Optical rotations were measured on a Perkin-Elmer 341 polarimeter. HRESIMS spectra were recorded on a Waters-Micromass Q-TOF Ultima Global electrospray mass spectrometer. NMR spectra were measured on a Bruker-DRX-500 spectrometer with the residual CHCl3 (δH 7.26 ppm, δC 77.0 ppm) as internal standard. Chemical shifts are expressed in δ (ppm) and coupling constants (J) in Hz. 1H and 13C NMR assignments were supported by 1H-1H COSY, HSQC, and HMBC experiments. Commercial silica gel (Qing Dao Hai Yang Chemical Group Co., 200–300 and 400–600 mesh), C18 reversed-phase silica gel (150–200 mesh, Merck) and Sephadex LH-20 (Amersham Biosciences) were used for column chromatography. Semi-preparative HPLC (Agilent 1100 series liquid chromatography using a VWDG1314A detector at 210 nm and a semi-preparative ODS-HG-5 [5 μm, 10 mm (i.d.) × 25 cm] column was also employed. Pre-coated silica gel GF254 plates (Qing Dao Hai Yang Chemical Group Co. Ltd. Qingdao, People’s Republic of China) were used for analytical thin-layer chromatography (TLC). All solvents used were of analytical grade (Shanghai Chemical Reagents Company, Ltd.).
C18 reversed phase silica gel
Manufactured by Merck Group
Sourced in Germany, China, Japan, Sweden
C18 reversed-phase silica gel is a type of stationary phase material used in liquid chromatography. It consists of a silica gel substrate with chemically bonded C18 alkyl chains. The primary function of C18 reversed-phase silica gel is to provide a hydrophobic surface for the separation and purification of a wide range of organic compounds.
Automatically generated - may contain errors
Lab products found in correlation
Silica gel, by Qingdao Marine Chemical (4 mentions)
341 polarimeter, by PerkinElmer (3 mentions)
Sephadex lh 20, by Cytiva (3 mentions)
Av 3 600 nmr spectrometer, by Bruker (3 mentions)
Ftir 8400s spectrometer, by Shimadzu (3 mentions)
Mci gel chp 20p, by Mitsubishi Chemical Corporation (3 mentions)
Avance 600 spectrometer, by Bruker (2 mentions)
Ods a column, by YMC (2 mentions)
Advance 500 spectrometer, by Bruker (2 mentions)
Pack c18 column, by YMC (2 mentions)
Mci gel chp 20p, by Mitsubishi (2 mentions)
Zorbax sb c18 column, by Agilent Technologies (2 mentions)
Pre coated silica gel gf254 plates, by Qingdao Haiyang Chemical (1 mentions)
Drx 500 spectrometer, by Bruker (1 mentions)
Uv 2600 spectrophotometer, by Shimadzu (1 mentions)
Silica gel gf254 plate, by Qingdao Marine Chemical (1 mentions)
820 spectropolarimeter, by Jasco (1 mentions)
Mcp 500 spectropolarimeter, by Anton Paar (1 mentions)
Affinity 1 spectrometer, by Shimadzu (1 mentions)
Ftir 8400, by Shimadzu (1 mentions)
18 protocols using c18 reversed phase silica gel
1
Spectroscopic Analysis of Natural Products
2
Spectroscopic Characterization of Natural Products
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HRESIMS data were collected on an MAT95XP machine (Thermo Fisher Scientific, Bremen, Germany). NMR spectra were acquired by an Avance-600 spectrometer (Bruker, Fällanden, Switzerland). Circular dichroism (CD) spectra were afforded by a Jasco 820 spectropolarimeter (Jasco Corporation, Kyoto, Japan). Optical rotations were obtained by an MCP-500 spectropolarimeter (Anton Paar, Graz, Austria). UV spectra were acquired using a UV-2600 spectrophotometer (Shimadzu, Kyoto, Japan). IR data were done with an Affinity-1 spectrometer (Shimadzu, Kyoto, Japan). Preparative HPLC was performed using an ODS-A column (250 × 20 mm, 5 μm, 12 nm, YMC Co., Ltd, Kyoto, Japan). An ODS-A/AQ column (250 × 10 mm, 5 μm, 12 nm, YMC CO., Ltd, Kyoto, Japan) was used for semipreparative HPLC separation and the CHIRALPAK IC column (250 × 10 mm, 5 μm) for chiral semipreparative HPLC separation. Silica gel (100–200 and 200-300 mesh, Qingdao Marine Chemical Inc., Qingdao, China), C18 reversed-phase Silica gel (40–63 μm, Merck, Darmstadt, Germany), and Sephadex LH-20 gel (Pharmacia Fine Chemical Co. Ltd., Uppsala, Sweden) were used in the chromatography processes. Fractions were monitored by TLC, and spots were detected on heated TLC plates (Silica gel GF254 plates, Qingdao Marine Chemical Inc., Qingdao, China) with 10% H2SO4 in EtOH under UV light.
