Antifouling terpenes and steroids against barnacle larvae from marine sponges

Biofouling

Volumn 11, Issue 4, 1997, Pages 283-291

  Tsukamoto, Sachiko ^a,b   Kato, Haruko ^a   Hirota, Hiroshi ^a   Fusetani, Nobuhiro ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Antifoulants; Barnacle; Marine sponge; Myrmekioderma dendyi; Smenospongia sp.; Topsentia sp.

Indexed keywords

ANTIFOULING SUBSTANCES; BARNACLE LARVAE; SPONGES;

BALANUS AMPHITRITE; CIRRIPEDIA; MYREMKIODERMA DENDYI; PORIFERA; SMENOSPONGIA; TOPSENTIA;

EID: 0031408375     PISSN: 08927014     EISSN: None     Source Type: Journal    
DOI: 10.1080/08927019709378337     Document Type: Article

References (33)

1. Abarzua S, Jakubowski S (1995) Biotechnological investigation for the prevention of biofouling. I. Biological and biochemical principles for the prevention of biofouling. Mar Ecol Prog Ser 123. 301-312
2. Alzieu Cl, Sanjuan J, Michel P, Borel M, Dreno J P (1989) Monitoring and assessment of butyltins in Atlantic coastal waters. Mar Pollut Bull 20: 22-26
3. Cambie R C, Craw P A, Berquist P R, Karuso P (1988) Chemistry of sponges, III. Manoalide monoacetate and thorectolide monoacetate, two new sesterterpenoids from Thorectandra excavatus. J Nat Prod 51: 331-334
4. Clare A S (1996) Marine natural product antifoulants: status and potential. Biofouling 9: 211-229
5. Clare A S, Rittschof D, Gerhart D J, Maki J S (1992) Molecular approaches to nontoxic anti-fouling Invertebr Reprod Dev 22: 67-76
6. Davis A R, Butler A J, van Altena I (1991) Settlement behavior of ascidian larvae: preliminary evidence for inhibition by sponge allelochemicals. Mar Ecol Prog Ser 72: 117-123
7. de Silva E D, Scheuer P J (1980) Manoalide, an antibiotic sesquiterpenoid from the marine sponge Luffariella variabiiis (Polejaeff) Tetrahedron Lett 21. 1611-1614
8. de Silva E D, Scheuer P J (1981) Three new sesterterpenoid antibiotics from the marine sponge Luffanella variabilis (Polejaeff). Tetrahedron Lett 22: 3147-3150
9. Ellis D V (1991) New dangerous chemicals in the environment: lessons from TBT. Mar Pollut Bull 22: 8-10
10. Fusetani N, Sugano M, Matsunaga S, Hashimoto K (1987) (+)-Curcuphenol and dehydrocurcuphenol, novel sesquiterpenes which inhibit H.K-ATPase, from a marine sponge Epipolasis sp. Experientia 43: 1234-1235
11. Fusetani N, Hirota H, Okino T, Toniono Y, Yoshimura E (1996) Antifouling activity of isocyanoterpenoids and related compounds isolated from a marine sponge and nudibranchs. J Nat Toxins 5: 249-259
12. Gerhart D J, Rittschof D, Mayo S W (1988) Chemical ecology and the search for marine antifoulants. J Chem Ecol 14: 1905-1917
13. Hirota H, Tomono Y, Fusetani N (1996) Terpenoids with antifouling activity against barnacle larvae from the marine sponge Acanthella cavernosa Tetrahedron 52: 2359-2368
14. Jacobs R S, Culver P, Langdon R, O'Brien T, White S (1985) Some pharmacological observations on marine natural products. Tetrahedron 41: 981-984
15. Keifer P A, Rinehart K, L Jr, Hooper I R (1986) Renillafoulins, antifouling diterpenes from the sea pansy Renilia reniformis (Ocxtocorallia). J Org Chem 51: 4450-4454
