참고문헌 (35)

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2. 2 Graham R.L. Donaldson E.F. Baric R.S. Nat Rev Microbiol 11 2013 836 848 24217413 

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10. 10 Hu J.N. Zhu X.M. Han L.K. Chem Pharm Bull 56 2008 12 16 18175967 

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11. 11 Piao S. Kang M. Lee Y.J. Urology 84 2014 982.e1？7 

12. 12 Sato I. Kofujita H. Suzuki T. Kobayashi H. Tsuda S. J Vet Med Sci 68 2006 487 489 16757892 

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13. 13 Yoshikawa M. Murakami T. Matsuda H. Yamahara J. Murakami N. Kitagawa I. Chem Pharm Bull 44 1996 1454 1464 8795266 

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14. 14 Wang P. Ownby S. Zhang Z. Yuan W. Li S. Bioorg Med Chem Lett 20 2010 2790 2796 20371180 

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18. 18 Mojzisova G. Mojzis J. Pilatova M. Phytother Res 27 2013 159 165 22451355 

19. 19 Podolak I. Galanty A. Sobolewska D. Phytochem Rev 9 2010 425 474 20835386 

20. 20 Rimmon A. Vexler A. Berkovich L. Earon G. Ron I. Lev-Ari S. Biochem Res Int 2013 251752 24282639 

21. 21 Sun H. Fang W. Wang W. Hu C. Botanical Studies 47 2006 339 368 

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22. 22 The seeds of A. turbinata were collected from Seoul in 2014 and authenticated by Prof. W.K. Oh. A voucher specimen (SNU2014-006) was deposited in the herbarium of the College of Pharmacy, Seoul National University, Korea. The dried seeds of A. turbinata (1？kg) were extracted by sonication with 70% EtOH. The extract (195.1？g) was partitioned successively with n -hexane, EtOAc and n -BuOH. Since the n -BuOH-soluble fraction (70.8？g) contains a large amount of mixed triterpenoidal saponins called escins, this fraction was directly applied to hydrolysis reactions of two steps. Acyl group hydrolysis was done at 90？°C with 0.5 N NaOH in 50% EtOH aqueous solution for 2？h. Further partial hydrolysis of the glucose moieties was also followed with 1.0？N HCl in 50% EtOH aqueous solution at 90？°C for 2？h. This reaction mixture was directly placed on an HP-20 CC (10？×？60？cm) to discard salt, washed with 10% EtOH (3？L), and finally eluted with EtOH (3？L) for the saponin fraction. The partial saponin fraction (5.59？g) was then chromatographed over an RP-C 18 CC (40？63？μm particle size) and eluted with a gradient solvent system of MeOH:H 2 O (from 4:6 to 1:0), to yield five fractions (F1？F5). Fraction F1 was further applied to semi-preparative HPLC [RS Tech Optima Pak C18 column (250？×？10？mm, particle size 5？μm)]; (0？5？min: A:B (75:25), 5？24？min: A:B (75:25？40:60), 24？34？min: B; 0.1% formic acid in H 2 O (A) and MeCN (B); flow rate 2？ml/min; UV detection at 205 and 254？nm) to isolate compounds 6 and 7 , respectively. Fraction F2 was also chromatographed by preparative HPLC (0？5？min; A:B (75:25), 5？25？min; A:B (75:25？ 60:40), 25？35？min; B) to provide compounds 2 , 3 and 5 . Purification of fraction F4 by preparative HPLC (mobile phase MeCN/H 2 O (30:70？60:40) over 25？min) resulted in the isolation of compound 4 . Fraction F5 was purified by preparative HPLC (mobile phase MeCN/H 2 O (30:70？60:40) over 25？min) to provide compound 1 . Compounds 8 ？ 10 were isolated from the n -BuOH fraction of the dried seeds of A. turbinata extract by semi-preparative HPLC using an isocratic solvent of 40% MeCN with 0.1% formic acid over 40？min. 

