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

  • Mar Drugs. 2019 Jun 26;17(7):383. doi: 10.3390/md17070383.
Hui-Min Zhang  1 Chuan-Xia Ju  2 Gang Li  3 Yong Sun  4 Yu Peng  5 Ying-Xia Li  6 Xiao-Ping Peng  7 Hong-Xiang Lou  8  9
Affiliations
  • 1. Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China. [email protected].
  • 2. Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China. [email protected].
  • 3. Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China. [email protected].
  • 4. Key Laboratory of Chemical Biology of Ministry of Education, Department of Natural Product Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China. [email protected].
  • 5. Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China. [email protected].
  • 6. Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China. [email protected].
  • 7. Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China. [email protected].
  • 8. Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China. [email protected].
  • 9. Key Laboratory of Chemical Biology of Ministry of Education, Department of Natural Product Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China. [email protected].
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.

Keywords
Penicillium sp.; antifungal activity; cytotoxicity; marine-derived fungus; quorum sensing; secondary metabolites.
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