Surfactin, a crystalline peptidelipid surfactant produced by Bacillussubtilis: Isolation, characterization and its inhibition of fibrin clot formation

Arima, Kei; Kakinuma, Atsushi; Tamura, Gakuzo

doi:10.1016/0006-291x(68)90503-2

Cited by 778 publications

(423 citation statements)

References 5 publications

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“…Surfactin is a lipopeptide antibiotic produced by Bacillus subtilis, and it was first identified as a potent inhibitor of fibrin clotting [24]. Surfactin contains the structure of a cyclic heptapeptide and a lipid portion represented by a mixture of several b-hydroxy fatty acids with chain lengths of 13ϳ15 carbon atoms [25].…”

Section: Discussionmentioning

confidence: 99%

Inhibition of Lipopolysaccharide Activity by a Bacterial Cyclic Lipopeptide Surfactin

et al. 2006

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Compounds that inactivate lipopolysaccharide (LPS) activity have the potential of being new antiinflammatory agents. Therefore, we searched among microbial secondary metabolites for compounds that inhibited LPS-stimulated adhesion between human umbilical vein endothelial cells (HUVEC) and HL-60 cells. By this screening, we found a cyclic lipopeptide surfactin from the culture broth of Bacillus sp. BML752-121F2 to be inhibitory. The addition of the surfactin prior to the LPS stimulation decreased HL-60 cell-HUVEC adhesion without showing any cytotoxicity. We confirmed that surfactin inhibited LPS-induced expression of ICAM-1 and VCAM-1 in HUVEC. It also inhibited the cellular adhesion induced by lipid A, the active component of LPS; but it did not inhibit TNF-a or IL-1b -induced cell adhesion. Then, surfactin was shown to suppress the interaction of lipid A with LPS-binding protein (LBP) that mediates the transport of LPS to its receptors. Finally, surface plasmon resonance (SPR) analysis revealed the surfactin to interact reversibly with lipid A. Thus, this Bacillus surfactin was shown to be an inhibitor of LPS-induced signal transduction, directly interacting with LPS.

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Section: Discussionmentioning

confidence: 99%

Inhibition of Lipopolysaccharide Activity by a Bacterial Cyclic Lipopeptide Surfactin

et al. 2006

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“…It contains ß-hydroxy fatty acids with side chains of 13-15 carbon atoms. Due to its amphiphilic structure it shows unique surface-, interface-and membrane-active properties [1,2,[8][9][10][11][12]] and a strong tendency for self-aggregation forming micelles and vesicles [13,14].…”

Section: Accepted M Manuscriptmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Surfactin, a lipopeptide which is produced by numerous Bacillus subtilis strains, is one of the most efficient biosurfactants so far known [1,2]. At a concentration of 20 μM (0.05%) it lowers the surface tension of water from 72 to 27 mN m -1 [1]. It is a cyclic lipoheptapeptide containing seven amino acids and a ß-hydroxy fatty acid of the following structure [3,4] Ring closure is achieved by lactone formation between the ß-hydroxyl group of the fatty acid component and the carboxyl group of the terminal L-Leu-residue [5].…”

Section: Introductionmentioning

confidence: 99%

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Physicochemical studies of the interaction of the lipoheptapeptide surfactin with lipid bilayers of l-α-dimyristoyl phosphatidylcholine

Kell

Holzwarth

Boettcher

et al. 2007

Biophysical Chemistry

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ochemical studies of the interaction of the lipoheptapeptide surfactin with lipid bilayers of L-α-dimyristoyl phosphatidylcholine. Biophysical Chemistry, Elsevier, 2007, 128 (2-3) This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. A C C E P T E D

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“…Many of these molecules with membrane active properties play an important role in the apoptosis induction process of tumor cells. For example, surfactin, a cyclic lipopeptide produced by Bacillus subtilis (Arima et al, 1968), is well-known for its antitumor activity on Ehrlich carcinoma tumor cells and LoVo cells (Kameda et al, 1974;Kim et al, 2007). In addition, surfactin can cause membrane leakage through pore formation (Grau et al, 1999), ion channel formation (Sheppard et al, 1991), action as a cation carrier (Sheppard et al, 1991) and detergent like effects (Heerklotz and Seelig, 2001), all of which eventually lead to cytotoxic effects.…”

Section: Introductionmentioning

confidence: 99%

Effect of themicrobial lipopeptide on tumor cell lines: apoptosis induced by disturbing the fatty acid composition of cell membrane

Tao

Zou

et al. 2010

Protein Cell

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Microbial lipopeptides play an important role in apoptosis induction of tumor cells. However, there is little knowledge about the relationship between apoptosis induction and membrane fatty acids. The present study focused on the effects of lipopeptides produced by Bacillus subtilis HSO121 on Bcap-37 cell lines. 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl (MTT) colorimetric assay and surface tension measurements, showed that the critical micelle concentration (CMC) was a critical level for the inhibitory activity of lipopeptides on the growth of Bcap-37 cells. Under the CMC, the order of least to greatest cytotoxicity effect on cancer cell lines by lipopeptides is C 13 -lipopeptide < C 14 -lipopepitde < C 15 -lipopeptide. Above CMC, all lipopeptides directly exert cytolytic activity. The flow cytometric analysis and Hoechst33258 staining experiments confirmed the apoptosis of Bcap-37 cell lines induced by lipopeptides in a dose-dependent manner. This apoptosis was associated with a significant decrease of the unsaturated degree of the cellular fatty acids of Bcap-37 cell lines due to the changes in the cellular fatty acids composition induced by the lipopeptide treatment. These results indicated that disturbance of the cellular fatty acid composition of breast cancer cell lines were related to in the cell apoptosis. Furthermore, significant difference in IC 50 values of tumor cells and normal cell showed that the lipopeptide exerted selective cytotoxicity on the cancer cells. Thus HSO121 lipopeptides may have potential applications as an anticancer leads.

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Surfactin, a crystalline peptidelipid surfactant produced by Bacillussubtilis: Isolation, characterization and its inhibition of fibrin clot formation

Cited by 778 publications

References 5 publications

Inhibition of Lipopolysaccharide Activity by a Bacterial Cyclic Lipopeptide Surfactin

Inhibition of Lipopolysaccharide Activity by a Bacterial Cyclic Lipopeptide Surfactin

Physicochemical studies of the interaction of the lipoheptapeptide surfactin with lipid bilayers of l-α-dimyristoyl phosphatidylcholine

Effect of themicrobial lipopeptide on tumor cell lines: apoptosis induced by disturbing the fatty acid composition of cell membrane

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