Journal of Microbiology and Biotechnology
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2012 ; 22(1): 69~79

AuthorAhmed Kamal, Anver Basha Shaik, C. Ganesh Kumar, Poornima Mongolla, P. Usha Rani, K.V.S. Rama Krishna, Suman Kumar Mamidyala, Joveeta Joseph
AffiliationChemical Biology Laboratory, Division of Organic Chemistry, Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500 607, India
TitleMetabolic Profiling and Biological Activities of Bioactive Compounds Produced by Pseudomonas sp. Strain ICTB-745 Isolated from Ladakh,India
PublicationInfo J. Microbiol. Biotechnol.2012 ; 22(1): 69~79
AbstractIn an ongoing survey of the bioactive potential of microorganisms from Ladakh, India, the culture medium of a bacterial strain of a new Pseudomonas sp., strain ICTB-745, isolated from an alkaline soil sample collected from Leh, Ladakh, India, was found to contain metabolites that exhibited broad-spectrum antimicrobial and biosurfactant activities. Bioactivity-guided purification resulted in the isolation of four bioactive compounds. Their chemical structures were elucidated by 1H and 13C NMR, 2D-NMR (HMBC, HSQC, 1H,1H-COSY, and DEPT- 135), FT-IR, and mass spectroscopic methods, and were identified as 1-hydroxyphenazine, phenazine-1-carboxylic acid (PCA), rhamnolipid-1 (RL-1), and rhamnolipid-2 (RL-2). These metabolites exhibited various biological activities like antimicrobial and efficient cytotoxic potencies against different human tumor cell lines such as HeLa, HepG2, A549, and MDA MB 231. RL-1 and RL-2 exhibited a dose-dependent antifeedant activity against Spodoptera litura, producing about 82.06% and 73.66% antifeedant activity, whereas PCA showed a moderate antifeedant activity (63.67%) at 60 μg/cm2 area of castor leaf. Furthermore, PCA, RL-1, and RL-2 exhibited about 65%, 52%, and 47% mortality, respectively, against Rhyzopertha dominica at 20 μg/ml. This is the first report of rhamnolipids as antifeedant metabolites against Spodoptera litura and as insecticidal metabolites against Rhyzopertha dominica. The metabolites from Pseudomonas sp. strain ICTB-745 have interesting potential for use as a biopesticide in pest control programs.
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Keywordsphenazine, rhamnolipids, Ladakh, bioactives, antifeedant, insecticidal
References
1. Abalos, A., A. Pinazo, M. R. Infante, M. Casals, F. Garcia, and A. Manresa. 2001 Physicochemical and antimicrobial properties of new rhamnolipids by Pseudomonas aeruginosa AT10 from soybean oil refinery wastes. Langmuir 17: 1367-1371.  : -
 

2. Abbott, W. S. 1925 A method of computing the effectiveness of an insecticide. J. Econ. Entomol. A method of computing the effectiveness of an insecticide. J. Econ. 18: 265-267


3. Abdel-Mawgoud, A. M., F. Lepine, and E. Deziel. 2010 Rhamnolipids: Diversity of structures, microbial origins and roles. Appl. Microbiol. Biotechnol. Rhamnolipids: Diversity of structures, microbial origins and roles. Appl. Microbiol. 86: 1323-1336
   

4. Abivardi, C. and G. Benz. 1984 Tests with extracts of 21 medicinal plants for anti-feedant activity against larvae of Pteris brassicae L. (Lepteridae). Bull. Soc. Entomol. Swisse 57: 383- 392.  : -


5. Bernays, E. A., S. Oppenheimer, R. F. Chapman, H. Kwon, and F. Gould. 2000 Taste sensitivity of insect herbivores to deterrents is greater in specialists than in generalists: A behavioural test of the hypothesis with two closely related caterpillars. J. Chem. Ecol. Taste sensitivity of insect herbivores to deterrents is greater in specialists than in generalists: A behavioural test of the hypothesis with two closely relate 26: 547-563
 

6. Bush, K., P. R. Henry, M. S. Woehleke, W. H. Trejo, and D. S. Slusarchyk. 1984 Phenacein - an angiotensin-converting enzyme inhibitor produced by a streptomycete. J. Antibiot. (Tokyo) 37: 1308-1312.  : -


7. Carpinella, M. C., M. T. Defago, G. Valladares, and S. M. Palacios. 2003 Antifeedant and insecticide properties of a limonoid from Melia azedarach (Meliaceae) with potential use for pest management. J. Agric. Food Chem. Antifeedant and insecticide properties of a limonoid from Melia azedarach (Meliaceae) with potential use for pest management. J. Agric. 51: 369-374
  

