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A New Phloroglucinol Glucoside from the Whole Plants of Glochidion eriocarpum
A New Phloroglucinol Glucoside from the Whole Plants of Glochidion eriocarpum
Bulletin of the Korean Chemical Society. 2014. Feb, 35(2): 631-634
Copyright © 2014, Korea Chemical Society
  • Received : September 16, 2013
  • Accepted : November 11, 2013
  • Published : February 20, 2014
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About the Authors
Yanming Wang
University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China
Hongtao Zhu
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China
Dong Wang
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China
Rongron Cheng
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China
Chongren Yang
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China
Min Xu
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China
Yingjun Zhang
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

Abstract
Keywords
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Experimental
General Procedures. Optical rotations were performed on a P-1020 polarimeter (JASCO, Tokyo, Japan). IR spectra were measured on a Bruker Tensor 27 spectrometer with KBr pellets. UV spectra were obtained on a 210A double-beam spectrophotometer (Shimadzu, Kyoto, Japan). 1D- and 2D-NMR spectra were run on Bruker DRX-500 and AV-600 instruments operating at 500 and 600 MHz for 1 H, and 125 and 150 MHz for 13 C, respectively. The MS data were recorded on a VG Auto Spec-3000 spectrometer (VG, Manchester, U.K.). HREIMS were recorded on a Waters Autospec Premier P776. Column chromatography (CC) was performed with Diaion HP20SS (Mitsubishi Chemical Industry, Ltd.), silica gel (200-300 mesh, Qingdao Haiyang Chemical Co., Ltd., Qingdao, People’s Republic of China), and Sephadex LH-20 (25-100 μm, Pharmacia Fine Chemical Co. Ltd. Japan).Thin-layer chromatography (TLC) was carried out on silica gel H-precoated plates (Qingdao Haiyang Chemical Co., Ltd., Qingdao, People’s Republic of China) with CHCl 3 /MeOH/H 2 O (8.5:1.5:0.1, 8:2:0.2 or 7:3:0.5, v/v) as develop-ing solvents. Spots were detected by spraying with 10% H 2 SO 4 in EtOH followed by heating. Semi-preparative HPLC separation was performed on an Agilent 1260 liquid chromatography with a 5 μm Waters Sunfire-C18 column (10 × 250 mm, Waters, Sunfire TM, USA).
Plant Material . The whole plants of G. eriocarpum were collected from Yunnan Province, People’s Republic of China, in May 2012. Voucher specimens (KUN_0186703) were deposited at the State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences.
Extraction and Isolation. The whole plants of G . eriocarpum (1.5 kg) were extracted with MeOH (3 times, each time 3h) under reflux at 60 °C. The resulting MeOH extract (64.5 g) was applied to Diaion HP20SS column chromatography (CC), eluting with MeOH/H 2 O (0:1–1:0), to give five fractions (Fr. 1–5). Fr. 2 (7.6 g) was subjected to CC over Sephadex LH-20 (MeOH/H 2 O, 0:100, 30:70, 60:90, 100:0) and silica gel (CHCl 3 /MeOH/H 2 O, 8:2:0.2–6:4:1) to give compounds 9 (6 mg), 13 (5 mg), and 15 (10 mg). Fr. 4 (15 g) was applied to CC over Sephadex LH-20 (MeOH/H 2 O, 0:100, 30:70, 60:90, 100:0) and silica gel (CHCl 3 /MeOH/H 2 O, 8:2:0.2–6:4:1), and then the semi-preparative HPLC with a isocratic flow of H 2 O/MeCN (flowing rate: 3 ml/min, 82:18) to afford compounds 4 (5 mg), 5 (13 mg), and 7 (13 mg). The residue was chromato-graphed over MCIgel CHP-20P (MeOH/H 2 O, 5% to 100% with a 10% increment), then purified by semi-preparative HPLC (flowing rate: 5 mL/min, 82:18) to afford 1 (2 mg), 6 (22 mg), 8 (5 mg), 3 (3 mg). Fr. 5 (8.2 g) was subjected to CC over Sephadex LH-20 (MeOH/H 2 O, 0:100, 30:70, 60:90, 100:0) and silica gel (CHCl 3 /MeOH/H 2 O, 8:2:0.2–6:4:1), and then purified through the semi-preparative HPLC to afford compounds 2 (2 mg), 10 (3 mg), 11 (3 mg), 12 (5 mg), 14 (6 mg), 16 and 17 (3 mg).
2-β-D-Glucopyranosyloxy-4-methoxy-6-hydroxyisovalerophenone (1). Amorphous white powder,
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−14.1 ( c 0.10, MeOH); UV (MeOH) λ max (log ε) 204 (4.15), 224 (4.17), 284 (4.20); IR (KBr) 𝒱 max 3450, 2925, 1627, 1597, 1427, 1384, 1276, 1220, 1167, 1083 cm -1 ; HREIMS m/z 386.1572 [M] + (calcd for C 18 H 26 O 9 , 386.1577); 1 H NMR (CD 3 OD, 500 MHz) and 13 C NMR (CD 3 OD, 125 MHz) are given in Table 1 .
Cannabiside D (2). Amorphous white powder,
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−42.0 ( c 0.10, MeOH); positive ESIMS m/z 425 [M+Na] + , C 19 H 30 O 9 ; 1 H NMR (CD 3 OD, 500 MHz) and 13 C NMR (CD 3 OD, 125 MHz) are given in Table 1 .
Glochidionionoside E (3). Amorphous white powder,
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−44.1 ( c 0.10, MeOH); negative ESIMS m/z 437 [M+Cl] - , C 19 H 30 O 9 ; 1 H NMR (CD 3 OD, 600 MHz) and 13 C NMR (CD 3 OD, 150 MHz) are given in Table 1 .
Acknowledgements
This work was supported by the NSFC 21002105, the 973 Program of Ministry of Science and Technology of P. R. China (2011CB915503), the Fourteenth Candidates of the Young Academic Leaders of Yunnan Province (Min XU, 2011CI044) and by West Light Foundation of the Chinese Academy of Sciences. And the publication cost of this paper was supported by the Korean Chemical Society.Supporting Information.The1H NMR,13C NMR, DEPT and ROESY spectra measured in methanol-d4of1-3, the HSQC, HMBC, and1H-1H COSY spectra of1, the1H and13C NMR data and spectra measured in DMSO-d6of2and3are provided.
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