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A New Stereoisomeric Acetogenic Glycoside from the Flower Buds of Buddleja officinalis
A New Stereoisomeric Acetogenic Glycoside from the Flower Buds of Buddleja officinalis
Bulletin of the Korean Chemical Society. 2014. Jul, 35(7): 2159-2161
Copyright © 2014, Korea Chemical Society
  • Received : January 17, 2014
  • Accepted : March 10, 2014
  • Published : July 20, 2014
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About the Authors
Chul Lee
Kwang-Woo Hwang
Laboratory of Host Defense Modulation, College of Pharmacy, Chung-Ang University, Seoul 156-756, Korea
So-Young Park
Laboratory of Pharmacognosy, College of Pharmacy, Dankook University, Cheonan 330-714, Korea

Abstract
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Experimental Section
General Experimental Procedures. NMR spectra were recorded on a Bruker Avance III 700 MHz NMR spectrometer using CD 3 OD as solvent, and TMS was used as an internal standard. Chemical shifts are presented in ppm. Optical rotation was evaluated on JASCO P-2000. TLC analysis was performed on a precoated silica gel 60 F 254 (0.24 mm, Merck). Open column chromatography was performed using a silica gel (Kieselgel 60, 70-230 mesh, Merck), RP 18 (Part NO. 5982-5752, Agilent), MCI CHP20P gel (75-150 μM, Mitsubishi), and Sephadex LH-20 (GE Healthcare). Semi-preparative HPLC was performed on a Shimadzu Prominence UFLC with UV detector. HRTOFMS and ESI-MS spectra were obtained using a Waters UPLC-QTOF micro, and a LCQ Fleet (Thermo Scientific), respectively. GC-MS spectra were acquired using an Agilent 6890/5973i.
Plant Materials. The flower buds of B. officianlis were purchased from a commercial market (Samhong medicinal herb market, Seoul, South Korea) in 2013. One of the authors (S.-Y. Park) performed botanical identification, and a voucher specimen has been deposited at the College of Pharmacy, Dankook University, South Korea.
Extraction and Isolation. The air-dried flower buds of B. officinalis (3 kg) were pulverized and then extracted with 100% methanol (24 L, three times) at room temperature. The methanolic filtrate was evaporated in vacuo to generate the methanolic extract (301 g), and the extract was partitioned with n -hexane, methylene chloride, ethyl acetate, n -butanol, and water, progressively. Among them, some of n -butanol extract (10 g) was loaded onto MCI gel to yield 4 subfractions (BOD1-BOD4) with a step gradient composed of methanol and water (40, 60, 80, 100% methanol). The subfraction BOD1 was further chromatographed on Sephadex LH-20 to give two portions (BOD1A-BOD1B), and BOD1A was then re-chromatographed on silica gel to generate 9 subfractions (BOD1A1-BOD1A9) with a step gradient solvent system composed of chloroform, methanol, and water (8:3:1 to 3:3:1). The subfractions BOD1A1, BOD1A6, and BOD1A7 was further purified by semi-preparative RP-HPLC (Ace, C 18 , 21.2 × 250 mm, flow rate 7 mL/min) to furnish 1 (4.5 mg), 2 (3.0 mg), 3 (5.0 mg), 4 (4.0 mg), 5 (3.0 mg), 6 (3.5 mg), 7 (7.4 mg), 8 (12 mg), and 9 (2.0 mg).
Compound 1: White powder;
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−17.0 ( c 0.15, MeOH); HRESIMS m/z 423.1860 (calcd for C 18 H 31 O 11 , 423.1866); 1 H and 13 C NMR in Table 1 .
Acid Hydrolysis of Compound 1 and Determination of Sugar Component. Compound 1 (1.0 mg) was dissolved in 1.0 N HCl (1 mL), followed by heating at 120 ℃ in a water bath for 3 h. The solvent was evaporated in vacuo , and mixture was extracted with chloroform three times over. The hydrolyzate containing sugar portion in a vial dissolved in dry pyridine (100 μL), and then L-cystein methyl ester hydrochloride in dry pyridine (0.06 M, 100 μL) was added. After heating the mixture at 60 ℃ for 2 h, NaBH 4 (2.0 mg) was added into vial, and the reaction mixture was stirred for 1 h at room temperature. Trimethylsilylimidazole solution (100 μL) was added and the reaction mixture was then heated at 60 ℃ for 2 h. The reaction mixture was evaporated in vacuo , and the dried product was then partitioned with nhexane and water. The n -hexane layer was analyzed by GCMS: the standard sugar generated peak at t R 18.95 for D-glucose.
Acknowledgements
Supporting Information.Spectroscopic data including 1D, 2D NMR, and HRTOF-MS are available as supporting information.
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