Glutinoin, a novel antioxidative ellagitannin from Alnus glutinosa cones with glutinoic acid dilactone moiety

Abstract

The crude aqueous ethanol extract of the cones of Alnus glutinosa (L.) Gaertn. (Betulaceae; black alder, European alder) was obtained and further partitioned between water and various organic phases. The active water and butanol phases were subjected to assay-guided (DPPH) fractionation using repetitive RP HPLC until individual compounds were isolated. Their antioxidative activities, measured as SC₅₀ values, were evaluated. The chemical structures of the isolated compounds were elucidated with the help of mass spectroscopy, (1)H NMR technique, UV spectroscopy, and chemical approaches. One novel ellagitannin, glutinoin (2), along with two known compounds, pedunculagin (1) and praecoxin D (3), were isolated and found to contribute to antioxidative activity of the A. glutinosa cones extract. The activities (SC₅₀) of 1-3 were evaluated as 0.95 (1), 1.00 (2) and 1.01 µg mL⁻¹ (3). The scavenging effects of glutinoin (2) and praecoxin D (3) were reported for the first time.