3
Spectroscopic Analysis of Natural Compounds
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IR spectra and UV absorption spectra were measured using FTIR-8400S and Shimadzu UV2550 spectrometers, respectively. Optical rotations were determined using a Jasco P-1010 polarimeter. TNMR spectra were recorded with a Bruker AV III 600 NMR spectrometer using trimethylsilyl (TMS) as the internal standard. HR-ESIMS spectra were obtained using a LTQ-Obitrap XL spectrometer. Preparative HPLC was performed using a Shimadzu analytic LC furnished with two LC-6AD pumps, a SPD-20A UV detector, and a Venusil C18 column (250 mm × 10 mm, i.d., 5 μM, Agela Technologies Ltd., the U.S.) Elution was carried out with CH3OH-H2O at a flow rate of 2 mL/min. C18 reversed-phase silica gel (40~63 μM, Merck, Darmstadt, Germany), MCI gel (CHP 120 P, 75~150 μM, Mitsubishi, Japan), and silica gel (SiO2 100~200 mesh, Qingdao Marine Chemical Plant, Qingdao, PRC) were used for column chromatography. GF254 precoated silica gel plates were used for thin-layer chromatography (TLC) VWR International Ltd. (Lutterworth, UK). Analytical grade solvents were used in all of the experiments (Beijing Chemical Works).
4
Characterization of Compound 1
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Optical rotation was measured on a Perkin-Elmer 341 polarimeter (Perkin-Elmer, Boston, MA, USA). UV spectra were recorded in MeOH on a Perkin-Elmer Lambda 35 UV–vis spectrophotometer (Perkin-Elmer, Boston, MA, USA). 1D and 2D NMR spectra were recorded on a Bruker Advance-500 spectrometer with TMS as internal standard (Bruker BioSpin AG, Fällanden, Switzerland). HRESIMS data were obtained on a Bruker Bio TOF IIIQ mass spectrometer (Bruker Daltonics, Billerica, MA, USA). All solvents were analytical grade (Shanghai Chemical Plant, Shanghai, China). Silica gel (200–300 mesh) was used for column chromatography, and precoated silica gel GF254 plates (Qingdao Haiyang Chemical Plant, Qingdao, China) were used for TLC analysis. C18 reversed-phase silica gel (150–200 mesh, Merck), MCI gel (CHP20P, 75–150 μm, Mitsubishi Chemical Industries Ltd.), and Sephadex LH-20 gel (Amersham Biosciences) were also used for column chromatography. TLC spots were visualized under UV light and by dipping into 5% H2SO4 in alcohol, followed by heating. In the biological and biophysical experiments, the solvent used to dissolve 1 were DMSO.
