Optical rotations were recorded using MCP 200 Polarimeter (Anton Paar GmbH, Graz, Austria). Optical density (OD) values were read on a Multiskan Spectrum Microplate Reader (Thermo Scientific Inc., Shanghai, China). CD spectra were acquired on a Chirascan Spectrometer (Applied Photophysics Ltd., Surrey, UK). IR spectra were carried out on a Nicolet Nexus 670 spectrophotometer, in KBr discs. NMR spectra were obtained on a Bruker AVANCE 400 (Bruker Co. Ltd., Zurich, Switzerland). Thin-layer chromatography (TLC) was carried out on pre-coated silica gel GF-254 plates (Qingdao Haiyang Chemical Co., Ltd., Qingdao, China) and column chromatography (CC) was performed over silica gel (Qingdao Haiyang Chemical Co., Ltd., Qingdao, China, 200–300 mesh) on a Sephadex LH-20 (GE healthcare, Buckinghamshire, UK). Semi-preparative HPLC was performed on a Waters 1525 system using a semi-preparative Ultimate XB-C18 column (5 μm, 21.2 mm × 250 mm; Welch) coupled with a Waters 2998 photodiode array detector (Waters Corp., Milford, MA, USA). ESIMS data were measured on a Thermo LCQ DECA XP plus mass spectrometer (Thermo Scientific, Waltham, MA, USA). All reagents and solvents were of commercial quality.
Lh 20
Manufactured by GE Healthcare
Sourced in China, Sweden
The LH-20 is a laboratory equipment product manufactured by GE Healthcare. It is a versatile instrument designed for performing liquid chromatography. The LH-20 allows for the separation, identification, and purification of various chemical compounds and biomolecules. It features robust construction and reliable performance to support research and analytical needs in a wide range of scientific applications.
Automatically generated - may contain errors
Lab products found in correlation
Gf254 plates, by Qingdao Haiyang Chemical (3 mentions)
Mcp 200 polarimeter, by Anton Paar (2 mentions)
Chelex 100 resin, by Merck Group (2 mentions)
Ultimate xb c18 column, by Hill-Rom (1 mentions)
Waters 2998 photodiode array detector, by Waters Corporation (1 mentions)
Multiskan spectrum microplate reader, by Thermo Fisher Scientific (1 mentions)
Avance 400, by Bruker (1 mentions)
Chirascan spectrometer, by Applied Photophysics (1 mentions)
Trypsin, by Atlanta Biologicals (1 mentions)
Dulbecco modified eagle medium (dmem), by Atlanta Biologicals (1 mentions)
Live dead fixable green dead cell stain, by Thermo Fisher Scientific (1 mentions)
Lysotracker blue dnd 22, by Thermo Fisher Scientific (1 mentions)
Tris 3 hydroxypropyltriazolylmethyl amine thpta, by Merck Group (1 mentions)
Sephadex g 50, by GE Healthcare (1 mentions)
1 2 dipalmitoyl sn glycero 3 phosphocholine, by Avanti Polar Lipids (1 mentions)
Cholesterol chol, by Avanti Polar Lipids (1 mentions)
1 2 distearoyl sn glycero 3 phosphoethanolamine, by Avanti Polar Lipids (1 mentions)
Fetal bovine serum (fbs), by Atlanta Biologicals (1 mentions)
Fmoc protected amino acids, by Merck Group (1 mentions)
Cyanine5.5 nhs ester, by Lumiprobe (1 mentions)
18 protocols using lh 20
1
Structural Elucidation of Natural Compounds
2
Solid-Phase Synthesis of Lipid Nanoparticles
3
Chromatography and NMR Analysis of Bioactive Compounds
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Column chromatography was performed using silica gel (Kieselgel 60, 70–230 and 230–400 mesh, Merck, Darmstadt, Germany), Sephadex LH-20 (GE Healthcare, Uppsala, Sweden), and C-18 (ODS-A 12 nm S-150, S-75 μm; YMC Co., Kyoto, Kansai, Japan) resins. Thin-layer chromatography (TLC) was performed using pre-coated silica gel 60 F254 and RP-18 F254S plates (both 0.25 mm, Merck). Spots in the TLC were visualized by spraying with 10% aqueous H2SO4 solution followed by heating to 300℃ in dried air. Nuclear magnetic resonance (NMR) spectra were recorded using the JEOL ECA 500 spectrometer (1H, 500 MHz; 13C, 125 MHz) (JEOL, Tokyo, Japan) (Supplementary Materials ). AUDA (10007927), soluble epoxide hydrolase (10011669) and PHOME (10009134) were purchased from Cayman (Cayman, Ann Arbor, MI, USA).
