Chemical defenses of tunicates of the genus Aplidium from the Weddell Sea (Antarctica)

Polar Biology

Volumn 33, Issue 10, 2010, Pages 1319-1329

  Nunez Pons L ^a   Forestieri, R ^b   Nieto, R M ^c   Varela, M ^d,e   Nappo, M ^a,b   Rodriguez J ^c   Jimenez C ^c   Castelluccio, F ^b   Carbone, M ^b   Ramos Espla, A ^d   Gavagnin, M ^b   Avila, C ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b CNR Consiglio Nazionale delle Ricerche   (Italy)

^c UNIVERSITY OF A CORUÑA   (Spain)

^d UNIVERSITY OF ALICANTE   (Spain)

^e UNIVERSITY OF VIGO   (Spain)

Author keywords

Antarctic tunicates; Aplidium species; Chemical defense; Deterrent activity; Indole alkaloids; Odontaster validus

Indexed keywords

ALKALOID; BENTHOS; BIOACTIVITY; CHEMICAL COMPOUND; CHEMICAL DEFENSE; OMNIVORY; VERTEBRATE;

SOUTHERN OCEAN; WEDDELL SEA;

ANIMALIA; APLIDIUM; APLIDIUM MERIDIANUM; ASCIDIA; ASCIDIACEA; ASTEROIDEA; ODONTASTER VALIDUS; UROCHORDATA;

EID: 77956549597     PISSN: 07224060     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00300-010-0819-7     Document Type: Article

References (78)

