Chemical and pharmacological characterization of halitoxin from Amphimedon viridis (porifera) from the southeastern Brazilian coast

Comparative Biochemistry and Physiology - C Pharmacology Toxicology and Endocrinology

Volumn 115, Issue 2, 1996, Pages 155-163

  Berlinck, Roberto G S ^a   Ogawa, Cláudia A ^a   Almeida, Adaíla M P ^a   Sanchez, Marco Aurélio A ^a   Malpezzi, Elena L A ^a   Costa, Letícia V ^a   Hajdu, Eduardo ^a   De Freitas, J C ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

alkylpyridine alkaloid; Amphimedon viridis; chemotaxonomy; cytotoxicity; halitoxin; Haplosclerida; hemolytic activity; marin sponge; marine pharmacology; neurotoxicity

Indexed keywords

ALKALOID; NEUROTOXIN; TOXIN;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BRAZIL; CYTOTOXICITY; HEMOLYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MITOSIS; MOUSE; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; SPONGE; TOXIN ANALYSIS;

ACTION POTENTIALS; ANIMALS; BRACHYURA; BRAZIL; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, ION EXCHANGE; DOSE-RESPONSE RELATIONSHIP, DRUG; HEMOLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; NEUROMUSCULAR DEPOLARIZING AGENTS; OVUM; PORIFERA; PYRIDINIUM COMPOUNDS; SEA URCHINS;

EID: 0030267231     PISSN: 07428413     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0742-8413(96)00107-7     Document Type: Article

References (48)

