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• Galeano, E
• Thomas, O
• Robledo, S
• Munoz, D
• Martinez, A
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• Galeano, E
• Thomas, O
• Robledo, S
• Munoz, D
• Martinez, A
• [+] on PubMed
• Galeano, E
• Thomas, O
• Robledo, S
• Munoz, D
• Martinez, A

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Mar. Drugs 2011, 9(10), 1902-1913; doi:10.3390/md9101902

Article

Antiparasitic Bromotyrosine Derivatives from the Marine Sponge Verongula rigida

Elkin Galeano ^1,* , Olivier P. Thomas ² , Sara Robledo ³ , Diana Munoz ³  and Alejandro Martinez ¹

¹ Marine Natural Products Research Group, Pharmaceutical Chemistry Faculty, University of Antioquia, Medellin AA 1226, Colombia ² Chemical Institute of Nice, UMR 6001 CNRS, University of Nice—Sophia Antipolis, Parc Valrose, 06108, Nice Cedex 02, France ³ Program for the Study and Control of Tropical Diseases (PECET), University of Antioquia, Medellin AA 1226, Colombia

* Author to whom correspondence should be addressed.

Received: 6 September 2011; in revised form: 21 September 2011 / Accepted: 30 September 2011 / Published: 14 October 2011

Download PDF Full-Text [218 KB, uploaded 14 October 2011 10:20 CEST]

Abstract: 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.

Keywords: bromotyrosines; Verongula rigida; antiplasmodial activity; leishmanicidal activity; trypanocidal activity

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