Institutional Repository of Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences
| First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-Derived Monoterpenoid, and Its Various Derivatives | |
Zhao, Jian-Chun1,2; Li, Xiao-Ming1; Gloer, James B.3; Wang, Bin-Gui1 ; Wang, BG (reprint author), Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266071, Peoples R China.
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| 2014-06-01 | |
| 发表期刊 | MARINE DRUGS
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| 卷号 | 12期号:6页码:3352-3370 |
| 文章类型 | Article |
| 摘要 | The first total synthesis of marine-derived penicimonoterpene (+/-)-1 has been achieved in four steps from 6-methylhept-5-en-2-one using a Reformatsky reaction as the key step to construct the basic carbon skeleton. A total of 24 new derivatives of 1 have also been designed and synthesized. Their structures were characterized by analysis of their H-1 NMR, C-13 NMR and HRESIMS data. Some of them showed significant antibacterial activity against Aeromonas hydrophila, Escherichia coli, Micrococcus luteus, Staphylococcus aureus, Vibrio anguillarum, V. harveyi and/or V. parahaemolyticus, and some showed activity against plant-pathogenic fungi (Alternaria brassicae, Colletotrichum gloeosporioides and/or Fusarium graminearum). Some of the derivatives exhibited antimicrobial MIC values ranging from 0.25 to 4 mu g/mL, which were stronger than those of the positive control. Notably, Compounds 3b and 10 showed extremely high selectively against plant-pathogenic fungus F. graminearum (MIC 0.25 mu g/mL) and pathogenic bacteria E. coli (MIC 1 mu g/mL), implying their potential as antimicrobial agents. SAR analysis of 1 and its derivatives indicated that modification of the carbon-carbon double bond at C-6/7, of groups on the allylic methylene unit and of the carbonyl group at C-1, effectively enhanced the antimicrobial activity. |
| 关键词 | (+/-)-penicimonoterpene Total Synthesis Antimicrobial Activity Structure-activity Relationship |
| 学科领域 | Pharmacology & Pharmacy |
| DOI | 10.3390/md12063352 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000338189200014 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.qdio.ac.cn/handle/337002/24114 |
| 专题 | 实验海洋生物学重点实验室 |
| 通讯作者 | Wang, BG (reprint author), Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266071, Peoples R China. |
| 作者单位 | 1.Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Univ Iowa, Dept Chem, Iowa City, IA 52242 USA |
| 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 | Zhao, Jian-Chun,Li, Xiao-Ming,Gloer, James B.,et al. First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-Derived Monoterpenoid, and Its Various Derivatives[J]. MARINE DRUGS,2014,12(6):3352-3370. |
| APA | Zhao, Jian-Chun,Li, Xiao-Ming,Gloer, James B.,Wang, Bin-Gui,&Wang, BG .(2014).First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-Derived Monoterpenoid, and Its Various Derivatives.MARINE DRUGS,12(6),3352-3370. |
| MLA | Zhao, Jian-Chun,et al."First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-Derived Monoterpenoid, and Its Various Derivatives".MARINE DRUGS 12.6(2014):3352-3370. |
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