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Effects of Secondary Metabolites from the Tropical Brazilian Brown Alga Dictyota Menstrualis on the Amphipod Parhyale Hawaiensis

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Effects of Secondary Metabolites from the Tropical Brazilian Brown Alga Dictyota Menstrualis on the Amphipod Parhyale Hawaiensis MARINE ECOLOGY PROGRESS SERIES Vol. 205: 95–100, 2000 Published October 19 Mar Ecol Prog Ser Effects of secondary metabolites from the tropical Brazilian brown alga Dictyota menstrualis on the amphipod Parhyale hawaiensis Renato C. Pereira1,*, Diana N. Cavalcanti1, 2, Valéria L. Teixeira1 1Departamento de Biologia Marinha, Instituto de Biologia, Universidade Federal Fluminense (UFF) CP 100.644, CEP 24001-970, Rio de Janeiro, Brazil 2Pós-Graduação em Química Orgânica, Instituto de Química, UFF 24020-150, Niterói, Rio de Janeiro, Brazil ABSTRACT: Diterpene metabolites produced by Dictyota species are known to inhibit feeding by several herbivorous species. We present the first evidence of feeding-deterrence of dictyotacean metabolites of an unusual compound belonging to a dichotomane diterpene skeleton type. Through experimental assay, we provide evidence of feeding-deterrent properties of lipid-soluble extracts of the Brazilian brown alga D. menstrualis (Hoyt) Schnetter, Hörnig & Weber-Peukert against the amphipod Parhyale hawaiensis Dana. Bioassay fractionation of this extract revealed the deterrent activity to be due to the diterpenoid (6R)-6-hydroxydichotoma-3,14-diene-1,17-dial, which was found to be the second most abundant metabolite (~0.2% dry mass) in D. menstrualis. In contrast to other studies, the major diterpenoid pachydictyol A, present as 0.4% (dry mass) in D. menstrualis, showed no anti-feeding properties. Our results suggest that chemical defense of Dictyota species may vary according to geographic region, thus explaining the presence of a metabolite other than pachydictyol A which functions as the anti-feedant metabolite in D. menstrualis from the Brazilian littoral zone. KEY WORDS: Amphipod · Chemical defense · Dictyota menstrualis · Herbivory · Parhyale hawai- ensis · Diterpenes Resale or republication not permitted without written consent of the publisher INTRODUCTION In the Phaeophyceae of both tropical and warm- temperate marine regions, Dictyota species have been Several chemical studies have indicated that sea- extensively studied and are known to produce sec- weeds produce hundreds of secondary metabolites, ondary metabolites, many of which are broad- including terpenoids (major sesqui- and diterpenes), spectrum feeding deterrents against herbivores. This acetogenins, amino acid-derived compounds, unusual broad-spectrum action is effected by the well-studied fatty acids, polyphenols (= ‘phlorotannins’) and meta- family of structurally similar dictyol diterpenes, includ- bolites produced through mixed biosynthesis that have ing pachydictyol A, dictyol E, dictyol B, dictyol B terpenoid and phenol portions (Faulkner 1998). Sev- acetate, and dictyol H, which have been shown to be eral seaweeds produce large numbers and types of active anti-feedant metabolites in ecological assays secondary metabolites capable of inhibiting herbivory (see Pereira et al. 1994 for Parhyale hawaiensis and or which exhibit a wide action against other adverse Hay & Steinberg 1992 for review about remaining her- agents in the marine environment (Hay & Steinberg bivore species). Natural concentrations of pachydictyol 1992, Paul 1992). A, found in some species of Dictyota, can inhibit her- bivory by tropical parrotfish species, by the temperate fishes Lagodon rhomboides Linnaeus and Diplobus *E-mail: [email protected] holbrooki Bean, and by the sea urchin Diadema antil- © Inter-Research 2000 96 Mar Ecol Prog Ser 205: 95–100, 2000 larum Philippi. On the other hand, this same metabo- Peukert, a common subtidal species, were collected at lite does not inhibit feeding by the sea urchin Arbacia Enseada do Forno (22° 45’ S, 41° 52’ W), Armação de punctulata (Lamarck) Phillipi, the cosmopolitan poly- Búzios (State of Rio de Janeiro, Brazil), during October chaete Platynereis dumerilii Audouin and M. Edwards, 1996, in shallow water at a depth of 2.0 to 5.0 m by or the amphipod Parhyale hawaiensis Dana, and has snorkeling. This region is characterized by high wave further been shown to increase feeding in the amphi- energy and by the presence of the seaweeds Dictyota pod Ampithoe longimana Smith. Dictyol E reduces spp., Sargassum cymosum C. Agardh and S. furcatum herbivory in L. rhomboides, D. holbrooki and Arbacia Kützing (Yoneshigue 1985). In the upper littoral, the punctulata, but is not an effective defense against coralline red algae Amphiroa spp. and Jania adherens Ampithoe longimana and Platynereis dumerilii. Finally, Lamouroux and the green alga Codium spongiosum pachydictyol A, dictyol B, and dictyol H significantly Harvey also characterize this region, where the