16. Keifer P A, Schwartz R E, Koker M E S, Hughes R G Jr, Rittchof D, Rinehart K L (1991) Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera. J Org Chem 56: 2965-2975
17. Kon-ya K, Shimidzu N, Adachi K, Miki W (1994) 2,5,6-Tribromo-1-methylgramine, an anti-fouling substances from the marine bryozoan Zoobotryon pellucudum. Fish Sci 60: 773-775
18. McEnroe F J, Fenical W (1978) Structures and synthesis of some new antibacterial sesquiterpenoids from the gorgonian coral Pseudopterogorgia rigida. Tetrahedron 34: 1661-1664
19. Nakagawa M, Ishihara M, Hamamoto Y, Endo M (1986) Aldose reductase inhibitor from Palauan sponges. Symposium Papers, 28th Symp Chem Nat Prod. Sendai 200-207
20. Okino T, Yoshimura E, Hirota H, Fusetani N (1995) Antifouling kalihinenes from the marine sponge Acanthella cavernosa. Tetrahedron Lett 36: 8637-8640
21. Okino T, Yoshimura E, Hirota H, Fusetani N (1996a) New antifouling sesquiterpenes from four nudibranchs of the family Phyllidiidae. Tetrahedron 52: 9447-9454
22. Okino T, Yoshimura E, Hirota H, Fusetani N (1996b) New antifouling kalihipyrans from the marine sponge Acanthella cavernosa. J Nat Prod 59: 1081-1083
23. Paul V J (1992) Chemical defenses of benthic marine invertebrates. In: Paul V J (ed) Ecological Roles of Marine Natural Products. Comstock Publishing Associates, Ithaca, pp 164-188
24. Potts B C M, Capon R J, Faulkner D J (1992) Luffalactone and (4E,6E)-dehydromanoalide from the sponge Luffariella variabiiis. J Org Chem 57: 2965-2967
25. Shimidzu N, Katsuoka M, Mizobuchi S, Ina K, Miki W (1993) Isolation of (-)-3-bisabolene as a repellent substance against blue mussel from an octocoral Sinularia sp. Nippon Suisan Gakkaishi 59: 1951
26. Tsukamoto S, Kato H, Hirota H, Fusetani N (1996a) Mauritiamine, a new antifouling oroidin dimer from the marine sponge Agelas mauritiana. J Nat Prod 59: 501-503
27. Tsukamoto S, Kato H, Hirota H, Fusetani N (1996b) Pseudoceratidine: a new antifouling spermidine derivative from the marine sponge Pseudoceratina purpurea. Tetrahedron Lett 37: 1439-1440
28. Tsukamoto S, Kato H, Hirota H, Fusetani N (1996c) Ceratinamine: an unprecedented anti-fouling cyanoformamide from the marine sponge Pseudoceratina purpurea. J Org Chem 61: 2936-2937
29. Tsukarnoto S, Kato H, Hirota H, Fusetani N (1996d) Ceratinamides A and B: new antifoulmg dibromotyrosine derivatives from the marine sponge Pseudoceratina purpurea Tetrahedron 52: 8181-8186
30. Tsukarnoto S, Kato H, Hirota H, Fusetani N (1997a) Seven new polyacetylene derivatives, which show both potent metamorphosis-inducing activity in ascidian larvae and antifouling activity against barnacle larvae, from the marine sponge Callyspongia truncata. J Nat Prod 60: 126-130
31. Tsukamoto S, Kato H, Hirota H, Fusetani N (1997b) Isolation of an unusual 2-aminoimidazolium salt of steroid trisulfate from a marine sponge Topsentia sp. Fish Sci 63: 310-312
32. Wahl M (1989) Marine epibiosis. I. Fouling and antifouling: some basis aspects. Mar Ecol Prog Ser 58: 175-189
33. Wright A E, Pompom S A, McConnell O J, Kohmoto S, McCarthy P J (1987) (+)-Curcuphenol and (+)-curcudiol, sesquiterpene phenols from shallow and deep water collections of the marine sponge Didiscus flavus. J Nat Prod 50: 976-978