Chemical defenses of the Caribbean sponges Agelas wiedenmayeri and Agelas conifera

Assmann, Michael; Lichte, Ellen; Pawlik, Joseph R.; Köck, Matthias

doi:10.3354/meps207255

Cited by 109 publications

(114 citation statements)

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“…If such a deterrent comprises, beside its unpalatability to the fish, any pharmacological potency was only known in part for oroidin. Oroidin is also present within the tissues of A. clathrodes, A. cervicornis, A. dispar and A. wiedenmayeri (Braekman et al, 1992;Assmann et al, 1999Assmann et al, , 2000Lindel et al, 2000;Assmann et al, in press) and has previously been shown to be cytotoxic (König et al, 1998).…”

Section: Discussionmentioning

confidence: 99%

“…One chance of survival is therefore to produce secondary metabolites to deter consumption by predatory fishes (e.g. Chanas et al, 1996;Wilson et al, 1999;Assmann et al, 2000;Kubanek et al, 2000;Assmann et al, 2004).…”

Section: Discussionmentioning

confidence: 99%

“…One example of these sponge secondary metabolites is 4,5-dibromopyrrole-2-carboxylic acid, which defends some Agelas species (A. clathrodes, A. cervicornis, A. dispar and A. wiedenmayeri) from common predatory reef fishes like Thalassoma bifasciatum (Chanas et al, 1996;Assmann et al, 2000Assmann et al, , 2004. If such a deterrent comprises, beside its unpalatability to the fish, any pharmacological potency was only known in part for oroidin.…”

Section: Discussionmentioning

confidence: 99%

“…Especially sponges are known to be a rich font for interesting secondary metabolites, for example the genus Agelas (Agelasidae) is well known to contain a variety of bromopyrrole alkaloids (reviewed in Braekman et al, 1992;Lindel et al, 2000). Recently, detailed studies have shown both at laboratory and field conditions, that brominated pyrrole alkaloids like 4,5-dibromopyrrole-2-carboxylic acid were the principal fish antifeedant metabolites within the sponge tissue of Agelas sponges at natural concentrations (Pawlik et al, 1995;Chanas et al, 1996;Assmann et al, 2000Assmann et al, , 2004. However, the chemosensory and cellular mechanisms of brominated pyrrole alkaloids to function as a feeding deterrent are not investigated so far.…”

Section: Introductionmentioning

confidence: 99%

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A secondary metabolite, 4,5-dibromopyrrole-2-carboxylic acid, from marine sponges of the genus Agelas alters cellular calcium signals

Bickmeyer¹,

Assmann²,

Köck³

et al. 2005

Environmental Toxicology and Pharmacology

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A secondary metabolite from sponges of the genus Agelas, 4,5-dibromopyrrole-2-carboxylic acid, which is well known as feeding deterrent, was investigated for effects on the cellular calcium homeostasis in PC12 cells. 4,5-Dibromopyrrole-2-carboxylic acid did not change intracellular calcium levels if applied alone without cell depolarization. During depolarization of the cellular membrane using high potassium solution, a dose dependent reduction of intracellular calcium elevation was revealed utilizing Fura II as calcium indicator. Significant reduction was seen at concentrations higher than 30 M in a series of experiments, but in single experiments a concentration of 300 nM was still reversible effective. In the same concentration range, the onset of depolarization induced calcium elevations was significantly delayed by 4,5-dibromopyrrole-2-carboxylic acid. Dose dependent reduction and delay of depolarization evoked calcium elevations are probably due to a reduction of calcium entry via voltage operated calcium channels. One cellular mode of action of the feeding deterrent potential of 4,5-dibromopyrrole-2-carboxylic acid to fishes may be an interaction with the cellular calcium homeostasis of exposed cells.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A secondary metabolite, 4,5-dibromopyrrole-2-carboxylic acid, from marine sponges of the genus Agelas alters cellular calcium signals