8. Chandrasekaran, E. V. and J. N. Bemiller. 1980 Constituent analyses of glycosamino-glycans, pp. 89-96. In R. L. Whistler (ed.). Methods in Carbohydrate Chemistry. Academic Press Inc., New York.  : -


9. Chin-A-Woeng, T. F. C., G. V. Bloemberg, and B. J. J. Lugtenberf. 2003 Phenazines and their role in biocontrol by Pseudomonas bacteria. New Phytol. Phenazines and their role in biocontrol by Pseudomonas bacteria. 157: 503-523
 

10. Cooper, D. G. and B. G. Goldenberg. 1987 Surface-active agents from two Bacillus species. Appl. Environ. Microbiol. Surface-active agents from two Bacillus species. Appl. Environ. 53: 224-229
  

11. Degiorgi, C. F., R. O. Fernandez, and R. A. Pizarro. 1996 Ultraviolet-B lethal damage on Pseudomonas aeruginosa. Curr. Microbiol. Ultraviolet-B lethal damage on Pseudomonas aeruginosa. Curr. 33: 141-146
  

12. Environmental Protection Agency Federal Register. 2004   69: 16796-16800


13. Fernandez, R. O. and R. A. Pizarro. 1996 Lethal effect induced in Pseudomonas aeruginosa exposed to ultraviolet-A radiation. Photochem. Photobiol. Lethal effect induced in Pseudomonas aeruginosa exposed to ultraviolet-A radiation. Photochem. 64: 334-339
 

14. Ganassi, S., A. De Cristofaro, P. Grazioso, C. Altomare, A. Logrieco, and M. A. Sabatini. 2007 Detection of fungal metabolites of various Trichoderma species by the aphid Schizaphis graminum. Entomol. Exp. Appl. Detection of fungal metabolites of various Trichoderma species by the aphid Schizaphis graminum. Entomol. Exp. 122: 77-86
 

15. Granousky, T. A. 1997 Stored product pests, pp. 635-728. In A. Mallis, S. A. Hedges, and D. Moreland (eds.). Handbook of Pest Control, 8th Ed. Mallis Handbook and Technical Training Co., Cleveland, OH.  : -


16. Gurusiddaiah, S., D. M. Weller, A. Sarkar, and R. J. Cook. 1986 Characterization of an antibiotic produced by a strain of Pseudomonas fluorescens inhibitory to Gaeumannomyces graminis var. tritici and Pythium spp. Antimicrob. Agents Chemother. Characterization of an antibiotic produced by a strain of Pseudomonas fluorescens inhibitory to Gaeumannomyces graminis var. tritici and Pythium spp. Antimicrob 29: 488-495
  

17. Hasan, M. M. and C. Reichmuth. 2004 Relative toxicity of phosphine against the bean bruchid Acanthoscelides obtectus (Say) (Col., Bruchidae). J. Appl. Entomol. Relative toxicity of phosphine against the bean bruchid Acanthoscelides obtectus (Say) (Col., Bruchidae). J. Appl. 128: 332-336
 

18. Haynes, W. C., F. H. Stodola, J. M. Locke, T. G. Pridham, H. F. Conway, B. E. Sohns, and R. W. Jackson. 1956 Pseudomonas aureofaciens Kluyver and phenazine-α-carboxylic acid, its characteristic pigments. J. Bacteriol. Pseudomonas aureofaciens Kluyver and phenazine-α-carboxylic acid, its characteristic pigments. J. 72: 412-417
  

19. He, L., Y.-Q. Xu, and X.-H. Zhang. 2008 Medium factor optimization and fermentation kinetics for phenazine-1-carboxylic acid production by Pseudomonas sp. M18G. Biotechnol. Bioeng. Medium factor optimization and fermentation kinetics for phenazine-1-carboxylic acid production by Pseudomonas sp. M18G. Biotechnol. 100: 250-259
  

20. Höller, U., A. D. Wright, G. F. Matthee, G. M. Konig, S. Draeger, H. J. Aust, and B. Schulz. 2000 Fungi from marine sponges: Diversity, biological activity and secondary metabolites. Mycol. Res. Fungi from marine sponges: Diversity, biological activity and secondary metabolites. Mycol. 104: 1354-1365
 

21. Isono, K., K. Anzai, and S. Suzuki. 1958 Tubermycins A and B, new antibiotics. J. Antibiot. (Tokyo) 11: 264-267.  : -


22. Joshi, P. K., G. S. Rawat, H. Padilya, and P. S. Roy. 2006 Biodiversity characterization in Nubra Valley, Ladakh with special reference to plant resource conservation and bioprospecting. Biodivers. Conserv. Biodiversity characterization in Nubra Valley, Ladakh with special reference to plant resource conservation and bioprospecting. Biodivers. 15: 4253-4270
 

