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  • 1
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of natural products 52 (1989), S. 732-739 
    ISSN: 1520-6025
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    The @journal of organic chemistry 45 (1980), S. 3401-3407 
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
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  • 3
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    The @journal of organic chemistry 53 (1988), S. 3644-3646 
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
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  • 4
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of the American Chemical Society 110 (1988), S. 7920-7922 
    ISSN: 1520-5126
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 5
    ISSN: 1432-1939
    Keywords: Chemical defense ; Halimeda ; Nocturnal growth ; Plant-herbivore interactions ; Seaweeds
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Tropical seaweeds in the genus Halimeda reduce losses to grazing by capitalizing on diel patterns of herbivore activity. These seaweeds produce new, more herbivoresusceptible growth at night when herbivorous reef fishes are inactive. Plant portions more than 48 h old are low in food value, well defended morphologically (calcified and high in ash content), and relatively resistant to herbivory. Younger plant portions represent 3–4.5 times the food value (nitrogen or organic content) of older portions but are only moderately more susceptible to herbivores due to their high concentrations of the terpenoid feeding deterrents halimedatrial and halimedatetraacetate. Halimedatrial significantly deters grazing by both parrotfishes (Scaridae) and surgeonfishes (Acanthuridae) and occurs in high concentrations (2–4.5% of plant ash-free dry mass) in plant portions that are 4–12 h old, intermediate concentrations (0.3–2.3%) in portions that are 16–26 h old, and low concentrations (0.3%) in older plant portions. The related compound halimedatetraacetate is absent from the youngest plant portions, shows a rapid increase in concentration (from 0 to 1%) in plant material that is approximately 16 h old, and then rapidly declines to low levels (0.1 to 0.2%) in older plant portions. Thus, newly produced tissues are nutritionally valuable but contain high concentrations of defensive chemicals. As these tissues age, morphological defenses increase, the tissue becomes less valuable as a food for herbivores, and chemical defenses decrease. Additionally, new growth of Halimeda remains unpigmented until just before sunrise. Thus, the valuable, nitrogen-containing molecules associated with photosynthesis are not placed in the new, and more herbivore susceptible, growth until lights is available and they can start producing income for the plant. Experiments in a coral-reef microcosm, where diel patterns of light and water chemistry could be altered, indicated that Halimeda's growth pattern is cued by the timing of light-dark cycles rather than by co-occurring diel changes in water chemistry. Although the growth patterns of Halimeda seem unusual, similar patterns appear to occur in numerous other seaweeds and in microalgae such as diatoms and dinoflagellates.
    Type of Medium: Electronic Resource
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  • 6
    ISSN: 1432-1939
    Keywords: Brown algae ; Biogeography ; Chemical defenses ; Herbivory ; Polyphenolic compounds
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Many tropical brown algae have low levels of polyphenolic compounds and are readily consumed by herbivorous fish. In contrast, temperate brown algae often produce large quantities of phenolic compounds causing them to be distasteful to herbivorous gastropods and sea urchins. We hypothesized that tropical brown algae do not use phenolic compounds as antiherbivore defenses because these compounds are not effective deterrents against tropical fish. To test our hypothesis, we assessed the ability of extracts from 8 tropical and 13 temperate algae with a broad range of phenolic levels to deter feeding by herbivorous fishes on Guam. Extracts of the high-phenolic (〉2% d.w.) temperate brown algae consistently deterred feeding by herbivorous fishes, whereas extracts from low phenolic (〈2% d.w.) temperate and 6 of 8 low-phenolic tropical brown algae did not. Thus, phenolic compounds could be effective feeding deterrents towards herbivorous fishes on Guam, but for unknown reasons they are not used by Guamanian brown algae.
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  • 7
    ISSN: 1432-0975
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Geosciences
    Notes: Abstract Over a dozen species of the genus Halimeda have been chemically investigated and found to produce the diterpenoid metabolites halimedatrial (1) and halimedatetraacetate (2) in varying concentrations. These meabolites have been proposed to play a role in chemical defense against herbivores based on their chemical structures and their demonstrated biological activities in laboratory and aquarium assays. We examined and compared the feeding deterrent effects of these two compounds tovard herbivorous fishes in field experiments on Guam reefs. Halimedatrial is a more effective feeding deterrent than halimedatetraacetate. It is the major secondary metabolite in young Halimeda macroloba and in the newly produced segments of growing plants. The organic extracts from young plants and new segments were significantly more deterrent than extracts from mature plant tissue. Some populations of Halimeda growing in reef-slope habitats, where herbivory is intense, also have high concentrations of halimedatrial. We compared extracts between reef slope and reef flat collections of Halimeda opuntia on Guam and Pohnpei (= Ponape), and H. discoidea and H. macroloba on Guam. We found that halimedtrial was the major metabolite in reef-slope collections of H. opuntia from Pohnpei and Pago Bay, Guam, and that halimedatetraacetate was the major metabolite a non-reef slope populations. In the cases examined, chemical defenses were greatest in (1) plant parts and (2) populations that were at greatest risk to herbivores.
