Chemistry of Verongida Sponges, II. Constituents of the Caribbean Sponge Aplysina fistularis forma fulva

Ciminiello, Patrizia; Costantino, Valeria; Fattorusso, Ernesto; Magno, Silvana; Mangoni, Alfonso; Pansini, Maurizio

doi:10.1021/np50108a004

Cited by 64 publications

(64 citation statements)

References 13 publications

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“…The absolute stereochemistry was determined by X-ray crystallographic analysis and circular dichroism (60). The 13 C NMR chemical shift assignments of C-2 and C-4 were inverted based on the correlation peaks between H-1/H-1′ with C-2/C-2′ and between H-5/H-5′ and C-4/C-4′ in the COLOC NMR experiment (61).…”

Section: B Spirocyclohexadienylisoxazoline Bromotyrosine Derivativesmentioning

confidence: 99%

The Marine Bromotyrosine Derivatives

Peng¹,

Jing²,

Hamann³

2005

The Alkaloids: Chemistry and Biology

101

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Section: B Spirocyclohexadienylisoxazoline Bromotyrosine Derivativesmentioning

confidence: 99%

The Marine Bromotyrosine Derivatives

Peng¹,

Jing²,

Hamann³

2005

The Alkaloids: Chemistry and Biology

101

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“…Chemically, they are characterized by a high content of sterols, generally with the modified aplystane skeleton, and they all synthesize a series of brominated metabolites derived from tyrosine (Tymiak & Rinehart 1981, Bergquist & Wells 1983, Ciminiello et al 1994. The compounds derived from bromotyrosine appear to be stored in spherulous cells and are not associated with any of the diverse microbial symbionts found in the sponge mesohyl, suggesting that they are synthesized by the sponge (Thompson et al 1983, Turon et al 2000.…”

Section: Introductionmentioning

confidence: 99%

Are there activated chemical defenses in sponges of the genus Aplysina from the Caribbean?

Puyana¹,

Fenical²,

Pawlik³

2003

Mar. Ecol. Prog. Ser.

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The Mediterranean sponge Aplysina aerophoba has been proposed to rely on damageinduced activation of chemical defenses against pathogens and fish predators. High molecular weight brominated tyrosine derivatives have been suggested to undergo rapid, enzyme-mediated transformations into the metabolites aeroplysinin-1 and dibromocyclohexadienone following tissue damage, a process also called 'biotransformation'. These putative end-products were found to exhibit greater defensive activity compared to their precursors. Because sponges of the genus Aplysina possess similar chemical components worldwide, it has been suggested that the activation of chemical defenses is a common feature in this group. Herein, we report in situ and laboratory experiments conducted with living specimens of 2 species from the Caribbean, Aplysina insularis and A. archeri. Changes in sponge tissue secondary metabolites during time-course experiments were determined using diode-array high performance liquid chromatography coupled with mass spectrometry (LC-MS) analyses of extracts of flash frozen samples. We obtained no evidence of chemical transformation after tissue damage. In short (150 s) and long (30 and 120 min) time-course experiments, conversion of the major high molecular weight brominated constituents into the low molecular weight aeroplysinin-1 or dibromocyclohexadienone was not apparent: there was neither a reduction in the concentration of putative precursor metabolites, nor an increase in end products. Past observations of transformation may be the result of differential tissue extraction efficiency, hydrolysis from insoluble precursors or the heterogeneous distribution of metabolites in sponge tissue.

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“…Além disso, foram observados sinais de 5 carbonos sp 2 , sendo um em δ 173,7, que foi atribuído a um grupo carbonila de éster, três sinais em δ 151,2, 119,3, 107,6 atribuídos a carbonos sp 2 totalmente substituídos, e um sinal em δ 77,0 de carbono quaternário oxigenado. Após a análise dos dados acima descritos e comparação com dados da literatura 10 , a substância 3 foi identificada como sendo a aeroplisinina-2, previamente isolada das esponjas Aplysina aerophoba, A. fistularis forma fulva e A. archeri [10][11][12] 13,14 permitiram determinar a estrutura de 4 como sendo a 2,4-dibromo-1-hidroxi-3-metoxi-6-oxa-3-azaspiro[4.5]dec-2,4,8-trieno-8-carboxilato de etila. Embora esta substância seja inédita na literatura, o fato do ácido correspondente já ter sido isolado de Pseudoceratina sp.…”