Bickmeyer¹,

Assmann²,

Köck³

et al. 2005

Environmental Toxicology and Pharmacology

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show abstract

“…Brominated pyrrole-imidazole alkaloids are known to be fish feeding deterrent against the reef fish Thalassoma bifasciatum [6,7] and demonstrate antibiotic activity [8] even against pathogens like Helicobacter pylori [9]. Especially, the degree of bromination and the guanidine moieties have shown to be important for the alkaloids efficacy to disturb cellular calcium ion entry via voltage operated channels in neuroendocrine cells [10][11][12], which possess mainly L-and N-type calcium channels common in neuronal cells.…”

Section: Introductionmentioning

confidence: 99%

Ageladine A, a pyrrole–imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye

Bickmeyer

Grube

Klings

et al. 2008

Biochemical and Biophysical Research Communications

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a b s t r a c tThe alkaloid ageladine A, a pyrrole-imidazole alkaloid isolated from marine Agelas sponges shows fluorescence in the blue-green range during excitation with UV light with the highest absorption at 370 nm. The fluorescence of this alkaloid is pH dependent. Highest fluorescence is observed at pH 4, lowest at pH 9 with the largest fluorescence changes between pH 6 and 7. Ageladine A is brominated, which facilitates membrane permeation and therefore allows for easy staining of living cells and even whole transparent animal staining. To calculate the exact pH in solutions, cells, and tissues, the actual concentration of the alkaloid has to be known. A ratiometric measurement at the commonly used excitation wavelengths at 340/380 nm allows pH measurements in living tissues with an attenuated influence of the ageladine A concentration on calculated values. The fluorescence changes report small intracellular pH changes induced by extracellular acidification and alkalization as well as intracellular alkalization induced by ammonium chloride.Ó 2008 Elsevier Inc. All rights reserved.The pyrrole-imidazole alkaloid ageladine A was first isolated and described by Fujita et al.[1] using bioassay guided fractionation of extracts of the marine sponge Agelas nakamurai.The alkaloid showed biological effects such as the inhibition of matrix metallo-proteinases and the inhibition of cell migration of bovine endothelial cells. In 2006 the total synthesis of ageladine A was completed by the groups of Weinreb and Karuso [2,3] and later optimized [4,5].Brominated pyrrole-imidazole alkaloids are known to be fish feeding deterrent against the reef fish Thalassoma bifasciatum [6,7] and demonstrate antibiotic activity [8] even against pathogens like Helicobacter pylori [9]. Especially, the degree of bromination and the guanidine moieties have shown to be important for the alkaloids efficacy to disturb cellular calcium ion entry via voltage operated channels in neuroendocrine cells [10][11][12], which possess mainly L-and N-type calcium channels common in neuronal cells. During these fluorescence measurements of cellular effects by pyrrole-imidazole alkaloids, ageladine A was noticed to show fluorescence during UV excitation [12], which was also described earlier by Fujita et al. [1]. We demonstrate here other surprising properties of ageladine A such as its sensitivity to pH changes covering a wide range and because of its high membrane permeability an easy whole animal pH sensitive staining. Material and methodsCulture methods. PC12 cells from the DSMZ (Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH, Braunschweig, Germany) were kept in culture medium containing RPMI 1640, 10% fetal calf serum, 5% horse serum, and 100 U penicillin/streptomycin per milliliter. Cells were cultivated in an incubator at 37°C, 90% humidity and 5% CO 2 with regular medium changes twice a week or when additionally necessary. Cells grew in culture flasks and 1-2 days prior to the experiments were seeded into petri dishes coated with coll...

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The Associations between Fishes and Sponges

Karplus¹

2014

Symbiosis in Fishes

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Chemical defenses of the Caribbean sponges Agelas wiedenmayeri and Agelas conifera

Cited by 109 publications

References 15 publications

A secondary metabolite, 4,5-dibromopyrrole-2-carboxylic acid, from marine sponges of the genus Agelas alters cellular calcium signals

A secondary metabolite, 4,5-dibromopyrrole-2-carboxylic acid, from marine sponges of the genus Agelas alters cellular calcium signals

Ageladine A, a pyrrole–imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye

The Associations between Fishes and Sponges

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