Obesity, inflammation, insulin resistance, dyslipidemia, hyperglycemia and hypertension are risk factors for cardiovascular morbidity and mortality. Recently discovered fatty acids (Fatty acid esters of hydroxy fatty acids, FAHFA) provide antiinflammatory, insulin-sensitizing and glucose-lowering effect, and show a decreased level in insulin-resistant individuals. Aim of this study was a detailed qualitative and quantitative analysis of FAHFA in plant foods, as to date only partial analyses in apple, broccoli, egg, chicken and beef are performed. In this study, 20 plant foods from everyday meals and diet plans for metabolic normalization were analysed. Analysis included a new technique: negative ionization mode of nanoLC-ESI-mass spectrometry system and postcolumn modifier addition. 16 FAHFA were analysed (hydroxyesters of palmitic, oleic, palmitoleic and stearic acids). Nanogram levels were detected, showing a significant interfood variability. Highest concentrations were found in oat. In foods with metabolic benefits, SAHSA (stearic acid hydroxystearic acid) was the most abundant FAHFA, whereas PAHSA (palmitic acid hydroxystearic acid), the only FAHFA previously investigated in anti-hyperglycemic and insulin-sensitizing manner, showed no presence in some foods. This study, along with development of new analytic methods, provided new knowledge about FAHFA composition of foods and emphasized the importance of further research in extended number of foods. Future aims are to enable incorporation of FAHFA-rich foods into diet plans targeting metabolic control, and to find adequate FAHFA carriers that could enable food enrichment.