First total syntheses and antimicrobial evaluation of penicimonoterpene, a marine-derived monoterpenoid, and its various derivatives

Jian-Chun Zhao; Xiao-Ming Li; James B Gloer; Bin-Gui Wang

doi:10.3390/md12063352

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First total syntheses and antimicrobial evaluation of penicimonoterpene, a marine-derived monoterpenoid, and its various derivatives

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First total syntheses and antimicrobial evaluation of penicimonoterpene, a marine-derived monoterpenoid, and its various derivatives

Jian-Chun Zhao, Xiao-Ming Li, James B Gloer and Bin-Gui Wang

Marine drugs, Vol.12(6), pp.3352-3370

06/03/2014

DOI: 10.3390/md12063352

PMCID: PMC4071580

PMID: 24897384

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Abstract

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.

Antifungal Agents - pharmacology

Fungi - drug effects

Magnetic Resonance Spectroscopy

Bacteria - drug effects

Antifungal Agents - chemical synthesis

Antifungal Agents - chemistry

Structure-Activity Relationship

Caprylates - pharmacology

Caprylates - chemistry

Monoterpenes - chemical synthesis

Anti-Bacterial Agents - chemical synthesis

Microbial Sensitivity Tests

Monoterpenes - pharmacology

Anti-Bacterial Agents - chemistry

Caprylates - chemical synthesis

Monoterpenes - chemistry

Anti-Bacterial Agents - pharmacology

Details

Title: Subtitle: First total syntheses and antimicrobial evaluation of penicimonoterpene, a marine-derived monoterpenoid, and its various derivatives
Creators: Jian-Chun Zhao - Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. jianchun017@163.com
Xiao-Ming Li - Institute of Oceanology
James B Gloer - Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA. james-gloer@uiowa.edu
Bin-Gui Wang - Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. wangbg@ms.qdio.ac.cn
Resource Type: Journal article
Publication Details: Marine drugs, Vol.12(6), pp.3352-3370
DOI: 10.3390/md12063352
PMID: 24897384
PMCID: PMC4071580
NLM abbreviation: Mar Drugs
ISSN: 1660-3397
eISSN: 1660-3397
Publisher: Switzerland
Language: English
Date published: 06/03/2014
Academic Unit: Chemistry
Record Identifier: 9983985880902771

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