Browse > Article

Bioactive Metabolites from the Brittle Star Ophioplocus japonicus  

Wang, Wei-Hong (College of Pharmacy, Pusan National University)
Hong, Jong-Ki (Basic Science Institute)
Lee, Chong-Ok (Korea Research Institute of Chemical Technology)
Cho, Hee-Young (Korea Research Institute of Chemical Technology)
Shin, Sook (Sahmyook University)
Jung, Jee-H. (College of Pharmacy, Pusan National University)
Publication Information
Natural Product Sciences / v.10, no.6, 2004 , pp. 253-261 More about this Journal
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
brittle star; Ophioplocus japonicus; cytotoxicity; antibacterial activity;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By SCOPUS : 3
연도 인용수 순위
1 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)   DOI   PUBMED   ScienceOn
2 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)   DOI   ScienceOn
3 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)   DOI
4 Riccio, R, D'Auria, M. V., Minale, L. Unusual sulfated marine steroids from the ophiuroid Ophioderma longicaudum. Tetrahedron 41(24), 6041-6046 (1985)   DOI   ScienceOn
5 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)   DOI   ScienceOn
6 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)   DOI   ScienceOn
7 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)   DOI   ScienceOn
8 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)
9 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)   DOI   ScienceOn
10 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)   DOI   ScienceOn
11 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)   DOI   ScienceOn
12 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)   DOI   ScienceOn
13 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)   DOI   ScienceOn
14 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)   DOI   ScienceOn
15 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)   DOI
16 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)
17 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)   DOI   ScienceOn
18 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)
19 Strott, C. A., Higashi, Y Cholesterol sulfate in human physiology: What's it all about? J. Lipid Res. 44(7), 1268-1278 (2003)   DOI   ScienceOn
20 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)   DOI   ScienceOn
21 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)   DOI   ScienceOn
22 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)   DOI
23 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)   DOI   ScienceOn
24 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)   DOI
25 Kimura, J, Kamada, N., Tsujimoto, Y. Fourteen charnigrane derivatives from a red alga, Laurencia nidifica. Bull. Chern. Soc. Jpn. 72(2), 289-292 (1999)   DOI   ScienceOn
26 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)
27 Minale, L., Riccio, R, Zollo, F. Structural studies on chemical constituents of echinoderms. Stud. Nat. Prod. Chem. 15, 43110 (1995)   DOI