliable method for characterizing trace amounts of surfactin isomers from the bioactive fraction (061341-A9) of the mangrove bacterium Bacillus sp. based on rules deduced from the relationship between the fragmentation behaviors and characteristic structure features. At the same time, 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 simultaneously investigated.


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)

Chemical structures of compounds 1–9 obtained from the bacterium Bacillus sp.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f1-marinedrugs-08-02605: Chemical structures of compounds 1–9 obtained from the bacterium Bacillus sp.
Mentions: Surfactin isomers are cyclic lipopeptide biosurfactants consisting of seven amino acid units and one β-hydroxyl fatty acid side chain with diverse chain lengths of 13–15 carbons which are characteristic metabolites of the genus Bacillus. Surfactin isomers have received much attention during the last two decades since they exhibit numerous pharmaceutical activities including anticoagulation [1], anti-tumor [2], antiviral [3], anti-inflammatory, and immunosuppressive activities [4–7]. Surfactin isomers are best known for their multifaceted interactions with biological systems that result in a number of physiological and biochemical activities [8], and can incorporate into the phospholipid bilayer and induce permeabilization and perturbation of target cell owing to their amphipathic nature. These characteristics make them promising for the treatment of a number of global public health issues. High performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MSn) is one of the most powerful techniques for online analysis of complex components in a crude extract. A variety of natural products, such as flavonoids, alkaloids, saponins, and steroids [9–12], have been analyzed by HPLC-MSn. During our search for bioactive metabolites from marine microorganisms, a series of surfactin isomers was obtained from the bacterium Bacillus sp. (Figure 1) [13]. In this paper, we developed a fast and reliable method for characterizing trace amounts of surfactin isomers from the bioactive fraction (061341-A9) of the mangrove bacterium Bacillus sp. based on rules deduced from the relationship between the fragmentation behaviors and characteristic structure features. At the same time, 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 simultaneously investigated.

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