Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7

Abstract

Fifteen compounds, including six quinone/hydroquinone meroterpenoids, purpurogemutantin (1), macrophorin A (2), 4′-oxomacrophorin (3), 7-deacetoxyyanuthone A (4), 2,3-hydro-deacetoxyyanuthone A (5), 22-deacetylyanuthone A (6), anicequol (7), three roquefortine derivatives, roquefortine C (8), (16S)-hydroxyroquefortine C (9), (16R)-hydroxyroquefortine C (10), dihydroresorcylide (11), nectriapyrone (12), together with three fatty acid derivatives, methyl linoleate (13), phospholipase A₂ (14), methyl elaidate (15), were isolated from the sponge-derived fungus Gliomastix sp. ZSDS1-F7 isolated from the sponge Phakellia fusca Thiele collected in the Yongxing island of Xisha. Their structures were elucidated mainly by extensive NMR spectroscopic and mass spectrometric analyses. Among these compounds, compounds 1–3 and 5–7 showed significant in vitro cytotoxicities against the K562, MCF-7, Hela, DU145, U937, H1975, SGC-7901, A549, MOLT-4 and HL60 cell lines, with IC₅₀ values ranging from 0.19 to 35.4 μM. And compounds 2–4 exhibited antitubercular activity with IC₅₀ values of 22.1, 2.44 and 17.5 μM, respectively. Furthermore, compound 7 had anti-enterovirus 71 activity with MIC value of 17.8 μM. To the best of our knowledge, this is the first report to product two quinone/hydroquinone meroterpenoids skeletons (linear skeleton and drimane skeleton) from the same fungal strain.

Keywords:

• Sponge-derived fungus
• Phakellia fusca Thiele
• meroterpenoid
• roquefortine
• cytotoxic activity
• antitubercular activity
• anti-enterovirus 71 activity

Acknowledgements

We are grateful to Dr Z. Xiao, A. Sun, C. Li and Y. Zhang in the analytical facility at SCSIO for recording spectroscopic data.