5
Spectroscopic Analysis of Organic Compounds
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Optical rotations were measured on a Perkin-Elmer 341 polarimeter. IR spectra were recorded on a Perkin-Elmer 577 spectrometer with KBr disks. HRESIMS spectra were recorded on a Waters-Micromass Q-TOF Ultima Global electrospray mass spectrometer. NMR spectra were measured on a Bruker Avance III 500 and Varian INOVA 600 spectrometers with the residual CHCl3(δH 7.26 ppm, δC 77.0 ppm) as internal standard. Chemical shifts are expressed in δ(ppm) and coupling constants(J) in Hz. 1H and 13C NMR assignments were supported by 1H-1H COSY, HSQC, and HMBC experiments. Commercial Silica gel(Qing Dao Hai Yang Chemical Group Co., 200–300 and 400–600 mesh), C18 reversed-phase silica gel(150–200 mesh, Merck) and Sephadex LH-20(Amersham Biosciences) were used for column chromatography. Reversed phase HPLC(Agilent 1100 series liquid chromatography using a VWDG1314A detector at 210 nm and a semi-preparative ODS-HG-5 [5 μm, 10 mm(i.d.) × 25 cm] column was also employed. Pre-coated silica gel GF254 plates(Qing Dao Hai Yang Chemical Group Co. Ltd. Qingdao, People’s Republic of China) were used for analytical thin-layer chromatography(TLC). All solvents used were of analytical grade(Shanghai Chemical Reagents Company, Ltd.).
6
Analytical Techniques for Compound Characterization
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Electrospray ionization mass spectrometry (ESI MS) and liquid chromatography/mass spectrometry (LC/MS) analyses were performed using an LC/MS TOF system Agilent 6230B (Agilent Technologies, Milan, Italy), HPLC 1260 Infinity. A Phenomenex (Bologna, Italy) Luna (C18 (2) 5 mm, 150–4.6 mm column) was used to perform the high-performance liquid chromatography (HPLC) separations. Bruker 400 Anova Advance (Karlsruhe, Germany) was used to record the 1H NMR spectra at 400 MHz in CDCl3 at 298 K. Analytical, preparative, and reverse-phase thin-layer chromatography (TLC) were carried out on silica gel (Merck, Kieselgel 60, F254, 0.25, 0.5 mm, and RP-18 F254s, respectively) plates (Merck, Darmstadt, Germany). The spots were visualized as previously described [20 (link)]. Column chromatography (CC) was performed using silica gel (Kieselgel 60, 0.063–0.200 mm) and C18-reversed phase silica gel (230–400 mesh) (Merck, Darmstadt, Germany). Sigma-Aldrich Co. (St. Louis, MO, USA) supplied all the reagents and the solvents.
7
Isolation and Characterization of Compounds from E. chinensis
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The air-dried leaves of E. chinensis (23.00 kg) were crushed and extracted with 95% EtOH for 48 h (30 L × 3) at room temperature. All the extracts were combined and evaporated under reduced pressure to obtain brown ethanolic crude extract (4.03 kg), which was then suspended in water (3 L) and then extracted sequentially with n-hexane (3 L × 3) and ethyl acetate (3 L × 3) in order to obtain the n-hexane-soluble (0.06 kg), EtOAc-soluble (1.11 kg) and water-soluble (0.53 kg) fractions. The EtOAc-soluble fraction was subjected to silica gel column chromatography with a gradient of n-hexane/ethyl acetate (from 20: 1 to 0:1) to yield the subfractions (Er1–Er4). The subfractions were subjected to silica gel (200–300 mesh, Qingdao Marine Chemical Inc., Qingdao, China), Sephadex LH-20 gel (CHP20P, 75–150 μm, Mitsubishi Chemical Industries Ltd, Tokyo, Japan), C18 reversed-phase silica gel (150–200 mesh, Merck, Darmstadt, Germany) column chromatography to obtain the pure compounds by following similar procedures as we described previously (J. Song et al., 2018a (link), 2018b (link)) with minor modification. 1D and 2D NMR spectra were recorded on a Bruker Advance-500 spectrometer with TMS as internal standard (Bruker BioSpin AG, Fallanden, Switzerland). Spectroscopic data were presented in Supplementary materials .
