Unpalatable compounds in the marine gastropod Dolabella auricularia: Distribution and effect of diet

Journal of Chemical Ecology

Volumn 25, Issue 4, 1999, Pages 735-755

  Pennings, Steven C ^a,d   Paul, Valerie J ^a   Chuck Dunbar, D ^b   Hamann, Mark T ^b   Lumbang, Wilfred A ^a   Novack, Brandie ^a   Jacobs, Robert S ^c  

^a UNIVERSITY OF GUAM   (Guam)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d University of Georgia Marine Institute   (United States)

Author keywords

Anaspidea; Chemical defense; Dehydrocholesterol; Dolabella; Johnstonol; Prepacifinol epoxide; Sea hare; Secondary metabolites; Sequester

Indexed keywords

DIET; FUNCTIONAL ROLE; PALATABILITY; SECONDARY METABOLITE;

ARTICLE; BIOASSAY; CELL FRACTIONATION; DIETARY INTAKE; EXTRACTION; GASTROPOD; MARINE ENVIRONMENT; NONHUMAN; PALATABILITY; PREDATION; SAMPLING; TISSUE DISTRIBUTION;

ALGAE; ANASPIDEA; ANIMALIA; AURICULARIA; DOLABELLA; DOLABELLA AURICULARIA; GASTROPODA; INVERTEBRATA; LEPUS; PISCES;

EID: 0032964553     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1020832414766     Document Type: Article

References (38)

