Cytotoxic furanosesquiterpenoids and steroids from Ircinia mutans sponges

Abstract

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.

Neuroprotective and nephroprotective effects of Ircinia sponge in polycyclic aromatic hydrocarbons (PAHs) induced toxicity in animal model: a pharmacological and computational approach

“…This is due to the richness of the members of Ircinia with steroids, macrolides, peptides, and fatty acids (Rashid et al 2001 ). Bioactive metabolites previously detected in Ircinia species include furanosesquiterpenoids (Heidary Jamebozorgi et al 2021 ), scalarane and cheilanthane sesterterpenoids (Buchanan et al 2001 ; Lai et al 2015 ), polyhalogenated peptides (Fernández et al 2020 ), indole alkaloids (Shinonaga et al 1994 ; Abdjul et al 2015 ), and terpenoids and their derivatives (Su et al 2011 ).…”

Ircinia ramosa Sponge Extract (iSP) Induces Apoptosis in Human Melanoma Cells and Inhibits Melanoma Cell Migration and Invasiveness

“…In the last few years, new data have emerging on the anticancer effect of extracts from marine sponges of the genus Ircinia. For instance, it has been recently described that Ircinia mutans (Wilson, 1925) extracts demonstrate potent cytotoxic effects on human lymphoblastic leukaemia, colorectal cancer and breast cancer cells thanks to the rich presence of furanosesquiterpoids and sterols [44]. Likewise, the dichloromethanemethanol extract of the Indo-Pacific marine sponge, Ircinia ramosa, significantly impaired the proliferation of different human cancer cell lines [15].…”

Marine natural products

“…450 More heavily rearranged sesquiterpenoids were reported from Persian Ircinia 1068 and Indonesian Lamellodysidea 1069 sponges. 451,452 Enantiomeric (+)-1070 and (−)-1071 spongiterpenes are likely artefacts of isolation from a Spongia sp. collected in China.…”