Trisoxazole Macrolide from a Marine Sponge Sarcotragus Species

  • Liu, Yong-Hong (College of Pharmacy, Pusan National University) ;
  • Shinde, Pramod B. (College of Pharmacy, Pusan National University) ;
  • Hong, Jong-Ki (Hazardous Substance Research Team, Korea Basic Science Institute) ;
  • Lee, Chong-O. (Pharmaceutical Screening Center, Korea Research Institute of Chemical Technology) ;
  • Im, Kwang-Sik (College of Pharmacy, Pusan National University) ;
  • Jung, Jee-H. (College of Pharmacy, Pusan National University)
  • Published : 2005.03.01

Abstract

Bioassay-directed fractionation of the lipophilic extract of a marine sponge Sarcotragus sp. led to the isolation of a known trisoxazole containing macrolide, mycalolide B (1). Its structure was identified by NMR and MS analyses. This is the first report on the isolation of macrolide from a sponge of the genus Sarcotragus (Order: Dictyoceratida).

Keywords

References

  1. Faulkner, D.J. Nat. Prod. Rep. 18, 1-49 (2001) and earlier reviews cited therein https://doi.org/10.1039/b006897g
  2. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Mycalolides A-C, hybrid macrolides of ulapualides and halichondrarnide, from a sponge of the genus Mycale. Tetrahedron Lett. 30, 2809-2812 (1989) https://doi.org/10.1016/S0040-4039(00)99131-7
  3. Kernan, M.R.; Faulkner, D.J. Halichondrarnide, an antifungal macrolide from the sponge Halichondria sp. Tetrahedron Lett. 28, 2809-2812 (1987) https://doi.org/10.1016/S0040-4039(00)96215-4
  4. Kernan, M.R.; Molinski, T.E; Faulkner, D.J. Macrocyclic antifungal metabolites from the Spanish dancer nudibranch Hexabranchus sanguineus and sponges of the genus Halichondria. J. Org. Chem. 53, 5014-5020 (1988) https://doi.org/10.1021/jo00256a021
  5. Kobayashi.T; Murata, O.; Shigemori, H. Jaspisarnides A-C, new cytotoxic macrolides from the Okinawan sponge Jaspis sp. J. Nat. Prod. 56, 787-791 (1993) https://doi.org/10.1021/np50095a021
  6. Kobayashi, J.; Tsuda, M.; Fuse, H.; Sasaki, T.; Mikarni, Y Halishigamides A-D, new cytotoxic oxazole containing metabolites from okinawan sponge Halichondria sp. J. Nat. Prod. 60, 150-154 (1997) https://doi.org/10.1021/np960558d
  7. Liu, Y; Bae, B.H.; Alam, N.; Hong, I; Sim C.J.; Lee, C-O.; Im, KS.; Jung, J.H. New cytotoxic sesterterpenes from the sponge Sarcotragus sp. J. Nat. Prod. 64, 1301-1304 (2001) https://doi.org/10.1021/np0101494
  8. Liu, Y; Hong, J; Lee, C-O.; Im, KS.; Kim, N.D.; Choi, J.S.; Jung, J.H. Cytotoxic pyrrolo- and furanoterpenoids from the sponge Sarcotragus sp. J. Nat. Prod. 65, 1307-1314 (2002a) https://doi.org/10.1021/np020145e
  9. Liu, Y; Lee, C-O.; Hong, J; Jung, J.H. Cyclitol derivatives from the sponge Sarcotragus sp. Bull. Korean Chem. Soc. 23, 1-3 (2002b)
  10. Liu, Y; Mansoor, T.A.; Hong, J; Lee, C-O.; Sim, C.J.; Im, K.S.; Kim, N.D.; Jung, J.H. New cytotoxic sesterterpenoids and norsesterterpenoids from two sponges of the genus Sarcotragus. J. Nat. Prod. 66, 1451-1458 (2003) https://doi.org/10.1021/np030268e
  11. Matsunaga, S.; Fusetani, N.; Hashimoto, K Kabirarnide C, a novel antifungal macrolide from nudibranch egg masses. J. Am. Chem. Soc. 108, 847-849 (1986) https://doi.org/10.1021/ja00264a053
  12. Matsunaga, S.; Fusetani, N.; Hashimoto, K Further kabirarnides and halichondramides, cytotoxic macrolides embracing trisoxazole, from the Hexabranchus egg masses. J. Org. Chem. 54, 1360-1363 (1989) https://doi.org/10.1021/jo00267a024
  13. Matsunaga, S.; Nogata, Y; Fusetani, N. Thiomycalolides: new cytotoxic trisoxazole-containing macrolides isolated from a marine sponge Mycale sp. J. Nat. Prod. 61, 663-666 (1998a) https://doi.org/10.1021/np9704866
  14. Matsunaga, S.; Sugawara, T.; Fusetani, N. New mycalolides from the marine sponge Mycale magellanica and their interconversion. J. Nat. Prod. 61, 1164-1167 (1998b) https://doi.org/10.1021/np980102r
  15. Phuwapraisirian, P.; Matsunaga, S.; Soest, R W. M. V., Fusetani, N. Isolation of a new mycalolide from the marine sponge Mycale izuensis. J. Nat. Prod. 65, 942-943 (2002) https://doi.org/10.1021/np010663+
  16. Rashid, M. A.; Gustafson, K R; Cardellina II, J. H.; Boyd, M. R Mycalolides D and E, new cytotoxic macrolides from a collection of the stony coral Tubastrea faulkneri. J. Nat. Prod. 58, 1120-1125 (1995) https://doi.org/10.1021/np50121a025
  17. Roesener, J. A.; Scheuer, P. J. Ulapualide A and B, extraordinary antitumor macrolides from nudibranch egg masses. J. Am. Chem. Soc. 108, 846-847 (1986) https://doi.org/10.1021/ja00264a052
  18. Saito, S.; Watabe, S.; Ozaki, H.; Fusetani, N.; Karaki, H. Mycalolide B, a novel depolymerizing agent. J. Biol. Chem. 269, 29710-29714 (1994)
  19. Wada, S.; Matsunaga, S.; Saito, S.; Fusetani, N.; Watabe, S. Actin-binding specificity of marine macrolide toxins, mycalolide B and kabiramide D. J. Biol. Chem. 123, 946-952 (1998)