Lipopeptides from the banyan endophyte, Bacillus subtilis K1: Mass spectrometric characterization of a library of fengycins

Journal of the American Society for Mass Spectrometry

Volumn 23, Issue 10, 2012, Pages 1716-1728

  Pathak, Khyati V ^a,b   Keharia, Haresh ^b   Gupta, Kallol ^a   Thakur, Suman S ^a   Balaram, Padmanabhan ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b SARDAR PATEL UNIVERSITY   (India)

Author keywords

Cyclic lipopeptides; Fengycin; Isotopic multiplet; Iturins; Mass spectrometry; Surfactins

Indexed keywords

CYCLIC LIPOPEPTIDES; FENGYCINS; ISOTOPIC MULTIPLET; ITURINS; SURFACTINS;

ELECTROSPRAY IONIZATION; ISOTOPES; MASS SPECTROMETRY;

MASS SPECTROMETERS;

FENGYCIN A; FENGYCIN A2; FENGYCIN B; FENGYCIN B2; FENGYCIN C; FENGYCIN DERIVATIVE; ITURIN DERIVATIVE; LIPOPEPTIDE; NATURAL PRODUCT; SURFACTIN; UNCLASSIFIED DRUG;

AMINO ACID COMPOSITION; AMINO ACID SUBSTITUTION; AMINO TERMINAL SEQUENCE; ANTIFUNGAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG DETERMINATION; DRUG HYDROLYSIS; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG MIXTURE; ENDOPHYTE; FATTY ACID DESATURATION; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; OPTICAL RESOLUTION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

BACILLUS SUBTILIS; BACTERIAL PROTEINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; LIPOPEPTIDES; MASS SPECTROMETRY; PEPTIDES, CYCLIC;

BACILLUS SUBTILIS; FICUS BENGHALENSIS;

EID: 84868249364     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-012-0437-4     Document Type: Article

References (38)

