Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa

Galeano, Elkin; Martínez, Alejandro Martínez; Thomas, Olivier P.; Robledo, Sara M.; Muñoz, Diego A.

doi:10.1590/s0100-40422012000600023

Cited by 13 publications

(11 citation statements)

References 11 publications

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“…A collection of 11 well-known bromotyrosines that was isolated from the Columbian sponges Verongula rigida [ 107 , 116 ] and Aiolochoria crassa [ 117 ] were examined for in vitro inhibition of HIV-1 replication [ 118 ]. Of these 11, six inhibit HIV-1 replication at different steps.…”

Section: Antiviral Compoundsmentioning

confidence: 99%

Biological Activity of Recently Discovered Halogenated Marine Natural Products

2015

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Section: Antiviral Compoundsmentioning

confidence: 99%

Biological Activity of Recently Discovered Halogenated Marine Natural Products

2015

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“…[5][6][7][8] We reported isolations and identifications of more than sixteen bromotyrosine isolated from sponges Verongula rigida and Aiolochroia crassa with antiparasitic activity, and we found a close relationship between the degree of bromination in the aromatic ring, the methylation in the amino group and their influence in the antiparasitic activity. 9 Due to the emerging resistance against current drugs, it is mandatory to develop new, safer and more effective antiparasitic agents. For that reason, in the present study, the potentials of marine natural products derivatives compounds, based on bioactive L-bromotyrosines, were evaluated as new antiparasitic compounds.…”

Section: Introductionmentioning

confidence: 99%

Anti-Parasite and Cytotoxic Activities of Chloro and Bromo L-Tyrosine Derivatives

Restrepo¹,

Galeano²,

Martínez³

et al. 2018

J. Braz. Chem. Soc.

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A series of twenty-one L-tyrosine derivatives with modifications in the halogenation pattern of the aromatic ring and different degree of methylations on the amine and phenolic hydroxyl groups were synthesized. The structures of all the intermediates and target compounds were confirmed unambiguous by spectroscopy analysis. Additionally, all compounds were evaluated against Plasmodium falciparum and Leishmania panamensis parasites between 20-702 µg mL -1 . The cytotoxic evaluation was done to determine the selectivity index for each compound. Six compounds had the lower EC 50 (effective concentration 50) against L. panamensis. One of these compounds was the most active with an EC 50 at 24.13 µg mL -1 (76.07 µM). All derivatives showed no significant activity against P. falciparum and no compound has in vitro antifungal activity at 500 µg mL -1 .

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“…The ICP-MS EICs, selected for the 127 I and 79 Br isotopes, together with the matching HRESI EICs and the corresponding mass spectra of selected peaks from LC-ICP-MS/ESI-MS of the methanolic extract from Didemnum sp 2 are presented in 26 and was found to be inactive in both anti-fouling and anti-parasitic bioassays. 30,31 The iodine ( 127 I) ICP-MS EIC (Fig. 5a) (Fig.…”

Section: Resultsmentioning

confidence: 99%

Hyphenated LC-ICP-MS/ESI-MS identification of halogenated etabolites in South African marine ascidian extracts

et al. 2018

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Extracts of 13 species of marine ascidian collected in Algoa Bay were analyzed by LC-ICP-MS/ESI-MS. This technique allows parallel analysis of the molecular species and the presence of certain elements. The LC-ICP-MS/ESI-MS technique was used to target iodinated metabolites in this study. Three ascidian species afforded the known 3,5-diiodo-4-methoxyphenethylamine (12), which was confirmed by the isolation of this metabolite from Aplidium monile. MS also suggested the presence of the known 3,5-dibromo-4-methoxyphenethylamine (10) and the new 3-bromo-5-iodo-4-methoxyphenethylamine (11) in the A. monile extract. The presence of the known 3,5-dibromotetramethyltyrosine (21) and the new 3-iodotetramethyltyrosine (23) in extracts of an unidentified Didemnum species was similarly proposed from MS evidence. This is the first report of the occurrence of iodinated metabolites in South African marine invertebrates. KEYWORDS Marine, ascidian, iodinated tyramine, iodinated tyrosine, LC-ICP-MS/ESI-MS.

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Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa

Cited by 13 publications

References 11 publications

Biological Activity of Recently Discovered Halogenated Marine Natural Products

Biological Activity of Recently Discovered Halogenated Marine Natural Products

Anti-Parasite and Cytotoxic Activities of Chloro and Bromo L-Tyrosine Derivatives

Hyphenated LC-ICP-MS/ESI-MS identification of halogenated etabolites in South African marine ascidian extracts

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