Marine natural products: metabolites of marine algae and herbivorous marine molluscs

Faulkner, D. John

doi:10.1039/np9840100251

Cited by 359 publications

(146 citation statements)

References 137 publications

(194 reference statements)

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“…397 Additionally, some grazers such as sea hares may be partly acclimatized to these active molecules, for example, palisadins A (195) and B (196) from L. obtusa, 512 and even use them to defend against their own predators. 511,512 Defensive effects of halogenated molecules have also been suggested by direct antifeedant assays. A halosesquiterpene of the chamigrane class, pacifenol (29), exhibited antifeedant activity against the aphid Schizaphis graminum, 513 while the halogenated diterpenes deoxyparguerol (302), 2-deacetoxydeoxyparguerol (306), and parguerol triacetate (704) ( Figure 57) displayed potent feeding-deterrent activity against the young abalone Huliotis discus hannai.…”

Section: Biological Functionsmentioning

confidence: 99%

“…Numerous dietary halogenated structures, such as the sesquiterpenes prepacifenol acetate (53), 62 prepacifenol epoxide (54), 44 laurenisol acetate (137), 119 and aplysistatin (199), 151 as well as the triterpene derivative aurilol (388), 252 were reported from both sea hares and their algal diets, and some of these compounds display toxicity to cell lines and/or brine shrimp in laboratory assays. 62,500,511 The occurrence of algal dietary toxins in sea hares does not prove a defensive function. However, it is interesting that some of these halogenated molecules were found in less toxic acetylated forms in sea hares.…”

Section: Biological Functionsmentioning

confidence: 99%

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Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

et al. 2013

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Section: Biological Functionsmentioning

confidence: 99%

Section: Biological Functionsmentioning

confidence: 99%

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

et al. 2013

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“…Bakus and Green (1974) found an inverse relationship between latitude and ichthyotoxicity in sponges and holothurians, suggesting that fish predators and grazers provide a selective pressure for the production and maintenance of chemical defenses. Similarly, tropical algae seem to be quantitatively and qualitatively better defended than temperate algae, since the former have greater numbers of secondary metabolites (Fenical 1980;Faulkner 1984;Hay and Fenical 1988) and stronger deterrent properties (Bolser and Hay 1996). Herbivorous fishes are more abundant on tropical reefs than on temperate reefs, creating greater herbivore pressure in the tropics (Meekan and Choat 1997), which may have selected for increased defenses in tropical seaweeds (Hay 1991;Bolser and Hay 1996).…”

Section: Introductionmentioning

confidence: 99%

Biogeography of sponge chemical ecology: comparisons of tropical and temperate defenses

et al. 2003

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Examples from both marine and terrestrial systems have supported the hypothesis that predation is higher in tropical than in temperate habitats and that, as a consequence, tropical species have evolved more effective defenses to deter predators. Although this hypothesis was first proposed for marine sponges over 25 years ago, our study provides the first experimental test of latitudinal differences in the effectiveness of sponge chemical defenses. We collected 20 common sponge species belonging to 14 genera from tropical Guam and temperate Northeast Spanish coasts (Indo-Pacific and Mediterranean biogeographic areas) and conducted field-based feeding experiments with large and small fish predators in both geographic areas. We use the term global deterrence to describe the deterrent activity of a sponge extract against all of the predators used in our experiments and to test the hypothesis that sponges from Guam are chemically better defended than their Mediterranean counterparts. Sympatric and allopatric deterrence refer to the average deterrent activity of a sponge against sympatric or allopatric predators. All of the sponges investigated in this study showed deterrent properties against some predators. However, 35% of the sponge species were deterrent in at least one but not in all the experiments, supporting the idea that predators can respond to chemical defenses in a species-specific manner. Tropical and temperate sponges have comparable global, sympatric, and allopatric deterrence, suggesting not only that chemical defenses from tropical and temperate sponges are equally strong but also that they are equally effective against sympatric and allopatric predators. Rather than supporting geographic trends in the production of chemical defenses, our data suggest a recurrent selection for chemical defenses in sponges as a general life-history strategy.

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“…Hundreds of biologically active natural products have been isolated from marine algae (Scheuer 1978, Faulkner 1984. Recent studies pro-vide evidence that algal secondary metabolites function as defenses against herbivorous fishes (Paul & Fenical 1986, Paul & Hay 1986, Targett et al 1986, Paul 1987, b, Paul & Van Alstyne 1987, Paul et al 1987a.…”

Section: Introductionmentioning

confidence: 99%

Feeding preferences of the surgeonfish Zebrasoma flavescens in relation to chemical defenses of tropical algae

Wylie¹,

Paul²

1988

Mar. Ecol. Prog. Ser.

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Seaweed preferences of the tropical herbivorous surgeonfish Zebrasorna flavescens were examined in aquarium assays on Guam, in order to examine the role of secondary metabolites in determining its preferences. Of 55 species of macrophytes examined (49 algae, 5 cyanobactena, l seagrass), only 7 species were highly preferred. Seaweed extracts were examined by thin-layer chromatography (TLC) and proton nuclear magnetic resonance (NMR) spectroscopy to determine the presence or absence of secondary metabolites. Extracts from the non-preferred seaweeds and several pure major metabolites from these seaweeds were tested as feeding deterrents by applying them to the surface of Enterornorpha clathrata, a preferred alga. Extracts that contained secondary metabolites and were the most deterrent were from Bryopsis pennata, Chlorodesmis fastigiata, Desmia hornernanni, Microcoleus lyngbyaceus, Liagora farinosa, and Dictyota bartayresii. The deterrent pure metabolites were malygamide A (from M. lyngbyaceus), chlorodesmin (from C. fastigiata), pachydictyol A (from D. bartayresii), ochtodene (from D. hornernanni), and a fatty acid metabolite isolated from L. farinosa. Several extracts which did not contain metabolites based on our chemical analyses were also significantly deterrent including those from Codiurn geppii, Padina tenuis, Galaxaura oblongata, and Halyrnenia durvlllaei. Extracts from Caulerpa racernosa, Avrainvillea obscura, and Asparagopsis taxiformis contained secondary metabolites yet were non-deterrent. The pure metabolites caulerpin, caulerpenyne, and avrainvilleol from C, racernosa and A. obscura were also non-deterrent. Secondary metabolites appear to account for the low palatabhty of many of the seaweeds examined. However, not all secondary metabolites were effective deterrents toward this herbivore.

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Marine natural products: metabolites of marine algae and herbivorous marine molluscs

Cited by 359 publications

References 137 publications

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

Biogeography of sponge chemical ecology: comparisons of tropical and temperate defenses

Feeding preferences of the surgeonfish Zebrasoma flavescens in relation to chemical defenses of tropical algae

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