Bioactive Semisynthetic Dervatives of (S)-(+)-Curcuphenol (original) (raw)

Abstract

8 pages, figures, and tables statistics.New semisynthetic sesquiterpene derivatives (3-7, 10), together with two known ones (8-9) were prepared from (S)-(+)- curcuphenol (1), isolated from the Caribbean sponge Didiscus oxeata. The natural sesquiterpenes 1 and (S)-(+)-curcudiol (2), as well as semisynthetic derivatives 3-10, were evaluated against the herbivorous insect species Spodoptera littoralis, Leptinotarsa decemlineata and Rhopalosiphum padi. All compounds had an antifeedant effect on L. decemlineata. With R. padi, a structure-dependent antifeedant response was observed, with 1 being the most active, followed by 4 and 5. Furthermore, compounds 1, 4, 5, 7, 8 and 10 reduced S. littoralis larval weight, with 10 also reducing ingestion by S. littoralis larvae. Of the derivatives studied here, none showed stronger effects (either antifeedant or postingestive) than the parent compound 1. It can, therefore, be concluded that the structure of the side chain and the presence of the phe...

Loading...

Loading Preview

Sorry, preview is currently unavailable. You can download the paper by clicking the button above.

References (39)

  1. Blunt JW, Copp BR, Hu W-P, Munro MHG, Northcote PT, Prinsep MR. (2007) Marine natural products. Natural Product Reports, 24, 31-86.
  2. Cichewicz RH, Clifford LJ, Lassenm PR, Cao X, Freedman TB, Nafie LA, Deschamps JD, Keyon VA, Flanary JR, Holman TR, Crews P. (2005) Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus oxeata and synthesized through laccase biocatalysis. Bioorganic & Medicinal Chemistry, 13, 5600-5612.
  3. Braekman JC, Daloze D, Moussiaux B, Stoller C, Deneubourg F. (1989) Sponge secondary metabolites: new results. Pure & Applied Chemistry, 61, 509-512.
  4. Tsukamoto S, Kato H, Hirota H, Fusetani N. (1997) Antifouling terpenes and steroids against barnacle larvae from marine sponges. Biofouling, 11, 283-291.
  5. Takamatsu S, Hodges TW, Rajbhandari I, Gerwick WH, Hamann MT, Nagle DG. (2003) Marine natural products as novel antioxidant prototypes. Journal of Natural Products, 66, 605-608.
  6. Peng J, Kasanah N, Stanley CE, Chawick J, Fronczeck FR, Hamann MT. (2006) Microbial metabolism studies of cyanthiwigin B and synergetic antibiotic effects. Journal of Natural Products, 69, 727-730.
  7. Gaspar H, Feio SS, Rodrigues AI, Van Soest R. (2004) Antifungal activity of (+)-curcuphenol, a metabolite from the marine sponge Didiscus oxeata. Marine Drugs, 2, 8-13.
  8. El Sayed KA, Yusaf M, Hamann MT, Avery MA, Kelly M, Wipf P. (2002) Microbial and chemical transformation studies of the bioactive marine sesquiterpenes (S)-(+)-curcuphenol and curcudiol isolated from a deep reef collection of the Jamaica sponge Didiscus oxeata. Journal of Natural Products, 65, 1547-1553.
  9. Peng J, Franzblau SG, Zhang F, Hamann MT. (2002) Novel sesquiterpenes and a lactone from the Jamaica sponge Myrmekioderma styx. Tetrahedron Letters, 43, 9699-9702.
  10. Wright AE, Pomponi SA, McConnell OJ, Kohmoto S, McCarthy PJ. (1987) (+)-Curcuphenol and (+)-curcudiol, sesquiterpene phenols from shallow and deep water collections of the marine sponge Didiscus flavus. Journal of Natural Products, 50, 976-978.
  11. Duque C, Zea S, De Silvestre S, Calderón A, Medina A. (1988) Actividad biológica vs. composición química del extracto uílorofórmico de la esponja marina Didiscus oxeata. Revista Colombiana de Química, 17, 39-46.
  12. Fusetani N, Sugano M, Matsunga S, Hashimoto K. (1987) (+)-Curcuphenol and dehydrocurcuphenol, novel sesquiterpenes which inhibit H, K-ATPase, from a marine sponge Epipolasis sp. Experientia, 43, 1234-1235.
  13. McEnroe FJ, Fenical W. (1978) Structure and synthesis of some new antibacterial sesquiterpenoids from the gorgonian coral. Tetrahedron, 34, 1661-1664.
  14. Harrison B, Crews P. (1997) The structure and probable biogenesis of helianane, a heterocyclic sesquiterpene, from the Indo- Pacific sponge Haliclona fascigera. Journal of Organic Chemistry, 62, 2646-2648.
  15. McBrien HL, Millar JG, Gottlieb L, Chen X, Rice RE. (2001) Male produced sex attractant pheromone of the green stink bug, Acrosternum halare. Journal of Chemical Ecology, 27, 1821-1839.
  16. Lu F, Teal PEA. (2001) Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew). Archives of Insect Biochemistry and Physiology, 48, 144-154.
  17. Pandji C, Grima C, Wray V, Witte L, Proksch P. (1993) Insecticidal constituents from four species of the Zingiberaceae. Phytochemistry, 34, 415-419.