1. Aiello A, Borrelli F, Capasso R, Fattorusso E, Luciano P, Menna M (2003) Conicamin, a novel histamine antagonist from the Mediterranean tunicate Aplidium conicum. Bioorg Med Chem Lett 13: 4481-4483.
2. Amsler CD, McClintock JB, Baker BJ (2000) Chemical defences of Antarctic marine organisms: a reevaluation of the latitudinal hypothesis. In: Davidson W, Howard-Williams C, Broady P (eds) Antarctic ecosystems: models for wider ecological understanding, Proceedings of the Seventh SCAR International Biology Symposium. NZ Natural Sciences, Christchurch, pp 158-164.
3. Arabshahi L, Schmitz FJ (1988) Thiazole and imidazole metabolites from the ascidian Aplidium pliciferum. Tetrahedron Lett 29: 1099-1102.
4. Arntz WE, Thatje S, Gerdes D, Gili JM, Gutt J, Jacob U, Montiel A, Orejas C, Teixido N (2005) The Antarctic-Magellan connection: macrobenthos ecology on the shelf and upper slope, a progress report. Sci Mar 69(Supl 2): 237-269.
5. Arntz WE, Thatje S, Linse K, Avila C, Ballesteros M, Barnes DKA, Cope T, Cristobo FJ, De Broyer C, Gutt J, Isla E, Lopez-Gonzalez P, Montiel A, Munilla T, Espla AAR, Raupach M, Rauschert M, Rodriguez E, Teixido N (2006) Missing link in the Southern Ocean: sampling the marine benthic fauna of remote Bouvet Island. Polar Biol 29: 83-96.
6. Avila C (2006) Molluscan natural products as biological models: chemical ecology, histology and laboratory culture. In: Muller WEG (ed) Progress in molecular and subcellular biology. Subseries marine molecular biotechnology. Springer, Berlin-Heidelberg, pp 1-23.
7. Avila C, Iken K, Fontana A, Gimino G (2000) Chemical ecology of the Antarctic nudibranch Bathydoris hodgsoni Eliot, 1907: defensive role and origin of its natural products. J Exp Biol Ecol 252: 27-44.
8. Avila C, Taboada S, Núñez-Pons L (2008) Marine Antarctic chemical ecology: what is next? Mar Ecol 29: 1-70.
9. Baker BJ, Kopitzke RW, Hamann M, McClintock JB (1993) Chemical ecology of Antarctic marine invertebrates in McMurdo Sound, Antarctica: chemical aspects. Antarct J US 28: 132-133.
10. Bakus GJ, Targett NM, Schulte B (1986) Chemical ecology of marine organisms: an overview. J Chem Ecol 12: 951-987.
11. Becerro MA, Turon X, Uriz MJ (1997) Multiple functions for secondary metabolites in encrusting marine invertebrates. J Chem Ecol 23: 1527-1547.
12. Blunt JW, Copp BR, Hu WP, Munro MH, Northcote PT, Prinsep MR (2009) Marine natural products. Nat Prod Rep 26: 170-244.
13. Carliste DB (1968) Vanadium and other metals in ascidians. Proc R Soc London Ser B 171: 31-42.
14. Carroll AR, Bowden BF, Coll JC (1993) Studies of Australian ascidians II. Novel cytotoxic iodotyrosine-based alkaloids from colonial ascidians, Aplidium sp. Aust J Chem 46: 825-832.
15. Chanas B, Pawlik JR (1995) Defenses of Caribbean sponges against predatory reef fish: II. Spicules, tissue toughness, and nutritional quality. Mar Ecol Prog Ser 127: 195-211.
16. Chanas B, Pawlik JR (1996) Does the skeleton of a sponge provide a defense against predatory reef fish? Oecologia 107: 225-231.
17. Davidson BS (1993) Ascidians: producers of amino acid derived metabolites. Chem Rev 93: 1771-1791.
18. Davis AR, Bremner JB (1999) Potential antifouling natural products from ascidians: a review. In: Fingerman M, Nagabhushanam R, Thompson M-F (eds) Marine biotechnology recent advances in marine biotechnology, Vol III. Biofilms, bioadhesion, corrosion and biofouling. Science Publishers, Enfield, pp 259-308.
19. Davis RA, Carroll AR, Quinn RJ (2002) Lepadins F-H, new cis-decahydroquinoline alkaloids from Australian ascidian Aplidium tabascum. J Nat Prod 65: 454-457.
20. Dayton PK, Robillia GA, Paine RT, Dayton LB (1974) Biological accommodation in benthic community at McMurdo Sound Antarctica. Ecol Monogr 44: 105-128.
21. Dearborn JH (1977) Food and feeding characteristics of Antarctic asteroids and ophiuroids. In: Llano GAE (ed) Adaptations within Antarctic ecosystems. Gulf Publications Co, Houston, pp 293-326.
22. Diyabalanage T, Amsler CD, Mcclintock JB, Baker BJ (2006) Palmerolide A, a cytotoxic macrolide from the Antarctic tunicate Synoicum Adareanum. J Am Chem Soc 128: 5630-5631.
23. Faulkner DJ (2000) Marine pharmacology. Antonie van Leeuwenhoek 77: 135-145.
24. Fenical W (2007) Marine natural products: where we've been and where we're going? 12th International Symposium on Marine Natural Products. Queenstown, New Zealand: Proceedings, 74.
