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Download PDF (Inglês) Quim. Nova, Vol. 35, No. 6, 1189-1193, 2012 ANTIPARASITIC BROMOTYROSINE DERIVATIVES FROM THE CARIBBEAN MARINE SPONGE Aiolochroia crassa Elkin Galeano* e Alejandro Martínez Marine Natural Products Research Group, University of Antioquia, Medellin AA 1226, Colombia Olivier P. Thomas Nice Institute of Chemistry, UMR 6001 CNRS, University of Nice - Sophia Antipolis, Parc Valrose, 06108, Nice Cedex 02, France Artigo Sara Robledo e Diana Munoz Program for the Study and Control of Tropical Diseases, University of Antioquia, Medellin, Colombia Recebido em 8/11/11; aceito em 27/1/12; publicado na web em 15/5/12 Six bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Aiolochroia crassa: 3-bromo-5-hydroxy- O-methyltyrosine (1), 3-bromo-N,N,N-trimethyltyrosinium (2), 3-bromo-N,N,N,O-tetramethyltyrosinium (3), 3,5-dibromo-N,N,N- trimethyltyrosinium (4), 3,5-dibromo-N,N,N,O-tetramethyltyrosinium (5), and aeroplysinin-1 (6). Structural determination was performed using NMR, MS and comparison with literature data. All isolated compounds were screened for their in vitro activity against Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compound 4 showed selective antiparasitic activity against Leishmania and Plasmodium parasites. This is the first report of compounds 1, 4 and 5 in the sponge A. crassa and the first biological activity reports for compounds 2-4. This work shows that bromotyrosines are potential antiparasitic agents. Keywords: bromotyrosines; Aiolochroia crassa; antiparasitic activity. INTRODUCTION Verongida, Aplysinidae). This sponge has been reported under different names, such as Suberea crassa (Hyatt, 1875), Aiolochroia ianthella Malaria, leishmaniasis and Chagas diseases number among the (De Laubenfels, 1949), Ianthella ianthella (De Laubenfels, 1949) and most common chronic infections afflicting the world’s poorest po- Ianthella ardis (De Laubenfels, 1950).6 Aiolochroia crassa, akin to pulations and represent the main causes of disability. These diseases other marine sponges of the order Verongida, is of great interest because occur mainly in poor areas of tropical and subtropical low-income this group of sponges is characterized by the production of bromina- countries. The most severe type of malaria is caused by the parasite ted metabolites which are biogenetically related to tyrosine. For this Plasmodium falciparum. In 2010, the World Health Organization reason, bromotyrosine metabolites have been considered as potential (WHO) reported 225 million malaria cases worldwide with a mortality chemotaxonomic markers of sponges of the order Verongida.7 A wide rate close to 781,000 cases/year.1 Leishmaniasis is an infection with range of biological activities have been reported for these compounds diverse clinical forms, which can cause skin ulcerations, mucosa and/ including antimicrobial, enzymatic, cytotoxic and antiparasitic activi- or severe visceral disease. Leishmaniasis is caused by trypanosomatid ties.8 A previous study on the sponge A. crassa led to the discovery of parasites from the genus Leishmania. According to WHO estimates, antimicrobial activity of its extracts,9 and the isolation and identification 350 million people are at risk of contracting leishmaniasis, approxi- of several bromotyrosine derivatives, namely: N-methylaerophobin-2, mately 12 million are infected and 2 million new cases are reported aerophobin-1, aerophobin-2, purealidin L, isofistularin-3, araplysillin each year worldwide.2 Chagas disease (American trypanosomiasis) III, hexadellin C, N,N,N-trimethyl-3-bromo-4-O-methyltyrosine and is caused by the parasite Trypanosoma cruzi. This zoonosis, in its N,N,N-trimethyl-3-bromotyrosine.6,10 Aeroplysinin 1 and ianthelline chronic phase, causes damage to the central nervous system, gas- were reported from the sponge Ianthella ardis.11 No chemical studies trointestinal system and heart and consequently is often fatal. The have been reported for the other synonyms of the sponge Aiolochroia WHO has reported nearly 10 million cases of Chagas disease, causing crassa.12 around 10,000 deaths per year, where Latin American countries have In this work, 6 known bromotyrosine derivatives were isolated the highest incidence of this disease.3 and tested for the first time against L. panamensis, P. falciparum The high prevalence of these three parasitic diseases the resistance and T. cruzi. Therapeutic indices were calculated by dividing the developed by these parasites to current treatments, the reduction of their antiparasitic activity of the compounds by their cytotoxicity against efficacy and consequent increase in the cost of conventional treatments, promonocytic macrophage cell line U937. highlights the need for novel and effective therapeutic