DOI QR코드

DOI QR Code

Coupling of ent-Cyclic Peroxide and Ircinol A, Two Biologically Active Natural Marine Products

  • Lim, Chi-Won (Biotechnology Research Center, National Fisheries R&D Institute) ;
  • Kim, Yeun-Kye (Biotechnology Research Center, National Fisheries R&D Institute) ;
  • Jang, Mi-Soon (Biotechnology Research Center, National Fisheries R&D Institute) ;
  • Park, Jin-Il (Biotechnology Research Center, National Fisheries R&D Institute) ;
  • Park, Hee-Yeun (Biotechnology Research Center, National Fisheries R&D Institute)
  • Published : 2006.12.30

Abstract

An acidic ent-cyclic peroxide was isolated from a sponge, Plakotis sp., and showed activity against leishmaniasis and pathogenic fungi. To improve the activity of this compound, we coupled the acidic ent-cyclic at the C1 position of ircinol A. Compound 3 exhibited significant activity against Leishmania mexican a and fungi with $IC_{50}$ values of 0.7 and $0.3-34{\mu}g/mL$, respectively. The yield of compound 3 was 98%.

Keywords

References

  1. Ang, K.K.H., M.J Holmes, T. Higa, M.T. Hamann and U.A.K. Kara. 2000. In vivo antimalarial activity of the $\beta$-carboline alkaloid manzamine A. Antimicrob. Agent. Chemother., 44, 1645-1649 https://doi.org/10.1128/AAC.44.6.1645-1649.2000
  2. Compagnone, S.R., C.I Pina, R.H. Rangel, F. Dagger, I.A. Suarez, R.Y.M. Reddy and J.D. Faulkner. 1998. Antileishmanial cyclic peroxides from the Palauan sponge Plakortis angulospiculatus. Tetrahedron, 54, 3057-3068 https://doi.org/10.1016/S0040-4020(98)00055-6
  3. EI Sayed, K.A., M. Kelly, U.A.K. Kara, K.K.H. Ang, I. Katswyama, D.C. Dunbar, A.A. Khan and M.T. Hamann. 2001. New manzamine alkaloids with potent activity against infectious disease. J. Am. Chem. Soc., 123, 1804-1808 https://doi.org/10.1021/ja002073o
  4. Gunasekera, P.S., M. Gunasekera, P. G. Gunawardana P McCarthy and N. Burres. 1990. Two new bioactive cyclic peroxides from the marine sponge Plakortis angulospiculatus. J. Nat. Prod., 53, 669-674 https://doi.org/10.1021/np50069a021
  5. Holla, P.S., M. Mahalinga, M.S. Karthikeyan, B. Poojary, P.M. Akberali and N.S. Kumari. 2005. Synthesis, chracterization and antimicrobial activity of some substituted 1,2,3-triazoles. Eur. J. Med. Chem., 40, 1173-1178 https://doi.org/10.1016/j.ejmech.2005.02.013
  6. Lim, C.W., Y.J., Cha and J.S. Kim. 2005. New cyclic peroxides from a sponge, Plakortis sp. J. Fish. Sci. Technol., 8, 6-9 https://doi.org/10.5657/fas.2005.8.1.006
  7. Lim, C.W., Y.K., Kim, H.D. Youn and H.Y Park. 2006. Enantiomeric compounds with antileishmanial activities from a sponge, Plakortis sp. Agric. Chem. Biotechnol., 49, 21-23
  8. Longley, R.E., O.J. McConnel, E. Essich and D. Harmody. 1993. Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity. J. Nat. Prod., 56, 915-920 https://doi.org/10.1021/np50096a015
  9. Masashi T., K. Naoko and J. Kobayashi. 1994. Ircinols A and B, first antipodes of manzamine-related alkaloids from an Okinawan marine sponge. Tetrahedron, 50, 7957-7960 https://doi.org/10.1016/S0040-4020(01)85280-7
  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 a Jamaican sponge Plakinastrella onkodes, with inhibitory activity against the AIDS opportunistic parasitic infection Toxoplasma gondii. Tetrahedron, 57, 1483-1487 https://doi.org/10.1016/S0040-4020(00)01134-0
  11. WHO. 2000. Leishmania/HIV w-infectious in south-western Europe 1990-1998: Retrospective analysis of 965 cases. WHO/LEISH/2000.42, 1-12

Cited by

  1. Chemistry and Selective Tumor Cell Growth Inhibitory Activity of Polyketides from the South China Sea Sponge Plakortis sp. vol.15, pp.5, 2017, https://doi.org/10.3390/md15050129
  2. Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products vol.10, pp.None, 2006, https://doi.org/10.3762/bjoc.10.6