Purification and identification of two antifungal cyclic dipeptides from Bacillus cereus subsp. thuringiensis associated with a rhabditid entomopathogenic nematode especially against Fusarium oxysporum

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 29, Issue 2, 2014, Pages 190-197

  Kumar, S Nishanth ^a   Nambisan, Bala ^a   Mohandas, C ^a  

^a CENTRAL TUBER CROPS RESEARCH INSTITUTE   (India)

Author keywords

Antimicrobial; Bacillus cereus subsp. thuringiensis; Cyclic dipeptides; Fusarium oxysporum

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENT; CARBENDAZIM; DIPEPTIDE; PIPERAZINEDIONE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; BACILLUS SUBTILIS; BACILLUS THURINGIENSIS; BACTERIAL STRAIN; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; ENTOMOPATHOGENIC NEMATODE; ESCHERICHIA COLI; FUSARIUM OXYSPORUM; FUSARIUM WILT; HETERONUCLEAR MULTIPLE BOND CORRELATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PENICILLIUM EXPANSUM; PRIORITY JOURNAL; PROTEIN ISOLATION; PROTEIN PURIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RHABDITOIDEA; RHIZOCTONIA SOLANI; ROOT ROT; STAPHYLOCOCCUS AUREUS;

ANIMALS; ANTIFUNGAL AGENTS; BACILLUS CEREUS; BACILLUS THURINGIENSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; FUSARIUM; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; PEPTIDES, CYCLIC; RHABDITOIDEA; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84896367209     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2013.765414     Document Type: Article

References (50)

