Isolation and purification of enniatins A, A1, B, B1, produced by Fusarium tricinctum in solid culture, and cytotoxicity effects on Caco-2 cells

Toxicon

Volumn 56, Issue 3, 2010, Pages 418-424

  Meca, G ^a   Ruiz, M J ^a   Soriano, J M ^a   Ritieni, A ^b   Moretti, A ^c   Font, G ^a   Manes J ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c INSTITUTE OF SCIENCES OF FOOD PRODUCTION   (Italy)

Author keywords

Caco 2 cells; Enniatins; LC MS MS; Liquid chromatography; MTT assay

Indexed keywords

ENNIATIN;

ARTICLE; CANCER CELL CULTURE; CELL ASSAY; CELL STRAIN CACO 2; CHEMICAL STRUCTURE; COLORECTAL CARCINOMA; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CORN; CYTOTOXICITY; FOOD CONTAMINATION; FUNGUS CULTURE; FUSARIUM; HEALTH HAZARD; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTEIN ISOLATION; PROTEIN PURIFICATION; TANDEM MASS SPECTROMETRY;

CACO-2 CELLS; CHROMATOGRAPHY, LIQUID; DEPSIPEPTIDES; FUSARIUM; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; TANDEM MASS SPECTROMETRY;

FUSARIUM; FUSARIUM TRICINCTUM; ZEA MAYS;

EID: 77954145774     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2010.04.008     Document Type: Article

References (35)

