Metabolic Profiling and Biological Activities of Bioactive Compounds Produced by Pseudomonas sp. Strain ICTB-745 Isolated from Ladakh, India = Metabolic Profiling and Biological Activities of Bioactive Compounds Produced by Pseudomonas sp. Strain ICTB-745 Isolated from Ladakh, India

다국어 초록 (Multilingual Abstract)

In 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.

참고문헌 (Reference)

1 Degiorgi, C. F., "Ultraviolet-B lethal damage on Pseudomonas aeruginosa" 33 : 141-146, 1996

2 Isono, K., "Tubermycins A and B, new antibiotics" 11 : 264-267, 1958

3 Vey, A., "Toxic metabolites of fungal biocontrol agents, In Fungi as Biocontrol Agents" CAB International 311-340, 2001

4 Sheppard, J. D., "The production of surfactin by Bacillus subtilis grown on peat hydrolysate" 27 : 110-116, 1987

5 Schmutterrer, H., "The Neem Tree Azadirachta indica A. Juss. and Other Meliaceous Plants" VCH Publishers 1995

6 Abivardi, C., "Tests with extracts of 21 medicinal plants for anti-feedant activity against larvae of Pteris brassicae L. (Lepteridae)" 57 : 383-392, 1984

7 Bernays, E. A., "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" 26 : 547-563, 2000

8 Cooper, D. G., "Surface-active agents from two Bacillus species" 53 : 224-229, 1987

9 Vichai, V., "Sulforhodamine B colorimetric assay for cytotoxicity screening" 1 : 1112-1116, 2006

10 Granousky, T. A., "Stored product pests, In Handbook of Pest Control, 8th Ed" Mallis Handbook and Technical Training Co. 635-728, 1997

11 Abdel-Mawgoud, A. M., "Rhamnolipids: Diversity of structures, microbial origins and roles" 86 : 1323-1336, 2010

12 Environmental Protection Agency, "Rhamnolipid biosurfactant: Exemption from the requirement of a tolerance" 69 : 16796-16800, 2004

13 Hasan, M. M., "Relative toxicity of phosphine against the bean bruchid Acanthoscelides obtectus (Say) (Col., Bruchidae)" 128 : 332-336, 2004

14 Wang, Y., "Redox reactions of phenazine antibiotics with ferric (hydr)oxides and molecular oxygen" 42 : 2380-2386, 2008

15 Haynes, W. C., "Pseudomonas aureofaciens Kluyver and phenazine-α-carboxylic acid, its characteristic pigments" 72 : 412-417, 1956

16 Abalos, A., "Physicochemical and antimicrobial properties of new rhamnolipids by Pseudomonas aeruginosa AT10 from soybean oil refinery wastes" 17 : 1367-1371, 2001

17 Chin-A-Woeng, T. F. C., "Phenazines and their role in biocontrol by Pseudomonas bacteria" 157 : 503-523, 2003

18 Bush, K., "Phenacein - an angiotensin-converting enzyme inhibitor produced by a streptomycete" 37 : 1308-1312, 1984

19 Smitka, T. A., "PD 166, 152, a novel phenazine antitumor antibiotic. Discovery, fermentation, culture characterization and biological activity" 39 : 192-197, 1986

20 Rimando, A. M., "Natural products for pest management" American Chemical Society 2-21, 2006

21 Monteiro, S. A., "Molecular and structural characterization of the biosurfactant produced by Pseudomonas aeruginosa DAUPE 614" 147 : 1-13, 2007

22 Strobel, G. A., "Microbial gifts from rain forests" 24 : 14-20, 2000

23 He, L., "Medium factor optimization and fermentation kinetics for phenazine-1-carboxylic acid production by Pseudomonas sp. M18G" 100 : 250-259, 2008

24 Paul, V. J., "Marine chemical ecology" 23 : 153-180, 2006

25 Fernandez, R. O., "Lethal effect induced in Pseudomonas aeruginosa exposed to ultraviolet-A radiation" 64 : 334-339, 1996