25. Garrido L, Zubía E, Ortega MJ, Salva J (2003) Haouamines A and B: a new class of alkaloids from ascidian Aplidium haouarianum. J Org Chem 68: 293-299.
26. Gili JM, Orejas C, Ros JD, López PJ, Arntz WE (2000) La vida en los fondos antárticos. Invest Cienc 290: 64-74.
27. Gompel M, Leost M, Bal de Kier Joffé E, Puricelli L, Hernández Franco L, Palermo JA, Meijer L (2004) Meridianins, a new family of protein kinase inhibitors isolated from the Ascidian Aplidium meridianum. Bioorg Med Chem Lett 14: 1703-1707.
28. Goodbody L, Gibson J (1974) The biology of Ascidia nigra (Savigny) V. Survival in populations settled at different times of the year. Biol Bull 146: 217-237.
29. Gutt J (2000) Some "driving forces" structuring communities of the sublittoral Antarctic macrobenthos. Antarct Sci 12: 297-313.
30. Gutt J, Starmans A (1998) Structure and biodiversity of megabenthos in the Weddell and Lazarev Seas (Antarctica): ecological role of physical parameters and biological interactions. Polar Biol 20: 229-247.
31. Hernández Franco L, Bal de Kier Joffé E, Puricelli L, Tatián M, Seldes AM, Palermo JA (1998) Indole alkaloids from the Tunicate Aplidium meridianum. J Nat Prod 61: 1130-1132.
32. Iken K, Avila C, Fontana A, Gavagnin M (2002) Chemical ecology and origin of defensive compounds in the Antarctic nudibranch Austrodoris kerguelenensis (Opisthobranchia: Gastropoda). Mar Biol 141: 101-109.
33. Kim J, Pordesimo EO, Toth SI, Schmitz FJ, Vanaltena I (1993) Pantherinine, a cytotoxic aromatic alkaloid, and 7-deazainosine from ascidian Aplidium pantherinum. J Nat Prod 56: 1813-1816.
34. Koplovitz G, McClintock JB, Amsler CD, Baker BJ (2009) Palatability and anti-predatory chemical defenses in a suite of ascidians from the Western Antarctic Peninsula. Aquat Biol 7: 81-92.
35. Lambert G, Lambert CC (1987) Spicule formation in the solitary ascidian, Herdmania momus. J Morphol 192: 145-159.
36. Lebar MD, Heimbegner JL, Baker BJ (2007) Cold-water marine natural products. Nat Prod Rep 24: 774-797.
37. Lindquist N, Hay ME (1996) Palatability and chemical defense of marine invertebrate larvae. Ecol Monogr 66: 431-450.
38. Lindquist N, Hay ME, Fenical W (1992) Defense of ascidians and their conspicuous larvae: adult vs larval chemical defenses. Ecol Monogr 62: 547-568.
39. López-Legentil S, Turón X, Schupp P (2006) Chemical and physical defenses against predators in Cystodytes (Ascidiacea). J Exp Mar Biol Ecol 332: 27-36.
40. McClintock JB (1989) Toxicity of shallow-water Antarctic echinoderms. Polar Biol 9: 461-465.
41. McClintock JB (1994) Trophic biology of Antarctic echinoderms. Mar Ecol Prog Ser 111: 191-202.
42. McClintock JB, Baker BJ (1997) Palatability and chemical defense of eggs, embryos and larvae of shallow-water Antarctic marine invertebrates. Mar Ecol Prog Ser 154: 121-131.
43. McClintock JB, Baker BJ (2001) Marine chemical ecology. CRC Marine Science Series Press, Boca Raton.
44. McClintock JB, Heine J, Slattery M, Weston J (1991) Biochemical and energetic composition, population biology, and chemical defense of the Antarctic ascidian Cnemidocarpa verrucosa Lesson. J Exp Mar Biol Ecol 147: 163-175.
45. McClintock JB, Slattery M, Heine L, Weston J (1992) Chemical ecology of the Antarctic spongivorous seastar Perknaster fuscus. Antarct J US 27: 129-130.
46. McClintock JB, Baker BJ, Slattery M, Hamann M, Kopitzke R, Heine J (1994) Chemotactic tube-foot responses of a spongivorous sea star Perknaster fuscus to organic extracts from Antarctic sponges. J Chem Ecol 20: 859-870.
47. McClintock JB, Amsler MO, Amsler CD, Southworth KJ, Petrie C, Baker BJ (2004) Biochemical composition, energy content and chemical antifeedant and antifoulant defenses of the colonial Antarctic ascidian Distaplia cylindrica. Mar Biol 145: 885-894.
48. Mccoy MC, Faulkner DJ (2001) Uoamines A and B, piperidine alkaloids from the ascidian Aplidium uouo. J Nat Prod 64: 1087-1089.
49. Millar RH (1971) The biology of ascidians. Adv Mar Biol 9: 1-100.
50. Munro MHG, Blunt JW (2009) MarineLit. University of Canterbury.
51. Murray L, Lim TK, Currie G, Capon RJ (1995) Aplidites (A-G): macrocyclic orthonitrites from an Australian tunicate, Aplidium sp. Aust J Chem 48: 1253-1266.
52. Parry DL (1984) Chemical properties of the test ascidians in relation to predation. Mar Ecol Prog Ser 17: 279-282.
