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A new fusarielin analogue from Penicillium sp. isolated from the Mediterranean sponge Ircinia oros

Author:
Chen, Huiqin, Aktas, Nihal, Konuklugil, Belma, Mándi, Attila, Daletos, Georgios, Lin, Wenhan, Dai, Haofu, Kurtán, Tibor, Proksch, Peter
Source:
Tetrahedron letters 2015 v.56 no.39 pp. 5317-5320
ISSN:
0040-4039
Subject:
Ircinia, Penicillium, cell lines, chemical reactions, chemical structure, coculture, curvularin, cytotoxicity, dehydrocurvularin, fungi, griseofulvin, inhibitory concentration 50, lymphoma, mass spectrometry, mice, nuclear magnetic resonance spectroscopy, spectral analysis
Abstract:
The marine-derived fungus Penicillium sp. (strain IO1) isolated from the Mediterranean sponge Ircinia oros yielded a new fusarielin analogue (1) together with the known compounds griseofulvin (4) and dechlorogriseofulvin (5). The structure of 1 was unambiguously elucidated by comprehensive spectroscopic analysis (1D and 2D NMR, and mass spectrometry) as well as by comparison with the literature, while the absolute configuration of 1 was determined on the basis of TDDFT ECD calculations. A further Penicillium sp. (strain IO2) that was isolated from the same sponge I. oros yielded the known compounds dehydrocurvularin (6), curvularin (7), and trichodimerol (8). Co-cultivation of both Penicillium strains (IO1 and IO2) was found to induce the accumulation of the known norlichexanthone (2) and monocerin (3) that were not detected in either of the two axenic fungal controls. Compounds 3 and 6 showed pronounced cytotoxicity against the murine lymphoma (L5178Y) cell line with IC50 values of 8.4 and 4.7μM, respectively.
Agid:
6040459