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New Cyclic Peroxides from a Sponge, Plakortis sp.

  • Lim Chi Won (Marine Bio21 Center, National Fisheries R&D Institute) ;
  • Cha Yong Jun (Department of Food Science and Nutrition, Changwon National University) ;
  • Kim Jin Soo (Division of Marine Bioscience Institute of Marine Industry, Gyeongsang National University)
  • Published : 2005.03.01

Abstract

Two new cyclic peroxides were isolated from an undescribed sponge of the genus Plakortis sp. collected at Discovery Bay, Jamaica. The molecular structures were elucidated by interpreting ID and 2D NMR and HRMS data. The cyclic peroxides, Compound 1 and 2, exhibited significant antimicrobial activity against pathogenic bacteria and fungi with IC$_${50} values of 0.9-5.0$\mug/mL and 0.7-8.0$\mug/mL, respectively.

Keywords

References

  1. Chen, Y., J.M. Peter, K.H. Dedra, S.O. Rebeeca, C. Katherine, S. Claude, A.P. Shirley and E.W. Amy. 2002. New bioactive peroxides from marine sponges of the family Plakiniidae. J. Nat. Prod., 65, 1509-1512 https://doi.org/10.1021/np0200414
  2. Compagnone, R.S., l.C. Pina, H.R. Rangel, F. Dagger, A.I. Suarez, M.V.R. Reddy and D.J. Faulkner. 1998. Antileisharnanial cyclic peroxides from the Palauan sponge Plakortis aff. angulospiculatus. Tetrahedron, 54, 3057-3068 https://doi.org/10.1016/S0040-4020(98)00055-6
  3. Davidson, B.S. 1991. Cytotoxic five-membered cyclic peroxides from a Plakortis sponge. J. Org. Chem., 56, 6722-6724 https://doi.org/10.1021/jo00023a048
  4. Fontana, A., M. Ishibashi and J. Kobayashi. 1998. New cyclic polyketide peroxides from Okinawan marine sponge Plakortis sp. Tetrahedron, 54, 2041-2048 https://doi.org/10.1016/S0040-4020(97)10414-8
  5. Gunasekera, S.P., M. Gunasekera, G.P. Gunawardana, P. McCarthy and N. Burrers. 1990. Two new bioactive cyclic peroxides from the marine sponge Plakortis angulospiculatus. J. Nat. Prod., 53, 669-674 https://doi.org/10.1021/np50069a021
  6. Hu, J.F., H.F. Gao, M. Kelly and M.T. Hamann. 2001. Plakortides I-L, four new cyclic peroxides from an undescribed Jamaican sponge Plakortis sp. (Homosclerophorida, Plakinidae). Tetrahedron, 57, 9379-9383 https://doi.org/10.1016/S0040-4020(01)00947-4
  7. Patil, A.D., A.J. Freyer, M.F. Bean, B.K. Carte, J.W. Westly and R.K. Johnson. 1996a. The plakortones, novel bicyclic lactones from the sponge Plakortis halichondrioides : Activators of cardiac SR-$Ca^{2+}$ -pumping ATPase. Tetrahedron, 52, 377-394 https://doi.org/10.1016/0040-4020(95)00856-X
  8. Patil, A.D., A.J. Freyer, B.K. Carte, R.K. Johnson and P. Lahouratate. 1996b. Plakortides, novel cyclic peroxides from the sponge Plakortis halichondrioides : Activators of cardiac SR-$Ca^{2+}$ -pumping ATPase. J. Nat. Prod., 59, 219-223 https://doi.org/10.1021/np960087v
  9. Peng, J., K. Walsh, V. Weedman, J.D. Bergthold, J. Lynch, K.L. Lieu, I.A. Braude, M. Kelly and M.T. Hamann. 2002. The new bioactive diterpenes cyanthiwigins E-AA from the Jamaican sponge Myrmekioderma styx. Tetrahedron, 58, 7809-7819 https://doi.org/10.1016/S0040-4020(02)00937-7
  10. Perry, T.L., A. Dickerson, A.A. Khan, R.K. Kondru, D.N. Beratan, P. Wipf, M. Kelly and M.T. Hamann. 2001. New peroxylactones from the Jamaican sponge Plakinastrella onkodes, with inhibitory activity against the AIDS opportunistic parasitic infectious Toxoplasma gondii. Tetrahedron, 57, 1483-1487 https://doi.org/10.1016/S0040-4020(00)01134-0
  11. Stierle, D.B. and D.J. Faulkner. 1980. Metabolites of three marine sponges of the genus Plakortis. J. Org. Chem., 45, 3396-3401 https://doi.org/10.1021/jo01305a005

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