Cytotoxic furanosesquiterpenoids and steroids from Ircinia mutans sponges.

Context: Ircinia mutans Wilson (Irciniidae) is a sponge with antimicrobial and cytotoxic constituents.
Objective: Our objective was to characterise the cytotoxic constituents of two seasonal collections of I. mutans .
Materials and Methods: The sponges were extracted in methanol-dichloromethane and their constituents were purified and characterised using column chromatography, GC-MS, 1 D and 2 D NMR. Anti-proliferative activities of the compounds, were evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay (0.25-100 μg/mL, 72 h) against leukaemia (MOLT-4), breast (MCF-7) and colon cancer (HT-29) human cells.
Results: Three furanosesquiterpoids; furodysin ( 1 ), ent -furodysinin ( 2 ) and furoircin ( 3 ) and ten sterols were characterised in I. mutans , for the first time. Cholesterol ( 4 ), cholesta-5, 7-dien-3β-ol ( 5 ) and ergosterol ( 6 ) were determined in the sponge from the winter collections, while cholesta-5, 22-dien-3β-ol ( 7 ), 24-methyldesmosterol ( 8 ), campesterol ( 9 ), stigmasterol ( 10 ), γ-ergostenol ( 11 ), chondrillasterol ( 12 ) and γ-sitosterol ( 13 ) were detected in the summer samples. The steroids from the winter collection exhibited cytotoxic activity with IC ₅₀ values of 13.0 ± 0.9, 11.1 ± 1.7 and 1.1 ± 0.4 µg/mL, against the mentioned cancer cell lines, respectively, while those from the summer sample, showed greater activity, IC ₅₀ = 1.1 ± 0.2 μg/mL against MOLT-4. The purified steroids showed potent MOLT-4 cytotoxic activity, IC ₅₀ values = 2.3-7.8 µg/mL.
Discussion and Conclusion: The present study suggests that I. mutans is a rich source of cytotoxic steroids, and introduces 3 as new natural product. Considering the high cytotoxic activity of the steroids, these structures could be candidates for anticancer drug development in future research.