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Eggplant fruits are normally harvested and marketed when they reach the commercial maturity, that precedes the physiological ripening when dramatic changes in taste, composition and peel color take place. The biochemical changes in fruit peel across the developmental stages, characterized also by a sizeable decrement of anthocyanins, were studied in four eggplant genotypes differing for fruit pigmentation. HPLC-DAD, HPLC-ESI-MS and NMR analyses identified naringenin chalcone and naringenin 7-O-glucoside as the main phenolic compounds in extracts from the physiological ripe stage, along with compounds tentatively identified as glycosylated naringenin chalcone, naringenin and kaempferol. On average, the levels of anthocyanins, responsible for the peel pigmentation, dropped by 75% during development, while, surprisingly, the level of total phenols showed a slight decrease of 16%, with a final concentration of more than 1000 mg/100g dw. RT-qPCR expression profiling of nine genes coding for enzymes putatively acting at different steps of the involved pathways showed modulation mostly consistent with the observed changes in phenolic composition, with a remarkable decrease in the activity of flavonol reductase and an increase in flavonol synthase during berry development. Antioxidant activity monitored by peroxyl scavenging was similar at all developmental stages while Fremy's analysis evidenced a slight decrement at full physiological ripening. These results are valuable to address the improvement of eggplant commercial fruit quality and the valorization of unmarketable physiological ripe fruits, especially for the newly accumulation of the health-promoting compounds chalcones and flavanones., (Copyright © 2021 Elsevier Masson SAS. All rights reserved.)