Synthesis of a New Benzylated Derivative of Rutin and Study of Its Cosmetic Applications

This study aimed to obtain a derivative of rutin that has biological activities for cosmetic applications. The benzylated derivative of rutin was prepared through a substitution reaction of the hydrogens and aromatic rings of rutin by benzylation with benzyl bromide, and the product of this synthesis was encoded as RuDiOBn. The structural elucidation of the compound was performed using NMR and LC-MS/MS. Assays were performed to examine antioxidant (DPPH, ABTS, and cellular antioxidant) content, enzyme and glycation inhibition, cytotoxicity, proliferation, and inhibition of collagen production. In the in vitro glycation assay, RuDiOBn inhibited the formation of advanced glycation end products in collagen via the glyoxal pathway, with an IC₅₀ (μg/mL) equal to 2.45 ± 0.47. In the cytotoxicity evaluation, RuDiOBn showed no toxicity to human fibroblasts. Regarding its proliferative activity, there was a significant stimulation in cell proliferation and migration, and it increased the synthesis of collagen deposited in the cell matrix. In the inhibitory activity on collagenase, using the zymographic method, RuDiOBn showed the inhibition of metalloproteinases. Our study presents a benzylated derivative of rutin and aspects of its efficacy and safety for application as a new bioactive cosmetic product.