and visualization of the surface with BAM revealed a pronounced monolayer stabilization effect 10 with both quercetin and tiliroside, whereas rutin disrupted the monolayer structure rendering the 11 surface entirely smooth. SAXS showed a monotonous membrane thinning for all compounds 12 studied associated with an increase in the root mean square fluctuations of the membrane. Rutin, 13 quercetin and tiliroside decreased the bilayer thickness of DOPC by ~0.45 Å, 0.8 Å, and 1.1 Å at 14 6 mol %, respectively. In addition to the novelty of using lipid monolayers to systematically 15 characterize the structure activity relationship (SAR) of a variety of flavonoids; this is the first 16 report investigating the effect of tiliroside with biomimetic membrane models. All the flavonoids 17 studied are believed to be localized in the lipid/water interface region. Both this localization and 18 the membrane perturbations have implications for their therapeutic activity.