  18. Porter R, Reese P, Williams LAD, Williams D. (1995) Acaricidal and insecticidal activities of cadina-4,10 (15)-dien-3-one. Phytochemistry, 40, 735-738.
  19. He K, Shi G, McLaughlin JL. (1997) Konishiol, a new sesquiterpene, and bioactive components from Cunninghamia konishii. Planta Medica, 63, 158-160.
  20. Bohlmann J, Crock J, Jetter R, Croteau R. (1998) Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E)-α-bisabolene synthase from grand fir (Abies grandis). Proceedings of the National Academy of. Sciences U.S.A., 95, 6756-61.
  21. González-Coloma A, Reina M, Cabrera R, Gutiérrez C. (1995) Antifeedant and toxic effects of sesquiterpenes from Senecio palmensis to Colorado potato beetle. Journal of Chemical Ecology, 21, 1255-1270.
  22. Gutiérrez C, Fereres A, Reina M, Cabrera R, González-Coloma A. (1997) Behavioral and sub-lethal effects of structurally-related lower terpenes on Myzus persicae. Journal of Chemical Ecology, 23, 1641-1650.
  23. Reina M, Nold M, Orihuela JC, Santana O, González-Coloma A. (2002) C-5-Subsituted antifeedant silphinene sesquiterpenes from Senecio palmensis. Journal of Natural Products, 65, 448-453.
  24. Lu J, Xie X, Chen B, She X, Pan X. (2005) An enantioselective synthesis of (S)-and (R)-curcuphenol. Tetrahedron: Asymmetry, 16, 1435-1438.
  25. Ono M, Ogura Y, Hatogai K, Akita H. (2001) Total synthesis of (S)-(+)-curcudiol, and (S)-(+)-and (R)-(-)-curcuphenol. Chemical & Pharmaceutical Bulletin, 12, 1581-1585.
  26. Gul W, Hammond NL, Yousaf M. (2007) Chemical transformation and biological studies of marine sesquiterpene (S)-(+)- curcuphenol and its analogs. Biochimica et Biophysica Acta, 1770, 1513-1519.
  27. Bair Jr. WC, Surridge JH, Buza M. (1971) Halogenation with copper (II) halides. Halogenation of olefins with complexed copper (II) halides. Journal of Organic Chemistry, 36, 22, 3324-3330.
  28. Mohammadpoor-Baltork, Tangestaninejad S, Aliyan H, Mirkhani V. (2000) Bismuth(III) chloride (BiCl 3 ); An efficient catalyst for mild, regio-and stereoselective cleavage of epoxides with alcohols, acetic acid and water. Synthetic Communications, 30, 2365-2374.
  29. González-Coloma A, Valencia F, Martín N, Hoffmann JJ, Hutter L, Marco JA, Reina M. (2002) Silphinene sesquiterpenes as model insect antifeedants. Journal of Chemical Ecology, 28, 117-129.
  30. González-Coloma A, Guadaño A, De Inés C, Martínez-Díaz R, Cortés D. (2002) Selective action of acetogenin mitochondrial complex I inhibitors. Zeitschrift für Naturforschung, 57c, 1028-1034.
  31. Mohammadi B, Haeseler G, Leuwer M, Dengler R, Krampfl K, Bufler J. (2001) Structural requirements of phenol derivatives for direct activation of chloride currents via GABA(A) receptors. European Journal of Pharmacology, 421, 85-91.
  32. Bloomquist JR, Boina DR, Chow E, Paul R, Carlier PR, Reina M, Gonzalez-Coloma A. (2008) Mode of action of the plant-derived silphinenes on insect and mammalian GABAA receptor/chloride channel complex. silphinenes Pesticide Biochemistry and Physiology, 91, 17-23.
  33. Mullin C, González-Coloma A, Gutiérrez C, Reina M, Eichenseer H, Hollister B, Chyb, S. (1997) Antifeedant effects of some novel terpenoids on Chrysomelidae beetles: Comparisons with alkaloids on an alkaloid-adapted and non-adapted species. Journal of Chemical Ecology, 23, 1851-1865.
  34. Tasdemir D, Bugni TS, Mangalindan GC, Concepción GP, Harper MK, Ireland, CM. (2003) Bisabolane-type sesquiterpenes from a marine didiscus sponge. Turkish Journal of Chemistry, 27, 273-279.
  35. Poitout S, Bues R. (1974) Élevage de plusieurs espéces de Lépidoptères sur milieu artificial simplifié. Annales de Zoologie Ecologie Animale, 2, 79-91.
  36. Reina M, González-Coloma A, Gutiérrez C, Cabrera R, Rodríguez ML, Fajardo V, Villarroel L. (2001) Defensive chemistry of Senecio miser Hook. Journal of Natural Products, 64, 6-11.
  37. Priestley CM, Sattelle DB, Williamson EM. (1999) An investigation into the action of naturally-occurring insecticidal monoterpenoids using recombinant homomeric insect GABA receptors. Journal of Pharmacy and Pharmacology, 51, 101.
  38. Priestley CM, Williamson EM, Wafford KA, Sattelle DB. (2003) Thymol, a constituent of thyme essential oil, is a positive allosteric modulator of human GABA A receptors and homo-oligomeric GABA receptor from Drosophila melanogaster. British Journal of Pharmacology, 140, 1363-1372.
  39. Hummelbrunner LA, Isman MB. (2001) Acute, sublethal, antifeedant, and synergistic effects of monoterpenoid essential oil compounds on the tobacco cutworm, Spodoptera litura (Lep., Noctuidae). Journal of Agricultural and Food Chemistry, 49, 715-720.