23. Kavitha, K., S. Mathiyazhagan, V. Sendhilvel, S. Nakkeeran, G. Chandrasekar, and W. G. D. Fernando. 2005 Broad spectrum action of phenazine against active and dormant structures of fungal pathogens and root knot nematode. Arch. Phytopathol. Plant Protect. Broad spectrum action of phenazine against active and dormant structures of fungal pathogens and root knot nematode. Arch. Phytopathol. 38: 69-76
 

24. Kim, S. K., Y. C. Kim, S. Lee, J. C. Kim, M. Y. Yun, and I. S. Kim. 2011 Insecticidal activity of rhamnolipid isolated from Pseudomonas sp. EP-3 against green peach aphid (Myzus persicae). J. Agric. Food Chem. Insecticidal activity of rhamnolipid isolated from Pseudomonas sp. EP-3 against green peach aphid (Myzus persicae). J. Agric. 59: 934-938
  

25. Kumar, C. G. and S. K. Mamidyala. 2011 Extracellular synthesis of silver nanoparticles using culture supernatant of Pseudomonas aeruginosa. Colloids Surf. B Biointerfaces 84: 462-466.  : -
  

26. Kumar, C. G., M. Mongolla, A. Basha, J. Joseph, U. V. M. Sarma, and A. Kamal. 2011 Decolorization and biotransformation of triphenylmethane dye, methyl violet, by Aspergillus sp. isolated from Ladakh, India. J. Microbiol. Biotechnol. Decolorization and biotransformation of triphenylmethane dye, methyl violet, by Aspergillus sp. isolated from Ladakh, India. J. Microbiol. 21: 267-273
 

27. Lin, Y., X. Wu, S. Feng, G. Jiang, J. Luo, S. Zhou, et al. 2001 Five unique compounds: Xyloketales from mangrove fungus Xylaria sp. from the South China Sea coast. J. Org. Chem. Five unique compounds: Xyloketales from mangrove fungus Xylaria sp. from the South China Sea coast. J. Org. 66: 6252-6256
  

28. Madigan, M. T. and B. L. Marrs. 1997 Extremophiles. Sci. Am. Extremophiles. Sci. 276: 82-87
  

29. Mata-Sandoval, J., J. Karns, and A. Torrents. 1999 Highperformance liquid chromatography method for the characterization of rhamnolipids mixture produced by Pseudomonas aeruginosa UG2 on corn oil. J. Chromatogr. Highperformance liquid chromatography method for the characterization of rhamnolipids mixture produced by Pseudomonas aeruginosa UG2 on corn oil. J. 864: 211-220
 

30. Matthews, G. A. 1993 Insecticide application in stores, pp. 305-315. In G. A. Matthews and E. C. Hislop (eds.). Application Technology for Crop Protection. CAB International, Wallingford, UK.  : -


31. Mendel, M. J., A. R. Alford, and M. D. Bentley. 1991 A comparison of the effects of limonin on Colorado potato beetle, Leptinotarsa decemlineata, and fall armyworm, Spodoptera frugiperda, larval feeding. Entomol. Exp. Appl. A comparison of the effects of limonin on Colorado potato beetle, Leptinotarsa decemlineata, and fall armyworm, Spodoptera frugiperda, larval feeding. Entomol. 58: 191-194
 

32. Monteiro, S. A., G. L. Sassaki, L. M. de Souza, J. A. Meira, J. M. de Araujo, D. A. Mitchell, et al. 2007 Molecular and structural characterization of the biosurfactant produced by Pseudomonas aeruginosa DAUPE 614. Chem. Phys. Lipids 147: 1-13.  : -
  

33. Paul, V. J., M. P. Puglisi, and R. R. Williams. 2006 Marine chemical ecology. Nat. Prod. Rep. Marine chemical ecology. Nat. Prod. 23: 153-180
  

34. Phoebe, C. H. Jr., J. Combie, F. G. Albert, K. Van Tran, J. Cabrera, H. J. Correira, et al. 2001 Extremophilic organisms as an unexplored source for antifungal compounds. J. Antibiot. (Tokyo) 54: 56-65.  : -


35. Quesada-Moraga, E., J. A. Carrasco-Diaz, and C. Santiago- Alvarez. 2006 Insecticidal and antifeedant activities of protein secreted by entomopathogenic fungi against Spodoptera littoralis (Lep, Noctuidae). J. Appl. Entomol. Insecticidal and antifeedant activities of protein secreted by entomopathogenic fungi against Spodoptera littoralis (Lep, Noctuidae). J. Appl. 130: 442-452
 

