Identification, quantification and antioxidant activity of acylated flavonol glycosides from sea buckthorn (Hippophae rhamnoides ssp. sinensis)

Abstract

A novel acylated flavonol glycoside: isorhamnetin (3-O-[(6-O-E-sinapoyl)-β-d-glucopyranosyl-(1→2)]-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside) (1), together with two known acylated flavonol glycosides: quercetin (3-O-[(6-O-E-sinapoyl)-β-d-glucopyranosyl-(1→2)]-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside) (2) and kaempferol (3-O-[(6-O-E-sinapoyl)-β-d-glucopyranosyl-(1→2)]-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside) (3) were isolated from the n-butanol fraction of sea buckthorn (Hippophae rhamnoides ssp. sinensis) berries for the first time by chromatographic methods, and their structures were elucidated using UV, MS, 1H and 13C NMR, and 2D NMR. Compounds 1–3 showed good scavenging activities, with respective IC50 values of 8.91, 4.26 and 30.90μM toward the 2,2′-diphenyl-1-picrylhydrazyl (DPPH) radical; respective Trolox equivalent antioxidant capacities of 2.89, 4.04 and 2.44μMμM−1 toward 2,2′-azino-bis-3-ethyl-benzothiazoline-6-sulphonate (ABTS) radical. The quantitative analysis of the isolated acylated flavonol glycosides was performed by HPLC–DAD method. The contents of compounds 1–3 were in the range of 12.2–31.4, 4.0–25.3, 7.5–59.7mg/100g dried berries and 9.1–34.5, 75.1–182.1, 29.2–113.4mg/100g dried leaves, respectively.