New Flavoalkaloids with Potent α-Glucosidase and Acetylcholinesterase Inhibitory Activities from Yunnan Black Tea ‘Jin-Ya’

Journal of Agricultural and Food Chemistry
2020.0

Abstract

As a subgroup of flavoalkaloids, N-ethyl-2-pyrrolidinone substituted flavan-3-ols are reported to possess various biological activities that may play important roles in the beneficial healthcare functions of tea. The HPLC and LC-MS analyses showed the existence of N-ethyl-2-pyrrolidinone substituted flavan-3-ols in 'Jin-Ya', which is a Yunnan black tea produced only from the buds of the tea plant Camellia sinensis var. assamica. Further phytochemical study on this precious black tea led to the identification of 8 flavoalkaloids, 1-8, along with 11 known flavan-3-ols (9-14) and flavonol glycosides (15-19). The new compounds, (-)-6-(5''S)-N-ethyl-2-pyrrolidinone-epiafzelechin (1), (-)-8-(5''R)-N-ethyl-2-pyrrolidinone-epiafzelechin-3-O-gallate (2a), and (-)-8-(5''S)-N-ethyl-2-pyrrolidinone-epiafzelechin-3-O-gallate (2b), were identified based on extensive spectroscopic analysis. Flavoalkaloids 2-6 showed inhibitory activity on alpha-glucosidase with IC(50) values ranging from 2.09 to 8.47 muM, compared to those of quercetin and acarbose (IC(50) = 6.87 and 228.9 muM, respectively). Moreover, compounds 2, 3, and 6 displayed an inhibitory effect on acetyl-cholinesterase with IC(50) values of 14.23, 33.79, and 34.82 muM, respectively, compared to tacrine (IC(50) = 0.223 muM).

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