Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A New Furfural Diglycoside and Other Carbohydrate Derivatives from Fermented Beverage of Prunus mume Fruit

  • Yan, Xi-Tao (College of Pharmacy, Chungnam National University) ;
  • Li, Wei (College of Pharmacy, Chungnam National University) ;
  • Sun, Ya-Nan (College of Pharmacy, Chungnam National University) ;
  • Yang, Seo Young (College of Pharmacy, Chungnam National University) ;
  • Song, Gyu Yong (College of Pharmacy, Chungnam National University) ;
  • Kim, Young Ho (College of Pharmacy, Chungnam National University)
  • Received : 2014.02.13
  • Accepted : 2014.03.10
  • Published : 2014.07.20
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Abstract

Keywords

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 CH2Cl2/MeOH/H2O (8:1:0.1 – 2:1:0.1) to afford 12 fractions (Frs. W1 – W12). Fr. W1 was separated by repeated RP-C18 CC (MeOH-H2O, 1:10) to yield 2 (11 mg) and 3 (5 mg). Fr. W4 was purified on a RP-C18 column (Me2CO-H2O, 1:20) to yield 14 (110 mg). Fr. W5 was subjected to RP-C18 CC (MeOH/H2O, 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 (CHCl3/94% 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-C18 column (MeOH/H2O, 1:25), respectively. The 50% MeOH elute (5.1 g) was subjected to silica gel CC eluted with CH2Cl2/MeOH/H2O 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-C18 column (MeOH/H2O, 1:15 – 1:5) and a silica gel column (CHCl3/94% EtOH, 30:1 – 10:1). Fr. M4 was subjected to RP-C18 CC (Me2CO /H2O, 1:20) to yield 4 (200 mg). Fr. M7 was purified on a silica gel column (CHCl3/MeOH, 5:1) and a RP-C18 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-C18 CC (MeOH/H2O, 1:12) to yield 12 (4 mg), 6 (105 mg), and 7 (135 mg). Fr. M9 was separated on a RPC18 column (MeOH/H2O, 1:7 – 1:2) to afford 10 (3 mg) and 9 (5 mg). Fr. M10 was subjected to RP-C18 CC (Me2CO/ MeOH/H2O, 0.2:1:10 – 0:1:3) and silica gel CC (CHCl3/ 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; +47.2 (c = 1.0, MeOH); UV (MeOH) λmax (logε): 278 nm (3.65); IR (KBr) νmax: 3362, 2927, 1666, 1027 cm−1; HRESI- MS (positive mode): m/z 473.1295 [M+Na]+ (calcd for C18H26O13Na, 473.1266); 1H- and 13C-NMR (600/150 MHz, CD3OD) data, see Table 1.

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