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Mar. Drugs 2014, 12(6), 3352-3370;

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

Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China
University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, China
Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA
Author to whom correspondence should be addressed.
Received: 28 February 2014 / Revised: 8 April 2014 / Accepted: 10 April 2014 / Published: 3 June 2014
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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 1H NMR, 13C 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 μg/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 μg/mL) and pathogenic bacteria E. coli (MIC 1 μg/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. View Full-Text
Keywords: (±)-penicimonoterpene; total synthesis; antimicrobial activity; structure-activity relationship (±)-penicimonoterpene; total synthesis; antimicrobial activity; structure-activity relationship

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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Zhao, J.-C.; Li, X.-M.; Gloer, J.B.; Wang, B.-G. First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-Derived Monoterpenoid, and Its Various Derivatives. Mar. Drugs 2014, 12, 3352-3370.

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