First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-Derived Monoterpenoid, and Its Various Derivatives

CORC > 海洋研究所 > 中国科学院海洋研究所 > 实验海洋生物学重点实验室

	First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-Derived Monoterpenoid, and Its Various Derivatives
	Zhao, Jian-Chun 1,2; Li, Xiao-Ming 1; Gloer, James B.3; Wang, Bin-Gui1
刊名	MARINE DRUGS
	2014-06-01
卷号	12 期号:6 页码:3352-3370
关键词	(+/-)-penicimonoterpene total synthesis antimicrobial activity structure-activity relationship
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.
英文摘要	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.
学科主题	Pharmacology & Pharmacy
收录类别	SCI
语种	英语
WOS记录号	WOS:000338189200014
内容类型	期刊论文
源URL	[http://ir.qdio.ac.cn/handle/337002/24114]
专题	海洋研究所_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.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
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.(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.