8
Spectroscopic Characterization of Compounds
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Optical rotation data were obtained using a Perkin-Elmer 341 digital polarimeter (PerkinElmer, Norwalk, CT, USA). UV and IR spectra were recorded on Shimadzu UV2550 and FTIR-8400S spectrometer (Shimadzu, Kyoto, Japan), respectively. NMR spectra were obtained with a Bruker AV Ⅲ 600 NMR spectrometer (chemical shift values are presented as δ values with TMS as the internal standard) (Bruker, Billerica, German). HR-ESI-MS were performed on a LTQ-Orbitrap XL spectrometer (Thermo Fisher Scientific, Boston, MA, USA). C 18 reversed-phase silica gel (40-63μm, Merck, Darmstadt, Germany), Sephadex LH-20 (Pharmacia, Uppsala, Sweden), MCI gel (CHP 20P, Mitsubishi Chemical Corporation, Tokyo, Japan) and silica gel (100-200 and 300-400 mesh, Qingdao Marine Chemical plant, Qingdao, China) were used for column chromatography (CC). And precoated silica gel GF 254 plates (Zhi Fu Huang Wu Pilot Plant of silica gel Development, Yantai, China) were used for TLC.
All solvents used were of analytical grade (Beijing Chemical Works, Beijing, China).
All solvents used were of analytical grade (Beijing Chemical Works, Beijing, China).
9
Analytical Techniques for Natural Products
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Optical rotations were obtained on a PerkinElmer 341 digital polarimeter. IR spectra were recorded on Shimadzu FTIR-8400S spectrometers. NMR spectra were obtained with a Bruker AV III 600 NMR spectrometer (chemical shift values are presented as δ values with TMS as the internal standard). HR-ESIMS spectra were performed on a LTQ-Obitrap XL spectrometer. Preparative HPLC was performed on a Lumtech K-1001 analytic LC equipped with two pumps of K-501, a UV detector of K-2600, and an YMC Pack C18 column (250 × 10 mm, i.d., 5 μm, YMC Co. Ltd., Japan) eluted with CH3OH-H2O at a flow rate of 2 ml/min. C18 reversed–phase silica gel (40–63 μm, Merk, Darmstadt, Germany), MCI gel (CHP 20P, 75–150 μm, Mitsubishi Chemical Corporation, Tokyo, Japan), and silica gel (100–200 mesh, Qingdao Marine Chemical plant, Qingdao, the People’s Republic of China) were used for column chromatography. Pre-coated silica gel GF254 plates (Zhi Fu Huang Wu Pilot Plant of Silica Gel Development, Yantai, the People’s Republic of China) were used for TLC. All solvents used were of analytical grade (Beijing Chemical Works).
10
Characterization of Natural Product Isolates
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Optical rotations were obtained on a PerkinElmer 341 digital polarimeter. IR spectra were recorded on Shimadzu FTIR-8400S spectrometers. NMR spectra were obtained with a Bruker AV III 600 NMR spectrometer (chemical shift values are presented as δ values with TMS as the internal standard). HR-ESIMS spectra were performed on an LTQ-Orbitrap XL spectrometer. Preparative HPLC was performed on a Lumtech K-1001 analytic LC equipped with two pumps of K-501, a UV detector of K-2600, and an YMC Pack C18 column (250 mm × 10 mm, i.d., 5 μM, YMC Co. Ltd., Kyoto, Japan) eluted with CH3OH-H2O at a flow rate of 2 mL/min. C18 reversed-phase silica gel (40~63 μM, Merk, Darmstadt, Germany), MCI gel (CHP 20P, 75~150 μM, Mitsubishi Chemical Corporation, Tokyo, Japan), and silica gel (100~200 mesh, Qingdao Marine Chemical plant, Qingdao, China) were used for column chromatography. Pre-coated silica gel GF254 plates (Zhi Fu Huang Wu Pilot Plant of Silica Gel Development, Yantai, China) were used for TLC. All solvents used were of analytical grade (Beijing Chemical Works).
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