    Type of Medium: Electronic Resource
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  • 8
    ISSN: 1432-0975
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Geosciences
    Notes: Abstract Cyphoma gibbosum is an ovulid predatory gastropod that specializes on gorgonians, many of which contain secondary metabolites and calcified sclerites that serve as antipredator defenses. In field and shipboard feeding assays, we examined the role of gorgonian crude extracts and sclerites as feeding deterrents to generalist predators and to C. gibbosum. Crude extracts and sclerites were isolated from Gorgonia ventalina, a Caribbean sea fan on which C. gibbosum feeds, and incorporated into a carrageenan-based artificial diet. In shipboard feeding experiments, artificial diet containing G. ventalina crude extracts was consumed 49% less by C. gibbosum, than artificial diet lacking extracts. The addition of G. ventalina sclerites to the diet also reduced feeding by Cyphoma by about one half. The addition of extracts to the artificial diet reduced feeding by natural assemblages of tropical fishes at Cross Harbor, Great Abaco Island, Bahamas by 87%; sclerites reduced feeding by fishes by 95%. Gorgonia ventalina extracts were composed of at least a dozen nonpolar terpenoids. Fractions containing these compounds were feeding deterrents towards fishes in the field. Unlike many terrestrial oligophagous specialists, C. gibbosum is not immune to the defenses produced by its prey.
    Type of Medium: Electronic Resource
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  • 9
    ISSN: 1573-1561
    Keywords: Acutilol diterpenes ; biogeography ; chemical defenses ; Dictyota ; diffuse coevolution ; fish ; plant–herbivore interactions ; sea urchin ; secondary metabolites
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Because herbivory is more intense in the tropics, tropical seaweeds may be better defended against herbivory than are temperate seaweeds. A “diffuse” coevolutionary corollary to this hypothesis is that tropical herbivores should be more resistant to seaweed defenses than temperate herbivores because tropical herbivores more commonly encounter heavily defended seaweeds. We begin to test the latter prediction using three newly discovered diterpenoid secondary metabolites from the tropical brown alga Dictyota acutiloba. We tested the feeding deterrent properties of these compounds against common herbivorous fishes and sea urchins from warm-temperate North Carolina versus tropical Guam using standardized laboratory feeding assays. The temperate herbivores were deterred by lower concentrations of secondary metabolites than the tropical herbivores. In no case was a tropical herbivore more deterred by a compound than a temperate herbivore, suggesting that temperate herbivores may be more strongly affected by seaweed chemical defenses. Feeding by the temperate pinfish Lagodon rhomboides was significantly reduced by two of the three diterpenes at a concentration that was only 13–18% of the natural concentration found in the alga. Feeding by four species of tropical fishes (two parrotfishes and two surgeonfishes) was unaffected by metabolite concentrations that deterred the temperate fish. At 100% of natural concentrations, only one of the three compounds deterred the two parrotfishes, and none of the three compounds deterred the surgeonfishes. Contrasts between the temperate sea urchin Arbacia punctulata and the tropical sea urchin Diadema savignyi showed a similar pattern; low concentrations of acutilol A acetate strongly deterred the temperate, but not the tropical, urchin. Tropical herbivores appear more resistant than temperate herbivores to seaweed chemical defenses.
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  • 10
    ISSN: 1573-1561
    Keywords: Herbivory ; chemical defense ; marine algae ; allelochemicals ; Caulerpa ; Sesquiterpenoids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Results of field feeding preference studies with 12 species of tropical green algae of the genusCaulerpa showed thatC. ashmeadii was preferred least by herbivorous fishes. Chemical investigations ofC. ashmeadii demonstrated the presence of high concentrations of sesquiterpenoid metabolites. The chemical isolation and structural elucidation of five majorC. ashmeadii metabolites, as well as the results of field feeding preference, antimicrobial, and ichthyotoxicity assays demonstrating the biological activities of these metabolites are reported here.
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