Journal
MARINE DRUGS
Volume 12, Issue 6, Pages 3352-3370Publisher
MDPI AG
DOI: 10.3390/md12063352
Keywords
(+/-)-penicimonoterpene; total synthesis; antimicrobial activity; structure-activity relationship
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Funding
- Ministry of Science and Technology of China [2013AA092901, 2010CB833800]
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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 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.
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