A novel approach for the identification and evaluation of Nonsteroidal Antiinflammatory Drugs (NSAIDs), found in olive oil is presented. The method is based on the exploitation of paper spray (PS) tandem mass spectrometry (MS/MS), which allows a high throughput screening of the active principles characterized by a dialdehyde moiety after an in situ derivatization with methoxyamine that leads to stable alkyloxime derivatives. The quantification analysis were performed in the precursor ion scan mode by comparing the signal intensity of the reference compound in the standard solution vs the signal intensity of the analytes obtained by the experiments performed on the olive oil. To verify the reliability of the proposed approach, a sample of seed oil spiked with a known amount of hydroxyoleocanthal has been analyzed leading to accuracy values in the range from 92% to 107%.The method here presented allows the direct analysis of olive oil samples in order to quickly verify its quality, providing molecular information on the presence of such anti-inflammatory molecules in a rapid and convenient way.