1. AMBROSE, H. W., III, and GIVENS, R. P. 1979. Distastefulness as a defense mechanism in Aplysia brasiliana (Mollusca: Gastropoda). Mar. Behav. Physiol. 6:57-64.
2. AVILA, C. 1995. Natural products of opisthobranch molluscs: A biological review. Oceanogr. Mar. Biol. Annu. Rev. 33:487-559.
3. BOBZIN, S. C., and FAULKNER, J. D. 1992. Chemistry and chemical ecology of the Bahamian sponge Aplysilla glacialis. J. Chem. Ecol. 18:309-332.
4. CAREFOOT, T. H. 1987. Aplysia: Its biology and ecology. Oceanogr. Mar. Biol. Annu. Rev. 25:167-284.
5. CAREFOOT, T. H., HARRIS, M., TAYLOR, B. E., DONOVAN, D., and KARENTZ, D. 1998. Mycosporine-like amino acids: Possible UV protection in eggs of the sea hare Aplysia dactylomela. Mar. Biol. 130:389-396.
6. CAREFOOT, T. H., PENNINGS, S. C., and DANKO, J. P. 1999. A test of novel function(s) for the ink of sea hares. J. Exp. Mar. Biol. Ecol. 234:185-197.
7. CHAPMAN, D. J., and FOX, D. L., 1969. Bile pigment metabolism in the sea-hare Aplysia. J. Exp. Mar. Biol. Ecol. 4:71-78.
8. DE NYS, R., STEINBERG, P. D., ROGERS, C. N., CHARLTON, T. S., and DUNCAN, M. W. 1996. Quantitative variation of secondary metabolites in the sea hare Aplysia parvula and its host plant, Delisea pulchra. Mar. Ecol. Prog. Ser. 130:135-146.
9. DIMATTEO, T. 1981. The inking behavior of Aplysia dactylomela (Gastropoda: Opisthobranchia): Evidence for distatefulness. Mar. Behav. Physiol 7:285-290.
10. DIMATTEO, T. 1982. The ink of Aplysia dactylomela (Rang, 1828) (Gastropoda: Opisthobranchia) and its role as a defense mechanism. J. Exp. Mar. Biol. Ecol. 57:169-180.
11. FAULKNER, D. J. 1984. Marine natural products: Metabolites of marine algae and herbivorous marine molluscs. Nat. Prod. Rep. 1:251-280.
12. FAULKNER, D. J. 1988. Feeding deterrents in molluscs, pp. 29-36, in D. G. Fautin (ed.). Biomedical Importance of Marine Organisms. California Academy of Sciences, San Francisco.
13. FAULKNER, D. J. 1992. Chemical defenses of marine molluscs, pp. 119-163 in V. J. Paul (ed.). Ecological Roles of Marine Natural Products. Comstock Publishing Associates, Ithaca, New York.
14. FAULKNER, D. J. 1997. Marine natural products. Nat. Prod. Rep. 14:259-302.
15. FAULKNER, D. J., STALLARD, M. O., and IRELAND, C. 1974. Prepacifenol epoxide: a halogenated sesquiterpene diepoxide. Tetrahedron Lett. 40:3571-3574.
16. FLURY, F. 1915. Uber das Apysiengift. Arch. Exp. Pathol. Pharmakol. 79:250-263.
17. GUNATILAKA, A. A. L., GOPICHAND, Y., SCHMITZ, F. J., and DJERASSI, C. 1981. Minor and trace sterols in marine invertebrates. 26. Isolation and structure elucidation of nine new 5α,8α-epidioxy sterols from four marine organisms. J. Org. Chem. 46:3860-3866.
18. IRELAND, C., STALLARD, M. O., FAULKNER, D. J., FINER, J., and CLARDY, J. 1976. Some chemical constituents of the digestive gland of the sea hare Aplysia californica. J. Org. Chem. 41:2461-2465.
19. KAMIYA, H., MURAMOTO, K., and OGATA, K. 1984. Antibacterial activity in the egg mass of a sea hare. Experientia 40:947-949.
20. MYERS, R. F. 1989. Micronesian Reef Fishes. Coral Graphics, Guam.
21. NOLEN, T. G., JOHNSON, P. M., KICKLIGHTER, C. E., and CAPO, T. 1995. Ink secretion by the marine snail Aplysia californica enhances its ability to escape from a natural predator. J. Comp. Physiol. A 176:239-254.
22. ORTEGA, M. J., ZUBÍA, E., and SALVÁ, J. 1997. 3-epi-Aplykurodinone B, a new degraded sterol from Aplysia fasciata. J. Nat. Prod. 60:488-489.
23. PAUL, V. J., and PENNINGS, S. C. 1991. Diet-derived chemical defenses in the sea hare Stylocheilus longicauda (Quoy et Gaimard, 1824). J. Exp. Mar. Biol. Ecol. 151:227-243.
24. PENNINGS, S. C. 1990. Multiple factors promoting narrow host range in the sea hare, Aplysia californica. Oecologia 82:192-200.
25. PENNINGS, S. C. 1994. Interspecific variation in chemical defenses in the sea hares (Opisthobranchia: Anaspidea). J. Exp. Mar. Biol. Ecol. 180:203-219.
26. PENNINGS, S. C., and PAUL, V. J. 1992. Effect of plant toughness, calcification, and chemistry on herbivory by Dolabella auricularia. Ecology 73:1606-1619.
27. PENNINGS, S. C., and PAUL, V. J. 1993. Sequestration of dietary secondary metabolites by three species of sea hares: Location, specificity and dynamics. Mar. Biol. 117:535-546.
28. PENNINGS, S. C., NADEAU, M. T., and PAUL, V. J. 1993. Selectivity and growth of the generalist herbivore Dolabella auricularia feeding upon complementary resources. Ecology 74:879-890.
29. PETERSON, C. H., and RENAUD, P. E. 1989. Analysis of feeding preference experiments. Oecologia 80:82-86.
30. PETTIT, G. R. 1996. Progress in the discovery of biosynthetic anticancer drugs. J. Nat. Prod. 59:812-821.
31. PETTIT, G. R., KAMANO, Y., KIZU, H., DUFRESNE, C., HERALD, C. L., BONTEMS, R. J., SCHMIDT, J. M., BOETTNER, F. E., and NIEMAN, R. A. 1989. Isolation and structure of the cell growth inhibitory depsipeptides dolastains 11 and 12. Heterocycles 28:553-558.
32. SIMS, J. J., FENICAL, W., WING, R. M., and RADLICK, P. 1972. Marine Natural Products III. Johnstonol; an unusual halogenated epoxide from Laurencia johnstonii. Tetrahedron Lett. 3:195-198.
33. SLATTERY, M., HAMANN, M. T., MCCLINTOCK, J. B., PERRY, T. L., PUGLISI, M. P., and YOSHIDA, W. Y. 1997. Ecological roles for water-borne metabolites from Antarctic soft corals. Mar. Ecol. Prog. Ser. 161:133-144.
34. STALLARD, M. O., and FAULKNER, D. J. 1974. Chemical constituents of the digestive gland of the sea hare Aplysia californica - I. Importance of diet. Comp. Biochem. Physiol. 49B:25-35.
35. SWITZER-DUNLAP, M., and HADFIELD, M. G. 1977. Observations on development, larval growth and metamorphosis of four species of aplysiidae (Gastropoda: Opisthobranchia) in laboratory culture. J. Exp. Mar. Biol. Ecol. 29:245-261.
36. SWITZER-DUNLAP, M., and HADFIELD, M. G. 1979. Reproductive patterns of Hawaiian aplysiid gastropods, pp. 199-210 in S. E. Stancyk (ed.). Reproductive Ecology of Marine Invertebrates, University of South Carolina Press, Colombia.
37. WINKLER, L. R. 1969. Distribution of organic bromide compounds in Aplysia californica Cooper, 1863. Veliger 11:268-271.
38. YAMADA, K., and KIGOSHI, H. 1997. Bioactive compounds from the sea hares of two genera: Aplysia and Dolabella. Bull. Chem. Soc. Jpn. 70:1479-1489.