26 Talukder, F. A., "Laboratory evaluation of toxic repellent properties of the pithsaj tree, Aphanamixis polystachya Wall and Parker against Sitophilus oryzae (L.)" 40 : 274-279, 1994

27 Matthews, G. A., "Insecticide application in stores, In ApplicationTechnology for Crop Protection" CAB International 305-315, 1993

28 Quesada-Moraga, E., "Insecticidal and antifeedant activities of protein secreted by entomopathogenic fungi against Spodoptera littoralis (Lep, Noctuidae)" 130 : 442-452, 2006

29 Kim, S. K., "Insecticidal activity of rhamnolipid Isolated from pseudomonas sp. EP-3 against green peach aphid (Myzus persicae)" AMER CHEMICAL SOC 59 (59): 934-938, 2011

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

31 Wildman, H., "Influence of habitation on the physiological and metabolic diversity of fungi" 73 : s907-s916, 1995

32 Mata-Sandoval, J., "Highperformance liquid chromatography method for the characterization of rhamnolipids mixture produced by Pseudomonas aeruginosa UG2 on corn oil" 864 : 211-220, 1999

33 Höller, U., "Fungi from marine sponges: Diversity, biological activity and secondary metabolites" 104 : 1354-1365, 2000

34 Lin, Y., "Five unique compounds: Xyloketales from mangrove fungus Xylaria sp. from the South China Sea coast" 66 : 6252-6256, 2001

35 Phoebe, C. H. Jr., "Extremophilic organisms as an unexplored source for antifungal compounds" 54 : 56-65, 2001

36 Madigan, M. T., "Extremophiles" 276 : 82-87, 1997

37 Kumar, C. G., "Extracellular synthesis of silver nanoparticles using culture supernatant of Pseudomonas aeruginosa" 84 : 462-466, 2011

38 Ganassi, S., "Detection of fungal metabolites of various Trichoderma species by the aphid Schizaphis graminum" 122 : 77-86, 2007

39 Kumar, C. Ganesh, "Decolorization and Biotransformation of Triphenylmethane Dye, Methyl Violet, by Aspergillus sp. Isolated from Ladakh, India" 한국미생물·생명공학회 21 (21): 267-273, 2011

40 Chandrasekaran, E. V., "Constituent analyses of glycosamino-glycans, In Methods in Carbohydrate Chemistry" Academic Press Inc. 89-96, 1980

41 Gurusiddaiah, S., "Characterization of an antibiotic produced by a strain ofPseudomonas fluorescens inhibitory to Gaeumannomyces graminisvar. tritici and Pythium spp" 29 : 488-495, 1986

42 Kavitha, K., "Broad spectrum action of phenazine against active and dormant structures of fungal pathogens and root knot nematode" 38 : 69-76, 2005

43 Wood, R. K. S., "Biological Control of Pests, Pathogens and Weeds: Development and Prospects" The Royal Society 1989

44 Joshi, P. K., "Biodiversity characterization in Nubra Valley, Ladakh with special reference to plant resource conservation and bioprospecting" 15 : 4253-4270, 2006

45 Valanarasu, M., "Antifungal and antifeedant activities of extracellular product of Streptomyces spp. ERI-04 isolated from Western Ghats of Tamil Nadu" 20 : 290-297, 2010

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

47 Carpinella, M. C., "Antifeedant and insecticide properties of a limonoid from Melia azedarach (Meliaceae) with potential use for pest management" 51 : 369-374, 2003

48 Wang, X., "Algicidal activity of rhamnolipid biosurfactants produced by Pseudomonas aeruginosa" 4 : 433-443, 2005

49 Tanaka, Y., "Agroactive compounds of microbial origin" 47 : 57-87, 1993

50 Abbott, W. S., "A method of computing the effectiveness of an insecticide" 18 : 265-267, 1925

51 Mendel, M. J., "A comparison of the effects of limonin on Colorado potato beetle, Leptinotarsa decemlineata, and fall armyworm, Spodoptera frugiperda, larval feeding" 58 : 191-194, 1991

52 Römer, A., "1H NMR spectra of substituted phenazines" 19 : 66-68, 1982