Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Bioactive Metabolites from the Brittle Star Ophioplocus japonicus

  • Published : 2004.12.30
Download PDF
⟨ Previous Next ⟩

Abstract

Ten terpenes (1-10), two sterols (11 and 12), and two unusual phenylpropanoids (13 and 14) were isolated from the brittle star Ophioplocus japonicus (Family Ophiuridae). Their structures were identified by analyses of the spectral data and by comparison with the literature data. The terpenes (1-10) and phenylpropanoids (13 and 14) are first encountered in brittle stars. These compounds were evaluated for cytotoxicity against a small panel of human solid tumor cell lines. Compounds 6-10 and 14 displayed moderate to significant cytotoxicity. The compounds were evaluated for antibacterial activity against 20 clinically isolated strains. Compound 5 exhibited antibacterial activities against three Streptococcus and three Staphylococcus strains.

Keywords

References

  1. Amico, V., Oriente, G., Piattelli, M., Tringali, C., Fattorusso, E., Magno, S., Mayol, L. Diterpenes based on the dolabellane skeleton from Dictyota dichotoma. Tetrahedron 36(10), 14091414 (1980) https://doi.org/10.1016/0040-4020(80)85055-1
  2. Argandona, V. H., San-Martin, A, Rovirosa, J. Halogenated sesquiterpenes pacifenol and pacifenol derivatives on the aphid Schizaphis graminum. Phytochemistry 32(5), 1159-1161 (1993) https://doi.org/10.1016/S0031-9422(00)95083-0
  3. Bouaicha, N., Tringali, C, Pesando, D., Mallea, M., Roussakis, C, Verbist, J. F. Bioactive diterpenoids isolated from Dilophus ligulatus. Planta Med. 59(3), 256-258 (1993) https://doi.org/10.1055/s-2006-959663
  4. D'Auria, M. V., Minael, L., Riccio, R., Uriarte, E. Dehy droophioxanthin, a new acetylenic carotenoid sulfate from the ophiuroid Ophiocomina nigra. J. Nat. Prod. 54(2), 606-608 (1991) https://doi.org/10.1021/np50074a044
  5. D' Auria, M. V., Gomez-Paloma, L., Minale, L., Riccio, R, Zampella, A On the composition of sulfated polyhydroxysteroids in some ophiuroids and the structure determination of six new constituents. J Nat. Prod. 58(2), 189-196 (1995) https://doi.org/10.1021/np50116a005
  6. De Rosa, S., De Stefano, S., Zavodnik, N. Chemical studies of North Adriatic seaweeds. Part 2. Hydroazulenoid diterpenes from the brown alga Dictyota dichotoma var. implexa. Phytochemistry 25(9), 2179-2181 (1986) https://doi.org/10.1016/0031-9422(86)80086-3
  7. Fedorov, S. N., Levina, E. V., Kalinovsky, A I., Dmitrenok, P S., Stonik, V. A Sulfated steroids from Pacific brittle stars Ophiopholis aculeata, Ophiura sarsi, and Stegophiura brachiactis. J. Nat. Prod. 57(12),1631-1637 (1994) https://doi.org/10.1021/np50114a004
  8. Finer, J., Clardy, J, Fenical, W, Minale, L., Riccio, R, Battaile, J., Kirkup, M., Moore, R E. Structures of dictyodia1 and dictyolactone, unusual marine diterpenoids. J Org. Chem. 44(12), 2044-2047 (1979) https://doi.org/10.1021/jo01326a040
  9. Hickman, C P, Roberts, C. S., Hickman, F. M. Integrated Principles of Zoology. $7^{th}$ edition. Times MirrorlMosby College Publishing, U. S. A, pp. 476(1984)
  10. Ivanchina, N. V., Kicha, A A, Kalinovsky, A I., Dmitrenok, P S., Stonik, V. A Hemolytic steroid disulfates from the Far Eastern starfish Pteraster pulvillus. J. Nat, Prod. 66(2), 298301 (2003) https://doi.org/10.1021/np010650w
  11. Jongaramruong, J, Blackman, A J, Skelton, B. W, White, A H. Chemical relationships between the sea hare Aplysia parvula and the red seaweed Laurencia filifonnis from Tasmania. Aust. J. Chem. 55(4), 275-280 (2002) https://doi.org/10.1071/CH01171