1. 1. Albrizio, S.; Ciminiello, P.; Fattorusso, E.; Magno, S.; Pawlik, J.R. Amphitoxin, a new high molecular weight anti-feedant pyridinium salt from the Caribbean sponge Amphimedon compressa. J. Nat. Prod. 58:647-652;1995.
2. 2. Baslow, M.H. Marine Pharmacology. Baltimore: The Williams & Wilkins Company; 1969:86-99.
3. 3. Baslow, M.H.; Read, G.W. Hypotensive and other pharmacological actions of agents from the sponges Toxadocia violacea, Haliclona viridis and Haliclona magnicanulosa. Proc. West. Pharmacol. Soc. 11:117-120; 1968.
4. 4. Baslow, M.H.; Turlapaty, P. In vivo antitumor activity and other pharmacological properties of halitoxin obtained from the sponge Haliclona viridis. Proc. West. Pharmacol. Soc. 12: 6;1969.
5. 5. Carballeira, N.M.; Shalabi, F. Unusual lipids in the Caribbean sponges Amphimedon viridis and Desmapsamma anchorata. J. Nat. Prod. 57:1152-1159;1994.
6. 6. Carballeira, N.; Negrón, V.; Reyes, E.D. Novel monounsaturated fatty acids from the sponges Amphimedon compressa and Mycale laevis. J. Nat. Prod. 55:333-339;1994.
7. 7. Carrol, A.R.; Scheuer, P.J. Four beta-alkylpyridines from a sponge. Tetrahedron. 46:6637-6644; 1990.
8. 8. Davies-Coleman, M.T.; Faulkner, D.J.; Dubowchik, G.M.; Roth, G.P.; Poison, C.; Fairchild, C. A new EGF-active polymeric pyridinium alkaloid from the sponge Callyspongia fibrosa. J. Org. Chem. 58:5925-5930;1993.
9. 9. Echavarren, A.M.; Stille, J.K. Total synthesis of amphimedine. J. Am. Chem. Soc, 110:4051-4053;1988.
10. 10. Faulkner, D.J. Marine natural products. Nat. Prod. Rep. 12: 223-269;1995.
11. 11. Freitas, J.C.; Sato, S.; Ogata, T.; Kodama, M. Guanidine neurotoxins are released with the digestive fluid of crabs (Crustacea, Brachyura). Toxicon 33:201-208;1995.
12. 12. Fusetani, N.; Asai, N.; Matsunaga, S.; Honda, K.; Yasumuro, K. Cyclostelletamines A-F, pyridine alkaloids which inhibit binding of methyl quinuclidinyl benzilate (QNB) to muscarinic acetylcholine receptors, from the marine sponge, Stelleta maxima. Tetrahedron Lett. 35:3967-3970; 1994.
13. 13. Gil, L.; Gateau-Olesker, A.; Wong, Y.-S.; Chernatova, L.; Marazano, C.; Das, B.C. Synthesis of macrocyclic or linear pyridinium oligomers from 3-substituted pyridines. Model synthetic studies toward macrocyclic marine alkaloids. Tetrahedron Lett. 36:2059-2062;1995.
14. 14. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G.; Siddiqui, M.A.; Snieckus, V. Combined metalation-palladium-catalyzed cross coupling strategies. A formal synthesis of the marine alkaloid amphimedine. J. Org. Chem, 60:292-296; 1995.
15. 15. Hajdu, E.; de Weerdt, W.H.; van Soest, R.W.M. Affinities of the "Mermaid's Glove" sponge lsodictya palmata with a discuss ion on the synapomorphic value of chelae microscleres. In: van Soest, R.W.M.; van Kemper, T.M.G., Braekman, J.C., eds. Sponges in time and space. Proc. IV Int. Porifera Congr. Balkema, Rotterdam; 1994:141-150.
16. 16. Hirsch, S.; Kashman, Y. New glycosphingolipids from marine organisms. Tetrahedron 45:3897-3906;1989.
17. 17. Jakowska, S.; Nigrelli, R.F. Antimicrobial substances from sponges. Ann. N.Y. Acad. Sci. 90:913-916;1960.
18. 18. Kaul, P.N.; Daftari, P. Marine pharmacology: bioactive molecules from the sea. Ann. Rev. Pharmacol. Toxicol, 26:117-142; 1986.
19. 19. Kobayashi, J.; Murayama, T.; Ohizumi, Y.; Sasaki, T.; Ohta, T.; Nozoe, S. Theonelladins A-D, novel antineoplastic pyridine alkaloids from the Okinawan marine sponge Theonella swinhoei. Tetrahedron Lett. 30:4833-4836;1989.
20. 20. Kobayashi, J.; Murayama, T.; Kosuge, S.; Kanda, F.; Ishibashi, M.; Kobayashi, H.; Ohizumi, Y.; Ohta, T.; Nozoe, S.; Sasaki, T. Niphatesines A-D, new antineoplastic pyridine alkaloids from the Okinawan marine sponge Nictates sp. J. Chem. Soc. Perkin Trans. 1:3301-3303;1990.
21. 21. Kobayashi, J.; Zeng, C.; Ishibashi, M.; Shigemori, H.; Sasaki, T.; Mikani, Y. Niphatesines E-H, new pyridine alkaloids from the Okinawan marine sponge Niphates sp. J. Chem. Soc. Perkin Trans. 1:1291-1294;1992.
22. 22. Kobayashi, J.; Tsuda, M.; Kawasaki, N.; Matsumoto, K.; Adachi, T. Keramaphidin B, a novel pentacyclic alkaloid from a marine sponge Amphimedan sp. - A plausible biogenetic precursor of manzamine alkaloids. Tetrahedron Lett. 35:4383-4386;1994.
23. 23. Lad, P.J.; Brown, J.W.; Shier, W.T. Activation of guanylate cyclase and inhibition of adenylate cyclase by cytotoxic preparations from marine sponges of Haliclona genus. Biochem. Biophys. Res. Commun. 85:1472-1479;1978.
24. 24. Malpezzi, E.L.A.; Freitas, J.C.; Muramoto, K.; Kamiya, H. Characterization of peptides in sea anemone venom collected by a novel procedure. Toxicon 31:853-864;1993.
