A New Furfural Diglycoside and Other Carbohydrate Derivatives from Fermented Beverage of Prunus mume Fruit

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Prunus mume Sieb. et Zucc. (Rosaceae) is a deciduous fruit tree that is distributed widely in East Asian. Its fruit, commonly known as Maesil in Korea, is a traditional raw ingredient used in herbal medicines and healthy foods in Korea, China, and Japan. In particular, a beverage produced by the fermentation of a mixture of green P. mume fruit and sugar is popular in Korea. Recent studies have shown that this fermented beverage, which contains a variety of probiotics, enhances immune activity and suppresses the development of atopic dermatitis-like skin lesions and 7,12-dimethylbenz[α]anthracene (DMBA)and 12-O-tetradecanoyl phorbol-13-acetate (TPA)-induced skin carcinogenesis in mice. Despite these findings, the chemical constituents of fermented P. mume beverage have yet to be characterized. In the present study, 19 compounds, including a new furfural diglycoside, 5-[β-D-fructopyranosyl-(2→6)-α-D-glucopyranosyloxymethyl]-2-furancarboxaldehyde (1), 16 carbohydrate derivatives (2-10 and 12-18), and two additional compounds (11 and 19) were isolated from samples of fermented P. mume fruit beverage. This is the first report detailing the chemical composition of fermented P. mume beverage and provides a useful reference for further biological investigation. This report describes the isolation and structural elucidation of compounds 1-19. The known compounds that were isolated from the fermented beverage of P. mume fruit were identified by comparisons of their physical and spectroscopic data with those reported in the literature. They were identified as 5hydroxymethyl-2-furfural (2), α-methoxy-2,5-furandimethanol (3), benzyl-β-D-glucopyranoside (4), benzyl-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside (5), benzyl-βD-xylopyranosyl-(1→6)-β-D-glucopyranoside (6), benzylα-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (7), benzyl-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (8), (2E)-7-hydroxy-3,7-dimethyl-2-octenyl α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (9), (2E)-7-hydroxy-3,7-dimethyl-2-octenyl α-L-arabinofuranosyl-(1→6)-βD-glucopyranoside (10), methyl (E)-p-coumarate (11), 3O-p-coumaroylsucrose (12), 3-O-feruloylsucrose (13), nbutyl-β-D-glucopyranoside (14), sucrose (15), methyl βD-fructopyranoside (16), D-glucopyranose (an equilibrium mixture of 64% β-D-glucopyranose and 36% α-D-glucopyranose in solution, 17), D-fructose (an equilibrium mixture of 70% β-D-fructopyranose and 22% β-D-fructofuranose in solution, 18), and tyrosol (19) (Figure 1). Compound 1 was obtained as a colorless syrup with a positive optical rotation of +47.2 (c = 1.0, MeOH). Its molecular formula was determined to be C18H26O13 by highresolution electrospray ionization mass spectrometry (HRESI-MS) at m/z 473.1295 [M+Na] (calcd for C18H26O13Na, α [ ]D 18