23. 23 β,16α,21β,22α)-16,21,22,28-tetrahydroxyolean-12-en-3-O-β- d -glucopyranosiduronic acid ( 2 ): amorphous powder; [α] D 25 +19.8 (c 0.1, MeOH); IR (KBr) νmax 3375, 2947, 2834, 1658, 1451, 1411, 1117, 1023？cm ？1 ; see Table 1 for 1 H (500？MHz) and 13 C NMR (125？MHz); HRESIMS m/z 665.3901 (calcd for C 36 H 57 O 11 [M？H] ？ , 665.3906). (3β,16α,21β,22α)-16,21,22,28-tetrahydroxyolean-12-en-3-yl-O-[β- d -glycopyranosyl-(1→4)]-β- d -glucopyranosiduronic acid ( 3 ): amorphous powder; [α] D 25 +12.5 (c 0.1, MeOH); IR (KBr) ν max 3390, 2952, 2834, 1658, 1456, 1412, 1028？cm ？1 ; see Table 1 for 1 H (500？MHz) and 13 C NMR (125？MHz); HRESIMS m/z 827.4434 (calcd for C 42 H 67 O 16 [M？H] ？ , 827.4435). (3β,16α,21β,22α)-16,21,22,24,28-pentahydroxyolean-12-en-3-O-β- d -glucopyranosiduronic acid ( 5 ): amorphous powder; [α] D 25 +32.7 (c 0.1, MeOH); IR (KBr) ν max 3385, 2952, 2834, 1657, 1456, 1412, 1028？cm ？1 ; see Table 1 for 1 H (800？MHz) and 13 C NMR (200？MHz); HRESIMS m/z 681.3852 (calcd for C 36 H 57 O 12 [M？H] ？ , 681.3856). (3β,16α,21β,22α)-16,21,22,24,28-pentahydroxyolean-12-en-3-yl-O-[β- d -glycopyranosyl-(1→4)]-β- d -glucopyranosiduronic acid ( 6 ): amorphous powder; [α] D 25 +10.9 (c 0.1, MeOH); IR (KBr) νmax 3405, 2942, 1604, 1051, 1033？cm ？1 ; see Table 1 for 1 H (800？MHz) and 13 C NMR (200？MHz); HRESIMS m/z 843.4384 (calcd for C 42 H 67 O 17 [M？H] ？ , 843.4384). 

24. 24 Konoshima T. Lee K.H. J Nat Prod 49 1986 650 656 3783160 

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25. 25 Chen Y.J. Takeda T. Ogihara Y. Iitaka Y. Chem Pharm Bull 33 1984 3378 3383 

26. 26 Yoshikawa M. Murakami T. Yamahara J. Matsuda H. Chem Pharm Bull 46 1998 1764 1769 9845957 

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27. 27 Vero cells (African green monkey kidney cell line; ATCC CCR-81) were obtained from American Type Culture Collection (ATCC, Manassas, VA, USA). Cells were grown in Dulbecco’s Modified Eagle’s Medium (DMEM) supplemented with 100？U/mL penicillin, 100？μg/mL streptomycin and 10% fetal bovine serum (FBS). PEDV was provided by Choong Ang Vaccine Laboratory, Korea. Virus stock was maintained at ？80？°C before use. To assess the cell viability, a MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2 H -tetrazolium bromide) assay was carried out. Vero cells were seeded for 24？h in 96-well plates at 1？×？10 5 ？cells per well. Then, the cells were exposed to different concentrations of fractions and compounds for 48？h. The final concentration of DMSO was maintained at 0.05% (v/v) to avoid solvent toxicity. Twenty microliters of MTT solution (2？mg/mL) was then added to cultures and incubated for 4？h. Formazan crystals were dissolved with 100？μL of DMSO, and the optimal densities (OD) were measured at 550？nm. 

