Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Polyketides from a Sponge-Derived Fungus, Aspergillus versicolor

  • Published : 2007.03.31
Download PDF
⟨ Previous Next ⟩

Abstract

Bioactivity guided fractionation of the cultured filtrates of Aspergillus versicolor, which was derived from a marine sponge Petrosia sp., yielded three polyketides: decumbenones A (1),B (2), and versiol (3). These compounds were identified on the basis of 1D and 2D NMR spectroscopic and MS analysis. The absolute configuration was defined by the modified Mosher's method. The isolated compounds were tested for cytotoxicity against a panel of five human solid tumor cell lines and antibacterial activity against twenty clinically isolated methicillin-resistant strains. This is the first report on the isolation of these compounds from a marine source.

Keywords

References

  1. Abrell, L.M., Borgeson, B., and Crews, P., Chloro polyketides from the cultured fungus (Aspergillus) separated from a marine sponge. Tetrahedron Lett., 37(14), 2331-2334 (1996) https://doi.org/10.1016/0040-4039(96)00277-8
  2. Belofsky, G.N., Jensen, P.R., Enner, M.K., and Fenical, W., New cytotxic sesquiterpenoid nitrobenzoyl esters from a marine isolate of the fungus Aspergillus versicolor. Tetrahedron, 54, 1715-1724 (1998) https://doi.org/10.1016/S0040-4020(97)10396-9
  3. Dale, J.A. and Mosher, H.S., Nuclear magnetic resonance enantiomer reagents: Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and ${\alpha}$-methoxy-${\alpha}$-trifluorometylphenylacetate (MTPA) esters. J. Am. Chem. Soc., 95(2), 512-519 (1973) https://doi.org/10.1021/ja00783a034
  4. Demarco, P.V., Farkas, E., Doddrell, D., Mylari, L.B., and Wenkert, E., Pyridine-induced solvent shifts in the nuclear magnetic resonance spactra of hydroxylic compounds. J. Am. Chem. Soc., 90(20), 5480-5486 (1968) https://doi.org/10.1021/ja01022a027
  5. Fujii, Y., Asahara, M., Ichinoe, M., and Nakajima, H., Fungal melanin inhibitor and related compounds from Penicillium decumbens. Phytochemistry, 60, 703-708 (2002) https://doi.org/10.1016/S0031-9422(02)00196-6
  6. Fukuyama, K., Katsube, Y.K., Hamasaki, T., and Hatsuda, Y., Struture and absolute configuration of versiol, a metabolite from Aspergillus versicolor. J. Chem. Soc. Perkin Trans., 2, 683-686 (1978)
  7. Hiort, J., Maksimenka, K., Reichert, M., Ottstadt, S.P., Lin, W.H., Wray, V., Steube, K., Schauma, K., Weber, H., Proksch, P., Ebel, R., Muller, W. E. G., and Bringmann, G., New natural products from the sponge-derived fungus Aspergillus niger. J. Nat. Prod., 67, 1532-1543 (2004) https://doi.org/10.1021/np030551d
  8. Holler, U., Wright, A.D., Matthee, G.F., Konig, G.M., Draeger, S., Aust, H.J., and Schulz, B., Fungi from marine sponges: diversity, biological activity and secondary metabolites. Mycol. Res., 104(11), 1354-1365 (2000) https://doi.org/10.1017/S0953756200003117
  9. Hyde, K.D., Farrant, C.A., and Jones, E.B.G., Isolation and culture of marine fungi. Botanica Marina, 30, 291-303 (1987) https://doi.org/10.1515/botm.1987.30.4.291
  10. Lim, Y.J., New Cytotoxic Polyacetylenes from the Marine Sponge, Petrosia sp., master degree thesis, Pusan National University, 25-26 (2000)
  11. Lin, H.W., Fu, Z.H., Li, J., and Proksche, P., Novel chromone derivatives from marine fungus Aspergillus versicolor isolated from the sponge Xestospongia exigua. Chinese Chem. Lett., 12(3), 235-238 (2001a)
  12. Lin, H.W., Fu, Z.H., Li, J., and Proksche, P., Four novel hydropyranoindeno-derivatives from marine fungus Aspergillus versicolor. Chinese Chem. Lett., 12(5), 435-438 (2001b)
  13. Lin, H.W., Brauers, G., Ebel, R., Wary, V., Berg, A., and Proksch, P., Novel chromone derivatives from the fungus Aspergillus versicolor isolated from the marine sponge Xestospongia exigua. J. Nat. Prod., 66, 57-61 (2003) https://doi.org/10.1021/np020196b
  14. Meyer, B.N., Ferrigni, N.R., Putnam, J.E., Jacobsen, L.B., Nichols, D.E., and McLaughlin, J.L., Brine Shrimp: A convenient general bioassay for active plant constituents. Planta Med., 45, 31-34 (1982) https://doi.org/10.1055/s-2007-971236
  15. Michael, S., Robert, J.C., Ernest, L., Shaun, T., Jennifer, H.G., and Calbistrin, E., Two other new metabolites from an Australian isolate of Penicillium striatisporum. J. Nat. Prod., 68, 581-584 (2005) https://doi.org/10.1021/np049614y
  16. Paul, M.D., Medicinal Natural Product-A Biosynthetic Approach, Willey 2nd, 2002, pp. 35-63
  17. Renner, M.K., Jensen, P.R., and William, F.P., Mangicols: Structures and biosynthesis of a new class of sesterterpene polyols from a marine fungus of the genus Fusarium. J. Org. Chem., 65, 4843-4852 (2000) https://doi.org/10.1021/jo000081h
  18. Tsukamoto, S., Miura, S., Yamashita, Y., and Ohta, T., Aspermytin A. : A new neurotrophic polyketide isolated from a marine- derived fungus of the genus Aspergillus. Bioorg. Med. Chem. Lett., 14, 417-420 (2004) https://doi.org/10.1016/j.bmcl.2003.10.053
  19. Varoglu, M. and Crews, P., Biosynthetically diverse compounds from a saltwater culture of sponge-derived Aspergillus niger. J. Nat. Prod., 63, 41-43 (2000) https://doi.org/10.1021/np9902892
  20. Ye, Y.H., Zhu, H.L., Song, T.C., Liu, J.Y., and Tan, R.X., Structural revision of aspernigrin A, reisolated from Cladosporium herbarum IFG-E002. J. Nat. Prod., 68, 1106-1108 (2005) https://doi.org/10.1021/np050059p