Bioactive Constituents from an Endophytic Fungus, Penicillium polonicum NFW9, Associated with Taxus fauna

Author(s): Nighat Fatima, Tawanun Sripisut, Ui J. Youn, Safia Ahmed, Ihsan ul-Haq, Ulyana Munoz-Acuna, Charles J. Simmons, Muneer A. Qazi, Muniba Jadoon, Ghee T. Tan, Esperanza J.C. de Blanco, Leng C. Chang*.

Journal Name: Medicinal Chemistry

Volume 13 , Issue 7 , 2017

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Abstract:

Background: Endophytic fungi are being recognized as vital and untapped sources of a variety of structurally novel and unique bioactive secondary metabolites in the field of natural products drug discovery. Herein, this study reports the isolation and characterization of secondary metabolites from an endophytic fungus Penicillium polonicum (NFW9) associated with Taxus fuana.

Method: The extracts of the endophytic fungus cultured on potato dextrose agar were purified using several chromatographic techniques. Biological evaluation was performed based on their abilities to inhibit tumor necrosis factor-alpha (TNF-α)-induced nuclear factor-kappa B (NF-κB) and cytotoxicity assays.

Results: Bioactivity-directed fractionation of the ethyl acetate extract of a fermentation culture of an endophytic fungus, Penicillium polonicum led to the isolation of a dimeric anthraquinone, (R)- 1,1',3,3',5,5'-hexahydroxy-7,7'-dimethyl[2,2'-bianthracene]-9,9',10,10'-tetraone (1), a steroidal furanoid (-)-wortmannolone (2), along with three other compounds (3−4). Moreover, this is the first report on the isolation of compound 1 from an endophytic fungus. All purified metabolites were characterized by NMR and MS data analyses. The stereo structure of compound 1 was determined by the measurement of specific optical rotation and CD spectrum. The relative stereochemistry of 2 was confirmed by single-crystal X-ray diffraction. Compounds 2−3 showed inhibitory activities in the TNF-α-induced NF-κB assay with IC50 values in the range of 0.47−2.11 µM. Compounds 1, 4 and 5 showed moderate inhibition against NF-κB and cancer cell lines.

Conclusion: The endophytic fungus Penicillium polonicum of Taxus fuana is capable of producing biologically active natural compounds. Our results provide a scientific rationale for further chemical investigations into endophyte-producing natural products, drug discovery and development.

Keywords: Taxus fuana, endophytic fungi, Penicillium sp., cytotoxicity, furanosteroids, natural products.

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Article Details

VOLUME: 13
ISSUE: 7
Year: 2017
Page: [689 - 697]
Pages: 9
DOI: 10.2174/1573406413666170216145121
Price: $58

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