Metabolism schemes of chlorogenic, quinic and caffeic acid derivatives in rats deduced by molecular fragments detected with optimized UPLC–APCI-MS/MS conditions

The synthesized chlorogenic, quinic, and caffeic acid derivatives with antifungal activity were investigated on their metabolism and biotransformation properties in rats detected by optimized UPLC–APCI-MS/MS conditions. The metabolic scheme was deduced from the molecular fragments detected in biotransformed samples in vivo. The ion sources of APCI and ESI under positive or negative ion polarity mode for detection molecular fragments were compared to create the optimized UPLC–MS/MS conditions. The plasma and biliary samples from rats after oral or intravenous administration of the compounds were analyzed for their biotransformation in vivo. The absorption, distribution, hepatic metabolism, and disposal from systemic circulation of the substrates, and isomerization of their metabolites would be finished in 4 h after oral administration. The detection of the metabolites after HCHO, H2N-orn-4-(octyloxy) aniline, and CH4 elimination, and isomerization of their metabolites illustrated for the metabolic pathway of chlorogenic and quinic acid derivates in vivo. Caffeic acid was found to dissociate easily from chlorogenic and caffeic acid derivatives in vivo, whereas quinic acid derivative seemed more stable in the systemic circulation of rats but had the tendency to isomerize in hepatic metabolism. In addition, in vitro incubation of the 3 substrates with pooled rat liver microsomes confirmed that CYP450 played the role in catalysis for biotransformation of these compounds.

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► Biotransformation of chlorogenic, quinic, caffeic acid derivatives was investigated.
► Metabolic scheme was deduced from the molecular fragments detected by UPLC–MS/MS.
► Isomerization of their metabolites was identified by extracted ion chromatography.