Feeding-deterrent properties of diterpenes of Dictyota mertensii (Phaeophyceae, Dictyotales)

Vallim, Magui Aparecida; Teixeira, Valéria Laneuville; Pereira, Renato Crespo

Abstracts

Crude extracts of the brown seaweed Dictyota mertensii (Martius) Kützing collected at two distant and different places on the Brazilian coast, Búzios (Rio de Janeiro) and Fernando de Noronha (PE), were evaluated for defensive chemistry against the crab Pachygrapsus transversus, and the sea urchin Lytechinus variegatus. The extract from Búzios specimens of D. mertensii significantly inhibited the consumption by both P. transversus and L. varigetaus. Fractionation of the extracts of specimens of D. mertensii from Búzios and F. de Noronha followed by complementary assays revealed one active fraction from each location, which contained distinct defensive secondary metabolites. In each active fractions prenylated guaiane diterpenes were the major compounds. Dictyol H and epoxypachydictyol A were the most abundant compounds in Búzios and F. de Noronha, respectively, followed by minor components. Our results show a differential production of secondary metabolites in the two distant and different populations of D. mertensii along the Brazilian coast. This suggests that defensive chemicals from this seaweed are not qualitatively absolute characteristics of the species, but may represent an ecological specialization to successfully prevent herbivory.

Diterpenes; Dictyota mertensii; Feeding; Chemical defense variation

Os espécimes da macroalga parda Dictyota mertensii coletados em dois diferentes locais no litoral brasileiro e distantes entre si, Búzios (Rio de Janeiro) e Fernando de Noronha (PE), foram avaliados quanto à atuação de seus extratos como defesa química contra o caranguejo Pachygrapsus transversus, e o ouriço do mar Lytechinus variegatus. O extrato dos espécimes de D. mertensii de Búzios inibiu o consumo por ambos P. transversus e L. variegatus. O fracionamento dos extratos dos espécimes de D. mertensii de Búzios e F. de Noronha avaliados em ensaios complementares revelaram uma fração ativa contendo distintos metabolitos secundários defensivos. Diterpenos do tipo guaiano prenilado foram as substâncias majoritárias em ambas as frações, mas dictyol H e epoxipachydictyol A foram os mais abundantes em Búzios e F. de Noronha, respectivamente, seguidos por componentes minoritários. Nossos resultados mostram uma produção diferencial de metabolitos secundários em duas populações distintas e distantes de D. mertensii no litoral brasileiro e sugerem que as defesas químicas desta macroalga marinha não são uma característica qualitativa absoluta desta espécie e pode representar uma especialização ecológica eficaz para prevenir a herbivoria.