sea- inhibit herbivory in the rabbitfish Siganus doliatus urchins Echinometra lucunter Linnaeus and Paracen- Cuvier. All these metabolites, collectively referred to trotus gaimardii Blainville (Blainville, 1825) are the as dictyols, represent the only structural class of the major invertebrate species (Yoneshigue 1985, Sabino prenylated guaiane diterpenes. & Villaça 1999) The amphipod Parhyale hawaiensis Besides the inherent variation in action against her- Dana is a common invertebrate species, usually found bivores, the presence of seaweed secondary metabo- with Sargassum spp., and has been used in previous lites may vary between tropical (more) and temperate studies of seaweed chemical defenses in Brazil (e.g. (less) seas, or may exhibit some other type of biogeo- Pereira et al. 1994, Pereira & Yoneshigue-Valentin graphic variation. For example, based on a common 1999). This amphipod is also found in other macroalgal biogenetic precursor, diterpene metabolites found in species (e.g. Ulva spp.), but is not closely related to D. Dictyota species belong to 3 different ‘chemical menstrualis. groups’ which are unequally distributed in the oceans Secondary metabolite extraction. A known weight (Teixeira & Kelecom 1987b). In the Atlantic Ocean, of fresh seaweed tissue (1416 g) was fully extracted 61% of the diterpenes found in Dictyota species pos- with CH2Cl2-MeOH (2:1). Evaporation of the solvent sess a dolastane (e.g. amijiol) or secodolastane (e.g. under reduced pressure yielded a brownish residue isolinearol) skeleton. In contrast, xeniane (e.g. dictyo- (22 g, 5.6% dry wt of the alga), which was subse- dial) skeletal compounds are more common in the quently partitioned between n-hexane, MeOH and Pacific Ocean, and prenylated guaiane (e.g. pachydic- CHCl3-H2O. The partitions resulted in 3 fractions of tyol A) skeletons have a more cosmopolitan distribu- different polarities (16.23, 4.03 and 1.46 g, respec- tion. Finally, within-species variance in secondary tively) which were tested in feeding assays. The metabolite production among different populations of hexane fraction (16.23 g, 4.17% dry wt of the alga) the same species appears to be considerable for some exhibited maximum anti-feedant activity compared to species of seaweeds (Paul & Fenical 1987, Paul & van the other 2 fractions, and was used in subsequent frac- Alstyne 1988) and invertebrates (Sammarco & Coll tionation. Rapid filtration on silica gel with n-hexane, 1992). CH2Cl2, EtOAc, and MeOH yielded 4 fractions which In this study, we assessed the chemical defenses of were then used in feeding assays. The compounds that Dictyota menstrualis against herbivory by the amphi- eluted with n-hexane (3.06 g) and CH2Cl2 (3.42 g) were pod Parhyale hawaiensis. A preliminary study of the major deterrents against herbivory by the amphipod crude extract of D. menstrualis from Brazilian littoral Parhyale hawaiensis. The compounds that eluted with zones indicated that the secondary metabolites present the CH2Cl2 fraction were further purified by silica-gel in this species acted as anti-feedant metabolites against column chromatography (with an eluent of n-hexane, crab and amphipod herbivores (Pereira et al. 2000). In CHCL3, EtOAc, and MEOH,) which yielded 7 addi- contrast, natural concentrations of the well-known tional fractions. Compounds that eluted with the n- pachydictyol A, also found in this species from the hexane fraction contained crude pachydictyol A Brazilian coast, were not deterrent to the same amphi- (250 mg), which was further purified by silica-gel col- pod species (Pereira et al. 1994). Here we determine umn chromatography (eluent: gradient of CHCL3 in what metabolite is responsible for the chemical defense EtOAc) giving pure pachydictyol A (152 mg). The frac- activity previously observed in this algal species. tion which eluted in CHCl3-EtOAc (9:1) gave crude dichotomane diterpene (545 mg). This fraction was purified by successive preparative TLC eluted with MATERIALS AND METHODS EtOAc in CHCl3 (1:4), giving pure dichotomane diter- pene (60 mg). The natural products were identified by Collection site and organisms. Specimens of Dic- comparison of UV, IR, mass, 1H-NMR (300MHz, 13 tyota menstrualis (Hoyt), Schnetter, Höring & Weber- CDCl3) and C-NMR (75 MHz, CDCl3) with spectral Pereira et al.: Secondary metabolites of Dictyota menstrualis 97 data and with previously published data (Blount et al. mated by comparing the number of squares consumed 1982). in both experimental and control foods. New speci- Chemical deterrence assays. The anti-feedant prop- mens of amphipods were used in each assay (with erty of all extracts, partitions, fractions, and pure com- crude extract, fractions and pure compound). pounds from Dictyota menstrualis were verified by Statistical analysis. Because paired-samples do not including natural concentrations of these components exhibit a normal distribution, the significance
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