53. Paul VJ (1992) Ecological roles of marine natural products. Comstock Publications Association, Ithaca, New York.
54. Paul VJ, Lindquist N, Fenical W (1990) Chemical defenses of the tropical ascidian Atapozoa sp. and its nudibranch predators Nembrotha spp. Mar Ecol Prog Ser 59: 109-118.
55. Paul VJ, Puglisi MP, Ritson-Williams R (2008) Marine chemical ecology. Nat Prod Rep 25: 662-695.
56. Pawlik JR (1993) Marine invertebrate chemical defenses. Chem Rev 93: 1911-1922.
57. Pawlik JR, Chanas RT, Toonen RT, Fenical W (1995) Defenses of Caribean sponges against predatory reef fish. I. Chemical deterrency. Mar Ecol Prog Ser 127: 183-194.
58. Peters KJ, Amsler CD, McClintock JB, van Soest RWM, Baker BJ (2009) Palatability and chemical defenses of sponges from the western Antarctic Peninsula. Mar Ecol Prog Ser 385: 179-187.
59. Pisut DP, Pawlik JR (2002) Anti-predatory chemical defenses of ascidians: secondary metabolites or inorganic acids? J Exp Mar Biol Ecol 270: 203-214.
60. Primo C, Vázquez E (2007) Zoogeography of the Antarctic ascidian fauna in relation to the Sub-Antarctic and South America. Antarct Sci 19: 321-336.
61. Puglisi MP, Paul VJ, Biggs J, Slattery M (2002) Co-occurrence of chemical and structural defenses in the gorgonian corals of Guam. Mar Ecol Prog Ser 239: 105-114.
62. Ramos-Esplá AA, Cárcel JA, Varela M (2005) Zoogeographical relationships of the littoral ascidiofauna around the Antarctic Peninsula, in the Scotia Arc and in the Magellan region. Sci Mar 69(Suppl 2): 215-223.
63. Reyes F, Fernández R, Rodríguez A, Francesch A, Taboada S, Avila C (2008) Aplicyanins A-F, new cytotoxic bromoindole derivates from the marine tunicate Aplydium cyaneum. Tetrahedron 64: 5119-5123.
64. Rhoades DF (1979) Evolution of plant chemical defenses against herbivores. In: Rosenthal GA (ed) Herbivores: their interaction with secondary plant metabolites. Academic Press, Orlando, pp 4-55.
65. Sahade R, Demarchi M, Chiappero M, Tatian M, Gardenal N (2003) Genetic differentiation between populations of the ascidian Aplidium falklandicum from South Georgia and South Orkney Islands. In: Thatje S, Calcagno J, Arntz W (eds) Interactions between Magellan region and the Antarctic-Antarctic benthic deep-sea biodiversity. Extended Abstracts of the IBMANT/ANDEEP International Symposium and Workshop, pp 95-96.
66. Seldes AM, Rodríguez Brasco MF, Hernández Franco L, Palermo JA (2007) Identification of two meridianins from the crude extract of the tunicate Aplidium meridianun by tandem mass spectometry. Nat Prod Res 21: 555-563.
67. Sokal RR, Rohlf FJ (1995) Biometry: the principles and practice of stadistics in biological research. Freeman WH and Co, New York.
68. Stoecker D (1980a) Chemical defenses of ascidians against predators. Ecology 61: 1327-1334.
69. Stoecker D (1980b) Relationships between chemical defense an ecology in benthic ascidians. Mar Ecol Prog Ser 3: 257-265.
70. Taboada S, García-Fernández LF, Bueno S, Vazquez J, Cuevas C Avila C (2010) Antitumoral activity in Antarctic and Sub-Antarctic benthic organisms. Antarct Sci (Accepted).
71. Tarjuelo I, López-Legentil S, Codina M, Turón X (2002) Defense mechanisms of adults and larvae of marine invertebrates: patterns of toxicity and palatability in colonial ascidians. Mar Ecol Prog Ser 235: 103-115.
72. Tatián M (1999) Diversidad, variabilidad y alimentación de ascidias (Tunicata, Ascidiacea) de la Isla 25 de Mayo. Dissertation. Universidad de Córdoba, Argentina.
73. Tatián M, Sahade RJ, Doucet ME, Esnal GB (1998) Ascidians (Tunicata, Ascidiacea) of Potter Cove South Shetland Islands, Antarctica. Antarct Sci 10: 147-152.
74. Tatián M, Antacli JC, Sahade RJ (2005) Ascidians (Tunicata, Ascidiacea): species distribution along the Scotia Arc. Sci Mar 69(Suppl 2): 205-214.
75. Varela M (2007) Contribución al conocimiento de las ascidias coloniales (Chordata: Tunicata) de la Antártida Occidental y Región Magallánica. Dissertation. Universitat d'Alacant, Spain.
76. Vervoort HC, Pawlik JR, Fenical W (1998) Chemical defense of the Caribean ascidian Didemnum conchyliatum. Mar Ecol Prog Ser 164: 221-228.
77. Young CM, Bingham BL (1987) Chemical defense and aposematic coloration in larvae of the ascidian Ecteinascidia turbinata. Mar Biol 96: 539-544.
78. Zubía E, Ortega MJ, Salvá J (2005) Natural products chemistry in marine ascidians of the genus Aplidium. Mini-Rev Org Chem 2: 389-399.