Institutional Repository of Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences
Comazaphilones A-F, Azaphilone Derivatives from the Marine Sediment-Derived Fungus Penicillium commune QSD-17 | |
Gao, Shu-Shan1,3; Li, Xiao-Ming1; Zhang, Yi2; Li, Chun-Shun1; Cui, Chuan-Ming1,3; 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 | |
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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