Dimeric 1,4-benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus Penicillium sp. L129.

Zhang Zhang,Peng Peng,Lou Lou,Sun Sun,Ju Ju,Li Li

doi:10.3390/md17070383

Zhang Zhang, Peng Peng + Show 4 more

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https://doi.org/10.3390/md17070383

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Journal: Marine drugs	Publication Date: Jun 26, 2019
Citations: 19	License type: CC BY 4.0

Affiliation: Qingdao University, Shandong University

Abstract

Two new dimeric 1,4-benzoquinone derivatives, peniquinone A (1) and peniquinone B (2), a new dibenzofuran penizofuran A (3), and a new pyrazinoquinazoline derivative quinadoline D (4), together with 13 known compounds (5–17), were isolated from a marine-derived fungus Penicillium sp. L129. Their structures, including absolute configurations, were elucidated by extensive spectroscopic data and electronic circular dichroism calculations. Compound 1 exhibited cytotoxicity against the MCF-7, U87 and PC3 cell lines with IC50 values of 12.39 µM, 9.01 µM and 14.59 µM, respectively, while compound 2 displayed relatively weak cytotoxicity activities against MCF-7, U87 and PC3 cell lines with IC50 values of 25.32 µM, 13.45 µM and 19.93 µM, respectively. Furthermore, compound 2 showed weak quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with an MIC value of 20 μg/well.

Highlights

Marine-derived fungi are an important resource of structurally novel and unique substances.These secondary metabolites often possess diverse biological activities, enabling producers to adapt to extremely challenging environments and contributing to the complex association with other organisms in certain ecological niches [1,2]
Its molecular formula was deduced as C17 H18 O6 with nine degrees of unsaturation according to the HRESIMS peak at m/z 319.1171 [M + H]+
The 1,4-benzoquinone ring system was confirmed by HMBC and NOESY correlations, which was further supported by comparing its NMR data with those of reported derivatives [23,24]

Summary

Introduction

Marine-derived fungi are an important resource of structurally novel and unique substances. These secondary metabolites often possess diverse biological activities, enabling producers to adapt to extremely challenging environments and contributing to the complex association with other organisms in certain ecological niches [1,2]. Enthusiasm for biologically active and novel molecules has presented opportunities in the realm of marine fungi-derived secondary metabolites. A novel diketopiperazine was characterized from the mangrove-derived Penicillium brocae. It exhibited potent cytotoxicity against both sensitive and cisplatin-resistant human ovarian cancer cells and established strong antimicrobial activity against pathogenic Staphylococcus aureus [3]. Marine-derived fungi hold great potential for the discovery of new bioactive natural products (NPs)

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