Section: Investigação Química Da Esponja Aplysina Spunclassified

Isolamento e atividades biológicas de produtos naturais das esponjas monanchora arbuscula, aplysina sp. petromica ciocalyptoides e topsentia ophiraphidites, da ascídia didemnum ligulum e do octocoral carijoa riisei

et al. 2007

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Recebido em 13/7/06; aceito em 18/1/07; publicado na web em 24/7/07 ISOLATION AND BIOLOGICAL ACTIVITIES OF SECONDARY METABOLITES FROM THE SPONGES Monanchora aff. arbuscula, Aplysina sp. Petromica ciocalyptoides AND Topsentia ophiraphidites, FROM THE ASCIDIAN Didemnum ligulum AND FROM THE OCTOCORAL Carijoa riisei. The investigation of extracts from six species of marine invertebrates yielded one new and several known natural products. Isoptilocaulin from the sponge Monanchora aff. arbuscula displayed antimicrobial activity at 1.3 μg/mL against an oxacillin-resistant strain of Staphylococcus aureus. Five inactive known dibromotyrosine derivatives, 2 -6, were isolated from a new species of marine sponge, Aplysina sp. The sponges Petromica ciocalyptoides and Topsentia ophiraphidites yielded the known halistanol sulfate A (7) as an inhibitor of the antileishmanial target adenosine phosphoribosyl transferase. The ascidian Didemnum ligulum yielded asterubin (10) and the new N,N-dimethyl-O-methylethanolamine (11). The octocoral Carijoa riisei yielded the known 18-acetoxypregna-1,4,20-trien-3-one (12), which displayed cytotoxic activity against the cancer cell lines SF295, MDA-MB435, HCT8 and HL60.Keywords: marine sponge; ascidian; octocoral. INTRODUÇÃONos últimos anos, investigações químicas e farmacológicas de organismos marinhos têm contribuído significativamente para a descoberta de novas substâncias químicas potencialmente bioativas para fins terapêuticos 1 . Embora o litoral brasileiro seja o segundo mais extenso depois da Austrália, o desenvolvimento da química de produtos naturais de organismos marinhos no Brasil foi negligenciado por muitos anos, porque o principal foco da química de produtos naturais brasileira foi direcionado ao estudo de plantas. Desta maneira, a fauna marinha brasileira ainda é pouco explorada na pesquisa por produtos naturais biologicamente ativos, estruturalmente inéditos ou taxonomicamente relevantes 2 .No presente trabalho relata-se a investigação química dos extratos brutos bioativos de quatro esponjas, uma ascídia e um octocoral. Descreve-se o isolamento de um alcalóide guanidínico a partir da esponja Monanchora aff. arbuscula, de cinco derivados da dibromotirosina, a partir da esponja Aplysina sp., o isolamento do mesmo esterol trissulfatado a partir de ambas esponjas Petromica ciocalyptoides e Topsentia ophiraphidites, o primeiro isolamento da asterubina, a partir de uma ascídia, Didemnum ligulum, da qual também foi isolada a N-N-dimetil-O-metiletanoamina, inédito na literatura, além do 18-acetoxipregna-1,4,20-trien-3-ona a partir do octocoral Carijoa riisei. Também são apresentados os resultados de testes de atividade biológica realizados com estes metabólitos secundários.

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Chemistry of Verongida Sponges, II. Constituents of the Caribbean Sponge Aplysina fistularis forma fulva

Cited by 64 publications

References 13 publications

The Marine Bromotyrosine Derivatives

The Marine Bromotyrosine Derivatives

Are there activated chemical defenses in sponges of the genus Aplysina from the Caribbean?

Isolamento e atividades biológicas de produtos naturais das esponjas monanchora arbuscula, aplysina sp. petromica ciocalyptoides e topsentia ophiraphidites, da ascídia didemnum ligulum e do octocoral carijoa riisei

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