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A New Furfural Diglycoside and Other Carbohydrate Derivatives from Fermented Beverage of Prunus mume Fruit
A New Furfural Diglycoside and Other Carbohydrate Derivatives from Fermented Beverage of Prunus mume Fruit
Bulletin of the Korean Chemical Society. 2014. Jul, 35(7): 2162-2164
Copyright © 2014, Korea Chemical Society
  • Received : February 13, 2014
  • Accepted : March 10, 2014
  • Published : July 20, 2014
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About the Authors
Xi-Tao Yan
Wei Li
Ya-Nan Sun
Seo Young Yang
Gyu Yong Song
Young Ho Kim

Abstract
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Experimental
Plant Materials. Fresh green fruits of P. mume (10 kg) were purchased from local markets (Yuseong, Daejeon, Korea) in June 2012 and authenticated by one of the authors, Prof. Young Ho Kim. Thick, fermented P. mume beverage was obtained by mixing cleaned fruits of P. mume (10 kg) with sugar (7 kg) and storing the mixture in the dark at room temperature for 3 months. During this time, the mixture was stirred weekly. To obtain the final beverage, fermentation residue and seeds were filtered from the fermentation broth.
Extraction and Isolation. Thick fermented beverage of P. mume fruit (4.5 L) were firstly diluted with distilled water (10.5 L) to 15 L. The dilution was subjected to adsorptive macroporous resins HP-20 column chromatography (CC) and eluted successively with distilled water, 25% aqueous MeOH, 50% aqueous MeOH, 75% aqueous MeOH, and 100% MeOH to yield 5 fractions, respectively. The 25% MeOH elute (9.4 g) was further subjected to silica gel CC eluted with CH 2 Cl 2 /MeOH/H 2 O (8:1:0.1 – 2:1:0.1) to afford 12 fractions (Frs. W1 – W12). Fr. W1 was separated by repeated RP-C 18 CC (MeOH-H 2 O, 1:10) to yield 2 (11 mg) and 3 (5 mg). Fr. W4 was purified on a RP-C 18 column (Me 2 CO-H 2 O, 1:20) to yield 14 (110 mg). Fr. W5 was subjected to RP-C 18 CC (MeOH/H 2 O, 1:30) to yield three subfractions (Frs. W5-1 – W5-3). Compound 1 (6 mg) was obtained by the separation of Fr. W5-2 on a silica gel column (EtOAc/MeOH, 10:1) and 16 (7 mg) was obtained by the separation of Fr. W5-3 on a silica gel column (CHCl 3 /94% EtOH, 5:2). 18 (426 mg), 17 (266 mg), and 15 (39 mg) were obtained by the separation of Frs. W9, W10, and W12 on a RP-C 18 column (MeOH/H 2 O, 1:25), respectively. The 50% MeOH elute (5.1 g) was subjected to silica gel CC eluted with CH 2 Cl 2 /MeOH/H 2 O in a gradient (8:1:0.1 – 3:1:0.1) to afford 11 fractions (Frs. M1 – M11). 11 (3 mg) and 19 (5 mg) were obtained by the separation of Fr. M1 on a RP-C 18 column (MeOH/H 2 O, 1:15 – 1:5) and a silica gel column (CHCl 3 /94% EtOH, 30:1 – 10:1). Fr. M4 was subjected to RP-C 18 CC (Me 2 CO /H 2 O, 1:20) to yield 4 (200 mg). Fr. M7 was purified on a silica gel column (CHCl 3 /MeOH, 5:1) and a RP-C 18 column (MeOH/H2O, 1:4) to yield 8 (9 mg). Fr. M8 was subjected to silica gel CC (EtOAc/94% EtOH, 5:1 – 5:2) and RP-C 18 CC (MeOH/H 2 O, 1:12) to yield 12 (4 mg), 6 (105 mg), and 7 (135 mg). Fr. M9 was separated on a RPC 18 column (MeOH/H 2 O, 1:7 – 1:2) to afford 10 (3 mg) and 9 (5 mg). Fr. M10 was subjected to RP-C 18 CC (Me 2 CO/ MeOH/H 2 O, 0.2:1:10 – 0:1:3) and silica gel CC (CHCl 3 / 94% EtOH, 4:1 – 3:2) to yield 5 (12 mg) and 13 (2 mg).
5-[β-D-Fructopyranosyl-(2→6)-α-D-glucopyranosyloxymethyl]- 2-furancarboxaldehyde (1): Colorless syrup;
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+47.2 ( c = 1.0, MeOH); UV (MeOH) λ max (log ε ): 278 nm (3.65); IR (KBr) ν max : 3362, 2927, 1666, 1027 cm −1; HRESI- MS (positive mode): m/z 473.1295 [M+Na] + (calcd for C 18 H 26 O 13 Na, 473.1266); 1 H- and 13 C-NMR (600/150 MHz, CD 3 OD) data, see Table 1 .
Acknowledgements
Supporting Information.General experimental procedures, hydrolysis procedure and NMR spectra of compound 1 are available as supporting information.
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