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Studies on Marine Natural Antifoulant Laurinterol  

유건식 (한밭대학교 환경개선형신소재개발센터)
윤오섭 (한밭대학교 환경공학과)
Publication Information
Journal of Environmental Health Sciences / v.29, no.3, 2003 , pp. 1-8 More about this Journal
Abstract
The development of environmentally nontoxic or non-polluting antifouling additives that can be formulated in practical coating requires assay involving target organisms. Described here are the simple laboratory assays that have been developed using the barnacle, Balanus amphitrite, a common fouling organism found throughout temperate and tropical seas. One of the assays depends on synchronous year-round mass culture, the procedure for which is described, of nauplii larvae and cyprids larvae. The laboratory assays provided quantitative estimates of toxicity and settlement inhibition of the test compounds. Laurinterol (1), isolaurinterol (2), alpysinal (3), and aplysin (4) have been isolated from the Korean red alga Laurencia okamurae. Their structures were identified by spectral data in comparison with the literature data. Compounds 1-4 inhibited larval settlement of the barnacle B. amphitrite with EC$_{50}$ values of 0.18- 36 $\mu\textrm{g}$/ml. Com-pounds 2-4 showed larval toxicity against nauplii of the barnacle B. amphitrite with 5-10 $\mu\textrm{g}$/ml, while laurinterol (1) exhibited no toxicity at even 100 $\mu\textrm{g}$/ml. Therefore, laurinterol was expected as a promising natural antifoulant.t.
Keywords
Antifoulant; Larval toxicity; Settlement inhibition; Laurencia okamurae; Laurinterol;
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1 Clare, A. S. : Marine natural product antifoulant: status and potential. Biofouling 10, 141-159, 1996   DOI   ScienceOn
2 Fusetani, N., Hirota, H., Okino, T., Tomono, Y. and Yoshimura, E. : Antifouling activity of isocyanoterpenoids and related compounds isolated from a marine sponge and nudibranchs. J. Nat. Toxins, 5, 249-259. 1996
3 Tsukamoto, S., Kato, H., Hirota, H. and Fusetani, N. : Seven new polyacetylene derivatives, showing both potent metamorphosis-inducing activity in ascidian larvae and antifouling activity against barnacle, from the marine sponge Callyspongia truncata. J. Nat. Prod., 60, 126-130, 1997   DOI   ScienceOn
4 lrie, T., Suzuki, M., Kurosawa, E. and Masamune, T.: Constituents from marine plants. XVI. Laurinterol, debromolaurinterol, and isolaurinterol, constituents of Laurencia saitoi, Phytochem., 47, 3271- 3277. 1970
5 Otha, K. and Tagaki, M.: Halogenated sesquiterpenes from the marine rd alga Marginisporum aberrans, Phytochem., 16, 1062-1063, 1977   DOI   ScienceOn
6 Bax, A., Azolos, A., Dinya, Z. and Sudo, K. : Structure elucidation of the antibiotic desertomycin through the use of new two-dimensional NMR tecniques. J. Am. Chem. Soc., 108, 8056-8053, 1986   DOI
7 Rittschof, D., Clare, A. S., Gerhart, D. J., Mary, S. A. and Bonaventura, J. : Barnacle in vitro assays for biologically active substances: toxicity and settlement inhibition assays using mass cultured Balnus amphitrite amphirite darwin, Biofouling, 6, 115-122, 1992   DOI   ScienceOn
8 Alberte, R. S., Snyder, S., Zahuranec. B. J. and Whetstone, M. Biofouling research needs for United States Navy: program history and goals. Biofouling 6, 91-95, 1992   DOI   ScienceOn
9 Winkler, L. R., Tilton, B. E. and Hardinge, M. G. : A choligernic agent extracted from sea hares. Arch. Intern. Pharmacodyn., 137, 76-83, 1962
10 Irie, T., Suzuki, M., Kurosawa, E. and Masamune, T. : Laurinterol and debromolaurinterol, constituents from Laurencia intermedia, Tetrahedron Lett., 17, 1837-1840, 1966
11 Vairappan, C. S., SuzukiAbe, T. and Masuda, M.: Halogenated metabolites with antibacterial activity from the Okinawa Laurencia species. Phytochemistry,58, 517-523, 2001   DOI   ScienceOn
12 Tsukamoto, S., Kato, H., Hirota, H. and Fusetani, N. : Mauritiamine, a new antifouling oroidin dimer from the marine sponge Agelas mauritiana. J. Nat. Prod., 59, 501-503, 1996   DOI   ScienceOn
13 Bodenhausen, G., Kogeler, H. and Ernst, R. R.: Selection of coherence transfer pathway in NMR pulse experiments. J. Magn. Reson., 58, 370-388, 1984
14 Rittschof, D., Kaki, J., Mitchell, R. and Costlow, J. D. : lon and neuropharmacological studies of barnacle settlement. Neth. J. Sea Res., 20, 269-275, 1986   DOI   ScienceOn
15 Tsukamoto, S., Kato, H., Hirota, H. and Fusetani, N. : Pseudoceratide: a new antifouling spermidine derivative from the marine sponge Pseudoceratina purpurea. Tetrahedron Lett., 37, 1439-1440, 1996   DOI   ScienceOn
16 Mizobuchi, S., Adachi, K. and Miki, W. : Antifouling polyhydroxysterols isolated from a Palauan octocoral of Sinularia sp. Fish Sci(Tokyo), 62, 98-100, 1996   DOI
17 Kon-ya, K. and Miki, W. : Effects of environmental factors on larval settlement of the barnacle Balanus amphitrite reared in the laboratory. Fish Sci(Tokyo), 60, 563-565, 1994   DOI
18 Kawamata, M., Kon-ya, K. and Miki, W. : Trigonelline, an antifouling substance isolted from an octocoral Dendronephthya sp. Fish Sci(Tokyo), 60, 485-486, 1994   DOI
19 Harrowven, D. C., Lucas, M. C. and Howes, P. D. : The synthesis of a natural product family: from debromoisolaurenterol to the aplysins. Tetrahedron, 57, 791-804, 2001   DOI   ScienceOn
20 Keifer, P. A., Rinehart, L. K. Jr. and Hooper, I. P.: Renillafoulins, antifouling diterpenes from the sea pansy Renilla reniformis (Octocorallia). J. Org Chem. , 51, 4450-4454, 1986   DOI