Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
권호 표지

Isolation and Structure Determination of Streptochlorin, an Antiproliferative Agent from a Marine-derived Streptomyces sp. 04DH110

  • Shin, Hee-Jae (Marine Natural Products Laboratory, Korea Ocean Research & Development Institute) ;
  • Jeong, Hyun-Sun (Marine Natural Products Laboratory, Korea Ocean Research & Development Institute) ;
  • Lee, Hyi-Seung (Marine Natural Products Laboratory, Korea Ocean Research & Development Institute) ;
  • Park, Song-Kyu (Bio-evaluation Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Hwan-Mook (Bio-evaluation Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kwon, Ho-Jeong (Chemical Genomics Laboratory, Department of Biotechnology, College of Engineering, Yonsei University)
  • Published : 2007.08.30
Download PDF
⟨ Previous Next ⟩

Abstract

An antiproliferative agent, streptochlorin, was isolated from the fermentation broth of a marine actinomycete isolated from marine sediment. Phylogenetic analysis of the 16S rRNA gene sequence indicated that the strain belongs to the genus Streptomyces. Bioactivity guided fractionation of the culture extract by solvent partitioning, ODS open flash chromatography, and reversed-phase HPLC gave a pure compound, streptochlorin. Its structure was elucidated by extensive 2D NMR and mass spectral analyses. Streptochlorin exhibited significant antiproliferative activity against human cultured cell lines.

Keywords

References

  1. Atlas, R. M. 1993. In L. C. Parks (ed.), Handbook of Microbiological Media, pp. 192-193. CRC Press, Raton, FL
  2. Cho, K. W., Y. Seo, T. Yoon, and J. Shin. 1999. Purification and structure determination of antifungal phospholipids from a marine Streptomyces. J. Microbiol. Biotechnol. 9: 709-715
  3. Hardt, I. H., P. R. Jensen, and W. Fenical. 2000. Neomarine, and new cytotoxic marinone derivatives, produced by a marine filamentous bacterium (Actinomycetales). Tetrahedron Lett. 41: 2073-2076 https://doi.org/10.1016/S0040-4039(00)00117-9
  4. Jensen, P. R. and W. Fenical. 1994. Strategies for the discovery of secondary metabolites from marine bacteria: Ecological perspectives. Annu. Rev. Microbiol. 48: 559-584 https://doi.org/10.1146/annurev.mi.48.100194.003015
  5. Jukes, T. H. and C. R. Cantor. 1969. Evolution of protein molecules, pp. 21-32. In H. N. Munro (ed.), Mammalian Protein Metabolism. Academic Press, New York
  6. Kim, D., Y. K. Park, J. S. Lee, J. Kim, H. Jeong, B. S. Kim, and C. H. Lee. 2006. Analysis of a prodigionsin biosynthetic gene cluster from the marine bacterium Hahella chejuensis KCTC 2396. J. Microbiol. Biotechnol. 16: 1912-1918
  7. Kumar, S., K. Tamura, I. B. Jakobsen, and M. Nei. 2001. MEGA2: Molecular evolutionary genetics analysis software. Bioinformatics 17: 1244-1245 https://doi.org/10.1093/bioinformatics/17.12.1244
  8. Li, X., S.-K. Kim, J. S. Kang, H. D. Choi, and B. W. Son. 2006. Radical scavenging hydroxyphenyl ethanoic acid derivatives from a marine-derived fungus. J. Microbiol. Biotechnol. 16: 637-638
  9. Miller, E. D., C. A. Kauffman, P. R. Jensen, and W. Fenical. 2007. Piperazimycins: Cytotoxic hexadepsipeptides from a marine-derived bacterium of the genus Streptomyces. J. Org. Chem. 72: 323-330 https://doi.org/10.1021/jo061064g
  10. Rainey, F. A., N. Ward-Rainey, R. M. Kroppenstedtk, and E. Stackebrandt. 1996. The genus Norcardiopsis represents a phylogenetically coherent taxon and a distinct actinomycete lineage: Proposal of Norcardiopsaceae fam. nov. Int. J. Syst. Bacteriol. 46: 1088-1092 https://doi.org/10.1099/00207713-46-4-1088
  11. Saitou, N. and M. Nei. 1987. The neighbor-joining method: A new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 24: 189-204
  12. Seo, Y., K. W. Cho, J.-R. Rho, S. J. Mo, and J. Shin. 2001. A new analog of antimycin from Streptomyces sp. M03033. J. Microbiol. Biotechnol. 11: 663-667
  13. Shirling, E. B. and D. Gottlieb. 1966. Methods for characterization of Streptomyces species. Int. J. Syst. Bacteriol. 16: 313-340 https://doi.org/10.1099/00207713-16-3-313
  14. Skehan, P., R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, and M. R. Boyd. 1990. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 82: 1107-1112 https://doi.org/10.1093/jnci/82.13.1107
  15. Thompson, J. D., D. G. Higgins, and T. J. Gibson. 1994. CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22: 4673-4680 https://doi.org/10.1093/nar/22.22.4673
  16. Watanabe, H., S. Amano, J. Yoshida, Y., Takase, S. Miyadoh, T. Sasaki, M. Hatsu, Y. Takeuchi, and Y. Komada. 1988. A new antibiotic SF2583A, 4-chloro-5-(3'-indolyl)oxazole, produced by Streptomyces. Meiji Seika Kenkyu Nenpo 27: 55-62