Aglycone, Glycoside, or Glucuronide? Experimental and Mechanistic Insights into the Antioxidative Potential of Gossypetin, Gossypin, and Hibifolin

Oxidative stress, caused by an imbalance between reactive oxygen species and antioxidants, drives chronic diseases such as cancer and neurodegeneration. This study investigates the antioxidant potential of three flavonoids from the <i>Malvaceae</i> family─gossypetin, gossypin, and hibifolin─using DPPH (radical scavenging) and FRAP (reducing power) assays, backed by quantum mechanical computations. Gossypetin displayed exceptional scavenging (TEAC: 111.53 mM/g) and reducing power (TEAC: 155.24 mM/g), thanks to its hydroxyl-rich structure, positioning it as a promising therapeutic option for oxidative stress-related conditions. Gossypin provided moderate scavenging (TEAC: 41.68 mM/g) but robust reducing capacity (TEAC: 126.28 mM/g), making it well-suited for food preservation. Hibifolin, with its stable glucuronyl group, showed balanced scavenging and reducing abilities (TEAC: 39.99 mM/g; 94.67 mM/g), ideal for nutraceuticals. Quantum mechanical analyses revealed the mechanisms behind these antioxidant effects, shedding light on their performance.