Introduction: studies performed to Myrmekioderma genus sponges show phospholipid fatty acids, volatile compounds, sterols, bioactive cyclic diterpenes, sesquiterpenes, lineal diterpenes and glycolipid ethers. Objetive: to evaluate the antiproliferative effect of seven fractions (F1-F7) obtained by flash column chromatography from the most bioactive extract of the sponge Myrmekioderma gyroderma, and to analyze the chemical composition of the most active fraction. Methods: samples of dried sponge were extracted with two different solvents: CH2Cl2 (2 x 50 mL), and CH3OH (2 x 50 mL). Each fraction was evaluated on tumor cell derived cell lines; and the cell growth, and viability were determined by a colorimeter assay using sulforhodamine B. Fatty acids structure of the most active fraction was possible by GC-MS analysis of the methyl ester, and pyrrolidine derivatives. Results: the fraction with higher activity on the assessed tumor cell lines is F4 due to it totally inhibited MDA-MB-231, and HT29 cell line growth to 5, and 25 µg/mL concentration (IC50< 1 µg/mL). Fatty acids identified in bioactive F4 fraction of the M. gyroderma sponge can be classified on the following groups: lineal chain saturated, branched-saturated, unsaturated, and a 3-hydroxy acid. Conclusions: 43 fatty acids among saturated, branched-saturated, and unsaturated were identified out of the F4 fraction with activity on the cell lines derived of breast cancer MDA-MB-231, colon carcinoma HT29, and lung carcinoma cells A-549. These results show the growth inhibitory effect shown by the fractions, on the tumor cell lines, depends on the dose.

Introducción: los estudios realizados a esponjas del género Myrmekioderma muestran la presencia de ácidos grasos de fosfolípidos, compuestos volátiles, esteroles, diterpenos cíclicos bioactivos, sesquiterpenos, diterpenos lineales y éteres glicolipídicos. Objetivo: evaluar el efecto antiproliferativo de siete fracciones (F1-F7) obtenidas por cromatografía en columna instantánea del extracto más activo de la esponja Myrmekioderma gyroderma, y analizar la composición química de la fracción más activa. Métodos: se extrajeron las muestras de esponja seca con dos solventes diferentes: CH2Cl2 (2 x 50 mL) y CH3OH (2 x 50 mL). Se evaluó cada fracción en líneas celulares derivadas de células tumorales, y se determinó el crecimiento celular y la viabilidad mediante un ensayo colorimétrico usando sulforhodamina B. Se realizó la identificación de los ácidos grasos de la fracción más activa mediante el análisis por cromatografía de gases acoplada a espectrometría de masas de los derivados ésteres metílicos y pirrolididas. Resultados: la fracción más activa fue la F4, debido a que inhibió totalmente el crecimiento de las líneas celulares MDA-MB-231 y HT29 a 5 y 25 µg/mL (IC50< 1 µg/mL). Los ácidos grasos identificados se pueden clasificar en los siguientes grupos: saturados de cadena lineal, saturados-ramificados, insaturados y un hidroxiácido. Se identificaron 43 ácidos grasos entre saturados, saturados-ramificados e insaturados en la fracción con mayor actividad sobre las líneas celulares derivadas de cáncer de mama MDA-MB-231, carcinoma de colon HT29 y carcinoma de pulmón A-549. Conclusiones: los resultados muestran que el efecto inhibitorio del crecimiento de las fracciones sobre las líneas celulares evaluadas depende de la dosis.

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.

Bioguided fractionation of Agelas cerebrum crude extract resulted in isolation of four bromopyrrole and four bromopyrrole aminoimidazole alkaloids, identified as 5-bromopyrrole-2-carboxylic acid (1), 4-bromopyrrole-2-carboxylic acid (2), 3,4-bromopyrrole-2-carboxylic acid (3), 4,5-bromopyrrole-2-carboxylic acid (4), oroidin (5), bromoageliferin (6), dibromoageliferin (7) and dibromosceptrin (8) on the basis of spectroscopic data analyses (UV, IR, HRMS, 1D and 2D NMR) and comparison with literature data. This is the first report of compounds 2 and 3 in a marine sponge belonging to the Agelas genus and the first evidence of the presence of 1 from a natural source.