28. 28 Vero cells were grown in 96-well plates at 1？×？10 5 ？cells per well. After 24？h, the medium was removed and washed with phosphate buffered saline (PBS). PEDV (0.01 MOI) were inoculated onto confluent monolayers of Vero cells for 2？h. The media were replaced by DMEM with different concentrations of compounds. After 72？h of incubation at 37？°C in a 5% CO 2 -balanced air incubator, cells were replaced with DMEM. Then, 20？μL of MTT solution (2？mg/mL) was added to each well and incubated for 4？h. 

29. 29 Song D. Park B. Virus Genes 44 2012 167 175 22270324 

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30. 30 Cruz D.J. Kim C.J. Shin H.J. Virus Res 132 2008 192 196 18067984 

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31. 31 Baric R.S. Nelson G.W. Fleming J.O. J Virol 62 1988 4280 4287 2845140 

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32. 32 Whole-cell lysates were prepared by scraping adherent-cultured cells with 100？μL of lysis buffer (0.5% NP-40, 50？mM NaF, 1？mM EDTA, 120？mM NaCl, and 50？mM Tris-HCl (pH 7.6)) and centrifuged at 12,000？rpm for 20？min. Protein concentrations of the supernatant were calculated using a protein assay kit (Bio-Rad Laboratories, Hercules, CA, USA). Aliquots of lysates were separated by 10？12% SDS-PAGE and electrophoretically transferred to PVDF membranes (PVDF 0.45？μm. Immobilon-P, USA). Membranes were incubated overnight with antibodies against spike (S) protein, nucleocapsid (N) (AbFrontier Co., Ltd., Seoul, Korea) or mouse monoclonal actin, and further incubated with secondary antibodies. Protein bands were detected using an enhanced chemiluminescence Western blotting detection kit (Thermo Scientific). 

33. 33 Quantitative real-time PCR was performed using the StepOnePlus Real-Time PCR System (Applied Biosystems, Foster City, CA, USA). Vero cells were seeded at 90% confluence in 6-well plates, infected with PEDV (0.01 MOI), and incubated for 2？h. Then, the medium was replaced by DMEM and cultured with different concentrations of compounds. After 24？h, total RNA from the cells was isolated by the TRIzol method and reverse transcribed using random primer (iNtRON Biotechnology, Seongman, Korea) according to the manufacturer’ protocol. Amplifications were carried out using selective primers for PEDV, which are listed in S-Table 1 (Supporting Information), using 2？μL of cDNA and Maxima SYBR Green qPCR master mix 2X (Thermo Scientific, Rockford, IL, USA). Cyclic conditions were as follows: initial denaturation at 95？°C for 10？min, 40 cycles with 95？°C for 15？s and 60？°C for 1？min. 

34. 34 Cells were grown on sterilized glasses slides, and PEDV (0.01 MOI) was inoculated to the cell monolayers for 2？h. The solution was replaced with DMEM, treated with compounds for 24？h, washed in PBS (pH 7.4) and fixed with a 4% paraformaldehyde solution for 30 min at room temperature. The slides were blocked with 1% BSA for 1？h, and incubated with monoclonal antibody against N protein of PEDV (AbFrontier Co., Ltd., Seoul, Korea) diluted 1:50 with PBS (pH 7.4) for 24？h. The slides were washed with PBS, and incubated with FITC-conjugated goat anti-RbIgG antibody (Abcam, Cambridge, UK) for 1？h. After washing three times with PBS (pH 7.4), the slides were stained with 500？nM DAPI solution for 10？min at room temperature and washed with PBS (pH 8.0) three times. Mounting reagent (Vectashield, Vector Laboratories Inc., Burlingame, CA, USA) was used. The slides were examined under a fluorescence microscope (Olympus ix70 Fluorescence Microscope, Olympus Corporation, Tokyo, Japan). 

35. 35 Jacobs J. Grum-Tokars V. Zhou Y. J Med Chem 56 2013 534 546 23231439 

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