ABSTRACT
Monogalactosyl diglycerides with medium to long fatty acid acyl chains, were prepared and examined for antimicrobial activity against Gram positive, Gram negative bacteria and fungi. The study of their in vitro antimicrobial activity confirms the significant activity of some monogalactosyl diacylglycerol analogues and establishes for the galactose series that the 1,2-disubstitution and the octanoyl chain are the proper structural features for the maximum activity.
Subject(s)
Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Diglycerides/chemical synthesis , Diglycerides/pharmacology , Anti-Infective Agents/chemistry , Bacteria/drug effects , Diglycerides/chemistry , Fungi/drug effects , Mass Spectrometry , Microbial Sensitivity TestsABSTRACT
Monoglucosyl and monogalactosyl diglycerides (MGDGs) with medium-long length acyl chains, identified as active components in Euphorbiaceae, were synthesized. They were examined for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. MGDGs with two octanoyl groups at both 1- and 2-positions showed the most potent activity. The stereoselectivity of pancreatic lipase was investigated in vitro where the preference for the 1 position in MGDGs is strictly related to the length of the acyl chains.
Subject(s)
Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Chemistry, Pharmaceutical/methods , Diglycerides/chemistry , Lipase/chemistry , Pancreas/enzymology , Animals , Anti-Infective Agents/chemistry , Antifungal Agents/chemistry , Drug Design , Fatty Acids/chemistry , Hydrolysis , Models, Chemical , Molecular Conformation , Mucor/metabolism , Pseudomonas/metabolism , TemperatureABSTRACT
Monoglucosyl diglycerides with medium-long length fatty acid acyl chains were prepared and examined for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The study of their in vitro antimicrobial activity confirms the significant activity of some monoglucosyl diacylglycerol analogues and establishes for the glucose series that the 1,2-disubstitution and the octanoyl chain are the proper structural features for the maximum activity.
Subject(s)
Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Glycolipids/chemical synthesis , Glycolipids/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Fungi/drug effects , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Indicators and Reagents , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Spectrometry, Mass, Electrospray IonizationABSTRACT
The synthesis of a series of alpha-methylene-gamma-butyrolactones (compounds 4a, 4b, 6-12, 16, 17) and alpha,beta-unsaturated-delta-lactones (compounds 19-23, 25, 26) starting from 4,4-dimethyldihydrofuran-2,3-dione (1) has been described. Their chemical structures were assigned by spectroscopic evidence. These new compounds exhibited significantly different antiproliferative properties against cultured human tumor cell lines with their IC(50) values ranging from 0.88 to>20.00 microM.
