Comazaphilones A-F, Azaphilone Derivatives from the Marine Sediment-Derived Fungus Penicillium commune QSD-17

doi:10.1021/np100788h

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	Comazaphilones A-F, Azaphilone Derivatives from the Marine Sediment-Derived Fungus Penicillium commune QSD-17
	Gao, Shu-Shan 1,3; Li, Xiao-Ming 1; Zhang, Yi 2; Li, Chun-Shun 1; Cui, Chuan-Ming 1,3; Wang, Bin-Gui1
	2011-02-01
发表期刊	JOURNAL OF NATURAL PRODUCTS
ISSN	0163-3864
卷号	74 期号:2 页码:256-261
文章类型	Article
摘要	Chemical investigation of Penicillium commune QSD-17, a fungus isolated from a marine sediment sample collected in the southern Chinai Sea, yielded six new azaphilone derivatives, namely, comazaphilones A-F (1-6). The structures of these compounds were established on the basis of spectroscopic analysis. Attempts to define the absolute configuration of these azaphilones through investigation of Mosher's esters failed, possibly due to steric crowding at C-6 and C-7 and due to the degradation of these azaphilone derivatives under the reaction conditions. The inhibitory activities of the six azaphilones against four bacteria, one pathogenic fungus, and seven tumor cell lines were evaluated. Compounds 3-5 displayed potent inhibitory activity against several of these bacteria, while compounds 4-6 showed cytotoxic activity against human pancreatic tumor cell line SW1990. The preliminary SAR results indicated that the double bond at C-10 and the location of the orsellinic acid unit at C-6 in these azaphilones are important for the antibacterial activity and cytotoxicity; respectively. This is the first report of the isolation of azaphilone derivatives from a marine sediment-derived fungus.; Chemical investigation of Penicillium commune QSD-17, a fungus isolated from a marine sediment sample collected in the southern Chinai Sea, yielded six new azaphilone derivatives, namely, comazaphilones A-F (1-6). The structures of these compounds were established on the basis of spectroscopic analysis. Attempts to define the absolute configuration of these azaphilones through investigation of Mosher's esters failed, possibly due to steric crowding at C-6 and C-7 and due to the degradation of these azaphilone derivatives under the reaction conditions. The inhibitory activities of the six azaphilones against four bacteria, one pathogenic fungus, and seven tumor cell lines were evaluated. Compounds 3-5 displayed potent inhibitory activity against several of these bacteria, while compounds 4-6 showed cytotoxic activity against human pancreatic tumor cell line SW1990. The preliminary SAR results indicated that the double bond at C-10 and the location of the orsellinic acid unit at C-6 in these azaphilones are important for the antibacterial activity and cytotoxicity; respectively. This is the first report of the isolation of azaphilone derivatives from a marine sediment-derived fungus.
学科领域	Plant Sciences ; Pharmacology & Pharmacy
DOI	10.1021/np100788h
URL	查看原文
收录类别	SCI ; IC
语种	英语
WOS记录号	WOS:000287637300021
引用统计	被引频次：64[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.qdio.ac.cn/handle/337002/11803
专题	实验海洋生物学重点实验室
作者单位	1.Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China 2.Dalian Jiaotong Univ, Sch Environm & Chem Engn, Dalian 116028, Peoples R China 3.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
第一作者单位	实验海洋生物学重点实验室
推荐引用方式 GB/T 7714	Gao, Shu-Shan,Li, Xiao-Ming,Zhang, Yi,et al. Comazaphilones A-F, Azaphilone Derivatives from the Marine Sediment-Derived Fungus Penicillium commune QSD-17[J]. JOURNAL OF NATURAL PRODUCTS,2011,74(2):256-261.
APA	Gao, Shu-Shan,Li, Xiao-Ming,Zhang, Yi,Li, Chun-Shun,Cui, Chuan-Ming,&Wang, Bin-Gui.(2011).Comazaphilones A-F, Azaphilone Derivatives from the Marine Sediment-Derived Fungus Penicillium commune QSD-17.JOURNAL OF NATURAL PRODUCTS,74(2),256-261.
MLA	Gao, Shu-Shan,et al."Comazaphilones A-F, Azaphilone Derivatives from the Marine Sediment-Derived Fungus Penicillium commune QSD-17".JOURNAL OF NATURAL PRODUCTS 74.2(2011):256-261.

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