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

Abstract

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.

Anti HSV-1 Activity of Halistanol Sulfate and Halistanol Sulfate C Isolated from Brazilian Marine Sponge Petromica citrina (Demospongiae)

“…The complete structure of compound 1 was determined based on HSQC, HMBC, and COSY spectra, as well as by ESI mass spectrometry and by comparison with literature data [29,30,31,32,33]. The presence of three sulfate groups in the structure could be clearly defined by ESI mass spectrometry ( m / z 731 [M − Na] − , m / z 611 [M − NaHSO 4 ], m / z 491 [M − (NaHSO 4 ) 2 ] and m / z 354 [M − (NaHSO 4 ) 3 ]).…”

“…[31], Epipolasis sp. [32], Petromica ciocalyptoides [29], Haliclona sp. [33], and Petromica citrina [30].…”

“…New compounds of the halistanol sulfate series (halistanol sulfates A to H) were isolated in the subsequent years [32,34], but the nomenclature and the chemical shift values in the 1 H NMR spectra of the side chain are still not completely defined [29,32]. Therefore, it is important that the details of the structural elucidation of compounds 1 and 2 are also presented.…”

“…Important biological activities have been reported for this steroid sulfate, such as anti-HIV effects [38], cytotoxic activity against human hepatoma cells (QGY-7701), and chronic myelogenous leukemia cells (K562) [40]. Afterwards, the same compound was isolated from Petromica ciocalyptoides and Topsentia ophiraphidites , showing inhibitory activity of Leishmania tarentola [29] and a wide spectrum of activity against resistant bacteria such as Staphylococcus aureus , Staphylococcus epidermidis , Enterococcus faecalis , Mycobacterium fortuitum , and Neisseria gonorrheae [30]. …”

“…There are few studies with this species, and most of them describe the evaluation of different pharmacological properties such as antibacterial and antiviral activities for its aqueous extracts [26,27] and n -butanol fraction [28]. Moreover, a restricted number of chemical investigations and a few bioactive constituents have been reported, in particular, a sulfated steroidal compound, identified as halistanol sulfate [29,30]. …”