1. De la Luz M., Chiericatti C., Aringoli E., Althaus R.L., Basilico J.C. Influence of environmental factors on airborne fungi in houses of Santa Fe City, Argentina. Sci. Total Environ. 2007, 376:143-150.
2. Ferrer E., Juan-García A., Font G., Ruiz M.J. Reactive oxygen species induced by beauvericin, patulin and zearalenone in CHO-K1 cells. Toxicol. in Vitro 2009, doi:10.1016/j.tiv.2009.07.009.
3. Fornelli F., Minervini F., Logrieco A. Cytotoxicity of fungal metabolites to lepidopteran (Spodoptera frugiperda) cell line (SF 9). J. Invertebr. Pathol. 2004, 85:74-79.
4. Gupta S., Montllor C., Hwang Y.S. Isolation of novel beauvericin analogues from the fungus Beauveria bassiana. J. Nat. Prod. 1995, 58:733-738.
5. Gutleb A.C., Morrison E., Murk A.J. Cytotoxicity assays for mycotoxins produced by Fusarium strains: a review. Environ. Toxicol. Pharmacol. 2002, 11:309-320.
6. Hanelt M., Gareis M., Kollarczik B. Cytotoxicity of mycotoxins evaluated by the MTT-cell culture assay. Mycopathologia 1994, 128:167-174.
7. Hiraga K., Yamamoto S., Fukuda H., Hamanaka N., Oda K. Enniatin has a new function as an inhibitor of Pdr5p, one of the ABC transporters in Saccharomyces cerevisiae. Biochem. Biophys. Res. Commun. 2005, 328:1119-1125.
8. Hyun U., Lee D.H., Lee C., Shin C.G. Apoptosis induced by enniatins H and MK1688 isolated from Fusarium oxysporum FB1501. Toxicon 2009, 53:723-728.
9. Ivanova L., Eystein Skjerve E., Eriksen G.S., Uhlig S. Cytotoxicity of enniatins A, A1, B, B1, B2 and B3 from Fusarium avenaceum. Toxicon 2006, 47:868-876.
10. Jestoi M. Emerging Fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin-a review. Crit. Rev. Food Sci. Nutr. 2008, 48:21-49.
11. Kamyar M., Rawnduzi P., Studenik C.R., Kouri K., Lemmens-Gruber R. Investigation of the electrophysiological properties of enniatins. Arch. Biochem. Biophys. 2004, 429:215-223.
12. Kelly S., Grimm L.H., Bendig C., Hempel D.C., Krull R. Effects of fluid dynamic induced shear stress on fungal growth and morphology. Process Biochem. 2006, 41:2113-2117.
13. Kouadio J.H., Mobio T.A., Baudrimont I., Moukha S., Dano S.D., Creppy E.E. Comparative study of cytotoxicity and oxidative stress induced by deoxynivalenol, zearalenone or fumonisin B1 in human intestinal cell line Caco-2. Toxicology 2005, 213:56-65.
14. Lee H.S., Song H.H., Jeong J.H., Shin C.G., Choi S.U., Lee C. Cytotoxicities of enniatins H, I, and MK1688 from Fusarium oxysporum KFCC 11363P. Toxicon 2008, 51:1178-1185.
15. Logrieco A., Rizzo A., Ferracane R., Ritieni A. Occurrence of beauvericin and enniatins in wheat affected by Fusarium avenaceum head blight. Appl. Environ. Microbiol. 2002, 68:82-85.
16. Mitchell D.A., Lonsane B.K. Definition, characterization and economic evaluation. General Principles of Solid Substrate Fermentation 1990, Rapid Publications of Oxford Ltd., UK. H.W. Doelle, C. Rolz (Eds.).
17. Monti S.M., Fogliano V., Logrieco A., Ferracane R., Ritieni A. Simultaneous determination of beauvericin, enniatins, and fusaproliferin by high performance liquid chromatography. J. Agric. Food Chem. 2000, 48:3317-3320.
18. Nilanonta C., Isaka M., Chanphen R., Thong-Orn N., Tanticharoen M., Thebtaranonth Y. Unusual enniatins produced by the insect pathogenic fungus Verticillium hemipterigenum: isolation and studies on precursor-directed biosynthesis. Tetrahedron 2003, 59:1015-1020.
19. Pandey A. Recent process developments in solid-state fermentation. Process Biochem. 1992, 27:109-117.
20. Pandey A. Solid-state fermentation. Biochem. Eng. J. 2003, 13:81-84.
21. Pandey A., Soccol C.R., Leo J.A.R., Nigam P. Solid-state Fermentation in Biotechnology 2001, Asiatech Publishers, Inc., New Delhi.
22. Plattner R.D., Nelson P.E. Production of beauvericin by a strain of Fusarium proliferatum isolated from corn fodder for swine. Appl. Environ. Microbiol. 2004, 60:3894-3896.
23. Ritieni A., Moretti A., Logrieco A., Bottalico A., Randazzo G., Monti S.M., Ferracane R., Fogliano V. Occurrence of fusaproliferin, fumonisin B1 and beauvericin in maize from Italy. J. Agric. Food Chem. 1997, 45:4011-4016.
24. Ruiz M.J., Festila L.E., Fernandez M. Comparison of basal cytotoxicity of seven carbamates in CHO-K1 cells. Toxicol. Environ. Chem. 2006, 88:345-354.
25. Sorensen J.L., Nielsen K.F., Rasmussen P.H., Thrane U. Development of a LC MS/MS method for the analysis of enniatins and beauvericin in whole fresh and ensiled maize. J. Agric. Food Chem. 2008, 56:10439-10443.
26. Supothina S., Isaka M., Kirtikara K., Tanticharoen M., Thebtaranonth Y. Enniatin production by the entomopathogenic fungus Verticillium hemipterigenum BCC 1449. J. Antibiot. 2004, 57:732-738.
27. Tomoda H., Huang X.H., Cao J., Nishida H., Nagao R., Okuda S., Tanaka H., Omura S., Arai H., Inoue K. Inhibition of acyl-CoA: colesterol acyltransferase activity in cyclodepsipedtide antibiotics. J. Antibiot. 1992, 45:1626-1632.
28. Tomoda H., Nishida H., Huang X.H., Masuna R., Kim Y.K., Smura S. New cyclodepsipeptides, enniatin D, E, and F produced by Fusarium sp. FO-1305. J. Antibiot. 1992, 45:1207-1215.
29. Uhlig, S., Gutleb, A., Thrane, U., Flaoyen, A., 2004a. Identification of cytotoxic principles of Fusarium avenaceum. In: Poster Presentation at the XI International IUPAC Synposium on Mycotoxins and Phycotoxins, May 2004, Betsheda, Maryland.
30. Uhlig S., Ivanova L. Determination of beauvericin and four other enniatins in grain by liquid chromatography-mass spectrometry. J. Chromatogr. A. 2004, 2:173-178.
31. Uhlig S., Jestoi M., Knutsen A.K., Heier B.T. Multiple regression analysis as a tool for the identification of relations between semi-quantitative LC-MS data and cytotoxicity of extracts of the fungus Fusarium avenaceum (syn. F-arthrosporioides). Toxicon 2006, 48:567-579.
32. Visconti A., Blais L.A., Simon J.W., Greenhalgh R., Miller D. Production of enniatins by Fusarium acuminatum and Fusarium compactum in liquid culture: isolation and characterization of three new enniatins, B2, B3, and B4. J. Agric. Food Chem. 1992, 40:1976-1982.
33. Vongvilai P., Isaka M., Kittakoop P., Srikitikulchai P., Kongsaeree P., Prabpai S., Thebtaranonth Y. Isolation and structure elucidation of enniatins L, M-1, M-2, and N: novel hydroxy analogs. Helv. Chem. Acta 2004, 87:2066-2073.
34. Watjen W., Debbab A., Hohlfeld A., Chovolou Y., Kampkotter A., Edrada R.A., Ebel R., Hakiki A., Mosaddak M., Totzke F., Kubbutat M.H.G., Proksch P. Enniatins A1, B and B1 from an endophytic strain of Fusarium tricinctum induce apoptotic cell death in H4IIE hepatoma cells accompanied by inhibition of ERK phosphorylation. Mol. Nutr. Food Res. 2009, 53:431-440.
35. Zhukhlistova N.E., Tishchenko G.N., Tolstykh I.V., Zenkova V.A. Molecular and crystal structure of the antibiotic enniatin B, a secondaty microbial metabolite. Crystallogr. Rep. 1999, 44:8-12.