alternatives with fewer or none side-effects. In the search for these new therapeutic op- EXPERIMENTAL tions, marine sponges have proven to be a source of bioactive molecules with high pharmacological potential.4 In this context, we evaluated the Instruments and reagent potential of Colombian sponges localized in Uraba Gulf, Southwestern Caribbean Sea, as sources of antiparasitic, cytotoxic, antimicrobial Optical rotations were measured on a BTI-162 polarimeter, and antitumor agents.4,5 In this study, we evaluated the in vitro antipa- while UV measurements were performed on a Varian Cary 300 Scan rasitic activity of molecules isolated from the purple-violet spherical UV–visible spectrophotometer. Infrared spectra were acquired on a morphotype of the marine sponge Aiolochroia crassa (Hyatt 1875, PerkinElmer Paragon 1000 FT-IR spectrophotometer. NMR data were collected on a Bruker Avance 500 MHz spectrometer using deuterated *e-mail: [email protected] NMR solvents supplied by Sigma-Aldrich. Spectra were referenced 1190 Galeano et al. Quim. Nova 1 13 -1 1 to residual H and C in the deuterated solvents. Low resolution 1150 and 750 cm ; H NMR data (500 MHz, CD3OD) δ 7.60 s (1H, electrospray ionization (ESI) mass spectra were obtained with a H-2), 7.38 s (1H, H-6), 3.83 m (1H, H-8), 3.75 s (3H, OMe), 3.17 m Bruker Esquire 3000 Plus spectrometer in the positive or negative (1H. H-7a), 3.23 m (1H, H-7b); ESI-MS m/z 290 (100%) [M+H]+, mode by the direct injection method. The solvents used (MeOH and 292 (96%). Spectroscopic NMR and MS data matched those pre- 13 H2O) were HPLC grade and obtained from Merck. The formic acid viously published. (FA) used was HPLC grade and supplied by Sigma-Aldrich. HPLC purifications were carried out on a Waters 600 system equipped with a 3-Bromo-N,N,N-trimethyltyrosinium (2) Waters 717 plus autosampler, a Waters 996 photodiode array detector Light brown solid; -8 (c 0.04, MeOH); UV (MeOH) λmax nm and a Sedex 55 evaporative light scattering detector (Sedere, France). (log ε) 278.5 nm (3.04); IR (neat) 3400, 1635, 1565, 1050 and 655 cm-1. ESI-MS m/z 302 (82%), 304 (100%) [M]+. Spectroscopic NMR Sponge material and MS data matched those previously published.14 A specimen of the marine sponge Aiolochroia crassa was col- 3-Bromo-N,N,N,O-tetramethyltyrosinium (3) lected at a depth of about 10 m from Urabá Gulf, Caribbean Sea, Brown solid; -5 (c 0.01, MeOH); UV (MeOH) λmax nm (log ε) Colombia (8°40’14”N, 77°21’28W) in October 2008 and identified 277.3 (3.0); IR (neat) 3350, 1630, 1550, 1055 and 650 cm-1. ESI-MS by S. Ospina. A voucher sample (INV-POR 0075) has been deposited m/z 316 (100%), 318 (90%) [M]+. Spectroscopic NMR and MS data in the sponge collection of Museo de Historia Natural Marina de matched those previously published.14 Colombia, Invemar. The sponge was kept frozen at -20 °C from time of collection until the extraction process. 3,5-Dibromo-N,N,N-trimethyltyrosinium (4) Yellow solid; -1 (c 0.03, MeOH); UV (MeOH) λmax nm (log ε) Extraction and isolation 288.0 (3.04); IR (neat) 3350, 2940, 1630, 1565 and 1150 cm-1; ESI- MS m/z 380 (39%), 382 (100%), 384 (38%) [M]+. Spectroscopic A portion of A. crassa (419 g wet) was freeze-dried and ground NMR and MS data matched those previously published.14 to obtain a dry powder (96 g), which was extracted three times with a mixture of MeOH/CH2Cl2 (1:1) at room temperature for 15 min in 3,5-Dibromo- N,N,N,O-tetramethyltyrosinium (5) an ultrasonic bath to give 20.5 g of crude extract after concentration Brown solid; -6 (c 0.02, MeOH); UV (MeOH) λmax nm (log ε) under reduced pressure. The crude extract was fractionated by RP- 282.0 (3.08); IR (neat) 3350, 2945, 1635, 1570 and 680 cm-1; ESI-MS C18 vacuum liquid chromatography (elution with 500 mL of each m/z 393 (46%), 395 (100%), 397 (44%) [M]+. Spectroscopic NMR 14 solvent in a decreasing polarity gradient of H2O 100% (F1, 749.3 and MS data matched those previously published. mg), H2O-MeOH 1:1 (F2, 657.2 mg), H2O-MeOH 1:3 (F3, 310.3 mg), MeOH 100% (F4, 364.3 mg), MeOH-CH2Cl2 3:1 (F5, 197.6 Aeroplysinin-1 (6) mg) and CH2Cl2 100% (F6, 43.1 mg)). Samples were further purified Yellow solid; +149 (c 0.04, MeOH); UV (MeOH) λmax nm (log ε) by phenyl-hexyl semi-preparative HPLC column chromatography 277.2 nm (3.8); IR (neat) 3390, 2265, 1635, 1575 and 700 cm-1; ESI- (Phenomenex Gemini, 10 mm x 250 mm, 5 µm, 3.0 mL/min), using MS m/z 338 (50%), 340 (100%), 341 (8%) 342 [M+H]+. Spectroscopic gradient elution from 20% MeOH+0.1%FA to 50% over 25 min. NMR and MS data matched those previously published.15 The following were isolated from F2: 1 (4.4 mg, 0.14%), 2 (1.06 mg, 0.03%), 3 (1.28 mg, 0.04%), 4 (0.77 mg, 0.02%), 5 (1.06 mg, Biological assay 0.03%) and 6 (1.54 mg, 0.05%), Figure 1.
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