25. 25. Malpezzi, E.L.A.; Davino, S.C.; Costa, L.V.; Freitas, J.C.; Giesbrecht, A.M.; Roque, N.F. Antimitotic action of extracts of Petiveria alliacea on sea urchin egg developments. Braz. J. Med. Biol. Res. 27:749-754;1994.
26. 26. Matsunaga, S.; Shinoda, K.; Fusetani, N. Cribrochalinamine oxides A and B, antifiingal β-substituted pyridines with an azomethine N-oxide from a marine sponge Cribrochalina sp. Tetrahedron Lett. 35:5953-5954:1994.
27. 27. Middlebrook, R.E.; Snyder, C.H.; Mercado, A.R.; Lane, C.E. Partial purification and biological properties of an extract of the green sponge, Haliclona viridis. In: Humm, H.J., Lane, C.E., eds. Bioactive compounds from the sea. New York: Marcel Dekker; 1974:175-182.
28. 28. Muricy, G.; Hajdu, E.; Araujo, F.V.; Hagler, A.N. Antimicrobial activity of southwestern Atlantic shallow-water marine sponges (Porifera). Sci. Mar. 57:427-432;1993.
29. 29. Nigrelli, R.F.; Baslow, M.; Jakowska, S. Further characterization of antimicrobial substances from the Bahamian sponges Haliclona viridis and Tedania ignis. First Interscience Conference on Antimicrobial Agents and Chemotherapy. Amer. Soc. Microbiol. Ann. Arbor: 83-84.
30. 30. Prager, R.H.; Topselas, C. A simple synthesis of amphimedine. Heterocycles 29:847-848;1989.
31. 31. Prager, R.H.; Topselas, C.; Hiesler, T. A simple synthesis of amphimedine. Aust. J. Chem. 44:277;1991.
32. 32. Quiñoá, E.; Crews, P. Niphatynes, methoxylamine pyridines from the marine sponge, Niphates sp. Tetrahedron Lett. 28: 2467-2468;1987.
33. 33. Ruggieri, G.D.; Baslow, M.H.; Jakowska, S.; Nigrelli, R.F. Developmental aberrations in sea-urchin eggs induced by sponge extracts. Amer. Zool. 1:384-385; 1961.
34. 34. Sakemi, S.; Totton, L.E.; Sun, H.H. Xestamines A, B and C, three new long-chain methoxylamine pyridines from the sponge Xestospongia wiedenmayeri. J. Nat. Prod. 53:995-999; 1990.
35. 35. Sarma, A.S.; Daum, T.; Müller, W.E.G. Secondary metabolites from marine sponges, Ullstein Mosby, Berlin; 1993.
36. 36. Schmitz, F.J.; Campbell, D.C.; Hollenbeak, K.; Vanderah, D.J.; Ciereszko, L.S.; Stendler, P.; Eckstrand, J.D.; van der Helm, D.; Kaul, P.; Kulkami, S. Chemistry related to the search for drugs from the sea, In: Faulkner, D.J.; Fenical, W.H., eds. Marine Natural Products Chemistry. Nato Conference Series IV, New York and London: Plenum Press, 1977: 293-310.
37. 37. Schmitz, F.I.; Hollenbeak, K.H.; Campbell, D.C. Marine nat-ural products: halitoxin, toxic complex of several marine sponges of the genus Haliclona. J. Org. Chem., 43:3916-3922; 1978.
38. 13C coupling constants. J. Am. Chem. Soc. 105:4835-4836; 1983.
39. 39. Sevcik, C.; Alvarez-Vasquez F.; Saavedra, J.A.; Cordovez, G. Blockage of resting potassium conductance in frog muscle fibers by a toxin isolated from sponge Holiclona viridis. Toxicon 24:851-860;1986.
40. 40. Sevcik, C.; Garcia-Rodriguez, A.I.; D'Suze, G.; Mijares, A.J. Specific blockage of squid axon resting potassium permeability by Haliclona viridis (Porifera: Haliclonidae) toxin (HvTX). Toxicon 32:773-788; 1994.
41. 41. Sigel, M.M.; Wellham, L.L.; Lichter, W.; Dudeck, L.E.; Gargus, J.L.; Lucas, A.H. Marine Tech. Soc., 281;1970.
42. 42. van Soest, R.W.M. Marine sponges from Curacao and other Caribbean localities. Part 2. Haplosclerida. Stud. Fauna Curaçao Caribb. IsI. 62:1-173;1980.
43. 43. van Soest, R.W.M. Phylogenetic exercises with monophyletic groups of sponges. In: Vacelet, J.; Boury-Esnault, N., eds. Taxonomy of Porifera from the Northeast Atlantic and Mediterranean Sea NATO ASI series G13, Berlin: Springer-Verlag; 1987:227-241.
44. 44. Stierle, D. B.; Faulkner, D.J. Antimicrobial N-methylpyridinium salts related to the xestamines from the Caribbean sponge Calyx podapyta. J. Nat. Prod. 54:1134-1136;1991.
45. 45. Talpir, R.; Rudi, A.; Han, M.; Kashman, Y. Niphatoxin A and B; two new ichtyo-and cytotoxic tripyridine alkaloids from a marine sponge. Tetrahedron Lett. 33:3033-3034; 1992.
46. 46. Tsuda, M.; Kawasaki, N.; Kobayashi, J. Ircinols A and B, first antipodes of manzamine-related alkaloids from an Okinawan marine sponge. Tetrahedron 50:7957-7960; 1994a.
47. 47. Tsuda, M.; Kawasaki, N.; Kobayashi, J. Keramaphidin C and keramamine C, plausible biogenetic precursors of manzamine C from an Okinawan marine sponge. Tetrahedron Lett. 35: 4387-4388; 1994b.
48. 48. Wang, C.M.; Narahashi, T.; Mende, T. Depolarizing action of Holiciona toxin on end-plate and muscle membranes. Toxicon 11:499-504;1973.