Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Secalonic acid D; A Cytotoxic Constituent from Marine Lichen-derived Fungus Gliocladium sp. T31

  • Ren, Hong (Key Laboratory of Marine Drug Chinese Ministry of Education, Institute of Marine Drug and Food, Ocean University of China) ;
  • Tian, Li (Science & technology college of Chemistry and Biology, Yantai University) ;
  • Gu, Qianqun (First Institute of Oceanography, State Oceanic Administration) ;
  • Zhu, Weiming (Qingdao University of Science & Technology)
  • Published : 2006.01.01
Download PDF
⟨ Previous Next ⟩

Abstract

Secalonic acid D(SAD) was isolated as the major secondary metabolite of the marine lichen-derived fungus Gliocladium sp. T31. Its structure was established on the basic of physicochemical and spectroscopic data. This is the first report on the isolation of SAD from this fungus, as well as its inhibitory effect on K562 cell cycle and its cytotoxicity against several tumor cell lines in vitro.

Keywords

References

  1. Alex, C., Wallace, A. H., and Ronald, F. V., Production and biological activity of Secalonic D. Applied and Environmental Microbiology, 39, 285-287 (1980)
  2. Bachanan, M. S., Melvyn, G., and Alberto, G., Pigments of fungi. XLVI. new dimeric dihydroanthracenones of the flavomannin type from an australian toadstool of the genus Dermocybe. J. Chem., 51, 103-110 (1998)
  3. Bugni, T. S. and Ireland, C. M., Marine-derived fungi: a chemically and biologically diverse group of microorganisms. Nat. Prod. Rep., 21, 143-163 (2004)
  4. Dhulipala, V. C., Welshons, W. V., and Reddy, C. S., Inhibition of human embryonic patatal mesenchymal cell cycle by secalonic acid D: a probable mechanism of its cleft palate induction. Orthod Craniofacial Res., 7, 227-236 (2004) https://doi.org/10.1111/j.1601-6343.2004.00299.x
  5. Ganesh, B. and Chada, S. R., Novel mechanism of protein kinase C inhibition involving the pseudosubstrate region by secalonic acid D in vitro. Toxicology and Applied Pharmacology, 163, 86-93 (2000) https://doi.org/10.1006/taap.1999.8850
  6. Hanumegowda, U. M., Barbara, M. J., Wade, V. W., and Chada, S. R., Selective inhibition of murine palatal mesenchymal cell proliferation in vitro by secalonic acid D. Toxicol. Sci., 66, 159-165 (2002b) https://doi.org/10.1093/toxsci/66.1.159
  7. Hanumegowda, U. M., Dhulipala, V. C., and Reddy, C. S., Mechanism of secalonic acid D-induced inhibition of transcription factor binding to cyclic AMP response element in the developing murine palate. Toxicol. Sci., 70, 55-62 (2002a) https://doi.org/10.1093/toxsci/70.1.55
  8. Jacqueb, P. B., Reaction of keten acetals. Part IV: Total syntheses of anthraquinones (${\pm}$)-nalyiovensin, (${\pm}$)-isorhodoptilometrin, and (${\pm}$)-rhodopilometrin [J]. JCS Perkin I, 613-619 (1976)
  9. Lu, Y. H., Wang, Z. T., Xu, L. S., and Wu, Z. B., Three Anthraquinones Isolated from Astertataricus. Journal of Chinese Pharmaceutical Science, 12, 112-113 (2003)
  10. Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods, 65, 55-63 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  11. Raymond, A., George, B., Brunhilde, K., and Arnold, L. D., Secalonic acid D and F are toxic metabolites of Aspergillus aculeatus. J. Org. Chem., 42, 352-353 (1977) https://doi.org/10.1021/jo00422a042
  12. Steyn, P. S., The isolation, structure and absolute configuration of secalonic acid D, the toxic metabolite of Penicillium Oxalicum. Tetrahedron, 26, 51-57 (1970) https://doi.org/10.1016/0040-4020(70)85006-2
  13. Tim, S. B. and Chris, M. I., Marine-derived Fungi: A Chemically and Biologically Diverse Group of Microorganisms. Nat. Prod. Rep., 21, 143-163 (2004)
  14. Viola, A., Lutz, N. W., Maroc, C., Julliard, M., and Cozzone, P. J., Metabolic effects of photodynamically induced apoptosis in an erythrolukemic cell line. A (31)P NMR spectroscopic study of Victoria-Blue-BO-sensitized TF-1 cells. Int. J. Cancer, 85, 733-739 (2000) https://doi.org/10.1002/(SICI)1097-0215(20000301)85:5<733::AID-IJC22>3.0.CO;2-C
  15. Wang, B. H. and Poya, G. M., The fungal teratogen secalonic acid D is an inhibitor of protein kinase C and of cyclic AMPdependent protein kinase. Planta Med., 62, 111-114 (1996) https://doi.org/10.1055/s-2006-957829