Reactive oxygen species (ROS) are known to contribute to intracellular oxidative damage, telomere attrition, and the induction of cellular senescence. Although plant-derived polyphenols show promise in mitigating this process, their poor water solubility and bioavailability limit their practical application. To address these limitations, transglycosylated polyphenols have been developed. In this study, we evaluated four transglycosylated polyphenols (αG-Resveratrol, αG-Hesperidin, αG-Naringin, and αG-Rutin) for their capacity to reduce intracellular ROS, prevent telomere attrition, and mitigate cellular senescence. Among them, αG-Rutin exhibited the most potent antioxidant effects in vitro. Cellular studies demonstrated that αG-Rutin significantly reduced intracellular ROS and 8-oxoguanine accumulation, attenuating telomere shortening under chronic oxidative stress and replicative aging. Finally, αG-Rutin prevented oxidative stress-induced cellular senescence, suppressing senescence-associated β-galactosidase activity and interleukin-6 secretion. These findings highlight the potential of αG-Rutin as a functional food ingredient to combat telomere attrition, prevent cellular senescence, and promote healthy aging.