Diterpenos; Dictyota mertensii; Herbivoria; Variação de defesa química

DE NYS, R. et al. Broad spectrum effects of secondary metabolites from the red alga Delisea pulchra in antifouling assays. Biofouling, v. 8, p. 259-271, 1995.
DE NYS, R.; DWORJANYN, A.; STEINBERG, P. D. A new method for determining surface concentrations of natural products on seaweeds. Mar. Ecol. Prog. Ser., v. 162, p. 79-87, 1998.
ESTON, V. R. et al Vertical distribution of benthic marine organisms on rocky coast of the Fernando de Noronha Archipelago (Brazil). Bolm Inst. oceanogr., S. Paulo, v. 34:37-53, 1986.
GERWICK, W. H.; FENICAL, W.; NORRIS, J. N. Chemical v ariation in the tropical seaweed Stypopodium zonale (Dictyotaceae). Phytochemistry, v. 24, p. 1279-1283, 1985.
GUNATILAKA, A. A. L. et al. Apakaochtodenes A and B: two tetrahalogenated monoterpenes from the red marine alga Portieria hornemannii J. Nat. Prod., v. 62, p. 1376-1378, 1999.
HAY, M. E. Marine chemical ecology: what's known and what's next? J. expl. Biol. Ecol., v. 200, p. 103-134, 1996.
HAY, M. E.; FENICAL, W. Marine plant-herbivore interactions: the ecology of chemical defense. Ann. Rev. Ecol. Syst., v. 19, p. 111-145, 1988.
HAY, M. E.; STEINBERG, P. D. The chemical ecology of plant herbivore interactions in marine versus terrestrial comunities. In: ROSENTHAL, G. A.; BERENBAUM, M. R. (Ed.). Herbivores - their interactions with secondary plant metabolites. New York: Academic Press, 1992. p. 371-413.
HAY, M. E.; KAPPEL, Q. E.; FENICAL, W. Synergisms in plants defenses against herbivores: intercations of chemistry, calcification, and plant quality. Ecology, v. 75, p. 1714-1726, 1994.
HAY, M. E. et al Bioassays with marine and freshwater macroorganisms. In: HAYNES, K. F.; MILLAR, J. G. (Ed.). Methods in chemical ecology, v.2. New York: Chapman and Hall, 1998. p.39-141.
KÖNIG, G. M. et al Four new hydroazulenoid diterpenes from the tropical marine brown alga Dictyota volubilis. Planta Med., v. 59, p. 174-178, 1993.
MAIDA, M.; FERREIRA, B. P. Coral reefs of Brazil: an overview. In: INTERNATIONAL CORAL REEF SYMPOSIUM, 8., 1996, Panama. Proceedings… Balboa, Panama: Smithsonian Tropical Research Institute, 1997. v. 1, p. 263-274.
MATLOCK, D. B.; GINSBURG, D. W.; PAUL, V. J. Spatial variability in secondary metabolite production by the tropical red alga Portieria hornemannii Hydrobiologia, v. 399, p. 267-273, 1999.
PAUL, V. J.; FENICAL, W. Chemical defense in tropical green algae, order Caulerpales. Mar. Ecol. Prog. Ser., v. 34, p. 157-169, 1986.
PAUL, V. J.; FENICAL, W. Natural products chemistry and chemical defense in tropical marine algae of the Phylum Chlorophyta. In: SCHEUER, P.J. (Ed.). Bioorganic marine chemistry v. I. Berlin: I. Springer-Verlag, 1987. p. 1-37.
PAUL, V. J.; VAN ALSTYNE, K. L. Antiherbivore defenses in Halimeda In: INTERNATIONAL CORAL REEF SYMPOSIUM, 6., 1988, Townsville. Proceedings… [Townsville, Qld.?]: Organizing Committee of the Sixth International Coral Reef Symposium, 1988a. v. 3, p. 133-138.
PAUL, V. J.; VAN ALSTYNE, K. L. Chemical defense and chemical variation in some tropical Pacific species of Halimeda (Chlorophyta, Halimedaceae). Coral Reefs, v. 6, p. 263-270, 1988b.
PAUL, V. J. et al. Evidence for chemical defense in the tropical green alga Caulerpa ashmeadii (Caulerpaceae: Chlorophyta): isolation of new bioactive sesquiterpenoids. J. chem. Ecol., v. 13, p. 1171-1185, 1987.
PAUL, V. J.; CRUZ-RIVERA, E.; THACKER, R. W. Chemical mediation of macroalgal herbivore interactions: ecological and evolutionary perspectives. In: MCCLINTOCK, J. B.; BAKER, B. J. (Ed.). Marine chemical ecology Baton rouge, Fla: CRC, 2001. p. 227-265.
PAUL, V. J.; PUGLISI, M. P.; RITSON-WILLIAMS, R. Marine chemical ecology. Nat. Prod. Rep., v. 23, p. 153-180, 2006.
PEREIRA, R. C.; YONESHIGUE-VALENTIN, Y. The role of polyphenols from the tropical brown alga Sargassum furcatum on the feeding by amphipod herbivores. Bot. Mar., v. 42, p. 441-448, 1999.
PEREIRA, R. C.; CAVALCANTI, D. N.; TEIXEIRA, V. L. Effects of secondary metabolites from the tropical Brazilian brown alga Dictyota menstrualis on the amphipod Parhyale hawaiensis Mar. Ecol. Prog. Ser., v. 205, p. 95-100, 2000.
PEREIRA, R. C. et al. Variation in chemical defenses against herbivory in southwestern Atlantic Stypopodium zonale (Phaeophyta). Bot. Mar., v. 47, p. 202-208, 2004.
PEREIRA, R. C.; TEIXEIRA, V. L.; KELECOM, A. Chemical defenses against herbivores in marine algae. I. The brown alga Dictyota dichotoma (Hudson) Lamouroux from Brazil. An. Acad. bras. Ci., v. 66, p. 229-235, 1994.
PUGLISI, M. P.; PAUL, V. J. Intraspecific variation in secondary metabolite production in the red alga Portieria hornemannii: monoterpene concentrations are not influenced by nitrogen and phosphorus enrichment. Mar. Biol., v. 128, p. 161-170, 1997.
RAGAN, M. A.; GLOMBITZA, K. W. Phlorotannins: brown algal polyphenols. Prog. Phycol. Res., v. 4, p. 129-241, 1986.
SCHMITT, T. M.; HAY, M. E.; LINDQUIST, N. Constraints on chemically mediated coevolution: Multiple functions for seaweed secondary metabolites. Ecology, v. 76, p. 107-123, 1995.
Targett, N. M. et al Biogeographic comparisons of marine algal polyphenolics: evidence against a latitudinal trend. Oecologia, v. 89, p. 464-470, 1992.
VAN ALSTYNE, K. L. et al Geographic variation in polyphenolic levels of Northeastern Pacific kelps and rockweeds. Mar. Biol., v. 133, p. 371-379, 1999.
VAN ALSTYNE, K. L.; DETHIER, M. N.; DUGGINS, D. O.. Spatial patterns in macroalgal chemical defenses. In: MCCLINTOCK, J. B.; BAKER, B. J. (Ed.). Marine chemical ecology Boca Raton, Fla: CRC, 2001. p. 301-324.
WRIGHT, A. D.; KÖNIG, G. M.; STICHER, O. New and highly oxidised hydroazulenoid diterpenes from the tropical marine brown alga Dictyota volubilis. Tetrahedron, v. 49, p. 571-580, 1993.
ZAR, J. H. Biostatistical analysis 4. ed. Englewood Cliffs, NJ: Prentice-Hall, 1998. p. 929.
YONESHIGUE, Y. Taxonomie et ecologie des algues marines dans la région de Cabo Frio (Rio de Janeiro, Brésil) 1985. 466 f. Thesis (PhD. Sci.) - Fac. Sci. Luminy, Univ. Aix-Marseille II.

