A-type procyanidin derivatives with antioxidant and much enhanced α-glucosidase inhibitor activities

doi:10.5246/jcps.2021.04.023

Abstract

Abstract:

Procyanidins are natural compounds with good biological activity. However, due to a large number of phenolic hydroxyl groups in the structure, they have high polarity and low bioavailability. The preparation of A-type proanthocyanidin derivatives is an effective way to change their polarity and biological activity. In this paper, a series of A-type procyanidin derivatives were designed and synthesized by two practical and safe methods, and two new dimeric A-type procyanidin derivatives, procyanidin A1-acetone conjugate (6) and procyanidin A2-cystein conjugate (9) were obtained and reported for the first time. Their structures were characterized and confirmed by ¹H NMR, ¹³C NMR, HMBC, ¹H-¹H COSY and MS. All the compounds showed strong DPPH scavenging activities. Compound 6 showed inhibitory effects on α-glucosidase with an IC₅₀ value of 8.7 μg/mL, while its parental compound, procyanidin A1, had no inhibitory effects. Degradation of procyanidins from peanut skin by L-cystein was studied. The results showed that the main structural unit of procyanidins in peanut skin was A-type proanthocyanidins dimer.

Key words: Peanut skin, A-type procyanidin-acetone conjugate, A-type procyanidin-cystein conjugate, Inhibition on α-glucosidase

Supporting:

Huiwen Zhang, Haiyan Xu, Yu Zhang, Chaomei Ma. A-type procyanidin derivatives with antioxidant and much enhanced α-glucosidase inhibitor activities[J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(4): 280-288.

Figures/Tables 7

Table 1. The contents of the degradation products of procyanidin polymers*.

Table 2. Comparison of 1H and 13C NMR data of compounds 3, 4, 6 and 9 (methanol-d4).

Table 3. The bioactivities of peanut skin procyanidin monomers, oligomers and their derivatives.

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