Abstract
A variety of structural analogues of streptolydigin exists in the cultural supernatants of Streptomyces lydicus AS 4.2501. The degradation of streptolydigin in cultural supernatants with different pH values kept at 25°C in a thermostatic bath was investigated using LC-MS/MS detection. Analysis of the alkaline supernatants (pH 9.50) provides evidence of degradation and conversion between streptolydigin and its structural analogues. Interestingly, a new streptolydigin analogue was detected by LC-MS and photo-diode array (PDA) detection in the process of alkaline degradation. After 48 h in a thermostatic bath, the degradation of streptolydigin and its two analogues at pH 9.50 approached pseudo-first order kinetics. Comparatively, the degradation of streptolydigin was much more rapid in the cultural supernatants with pH 3.05, only requiring 2 hours. Qualitative analysis of the degradation products by LC-MS/MS and PDA indicated that hydrolysis of the epoxy ether bond and acid amide bond was the major mechanism of degradation in acidic cultural supernatants. Two degradation products in the acid supernatant were assumed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Aga, D. S., O’Connor, S., Ensley, S., Payero, J. O., Snow, D., & Tarkalson, D. (2005). Determination of the persistence of tetracycline antibiotics and their degradates in manure-amended soil using enzyme-linked immunosorbent assay and liquid chromatography-mass spectrometry. Journal of Agricultural and Food Chemistry, 53, 7165–7171. DOI: 10.1021/jf050415+.
Bersanetti, P. A., Almeida, R. M. R. G., Barboza, M., Araújo, M. L. G. C., & Hokka, C. O. (2005). Kinetic studies on clavulanic acid degradation. Biochemical Engineering Journal, 23, 31–36. DOI: 10.1016/j.bej.2004.10.007.
Chai, W., Handa, Y., Suzuki, M., Saito, M., Kato, N., & Horiuchi, C. (2000). Biodegradation of bisphenol A by fungi. Applied Biochemistry and Biotechnology, 120, 175–182. DOI: 10.1385/ABAB:120:3:175.
Cirilli, R., Costi, R., Di Santo, R., Artico, M., Roux, A., Gallinella, B., Zanitti, L., & La Torre, F. (2003). Enantioselective liquid chromatography of C3-chiral 2,3-dihydro-1,2,5-benzothiadiazepin-4(5H)-one and thione 1,1-dioxides on polyacrylamide- and polysaccharide-based chiral stationary phases. Journal of Chromatography A, 993, 17–28. DOI: 10.1016/S0021-9673(03)00321-2.
Fagerquist, C. K., Lightfield, A. R., & Lehotay, S. J. (2005). Confirmatory and quantitative analysis of β-lactam antibiotics in bovine kidney tissue by dispersive solid-phase extraction and liquid chromatography-tandem mass spectrometry. Analytical Chemistry, 77, 1473–1482. DOI: 10.1021/ac040 138q.
Kozlova, E. V., Puntus, I. F., Slepenkin, A. V., & Boronin, A. M. (2004). Naphthalene degradation by Pseudomonas putida strains in soil model systems with arsenite. Process Biochemistry, 39, 1305–1308. DOI: 10.1016/j.procbio.2003.09.015.
Lee, S. H., Raboune, S., Walker, J. M., & Bradshaw, H. B. (2010). Distribution of endogenous farnesyl pyrophosphate and four species of lysophosphatidic acid in rodent brain. International Journal of Molecular Sciences, 11, 3965–3976. DOI: 10.3390/ijms11103965.
Li, L. Z., Qiao, B., & Yuan, Y. (2007). Nitrogen sources affect streptolydigin production and related secondary metabolites distribution of Streptomyces lydicus AS 4.2501 Chinese Journal of Chemical Engineering, 15, 403–410. DOI: 10.1016/S1004-9541(07)60099-8.
Li, X.-B., Qiao, B., & Yuan, Y.-J. (2006). Differential analysis of secondary metabolites by LC-MS following strain improvement of Streptomyces lydicus AS 4.2501. Biotechnology and Applied Biochemistry, 45, 107–118. DOI: 10.1042/BA20060 042.
Lim, S.-P., Gan, S.-N., & Tan, I. K. P. (2005). Degradation of medium-chain-length polyhydroxyalkanoates in tropical forest and mangrove soils. Applied Biochemistry and Biotechnology, 126, 23–33. DOI: 10.1007/s12010-005-0003-7.
Marriott, P., Aryusuk, K., Shellie, R., Ryan, D., Krisnangkura, K., Schurig, V., & Trapp, O. (2004). Molecular interconversion behaviour in comprehensive two-dimensional gas chromatography. Journal of Chromatography, 1033, 135–143. DOI: 10.1016/j.chroma.2004.01.035.