1. Gordon TR, Martyn RD. The evolutionary biology of Fusarium oxysporum. Annu Rev Phytopathol 1997;35:111-28.
2. Brayford D. Fusarium oxysporum f. sp. radicis-lycopersici, IMI descriptions of fungi and bacteria no. 1270. Mycopathol 1996;133:61-3.
3. Ploetz RC. Population biology of Fusarium oxysporum f. sp. cubense. In: Ploetz RC, ed. Fusarium wilt of banana. St. Paul (MN): APS Press; 1990:63-76.
4. Albisetti M, Lauener RP, Gungor T, et al. Disseminated Fusarium oxysporum infection in hemophagocytic lymphohistiocytosis. Infection 2004;32:364-6.
5. Biondi N, Piccardi R, Margheri MC, et al. Evaluation of Nostoc strain ATCC 53789 as a potential source of natural pesticides. Appl Environ Microbiol 2004;70:3313-20.
6. Khan Z, Kim YH, Kim SG, Kim HW. Observation of the suppression of root-knot nematode (Meloigogyne arenaria) on tomato by incorporation of cyanobacteria power (Oscillatoria chlorine) into potting filed soil. Bioresour Technol 2007;98:69-73.
7. Khalifa EZ, El-Shenawy Z, Awad HM. Biological control of damping-off and root-rot of sugar beet. Egypt J Phytopathol 1995;23:39-51.
8. Lewis JA, Lumsden RD, Locke JC. Biocontrol of damping-off diseases caused by Rhizoctonia solani and Pythium ultimum with alginate prills of Gliocladium virens, Trichoderma hamatum and various food bases. Biocont Sci Technol 1996;6:163-73.
9. Sutton TB. Changing options for the control of deciduous fruit tree diseases. Annu Rev Phytopathol 1996;34:527-47.
10. Burnell AM, Stock SP. Heterorhabditis, Steinernema and their bacterial symbionts - lethal pathogens of insects. Nematol 2000;2:31-42.
11. Dowds BCA, Peters A. Virulence mechanisms. In: Gaugler R, ed. Entomopathogenic nematology. New York (NY): CABI; 2002:79-98.
12. Akhurst RJ. Antibiotic activity of Xenorhabdus spp., bacteria symbiotically associated with insect pathogenic nematodes of the families Hettrorhabditidae and Steinernematidae. J Gen Microbiol 1982;128:3061-5.
13. Chen G, Dunphy GB, Webster JM. Antifungal activity of two Xenorhabdus species and Photorhabdus luminescens, bacteria associated with the nematodes Steinernema species and Heterorhabditis megidis. Biol Cont 1994;4:157-62.
14. Chen G, Maxwell P, Dunphy GB, Webster JM. Culture conditions for Xenorhabdus and Photorhabdus symbionts of entomopathogenic nematodes. Nematologica 1996;42:124-7.
15. Paul VJ, Frautschy S, Fenical W, Nealson KH. Antibiotics in microbial ecology, isolation and structure assignment of several new antibacterial compounds from the insect symbiotic bacteria Xenorhabdus spp. J Chem Ecol 1981;7:589-97.
16. Hu K, Li J, Webster JM. Nematicidal metabolites produced by Photorhabdus luminescens (Enterobacteriaceae), bacterial symbiont of entomopathogenic nematodes. Nematol 1999;1:457-69.
17. McInerney BV, Gregson RP, Lacey MJ, et al. Biologically active metabolites from Xenorhabdus spp. Part 1. Dithiolopyrrolone derivatives with antibiotic activity. J Nat Prods 1991;54:774-84.
18. McInerney BV, Taylor WC, Lacey MJ, et al. Biologically active metabolites from Xenorhabdus spp. Part 2. Benzopyran-1-one derivatives with gastroprotective activity. J Nat Prods 1991;54:785-95.
19. Li JX, Chen GH, Webster JM. Nematophin, a novel antimicrobial substance produced by Xenorhabdus nematophilus (Enterobactereaceae). Canadian J Microbiol 1997;43:770-3.
20. Ji DJ, Yi YK, Kang GH. Identification of an antibacterial compound, benzylideneacetone, from Xenorhabdus nematophila against major plant-pathogenic bacteria. FEMS Microbiol Lett 2004;239:241-8.
21. Lang, G, Kalvelage T, Peters A, et al. Peptides from the entomopathogenic bacterium Xenorhabdus nematophilus. J Nat Prods 2008;71:1074-7.
22. Gualtieri M, Aumelasm A, Thaler JO. Identification of a new antimicrobial lysine-rich cyclolipopeptide family from Xenorhabdus nematophila. J Antibiot 2009;62:295-302.
23. Deepa I, Mohandas C, Makesh KT, et al. Identification of new entomopathogenic nematodes (EPNs) based on sequences of D2-D3 expansion fragments of the 28SrRNA. J Root Crops 2010;36:227-32.
24. Mohandas C, Sheeba M, Firoza AJ, Rajamma P. Bacteria associated with Rhabditis (Oscheius) spp. (Rhabditidae: Nematoda) for the biocontrol of insect pests. Proc Nat Seminar on Achievements and Opportunities in Post harvest Management and Value Addition in Root and Tuber Crops (NSRTC - 2);2007:195-8.