1. Strobel, G., Daisy, B.: Bioprospecting for microbial endophytes and their natural products. Micorbiol. Mol. Biol. Rev. 67, 491-502 (2003)
2. Zhang, H.W., Song, Y.C., Tan, R.X.: Biology and chemistry of endophytes. Nat. Prod. Rep. 23, 753-771 (2006)
3. Khare, C.P.: Indian Medicinal Plants, An Illustrated Dictionary, p. 264. Springer Reference, New York (2007)
4. Sieber, T.: Endophytic fungi of forest trees: Are they mutualists? Fungal Biol. Rev. 21, 75-89 (2007)
5. Suryanarayanan, T.S., Vijaykrishna, D.: Fungal endophytes of aerial roots of Ficus benghalensis. Fungal Diversity. 8, 155-161 (2001)
6. Stein, T.: Bacillus subtilis antibiotics: Structures, synthesis and specific functions. Mol. Microbiol. 56, 845-847 (2005)
7. Ng, J., Bandeira, N., Liu, W.T., Ghassemian, M., Simmons, T.L., Gerwick, W.H., Linington, R., Dorrestein, P.C., Pevzner, P.A.: Dereplication and De Novo sequencing of nonribosomal peptides. Nat. Methods 6, 596-599 (2009)
8. Caboche, S., Leclere, V., Pupin, M., Kuchrov, G., Jacques, P.: Diversity of monomers in nonribosomal peptides: Towards the prediction of origin and biological activity. J. Bacteriol. 192, 5143-5150 (2010)
9. Aric, A., Jacques, P., Wathelet, B., Paquot, M., Fuchs, R., Budzikiewics, H., Thonart, P.: Influence of culture conditions on lipopeptide production by Bacillus subtilis. Appl. Biochem. Biotechnol. 91/93, 1-9 (2001)
10. Yu, G.Y., Sinclair, J.B., Hartman, G.L., Bertagnolli, B.L.: Production of Iturin A by Bacillus amyloliquefaciens suppressing Rhizoctonia solani. Soil Biol. Biochem. 34, 955-963 (2002)
11. Vater, J., Kablitz, B., Wilde, C., Franke, P., Mehta, N., Cameotra, S.S.: Matrix-assisted laser desorption ionization-time of flight mass spectrometry of lipopeptide biosurfactants in whole cells and culture filtrates of Bacillus subtilis C-1 isolated from petroleum sludge. Appl. Environ. Microbiol. 68, 6210-6219 (2002)
12. Pueyo, M.T., Bloch Jr., C., Carmon-Ribeiro, A.M., di Mascio, P.: Lipopeptides produced by a soil Bacillus megaterium Strain. Microb. Ecol. 57, 367-378 (2005)
13. Nagorska, K., Bikowski, M., Obuchowski, M.: Multicellular behaviour and production of a wide variety of toxic substances support usage of Bacillus subtilis as a powerful biocontrol agent. Acta Biochim. Pol. 54, 495-508 (2007)
14. Ongena, M., Jacques, P.: Bacillus lipopeptides: Versatile weapons for plant disease biocontrol. Trends Microbiol. 16, 115-125 (2008)
15. Arguelles-Aria, A., Ongena, M., Halimi, B., Lara, Y., Brans, A., Joris, B., Fickers, P.: Microb.: Bacillus amyloliquefaciens GA1 as a source of potent antibiotics and other secondary metabolites for biocontrol of plant pathogens. Microb. Cell Fact. 26, 1-12 (2009)
16. Arima, K., Kakinuma, A., Tamura, G.: Surfactin, a crystalline peptidelipid surfactant produced by Bacillus subtilis: Isolation, characterization and its inhibition of fibrin clot formation. Biochem. Biophys. Res. Commun. 31, 88-494 (1968)
17. Garbay-Jaureguiberry, C., Roques, B.P., Delcambe, L., Peypoux, F., Michel, G.: NMR conformational study of Iturin A, an antibiotic from Bacillus subtilis. FEBS Lett. 93, 151-156 (1978)
18. Winkelmann, G., Allgaier, H., Lupp, R., Jung, G.: Iturin AL-A new long chain iturin a possessing an unusual high content of C16-beta-amino acids. J. Antibiot. 36, 1451-1457 (1983)
19. Vanittanakom, N., Loeffler, W., Koch, U., Jung, G.: Fengycin-A novel antifungal lipopeptide antibiotic produced by Bacillus subtilis F-29-3. J. Antibiot. 39, 888-901 (1986)
20. Kowall, M., Vater, J., Kluge, T., Stein, P., Ziessow, D.: Separation and characterization of surfactin isoforms produced by Bacillus subtilis OKB 105. J. Colloid Interface Sci. 204, 1-8 (1998)
21. Volpon, L., Besson, F., Lancelin, J.M.: NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A(2). FEBS Lett. 485, 76-80 (2000)
22. Madonna, J., Voorhees, K.J., Taranenko, N.I., Laiko, V.V., Doroshenko, V.M.: Detection of cyclic lipopeptide biomarkers from Bacillus species using atmospheric pressure matrix-assisted laser desorption/ionization mass spectrometry. Anal. Chem. 75, 1628-1637 (2003)
23. Pecci, Y., Rivardo, F., Martinotti, M.G., Allegrone, G.: LC/ESI-MS/MS characterisation of lipopeptide biosurfactants produced by the Bacillus licheniformis V9T14 strain. J. Mass Spectrom. 45, 772-778 (2010)
24. Williams, B.H., Hathout, Y., Fenselau, C.: Structural characterization of lipopeptide biomarkers isolated from Bacillus globigii. J. Mass Spectrom. 37, 259-264 (2002)
25. Kim, P.I., Bai, H., Bai, D., Chae, H., Chung, S., Kim, Y., Park, R., Chi, Y.T.: Purification and characterization of a lipopeptide produced by Bacillus thuringiensis CMB26. J. Appl. Microbiol. 97, 942-949 (2004)
26. Nihorimbere, V., Cawoy, H., Seyer, A., Brunelle, A., Thonart, P., Ongena, M.: Impact of rhizosphere factors on cyclic lipopeptide signature from the plant beneficial strain Bacillus amyloliquefaciensS499. FEMS Microbiol. Ecol. 79, 176-191 (2012)
27. Nishikiori, T., Naganawa, H., Muraoka, Y., Aoyagi, T., Umezawa, H.: Plipastatins: New inhibitors of phospholipase A2, produced by Bacillus cereus BMG302-fF67. III. Structural elucidation of plipastatins. J. Antibiot. 39, 755-761 (1986)
28. Peypoux, F., Besson, F., Michel, G., Delcambe, L.: Structure of bacillomycin D, a new antibiotic of the Iturin group. Eur. J. Biochem. 118, 323-327 (1981)
29. Peypoux, F., Pommier, M.T., Das, B.C., Besson, F., Delcambe, L., Michel, G.: Structures of bacillomycin D and bacillomycin L peptidolipid antibiotics from Bacillus subtilis. J. Antibiot. 37, 1600-1604 (1984)
30. Peypoux, F., Pommier, M.T., Marion, D., Ptak, M., Das, B.C., Michel, G.: Revised structure of mycosubtilin, a peptidolipid antibiotic from Bacillus subtilis. J. Antibiot. 39, 636-641 (1986)
31. Grangemard, I., Wallach, J., Maget-Dana, R., Peypoux, F.: Lichenysin: A more efficient cation chelator than surfactin. Appl. Biochem. Biotechnol. 90, 199-210 (2001)
32. Naruse, N., Tenmyo, O., Kobaru, S., Kamei, H., Miyaki, T., Konishi, M., Oki, T.: Pumilacidin, a complex of new antiviral antibiotics. Production, isolation, chemical properties, structure and biological activity. J. Antibiot. 43, 267-280 (1990)
33. Isogai, A., Takayama, S., Murakoshi, S., Suzuki, A.: Structure of β-amino acids in antibiotics Iturin A. Tetrahedron Lett. 23, 3065-3068 (1982)
34. Gong, M., Wang, J.D., Zhang, J., Yang, H., Lu, X.F., Pei, Y., Cheng, J.Q.: Study of the antifungal ability of Bacillus subtilis strain PY-1 in vitro and identification of its antifungal substance (iturin A). Acta Biochim. Biophys. Sin. (Shanghai) 38, 233-240 (2006)
35. Pathak, K.V.: Purification and Characterization of Antifungal Compounds Produced by Banyan Endophytic Bacilli. Ph.D. Thesis, Sardar Patel University, Vallabh Vidynagar, India, p 42 (2011)
36. Sabareesh, V., Ranganayaki, R.S., Raghothama, S., Bopanna, M.P., Balaram, H., Srinivasan, M.C., Balaram, P.: Identification and characterization of a library of microheterogeneous cyclohexadepsipeptides from the fungus isaria. J. Nat. Prod. 70, 715-729 (2007)
37. Kubinyi, H.: Calculation of isotope distributions in mass spectrometry. A trivial solution for a non-trivial problem. Anal. Chim. Acta 247, 107-119 (1991)
38. Sieber, S.A., Marahiel, M.A.: Molecular mechanisms underlying non-ribosomal peptide synthesis: Approaches to new antibiotics. Chem. Rev. 105, 715-738 (2005)