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

Huiqin Chen, Nihal Aktas, Belma Konuklugil, Attila Mándi, Georgios Daletos, Wenhan Lin, Haofu Dai, T. Kurtán, Peter Proksch

Research output: Contribution to journalArticle

12 Citations (Scopus)

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 4.7 μM, respectively.

Original languageEnglish
Pages (from-to)5317-5320
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number39
DOIs
Publication statusPublished - Aug 22 2015

Fingerprint

Penicillium
Porifera
Griseofulvin
Spectroscopic analysis
Cytotoxicity
Fungi
Inhibitory Concentration 50
Mass spectrometry
Lymphoma
Mass Spectrometry
Cells
Nuclear magnetic resonance
Cell Line

Keywords

  • Absolute configuration
  • Co-cultivation
  • Cytotoxicity
  • Penicillium sp.
  • Sponge-derived fungus

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chen, H., Aktas, N., Konuklugil, B., Mándi, A., Daletos, G., Lin, W., ... Proksch, P. (2015). A new fusarielin analogue from Penicillium sp. isolated from the Mediterranean sponge Ircinia oros. Tetrahedron Letters, 56(39), 5317-5320. https://doi.org/10.1016/j.tetlet.2015.07.072

A new fusarielin analogue from Penicillium sp. isolated from the Mediterranean sponge Ircinia oros. / Chen, Huiqin; Aktas, Nihal; Konuklugil, Belma; Mándi, Attila; Daletos, Georgios; Lin, Wenhan; Dai, Haofu; Kurtán, T.; Proksch, Peter.

In: Tetrahedron Letters, Vol. 56, No. 39, 22.08.2015, p. 5317-5320.

Research output: Contribution to journalArticle

Chen, H, Aktas, N, Konuklugil, B, Mándi, A, Daletos, G, Lin, W, Dai, H, Kurtán, T & Proksch, P 2015, 'A new fusarielin analogue from Penicillium sp. isolated from the Mediterranean sponge Ircinia oros', Tetrahedron Letters, vol. 56, no. 39, pp. 5317-5320. https://doi.org/10.1016/j.tetlet.2015.07.072
Chen, Huiqin ; Aktas, Nihal ; Konuklugil, Belma ; Mándi, Attila ; Daletos, Georgios ; Lin, Wenhan ; Dai, Haofu ; Kurtán, T. ; Proksch, Peter. / A new fusarielin analogue from Penicillium sp. isolated from the Mediterranean sponge Ircinia oros. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 39. pp. 5317-5320.
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