  12. Kapustina, I. I., Ponomarenko, L. P, Moiseenko, O. P, Stonik, V. A Free and sulfated sterols of two far-east Leptasterias starfish. Chem. Nat. Compo 37(6), 515-519 (2001) https://doi.org/10.1023/A:1014856530108
  13. Kimura, J, Kamada, N., Tsujimoto, Y. Fourteen charnigrane derivatives from a red alga, Laurencia nidifica. Bull. Chern. Soc. Jpn. 72(2), 289-292 (1999) https://doi.org/10.1246/bcsj.72.289
  14. Koenig, G. M., Wright, A D., Sticher, O., Angerhofer, C K., Pezzuto, J. M. Biological activities of selected marine natural products. Planta Med. 60(6), 532-537 (1994) https://doi.org/10.1055/s-2006-959565
  15. Lee, S., Williams, G. A, Brown, G. D. Tribenzylbutyrolactones and dibenzyldiphenyl-4,5,6,7-tetrahydrobenzofuranones from Kyrtuthrix maatlans. J. Nat. Prod. 61(1), 29-33 (1998) https://doi.org/10.1021/np970322p
  16. Liu, S., Sjoevall, J., Griffiths, W. J. Neurosteroids in rat brain: extraction, isolation, and analysis by nanoscale liquid chromatography-electrospray mass spectrometry. Anal. Chem. 75(21), 5835-5846 (2003) https://doi.org/10.1021/ac0346297
  17. Maier, M. S., Araya, E., Seldes, A M. Sulfated polyhy droxysteroids from the antarctic ophiuroid Gorgonocephalus chilensis. Molecules (Electronic Publication) 5(3), 348-349 (2000)
  18. McPhail, K. L., Davies-Coleman, M. T., Copley, ReB., Eggleston, D. S. New halogenated sesquiterpenes from South African specimens of the circumtropical sea hare Aplysia dactylomela, J. Nat. Prod. 62(12), 1618-1623 (1999) https://doi.org/10.1021/np990229w
  19. Midland, S. L., Wing, R M., Sims, J. J. New crenulides from the sea hare, Aplysia vaccaria. J. Org. Chon. 48(11), 1906-1909 (1983) https://doi.org/10.1021/jo00159a026
  20. Minale, L. Riccio, R Constituents of the digestive gland of the molluscs of the genus Aplysia. 1. Novel diterpenes from Aplysia depilans. Tetrahedron Lett. 31, 2711-2714 (1976)
  21. Minale, L., Riccio, R, Zollo, F. Structural studies on chemical constituents of echinoderms. Stud. Nat. Prod. Chem. 15, 43110 (1995) https://doi.org/10.1016/S1572-5995(06)80130-4
  22. Riccio, R, D'Auria, M. V., Minale, L. Unusual sulfated marine steroids from the ophiuroid Ophioderma longicaudum. Tetrahedron 41(24), 6041-6046 (1985) https://doi.org/10.1016/S0040-4020(01)91445-0
  23. Roccatagliata, A. J., Maier, M. S., Seldes, A. M., Pujol, C. A., Damonte, E. B. Antiviral sulfated steroids from the ophiuroid Ophioplocus januarii. J. Nat. Prod. 59(9), 887-889 (1996) https://doi.org/10.1021/np960171a
  24. Ryu, G., Park, S. H., Choi, B. W., Lee, N. H., Hwang, H. J., Ryu, S. Y, Lee, B. H. Cytotoxic actlVlt1es of brominated sesquiterpenes from the red alga Laurencia okamurae. Nat. Prod. Sci. 8(3), 103-107 (2002)
  25. Strott, C. A., Higashi, Y Cholesterol sulfate in human physiology: What's it all about? J. Lipid Res. 44(7), 1268-1278 (2003) https://doi.org/10.1194/jlr.R300005-JLR200
  26. Suzuki, M., Kurosawa, E., Furusaki, A. Constituents of marine plants. 73. The structure and absolute stereochemistry of a halogenated chamigrene derivative from the red alga Laurencia species. Bull. Chem. Soc. Jpn. 61(9), 3371-3373 (1988) https://doi.org/10.1246/bcsj.61.3371
  27. Vairappan, C. S., Suzuki, M., Abe, T., Masuda, M. Halogenated metabolites with antibacterial activity from the Okinawan Laurencia species. Phytochemistry, 58(3), 517-523 (2001) https://doi.org/10.1016/S0031-9422(01)00260-6