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. 2018 Feb 12;23(2):394.
doi: 10.3390/molecules23020394.

Cytotoxic and Antimicrobial Compounds from the Marine-Derived Fungus, Penicillium Species

Diaa T A Youssef  1 , Abdulrahman M Alahdal  2
Affiliations

Cytotoxic and Antimicrobial Compounds from the Marine-Derived Fungus, Penicillium Species

Diaa T A Youssef et al. Molecules. .

Abstract

The organic extract of liquid cultures of the marine-derived Penicillium sp. was investigated. Fractionation of the extracts of the fungus led to the purification and identification of two new compounds, penicillatides A (1) and B (2), together with the previously reported cyclo(R-Pro-S-Phe) (3) and cyclo(R-Pro-R-Phe) (4). The structures of compounds 1-4 were assigned by extensive interpretation of their NMR and high-resolution mass spectrometry (HRMS). The antiproliferative and cytotoxic activities of the compounds against three human cancer cell lines as well as their antimicrobial activity against several pathogens were evaluated. Compounds 2-4 displayed variable cytotoxic and antimicrobial activities.

Keywords: 2,5-diketopiperazines; cytotoxic and antimicrobial activities; marine Penicillium sp..

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of compounds 1–4.
Figure 2
Figure 2
Key COSY and HMBC correlations of 1 and 2.
Scheme 1
Scheme 1
Reaction of 1-fluoro-2,4-dinitrophenyl-5-l-alanine amide (FDAA) with the hydrolytic product of compound 1 (l-leucine).
Scheme 2
Scheme 2
Reaction of FDAA with the hydrolytic product of compound 2 (l-proline).
Figure 3
Figure 3
MM2 energy-minimized drawing of 2 showing an important NOE correlation.
See this image and copyright information in PMC

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