Publication Dates

Publication in this collection
06 Nov 2007
Date of issue
Sept 2007

History

Accepted
08 May 2007
Reviewed
16 Apr 2007
Received
09 June 2006

This work is licensed under a Creative Commons Attribution 4.0 International License.

[1] DE NYS, R. et al. Broad spectrum effects of secondary metabolites from the red alga Delisea pulchra in antifouling assays. Biofouling, v. 8, p. 259-271, 1995.

[2] DE NYS, R.; DWORJANYN, A.; STEINBERG, P. D. A new method for determining surface concentrations of natural products on seaweeds. Mar. Ecol. Prog. Ser., v. 162, p. 79-87, 1998.

[3] ESTON, V. R. et al Vertical distribution of benthic marine organisms on rocky coast of the Fernando de Noronha Archipelago (Brazil). Bolm Inst. oceanogr., S. Paulo, v. 34:37-53, 1986.

[4] GERWICK, W. H.; FENICAL, W.; NORRIS, J. N. Chemical v ariation in the tropical seaweed Stypopodium zonale (Dictyotaceae). Phytochemistry, v. 24, p. 1279-1283, 1985.

[5] GUNATILAKA, A. A. L. et al. Apakaochtodenes A and B: two tetrahalogenated monoterpenes from the red marine alga Portieria hornemannii J. Nat. Prod., v. 62, p. 1376-1378, 1999.

[6] HAY, M. E. Marine chemical ecology: what's known and what's next? J. expl. Biol. Ecol., v. 200, p. 103-134, 1996.

[7] HAY, M. E.; FENICAL, W. Marine plant-herbivore interactions: the ecology of chemical defense. Ann. Rev. Ecol. Syst., v. 19, p. 111-145, 1988.

[8] HAY, M. E.; STEINBERG, P. D. The chemical ecology of plant herbivore interactions in marine versus terrestrial comunities. In: ROSENTHAL, G. A.; BERENBAUM, M. R. (Ed.). Herbivores - their interactions with secondary plant metabolites. New York: Academic Press, 1992. p. 371-413.

[9] HAY, M. E.; KAPPEL, Q. E.; FENICAL, W. Synergisms in plants defenses against herbivores: intercations of chemistry, calcification, and plant quality. Ecology, v. 75, p. 1714-1726, 1994.

[10] HAY, M. E. et al Bioassays with marine and freshwater macroorganisms. In: HAYNES, K. F.; MILLAR, J. G. (Ed.). Methods in chemical ecology, v.2. New York: Chapman and Hall, 1998. p.39-141.

[11] KÖNIG, G. M. et al Four new hydroazulenoid diterpenes from the tropical marine brown alga Dictyota volubilis. Planta Med., v. 59, p. 174-178, 1993.

[12] MAIDA, M.; FERREIRA, B. P. Coral reefs of Brazil: an overview. In: INTERNATIONAL CORAL REEF SYMPOSIUM, 8., 1996, Panama. Proceedings… Balboa, Panama: Smithsonian Tropical Research Institute, 1997. v. 1, p. 263-274.

[13] MATLOCK, D. B.; GINSBURG, D. W.; PAUL, V. J. Spatial variability in secondary metabolite production by the tropical red alga Portieria hornemannii Hydrobiologia, v. 399, p. 267-273, 1999.

[14] PAUL, V. J.; FENICAL, W. Chemical defense in tropical green algae, order Caulerpales. Mar. Ecol. Prog. Ser., v. 34, p. 157-169, 1986.

[15] PAUL, V. J.; FENICAL, W. Natural products chemistry and chemical defense in tropical marine algae of the Phylum Chlorophyta. In: SCHEUER, P.J. (Ed.). Bioorganic marine chemistry v. I. Berlin: I. Springer-Verlag, 1987. p. 1-37.

