Bromoisoxazoline Alkaloids from the Caribbean Sponge Aplysina insularis

Fendert, T.; Wray, Victor; Soest, R.W.M. van; Proksch, Peter

doi:10.1515/znc-1999-3-415

Cited by 15 publications

(10 citation statements)

References 10 publications

(13 reference statements)

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“…The present study also demonstrated that the crude extract of A. fulva did not inhibit the establishment of fouling. However, species of Aplysina are known to produce a diverse array of secondary metabolites (Goo, 1980;Gopichand & Schmitz, 1979;McMillan et al, 1981;Ziefer et al, 1995;Fendert et al, 1999), exhibiting cytotoxic (Gopichand & Schmitz, 1979;Compagone et al, 1999), anti-microbial (Goo, 1980) and anti-bacterial activities Muricy et al, 1993;Newbold et al, 1999). Thus, although a number of metabolites from Aplysina species have been screened for biological activity in a variety of pharmacological assays, the value of these assays for predicting the anti-fouling effect may be questionable.…”

Section: Discussionmentioning

confidence: 99%

Field experimental evaluation of secondary metabolites from marine invertebrates as antifoulants

et al. 2002

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The crude organic extracts of the endemic gorgonian Phyllogorgia dilatata and two sponge species Aplysina fulva and Mycale microsigmatosa were evaluated for anti-fouling properties through field experiments. To investigate this property in ecologically meaningful conditions, crude extracts from these invertebrates were incorporated at concentrations naturally found in these marine organisms into a stable gel used as a substratum for fouling settlement. Crude extract from A. fulva showed no significant anti-fouling property at the natural concentrations used in the field experiments. In fact, fouling organisms settled significantly more on gels treated with A. fulva extract than on the control gel. On the other hand, both M. microsigmatosa and P. dilatata yielded crude extracts that exhibited a selective action inhibiting only the settlement of barnacles. The evidences obtained here by means of field experiments can provide a basis for future development of one kind of natural antifoulant technology to prevent marine biofouling.Key words: marine invertebrates, anti-fouling, secondary metabolites. RESUMO Avaliação experimental de metabólitos secundários de invertebrados marinhos como antiincrustantes em campoAs propriedades antiincrustantes dos extratos brutos da gorgônia endêmica Phyllogorgia dilatata e de duas espécies de esponja, Aplysina fulva e Mycale microsigmatosa, foram avaliadas por intermédio de ensaios de campo. Para investigar essas propriedades sob condições ecologicamente relevantes, as concentrações naturais dos extratos brutos encontrados nesses invertebrados foram incorporadas a um gel estável que serviu de substrato para o assentamento de organismos incrustantes. O extrato bruto de A. fulva não mostrou efeito antiincrustante na concentração natural usada nos experimentos. De fato, os organismos incrustantes colonizaram significativamente mais o gel contendo extrato de A. fulva do que o gel-controle. Por outro lado, ambos os invertebrados, M. microsigmatosa e P. dilatata, produzem extratos brutos que foram seletivamente ativos contra o estabelecimento de balanídeos. As evidências obtidas aqui, por meio de experimentos em campo, podem ser importantes subsídios para futuras investigações visando à aplicação industrial de produtos naturais antiincrustantes em tecnologias de prevenção da bioincrustação marinha.Palavras-chave: invertebrados marinhos, antiincrustação, metabólitos secundários.

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Section: Discussionmentioning

confidence: 99%

Field experimental evaluation of secondary metabolites from marine invertebrates as antifoulants

et al. 2002

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“…A wide range of biological activities has been reported for some of these secondary metabolites, including antimicrobial, anti-enzymatic, cytotoxic and antiparasitic activities [ 11 – 13 ]. Previous studies on the sponge V. rigida led to the discovery of antimicrobial and enzymatic activity of its extracts [ 14 , 15 ] and the isolation and structure identification of bromotyrosine-derived compounds [ 8 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Antiparasitic Bromotyrosine Derivatives from the Marine Sponge Verongula rigida

et al. 2011

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Nine bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Verongula rigida. Two of them, aeroplysinin-1 (1) and dihydroxyaerothionin (2), are known compounds for this species, and the other seven are unknown compounds for this species, namely: 3,5-dibromo-N,N,N-trimethyltyraminium (3), 3,5-dibromo-N,N,N, O-tetramethyltyraminium (4), purealidin R (5), 19-deoxyfistularin 3 (6), purealidin B (7), 11-hydroxyaerothionin (8) and fistularin-3 (9). Structural determination of the isolated compounds was performed using one- and two-dimensional NMR, MS and other spectroscopy data. All isolated compounds were screened for their in vitro activity against three parasitic protozoa: Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compounds 7 and 8 showed selective antiparasitic activity at 10 and 5 μM against Leishmania and Plasmodium parasites, respectively. Cytotoxicity of these compounds on a human promonocytic cell line was also assessed.

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“…Previous studies (Thompson et al 1983) of the congeneric species Aplysina fistularis (Pallas, 1776) have been used for interspecies comparison. Verongida sponges contain a variety of brominated metabolites (Thompson et al 1983;Teeyapant and Proksch 1993;Aiello et al 1995;Fendert et al 1999). Over 100 halotyrosine-derived compounds have been reported for sponges of this order (Carney and Rinehart 1995).…”

Section: Introductionmentioning

confidence: 99%

Distribution of brominated compounds within the sponge Aplysina aerophoba : coupling of X-ray microanalysis with cryofixation techniques

Turon

Becerro

Uriz

2000

Cell and Tissue Research

104

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The major secondary metabolites of the sponge Aplysina aerophoba are brominated compounds. X-ray energy dispersive microanalysis was therefore used to locate secondary metabolites via the Br signal in energy emission spectra from sponge sections. To test the reliability of this method in the face of the loss or redistribution of metabolites during processing, we compared the results obtained by conventional aldehyde fixation with those obtained by cryofixation and cryosubstitution with and without cryoembedding. Bromine appeared to be concentrated in two sponge structures, viz. fibres and spherulous cells, when cryofixed material was examined. However, X-ray microanalysis failed to demonstrate the presence of bromine in spherulous cells in chemically fixed samples, showing the need for cryotechniques to avoid the loss of compounds. Cryofixation plus cryosubstitution methods performed best regarding structural preservation and the immobilization of metabolites. The presence of bromine in the spherulous cells suggests that this cell type is the producer of the secondary metabolites, as described for other sponge species. Nevertheless, the presence of bromine in sponge fibres indicates that they can accumulate metabolic substances, although we have been unable to assess whether the chemicals are in their original form or in a modified state within the fibres. A. aerophoba has both bacterial and cyanobacterial symbionts in its mesohyl; the absence of brominated compounds in them contrasts with previous findings in other sponges with prokaryote symbionts.

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Bromoisoxazoline Alkaloids from the Caribbean Sponge Aplysina insularis

Cited by 15 publications

References 10 publications

Field experimental evaluation of secondary metabolites from marine invertebrates as antifoulants

Field experimental evaluation of secondary metabolites from marine invertebrates as antifoulants

Antiparasitic Bromotyrosine Derivatives from the Marine Sponge Verongula rigida

Distribution of brominated compounds within the sponge Aplysina aerophoba : coupling of X-ray microanalysis with cryofixation techniques

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