Sains Malaysiana 45(7)(2016): 1073–1077

Isolation and Identification of Metabolites from the Gram-negative Proteobacteria of Burkholderia cenocepacia and Serratia marcescens

(Pengasingan dan Pengenalpastian Metabolit daripada Proteobakteria Gram-negatif Burkholderia cenocepacia dan Serratia marcescens)

ANN-CHEE YAP, KOK-GAN CHAN & YEUN-MUN CHOO*

Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Federal Territory, Malaysia

Received: 30 June 2015/Accepted: 11 February 2016

ABSTRACT

Burkholderia cenocepacia and Serratia marcescens are Gram-negative proteobacteria commonly found in the natural environment and are also opportunistic pathogens that caused a number of human diseases. The fermentation culture of Burkholderia cenocepacia yielded three compounds, 4-(2-hydroxyethoxy)-phenol (1), Maculosin (2) and methyl myristate (3). Compound 2 was also isolated together with cyclo(L-Leu-L-Pro) (4) from Serratia marcescens. Compound 1 was isolated from a natural source for the first time and the first isolation of compounds 2-4 was also reported from both Burkholderia cenocepacia and Serratia marcescens.

Keywords: Burkholderia cenocepacia; Malaysia microorganism natural products; proteobacteria metabolites; Serratia marcescens

ABSTRAK

Burkholderia cenocepacia dan Serratia marcescens adalah proteobakteria Gram-negatif yang biasa dijumpai di alam semula jadi dan juga patogen yang boleh membawa penyakit kepada manusia. Tiga metabolit telah diasingkan daripada kultur fermentasi Burkholderia cenocepacia, iaitu 4-(2-hidroksietoksi)-fenol (1), Maculosin (2) dan metil miristat (3). Sebatian 2 juga diasingkan bersama siklo(L-Leu-L-Pro) (4) daripada Serratia marcescens. Sebatian 1 diasingkan untuk pertama kali daripada sumber hasil semula jadi dan pengasingan untuk sebatian 2-4 juga dilaporkan buat pertama kali daripada Burkholderia cenocepacia dan Serratia marcescens.

Kata kunci: Burkholderia cenocepacia; metabolit proteobakteria; sebatian semula jadi mikroorganisme Malaysia; Serratia marcescens

REFERENCES

Araujo, D.M., Yoshids, M.I., Takahashi, J.A., Carvalho, C.F. & Stapelfeldt, F. 2010. Biodegradation studies on fatty amines used for reverse otation of iron ore. Int. Biodeterioration & Biodegradation 64(2): 151-155.

Bouvet, O.M.M., Lenormand, P.L. & Grimont, P.A.D. 1989. Taxonomic diversity of the D-glucose oxidation pathyway in the Enterobacteriaeae. Int. J. Sys. Bacteriol. 39(1): 61-67.

Cimmino, A., Puopolo, G., Perazzolli, M., Andolfi, A., Melck, D., Pertot, I. & Evidente, A. 2014. Cyclo(L-pro-L-tyr), the fungicide isolated from Lysobacter capsici AZ78: A structure-activity relationship study. Chem. Heterocyclic Compounds. 50(2): 290-295.

de Boer, M.G.J., Brunsveld-Reinders, A.H., Salomons, E.M.A., Dijkshoorn, L., Bernards, A.T., van den Berg, P.C.M. & van den Broek, P.J. 2008. Multifactorial origin of high incidence of Serratia marcescens in a cardio-thoracic ICU: analysis of risk factors and epidemiological characteristics. J. Infect. 56(6): 446-453.

El-Banna, N. & Winkelmann, F. 1998. Pyrrolnitrin from Burkholderia cepacia: antibiotic activity against fungi and novel activities againts streptomycetes. J. Appl. Microb. 85(1): 69-78.

Fuller, A.T. & Horton, J.M. 1950. Marcescin, an antibiotic substance from Serratia marcescens. Microbiol. 4(3): 417- 433.

Hejazi, A. & Falkiner, F.R. 1997. Serratia marcescens. J. Med. Microbiol. 46(11): 903-912.

Holden, M.T.G., Chhabra, S.R., de Nys, R., Stead, P., Bainton, N.J., Hill, P.J., Manefield, M., Kumar, N., Labatte, M., England, D.R.S., Givskov, M., Salmond, G.P.C., Steward, G.S.A.B., Bycroft, B.W., Kjelleberg, S. & Williams, P. 1999. Quorum-sensing cross talk: isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other Gram-negative bacteria. Molecular Mirobiology 33(6): 1254-1266.

Mao, S., Lee, S.J., Hoon, H., Kim, Y.W., Park, K.H., Cha, G.S., Park, R.D. & Kim, K.Y. 2006. Isolation and characterization of antifungal substances from Burkholderia sp. culture broth. Curr. Microbiol. 53(5): 358-364.

Matsuyama, T., Tanikawa, T. & Nakagawa, Y. 2011. Serrawettins and other surfactants produced by Serratia. Biosurfactants 20: 93-120.

Montpas, S., Samson, J., Langlois, E., Lei, J., Piche, Y. & Chenevert, R. 1997. Degradation of 2,4,6-trinitrotoluene by Serratia marcescens. Biotechnol. Lett. 19(3): 291-294.

Perestelo, F., Dalcón, M.A. & de la Fuente, G. 1989. Production of vanillic acid from vanillin by resting cells of Serratia marcescens. Appl. Environ. Microbiol. 55(6): 1660-1662.

Read, R.R. & Miller, E. 1932. Some substituted phenols and germicidal activity. J. Am. Chem. Soc. 54: 1195-1199.

Singh, S., Chandra, R., Patel, D.K. & Rai, V. 2007. Isolation and characterization of novel Serratia marcescens (AY927692) for pentachlorophenol degradation from pulp and paper mill waste. World J. Microbiol Biotechnol. 23(12): 1747-1754.

Stierle, A.C., Cardellina, J.H. & Strobel, G.A. 1989. Phytotoxins from Alternaria alternata, a pathogen of spotted knapweed. J. Nat. Prod. 52(1): 42-47.

Su, L.H., Ou, J.T., Leu, H.S., Chiang, P.C., Chiu, Y.P., Chia, J.H., Kuo, A.J., Chiu, C.H., Chu, C., Wu, T.L., Sun, C.F., Riley, T.V., Chang, B.J. & The Infection Control Group. 2003. Extended epidemic of nosocomial urinary tract infections caused by Serratia marcescens. J. Clin. Microbiol. 41(10): 4726-4732.

Yan, P.S., Song, Y., Sakuno, E., Nakajima, H., Nakagawa, H. & Yabe, K. 2004. Cyclo(L-Leucyl-L-Prolyl) produced by Achromobacter xylosoxidans inhibits aflatoxin production by Aspergillus parasiticus. Appl. Environ. Microbio. 70(12): 7446-7473.

Yap, A.C., Teoh, W.Y., Chan, K.G., Sim, K.S. & Choo, Y.M. 2015a. A new oxathiolane from Enterobacter cloacae. Nat. Prod. Res. 29(8): 722-726.

Yap, A.C., Chan, K.G., Sim, K.S. & Choo, Y.M. 2015b. A new oxolane from Enterobacter cloacae. Nat. Prod. Res. 30(7). DOI: 10.1080/14786419.2015.1065492.

*Corresponding author; email: ymchoo@um.edu.my