Olano, C., Gómez, C., Pérez, M., Palomino, M., Pineda-Lucena, A., Carbajo, R. J., Braña, A. F., Méndez, C., & Salas, J. A. (2009). Deciphering biosynthesis of the RNA polymerase inhibitor streptolydigin and generation of glycosylated derivatives. Chemistry & Biology, 16, 1031–1044. DOI: 10.1016/j.chembiol.2009.09.015.
Olšovská, J., Šululc, M., Novák, P., Pažoutov M. (2008). Liquid chromatography-tandem mass spectrometry characterization of ergocristam degradation products. Journal of Chromatography B, 873, 165–172. DOI: 10.1016/j. jchromb.2008.08.004.
Pronin, S. V., & Kozmin, S. A. (2010). Synthesis of streptolydigin, a potent bacterial RNA polymerase inhibitor. Journal of the American Chemical Society, 132, 14394–14396. DOI: 10.1021/ja107190w.
Rinehart, K. L., Beck, J. R., Borders, D. B., Epstein, W. W., Kinstle, T. H., Spicer, L. D., Krauss, D., & Button, A. C. (1963). Structure of streptolydigin. Antimicrobial Agents and Chemotherapy, 161, 346–348.
Suzuki, T., Beuzenberg, V., Mackenzie, L., & Quilliam, M. A. (2003). Liquid chromatography-mass spectrometry of spiroketal stereoisomers of pectenotoxins and the analysis of novel pectenotoxin isomers in the toxic dinoflagellate Dinophysis acuta from New Zealand. Journal of Chromatography A, 992, 141–150. DOI: 10.1016/S0021-9673(03)00324-8.
Temiakov, D., Zenkin, N., Vassylyeva, M. N., Perederina, A., Tahirov, T. H., Kashkina, E., Savkina, M., Zorov, S., Nikiforov, V., Igarashi, N., Matsugaki, N., Wakatsuki, S., Severinov, K., & Vassylyev, D. G. (2005). Structural basis of transcription inhibition by antibiotic streptolydigin. Molecular Cell, 19, 655–666. DOI: 10.1016/j.molcel.2005.07.020.
Tuske, S., Sarafianos, S. G., Wang, X., Hudson, B., Sineva, E., Mukhopadhyay, J., Birktoft, J. J., Leroy, O., Ismail, S., Clark, A. D., Dharia, C., Napoli, A., Laptenko, O., Lee, J., Borukhov, S., Ebright, R. H., & Arnold, E. (2005). Inhibition of bacterial RNA polymerase by streptolydigin: Stabilization of a straight-bridge-helix active-center conformation. Cell, 122, 541–552. DOI: 10.1016/j.cell.2005.07.017.
Van Bocxlaer, J. F., Clauwaert, K. M., Lambert, W. E., Deforce, D. L., Van den Eeckhout, E. G., & De Leenheer, A. P. (2000). Liquid chromatography-mass spectrometry in forensic toxicology. Mass Spectrometry Reviews, 19, 165–214. DOI: 10.1002/1098-2787(200007)19:4〈165::AID-MAS1〉3.0.CO;2-Y.
Van Boekel, M. A. J. S. (1996). Statistical aspects of kinetic modeling for food science problems. Journal of Food Science, 61, 477–486. DOI: 10.1111/j.1365-2621.1996.tb13138.x.
Waterval, J. C. M., Bloks, J. C., Sparidans, R. W., Beijnen, J. H., Rodriguez-Campos, I. M., Bult, A., Lingeman, H., & Underberg, W. J. M. (2001). Degradation kinetics of aplidine, a new marine antitumoural cyclic peptide, in aqueous solution. Journal of Chromatography B: Biomedical Sciences and Applications, 754, 161–168. DOI: 10.1016/S0378-4347(00)00596-X.
Zhao, G.-R., Luo, T., Zhou, Y.-J., Jiang, X., Qiao, B., Yu, F.-M., & Yuan, Y.-J. (2009). fabC of Streptomyces lydicus involvement in the biosynthesis of streptolydigin. Applied Microbiology and Biotechnology, 83, 305–313. DOI: 10.1007/s00253-009-1872-4.
Zhao, Z. (Z.), Qin, X.-Z., & Reed, R. A. (2002). Identification by LC/MSn of degradates of a novel carbapenem antibiotic in an aqueous matrix. Journal of Pharmaceutical and Biomedical Analysis, 29, 173–181. DOI: 10.1016/S0731-7085(02)00008-0.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Li, L., Fu, J., Qiu, Y. et al. Analysis of streptolydigin degradation and conversion in cultural supernatants of Streptomyces lydicus AS 4.2501. Chem. Pap. 65, 652–659 (2011). https://doi.org/10.2478/s11696-011-0050-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-011-0050-1