25. Marfey P. Determination of D-amino acids. II. Use of a bifunctional reagents, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res Commun 1984;49:591-6.
26. Rollas S, Kalyoncuoglu N, Sur-Altiner D, Yegenglu Y. 5-(4- Aminophenyl)-4-substituted 2,4-dihydro-3H-1,2,4-triazole-3- thiones: synthesis, antibacterial and antifungal activities. Pharmazie 1993;48:308-9.
27. Clinical and Laboratory Standards Institute (CLSI). Reference methods for broth dilution antifungal susceptibility tests of yeasts. CLSI documents M27-S3. 940 West Valley Road, Suite 1400, Wayne, Pennsylvania, USA; 2008.
28. Clinical and Laboratory Standards Institute (CLSI). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. CLSI documents M27-S3. 940 West Valley Road, Suite 1400, Wayne, Pennsylvania, USA; 2006.
29. Murray PR, Baron EJ, Pfaller MA, et al. Manual of clinical microbiology. Washington (DC): ASM; 1995.
30. Gomez KA, Gomez AA. Presentation of research results. Statistical Procedures for Agricultural Research. New York: A Wiley- Interscience Publication; 1984.
31. Krejcarek GE, Dominy BH, Lawton RG. The interaction of reactive functional groups along peptide chains. A model for alkaloid biosynthesis. Chem Commun 1968:1450-2.
32. Prasad C. Bioactive cyclic dipeptides. Peptides 1995;16:151-64.
33. Rudi A, Kashman Y, Benayahu Y, Schleyer M. Amino acid derivatives from the marine sponge Jaspis digonoxea. J Nat Prod 1994;57:829-32.
34. Strom K, Sjogren J, Broberg A, Schnurer J. Lactobacillus plantarum MiLAB 393 produces the antifungal cyclic dipeptides cyclo(L-Phe- L-Pro) and cyclo(L-Phe-trans-4-OH-L-pro) and 3-phenyllactic acid. Appl Environ Microbiol 2002;68:4322-7.
35. Rosa SD, Mitova M, Tommonaro G. Marine bacteria associated with sponge as source of cyclic peptides. Biomol Eng 2003;20:311-16.
36. Lucietto FR, Milne PJ, Kilian G, et al. The biological activity of the histidine-containing diketopiperazines cyclo(His-Ala) and cyclo(His-Gly). Peptides 2006;26:2706-14.
37. Anteunis MJO. The cyclic dipeptides: proper model compounds in peptide research. Bull Chem Soc Belgium 1978;87:627-50.
38. Nicholson B, Lloyd GK, Miller BR, et al. NPI-2358 is a tubulindepolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent. Anticancer Drugs 2006;7:25-31.
39. Sinha S, Srivastava R, De Clercq E, Singh RK. Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazaadenine and diketopiperazine. Nucleos Nucleot Nucl Acids 2004;23:1815-24.
40. Houston DR, Synstad B, Eijsink VGH, et al. Structure-based exploration of cyclic dipeptide chitinase inhibitors. J Med Chem 2004;47:5713-20.
41. Kwon OS, Park SH, Yun B, et al. Cyclo(dehydroala-L-Leu), an aglucosidase inhibitor from Penicillium sp. F70614. J Antibiot 2000;53:954-8.
42. McCleland K, Milne PJ, Lucietto FR, et al. An investigation into the biological activity of the selected histidine-containing diketopiperazines cyclo(His-Phe) and cyclo(His-Tyr). J Pharm Pharmacol 2004;56:1143-53.
43. Stierle AC, Cardellina JH, Strobel GA. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternate. Proc Natl Acad Sci USA 1988;85:8008-11.
44. Cain CC, Dongho L, Robert H, et al. Synergistic antimicrobial activity of metabolites produced by a nonobligate bacterial predator. Antimicrob Agents Chemother 2003;47:2113-17.
45. Smaoui SF, Mathieu F, Elleuch L, et al. Taxonomy, purification and chemical characterization of four bioactive compounds from new Streptomyces sp. TN256 strain. World J Microbiol Biotechnol 2012;28:793-804.
46. Teasdale ME, Donovan KA, Forschner-Dancause SR, Rowley DC. Gram-positive marine bacteria as a potential resource for the discovery of quorum sensing inhibitors. Marine Biotechnol 2011;13:722-32.
47. Jayatilake GS, Thornton MP, Leonard AC, et al. Metabolites from an antarctic sponge-associated bacterium, Pseudomonas aeruginosa. J Nat Prod 1996;59:293-6.
48. Shin HJ, Mojid Mondol MA, Yu TK, et al. An angiogenesis inhibitor isolated from a marine-derived actinomycete, Nocardiopsis sp. 03N67. Phytochem Lett 2010;3:194-7.
49. Li J, Wangb W, Xua SX, et al. Lactobacillus reuteri-produced cyclic dipeptides quench agr-mediated expression of toxic shock syndrome toxin-1 in staphylococci. Proc Natl Acad Sci USA 2011;108:3360-5.
50. Holden MTG, Chhabra SR, de Nys R, et al. Quorem-sensing cross talk: isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other gram negative bacteria. Mol Microbiol 1999;33:1254-60.