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

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 (<b...

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Main Authors:	Hui-Min Zhang, Chuan-Xia Ju, Gang Li, Yong Sun, Yu Peng, Ying-Xia Li, Xiao-Ping Peng, Hong-Xiang Lou
Format:	Article
Language:	English
Published:	MDPI AG 2019-06-01
Series:	Marine Drugs
Subjects:	marine-derived fungus <i>Penicillium</i> sp. secondary metabolites quorum sensing cytotoxicity antifungal activity
Online Access:	https://www.mdpi.com/1660-3397/17/7/383

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spelling	doaj-76648a3a97604996a53dc1867c071cad2020-11-25T00:32:08ZengMDPI AGMarine Drugs1660-33972019-06-0117738310.3390/md17070383md17070383Dimeric 1,4-Benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. L129Hui-Min Zhang0Chuan-Xia Ju1Gang Li2Yong Sun3Yu Peng4Ying-Xia Li5Xiao-Ping Peng6Hong-Xiang Lou7Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, ChinaDepartment of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, ChinaDepartment of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, ChinaKey Laboratory of Chemical Biology of Ministry of Education, Department of Natural Product Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, ChinaDepartment of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, ChinaDepartment of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, ChinaDepartment of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, ChinaDepartment of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, ChinaTwo new dimeric 1,4-benzoquinone derivatives, peniquinone A (<b>1</b>) and peniquinone B (<b>2</b>), a new dibenzofuran penizofuran A (<b>3</b>), and a new pyrazinoquinazoline derivative quinadoline D (<b>4</b>), together with 13 known compounds (<b>5</b>−<b>17</b>), were isolated from a marine-derived fungus <i>Penicillium</i> sp. L129. Their structures, including absolute configurations, were elucidated by extensive spectroscopic data and electronic circular dichroism calculations. Compound <b>1</b> exhibited cytotoxicity against the MCF-7, U87 and PC3 cell lines with IC<sub>50</sub> values of 12.39 µM, 9.01 µM and 14.59 µM, respectively, while compound <b>2</b> displayed relatively weak cytotoxicity activities against MCF-7, U87 and PC3 cell lines with IC<sub>50</sub> values of 25.32 µM, 13.45 µM and 19.93 µM, respectively. Furthermore, compound <b>2</b> showed weak quorum sensing inhibitory activity against <i>Chromobacterium violaceum</i> CV026 with an MIC value of 20 μg/well.https://www.mdpi.com/1660-3397/17/7/383marine-derived fungus<i>Penicillium</i> sp.secondary metabolitesquorum sensingcytotoxicityantifungal activity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Hui-Min Zhang Chuan-Xia Ju Gang Li Yong Sun Yu Peng Ying-Xia Li Xiao-Ping Peng Hong-Xiang Lou
spellingShingle	Hui-Min Zhang Chuan-Xia Ju Gang Li Yong Sun Yu Peng Ying-Xia Li Xiao-Ping Peng Hong-Xiang Lou Dimeric 1,4-Benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. L129 Marine Drugs marine-derived fungus <i>Penicillium</i> sp. secondary metabolites quorum sensing cytotoxicity antifungal activity
author_facet	Hui-Min Zhang Chuan-Xia Ju Gang Li Yong Sun Yu Peng Ying-Xia Li Xiao-Ping Peng Hong-Xiang Lou
author_sort	Hui-Min Zhang
title	Dimeric 1,4-Benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. L129
title_short	Dimeric 1,4-Benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. L129
title_full	Dimeric 1,4-Benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. L129
title_fullStr	Dimeric 1,4-Benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. L129
title_full_unstemmed	Dimeric 1,4-Benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. L129
title_sort	dimeric 1,4-benzoquinone derivatives with cytotoxic activities from the marine-derived fungus <i>penicillium</i> sp. l129
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2019-06-01
description	Two new dimeric 1,4-benzoquinone derivatives, peniquinone A (<b>1</b>) and peniquinone B (<b>2</b>), a new dibenzofuran penizofuran A (<b>3</b>), and a new pyrazinoquinazoline derivative quinadoline D (<b>4</b>), together with 13 known compounds (<b>5</b>−<b>17</b>), were isolated from a marine-derived fungus <i>Penicillium</i> sp. L129. Their structures, including absolute configurations, were elucidated by extensive spectroscopic data and electronic circular dichroism calculations. Compound <b>1</b> exhibited cytotoxicity against the MCF-7, U87 and PC3 cell lines with IC<sub>50</sub> values of 12.39 µM, 9.01 µM and 14.59 µM, respectively, while compound <b>2</b> displayed relatively weak cytotoxicity activities against MCF-7, U87 and PC3 cell lines with IC<sub>50</sub> values of 25.32 µM, 13.45 µM and 19.93 µM, respectively. Furthermore, compound <b>2</b> showed weak quorum sensing inhibitory activity against <i>Chromobacterium violaceum</i> CV026 with an MIC value of 20 μg/well.
topic	marine-derived fungus <i>Penicillium</i> sp. secondary metabolites quorum sensing cytotoxicity antifungal activity
url	https://www.mdpi.com/1660-3397/17/7/383
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Dimeric 1,4-Benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. L129

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