[16] PAUL, V. J.; VAN ALSTYNE, K. L. Antiherbivore defenses in Halimeda In: INTERNATIONAL CORAL REEF SYMPOSIUM, 6., 1988, Townsville. Proceedings… [Townsville, Qld.?]: Organizing Committee of the Sixth International Coral Reef Symposium, 1988a. v. 3, p. 133-138.

[17] PAUL, V. J.; VAN ALSTYNE, K. L. Chemical defense and chemical variation in some tropical Pacific species of Halimeda (Chlorophyta, Halimedaceae). Coral Reefs, v. 6, p. 263-270, 1988b.

[18] PAUL, V. J. et al. Evidence for chemical defense in the tropical green alga Caulerpa ashmeadii (Caulerpaceae: Chlorophyta): isolation of new bioactive sesquiterpenoids. J. chem. Ecol., v. 13, p. 1171-1185, 1987.

[19] PAUL, V. J.; CRUZ-RIVERA, E.; THACKER, R. W. Chemical mediation of macroalgal herbivore interactions: ecological and evolutionary perspectives. In: MCCLINTOCK, J. B.; BAKER, B. J. (Ed.). Marine chemical ecology Baton rouge, Fla: CRC, 2001. p. 227-265.

[20] PAUL, V. J.; PUGLISI, M. P.; RITSON-WILLIAMS, R. Marine chemical ecology. Nat. Prod. Rep., v. 23, p. 153-180, 2006.

[21] PEREIRA, R. C.; YONESHIGUE-VALENTIN, Y. The role of polyphenols from the tropical brown alga Sargassum furcatum on the feeding by amphipod herbivores. Bot. Mar., v. 42, p. 441-448, 1999.

[22] PEREIRA, R. C.; CAVALCANTI, D. N.; TEIXEIRA, V. L. Effects of secondary metabolites from the tropical Brazilian brown alga Dictyota menstrualis on the amphipod Parhyale hawaiensis Mar. Ecol. Prog. Ser., v. 205, p. 95-100, 2000.

[23] PEREIRA, R. C. et al. Variation in chemical defenses against herbivory in southwestern Atlantic Stypopodium zonale (Phaeophyta). Bot. Mar., v. 47, p. 202-208, 2004.

[24] PEREIRA, R. C.; TEIXEIRA, V. L.; KELECOM, A. Chemical defenses against herbivores in marine algae. I. The brown alga Dictyota dichotoma (Hudson) Lamouroux from Brazil. An. Acad. bras. Ci., v. 66, p. 229-235, 1994.

[25] PUGLISI, M. P.; PAUL, V. J. Intraspecific variation in secondary metabolite production in the red alga Portieria hornemannii: monoterpene concentrations are not influenced by nitrogen and phosphorus enrichment. Mar. Biol., v. 128, p. 161-170, 1997.

[26] RAGAN, M. A.; GLOMBITZA, K. W. Phlorotannins: brown algal polyphenols. Prog. Phycol. Res., v. 4, p. 129-241, 1986.

[27] SCHMITT, T. M.; HAY, M. E.; LINDQUIST, N. Constraints on chemically mediated coevolution: Multiple functions for seaweed secondary metabolites. Ecology, v. 76, p. 107-123, 1995.

[28] Targett, N. M. et al Biogeographic comparisons of marine algal polyphenolics: evidence against a latitudinal trend. Oecologia, v. 89, p. 464-470, 1992.

[29] VAN ALSTYNE, K. L. et al Geographic variation in polyphenolic levels of Northeastern Pacific kelps and rockweeds. Mar. Biol., v. 133, p. 371-379, 1999.

[30] VAN ALSTYNE, K. L.; DETHIER, M. N.; DUGGINS, D. O.. Spatial patterns in macroalgal chemical defenses. In: MCCLINTOCK, J. B.; BAKER, B. J. (Ed.). Marine chemical ecology Boca Raton, Fla: CRC, 2001. p. 301-324.

[31] WRIGHT, A. D.; KÖNIG, G. M.; STICHER, O. New and highly oxidised hydroazulenoid diterpenes from the tropical marine brown alga Dictyota volubilis. Tetrahedron, v. 49, p. 571-580, 1993.

[32] ZAR, J. H. Biostatistical analysis 4. ed. Englewood Cliffs, NJ: Prentice-Hall, 1998. p. 929.

[33] YONESHIGUE, Y. Taxonomie et ecologie des algues marines dans la région de Cabo Frio (Rio de Janeiro, Brésil) 1985. 466 f. Thesis (PhD. Sci.) - Fac. Sci. Luminy, Univ. Aix-Marseille II.

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Feeding-deterrent properties of diterpenes of Dictyota mertensii (Phaeophyceae, Dictyotales)

Abstracts

Publication Dates

History