36. Rimando, A. M. and S. O. Duke. 2006 Natural products for pest management, pp. 2-21. ACS Symposium Series. American Chemical Society, Washington, DC.  : -


37. Römer, A. 1982 1H NMR spectra of substituted phenazines. Org. Magn. Reson. 1H NMR spectra of substituted phenazines. Org. Magn. 19: 66-68
 

38. Sadek, M. M. 2003 Antifeedant and toxic activity of Adhatoda vasica leaf extract against Spodoptera littoralis (Lep., Noctuidae). J. Appl. Entomol. Antifeedant and toxic activity of Adhatoda vasica leaf extract against Spodoptera littoralis (Lep., Noctuidae). J. Appl. 127: 396-404
 

39. Schmutterrer, H. 1995 The Neem Tree Azadirachta indica A. Juss. and Other Meliaceous Plants. VCH Publishers, Weinheim, Germany.  : -
 

40. Sheppard, J. D. and C. N. Mulligan, 1987 The production of surfactin by Bacillus subtilis grown on peat hydrolysate. Appl. Microbiol. Biotechnol. The production of surfactin by Bacillus subtilis grown on peat hydrolysate. Appl. Microbiol. 27: 110-116
 

41. Smitka, T. A., R. H. Bunge, J. H. Wilton, G. C. Hokanson, J. C. French, H. Cun-Heng, and J. Clardy. 1986 PD 166, 152, a novel phenazine antitumor antibiotic. Discovery, fermentation, culture characterization and biological activity. J. Antibiot. (Tokyo) 39: 192-197.  : -


42. Strobel, G. A. 2000 Microbial gifts from rain forests. Can. J. Plant Pathol. Microbial gifts from rain forests. Can. J. 24: 14-20
 

43. Talukder, F. A. and P. E. Howse. 1994 Laboratory evaluation of toxic repellent properties of the pithsaj tree, Aphanamixis polystachya Wall and Parker against Sitophilus oryzae (L.). Int. J. Pest Manage. Sci. 40: 274-279
 

44. Tanaka, Y. and S. Omura. 1993 Agroactive compounds of microbial origin. Annu. Rev. Microbiol. Agroactive compounds of microbial origin. Annu. Rev. 47: 57-87
  

45. Usha Rani, P. and P. Rajasekharreddy. 2010 Insecticidal activity of (2n-octyl-cyclo-prop-1-enyl)-octanoic acid (I) against three Coleopteran stored product insects from Sterculia foetida (L.). J. Pest Sci. Insecticidal activity of (2n-octyl-cyclo-prop-1-enyl)-octanoic acid (I) against three Coleopteran stored product insects from Sterculia foetida (L.). J. 83: 273-279
 

46. Valanarasu, M., P. Kannan, S. Ezhilvendan, G. Ganesan, S. Ignacimuthu, and P. Agastian. 2010 Antifungal and antifeedant activities of extracellular product of Streptomyces spp. ERI-04 isolated from Western Ghats of Tamil Nadu. J. Mycol. Méd. Antifungal and antifeedant activities of extracellular product of Streptomyces spp. ERI-04 isolated from Western Ghats of Tamil Nadu. J. Mycol. 20: 290-297
 

47. Vey, A., R. Hoagland, and T. M. Butt. 2001 Toxic metabolites of fungal biocontrol agents, pp. 311-340. In T. M. Butt, C. Jacskon, and N. Magan (eds.). Fungi as Biocontrol Agents. CAB International, Wallingford, UK.  : -
 

48. Vichai, V. and K. Kirtikara. 2006 Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat. Protoc. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat. 1: 1112-1116
  

49. Wang, Y. and D. K. Newman. 2008 Redox reactions of phenazine antibiotics with ferric (hydr)oxides and molecular oxygen. Environ. Sci. Technol. Redox reactions of phenazine antibiotics with ferric (hydr)oxides and molecular oxygen. Environ. Sci. 42: 2380-2386
 

50. Wang, X., L. Gong, S. Liang, X. Han, C. Zhu, and Y. Li. 2005 Algicidal activity of rhamnolipid biosurfactants produced by Pseudomonas aeruginosa. Harmful Algae 4: 433-443.  : -
 

51. Wildman, H. 1995 Influence of habitation on the physiological and metabolic diversity of fungi. Can. J. Bot. 73: s907-s916.  : -
 

52. Wood, R. K. S. and M. J. May. 1989 Biological Control of Pests, Pathogens and Weeds: Development and Prospects. The Royal Society, London.  : -


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