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• L. polystachyus (LP) attracts much attention for its hypoglycemic potency. • Simultaneous analysis of α -glucosidase inhibitors by affinity separation-UPLC-MS. • Fifty-four α -glucosidase inhibitors were first identified from this plant. • The top 3 inhibitors were astilbin, morin and naringenin with reversible mechanism. • They showed 2- to 4-fold higher potency than the clinical used drug acarbose. Lithocarpus polystachyus Rehd. known as Sweet Tea in China has attracted lots of interest for its good hypoglycemic effect and the potential as a hypoglycemic agent. Based on affinity separation-UPLC-Q-TOF-MS/MS, 54 potential α -glucosidase inhibitiors were identified and 44 were structurally determined. Out of them, 41 were identified for the first time from this plant including flavonoids, fatty acids, triterpenes, alkaloids, and coumarins. Enzyme assays revealed that flavonoids exhibited higher inhibitory activity against α -glucosidase than others with astilbin (IC 50 = 6.14 μg·mL−1), morin (IC 50 = 8.46 μg·mL−1), and naringenin (IC 50 = 10.03 μg·mL−1) showing 2- to 4-fold higher potency than the positive control acarbose. They were proved as reversible inhibitors with mixed inhibition mechanism. K i (K i ') values and molecular dockings strongly supported the potency order of astilbin, morin and naringenin that showed in the enzyme assays. [ABSTRACT FROM AUTHOR]