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Although tremendous efforts have been devoted to the structural and functional tailoring of natural polyphenol-functionalized nanoparticles,preparing ultrasmall sized (＜ 6 nm) particles with precisely-defined structures has remained a grand challenge.In this work,we reported the preparation of ultra-small and precisely structured polyhedral oligomeric silsesquioxanes (POSS)-based polyphenol nanoparticles (T8-,T10-,and T12-GAPOSS) by accurately functionalizing the POSS surface with plant polyphenol gallic acid units via thiol-Michael “click” reactions.Those polyphenol nanoparticles exhibited strong free radical scavenging capacity,good biocompatibility and ability to resist ceil oxidative damage,which demonstrated great potentials in inhibiting oxidative stress induced pathologies.