Synthesis and structure–activity relationships of novel abietane diterpenoids with activity against Staphylococcus aureus

2019 ◽  
Vol 11 (24) ◽  
pp. 3109-3124
Author(s):  
Macarena Funes Chabán ◽  
Antonia I Antoniou ◽  
Catherine Karagianni ◽  
Dimitra Toumpa ◽  
Mariana Belén Joray ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Minimum Inhibitory Concentration ◽  
Toxic Effect ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Inhibitory Concentration ◽  
Dehydroabietic Acid ◽  
Target Cells ◽  
Structure Activity ◽  
Abietane Diterpenoids ◽  
Relationship Study

Aim: To find alternative compounds against methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-susceptible S. aureus (MSSA), novel derivatives from dehydroabietic acid were synthesized. Methods & results: Compound 12 was the most effective against 15 MRSA and 11 MSSA with minimum inhibitory concentration values ranging from 3.9 to 15.6 μg/ml. Although less active than 12, compound 11, followed by 25 and 13, also exhibited anti-staphylococcal activity. Additional studies showed that compound 12 is devoid of toxic effect on non-target cells. A structure–activity relationship study revealed that an oxime at C-13 together with a hydroxyl at C-12 could play a key role in the activity. Conclusion: These structures, in particular compound 12, could arise as templates for the development of agents against MRSA and MSSA.

scholarly journals Synthesis and Antimicrobial Studies of Coumarin-Substituted Pyrazole Derivatives as Potent Anti-Staphylococcus aureus Agents

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2758 ◽  
Author(s):  
Rawan Alnufaie ◽  
Hansa Raj KC ◽  
Nickolas Alsup ◽  
Jedidiah Whitt ◽  
Steven Andrew Chambers ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Minimum Inhibitory Concentration ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Inhibitory Concentration ◽  
Fatality Rate ◽  
Pyrazole Derivatives ◽  
Methicillin Resistant ◽  
Antimicrobial Studies ◽  
Mrsa Strains

In this paper, synthesis and antimicrobial studies of 31 novel coumarin-substituted pyrazole derivatives are reported. Some of these compounds have shown potent activity against methicillin-resistant Staphylococcus aureus (MRSA) with minimum inhibitory concentration (MIC) as low as 3.125 µg/mL. These molecules are equally potent at inhibiting the development of MRSA biofilm and the destruction of preformed biofilm. These results are very significant as MRSA strains have emerged as one of the most menacing pathogens of humans and this bacterium is bypassing HIV in terms of fatality rate.

scholarly journals Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues

2019 ◽  
Vol 20 (5) ◽  
pp. 1083 ◽  
Author(s):  
Seindé Touré ◽  
Sandy Desrat ◽  
Léonie Pellissier ◽  
Pierre-Marie Allard ◽  
Jean-Luc Wolfender ◽  
...  
Keyword(s):  
Methicillin Resistant Staphylococcus Aureus ◽  
Inhibitory Concentration ◽  
Biological Evaluation ◽  
Comprehensive Analysis ◽  
Chain Fatty Acid ◽  
Long Chain Fatty Acid ◽  
Lipoamino Acids ◽  
Structure Activity ◽  
Relationship Study ◽  
Saturated Medium

A biological evaluation of a library of extracts from entomopathogen strains showed that Pantoea sp. extract has significant antimicrobial and insecticidal activities. Three hydroxyacyl-phenylalanine derivatives were isolated from this strain. Their structures were elucidated by a comprehensive analysis of their NMR and MS spectroscopic data. The antimicrobial and insecticidal potencies of these compounds were evaluated, and compound 3 showed 67% mortality against Aedes aegypti larvae at a concentration of 100 ppm, and a minimum inhibitory concentration (MIC) of 16 µg/mL against methicillin-resistant Staphylococcus aureus. Subsequently, hydroxyacyl-phenylalanine analogues were synthesized to better understand the structure-activity relationships within this class of compounds. Bioassays highlighted the antimicrobial potential of analogues containing saturated medium-chain fatty acids (12 or 14 carbons), whereas an unsaturated long-chain fatty acid (16 carbons) imparted larvicidal activity. Finally, using a molecular networking-based approach, several close analogues of the isolated and newly synthesized lipoamino acids were discovered in the Pantoea sp. extract.

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