This study investigates the interactions of Myrsinoic acid A, a natural compound with reported anti-inflammatory and antitumor properties, with lipid monolayers composed of dipalmitoylphosphatidylcholine (DPPC) and dipalmitoylphosphatidylserine (DPPS). Utilizing tensiometry, polarization-modulation infrared reflection-absorption spectroscopy (PM-IRRAS), Brewster Angle Microscopy (BAM), and surface rheology, we analyzed how Myrsinoic acid A affects the structural and mechanical properties of these lipid systems. The PM-IRRAS spectra revealed that Myrsinoic acid A induced disorder in the DPPC monolayer, shifting CHI asymmetric stretching peaks and decreasing packing order, while DPPS remained structurally stable. Surface rheology measurements showed reduced elasticity in both lipids, with differential effects on viscosity: a decrease for DPPC and an increase for DPPS, indicating varied molecular interactions. BAM images confirmed that DPPC maintained a homogeneous morphology, while DPPS displayed aggregate formation, suggesting distinct lipid-drug interactions. These findings highlight the importance of lipid composition in modulating the effects of Myrsinoic acid A on membrane properties, providing insights into its potential therapeutic applications in targeting tumorigenic versus non-tumorigenic cells.