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• Chestnut shells extract valorized as a promising nutraceutical ingredient. • Total phenolics improved during in-vitro digestion. • Hydroxybenzoic, phenylpropanoic, and phenylacetic acids identified upon digestion. • Proven bioactivity on α-amylase, acetylcholinesterase, and antioxidant enzymes. • Multivariate analysis predicted the role of phenolics in extract bioactivity. Chestnut (Castanea sativa) shells (CS) are an undervalued antioxidant-rich by-product. This study explores the impact of in-vitro digestion on the bioaccessibility, bioactivity, and metabolic profile of CS extract prepared by Supercritical Fluid Extraction, aiming its valorization for nutraceutical applications. The results demonstrated significantly (p < 0.05) lower phenolic concentrations retained after digestion (38.57 µg gallic acid equivalents/mg dry weight (DW)), reaching 30% of bioaccessibility. The CS extract showed antioxidant/antiradical, hypoglycemic, and neuroprotective properties after in-vitro digestion, along with upmodulating effects on antioxidant enzymes activities and protection against lipid peroxidation. The metabolic profile screened by LC-ESI-LTQ-Orbitrap-MS proved the biotransformation of complex phenolic acids, flavonoids, and tannins present in the undigested extract (45.78 µg/mg DW of total phenolic concentration) into hydroxybenzoic, phenylpropanoic, and phenylacetic acids upon digestion (35.54 µg/mg DW). These findings sustain the valorization of CS extract as a promising nutraceutical ingredient, delivering polyphenols with proven bioactivity even after in-vitro digestion. [ABSTRACT FROM AUTHOR]