4
Phytochemical Analysis of Natural Compounds
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Melting points were obtained on a SGW X-4 micromelting point apparatus (INESA Co., Shanghai, China). Optical rotations were measured on SGW-533 automatic polarimeter (INESA Co., Shanghai, China). HRESIMS spectra were taken on an API QSTAR mass spectrometer (Applied Biosystem/MSD Sciex, Concord, ON, Canada). The 1D- and 2D-NMR spectra were recorded on a Bruker Avance III 600MHz NMR spectrometer using TMS as an internal standard. Column chromatography was performed on silica gel (100–200 mesh, Qingdao Marine Chemical Ltd., Qingdao, China). Preparative TLC plates (HSGF254, Jiangyou silicone Development Co., Ltd., Yantai, China), Sephadex LH-20 (GE Healthcare, Uppsala, Sweden), and Develosil ODS (50 μm, Nomura Chemical Co. Ltd., Osaka, Japan) were used for the isolation experiments. Preparative HPLC was performed on a Waters 1525 Binary HPLC pump and a Waters 2414 refractive index detector (Waters Corp, Milford, MA, USA) using a YMC-Pack ODS-A column (250 mm ×10 mm I.D.; S-5 μm, 12 nm).
5
Synthesis of Farnesol Phosphate Derivative
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Farnesol phosphate 8 (78.6 mg, 266.1 μmol) was coevaporated from toluene (2 mL) two times and dissolved in 50% DMF/THF (3.82 mL). Carbonyldiimidazole (CDI, 170.2 mg, 1.06 mmol) was dissolved in 50% DMF/THF (3.82 mL) and added to the farnesol phosphate solution. The reaction was stirred for 2 h at rt and MeOH (76.3 μL) was added before stirring further 45 min at rt. The solvents were removed under reduced pressure and the synthesized phosphoimidazole intermediate was coevaporated from toluene (2 mL) twice before the addition of DMF (3.1 mL). Mass spectrometry showed the successful synthesis.
HRMS (ESI) m/z: calcd for C18H28N2O3P [M − H]−: 351.1843, found: 351.1835.
In the meantime phosphate 74 (37.1 mg, 27.9 μmol) was coevaporated first from 0.4 mL pyridine and then twice from 2 mL toluene under argon. DMF (3.1 mL) and the freshly prepared phosphoimidazole solution were added and the reaction was stirred for 3 d at rt. The solvent was removed under reduced pressure and the crude product was semi-purified by gel permeation chromatography (Sephadex® LH-20, GE Healthcare, 260 × 20 mm, methanol) to yield 53.9 mg (33.4 μmol, 90%) of a colorless, amorphous solid (75), which was used for the next reaction without further purification or analysis.
Rf 0.78 (4 MeOH/2 CHCl3/0.5 water). HRMS (ESI) m/z: calcd for C68H123N9O24P2Si3 [M − 2H]2−: 791.8737, found: 791.8740.
HRMS (ESI) m/z: calcd for C18H28N2O3P [M − H]−: 351.1843, found: 351.1835.
In the meantime phosphate 74 (37.1 mg, 27.9 μmol) was coevaporated first from 0.4 mL pyridine and then twice from 2 mL toluene under argon. DMF (3.1 mL) and the freshly prepared phosphoimidazole solution were added and the reaction was stirred for 3 d at rt. The solvent was removed under reduced pressure and the crude product was semi-purified by gel permeation chromatography (Sephadex® LH-20, GE Healthcare, 260 × 20 mm, methanol) to yield 53.9 mg (33.4 μmol, 90%) of a colorless, amorphous solid (75), which was used for the next reaction without further purification or analysis.
Rf 0.78 (4 MeOH/2 CHCl3/0.5 water). HRMS (ESI) m/z: calcd for C68H123N9O24P2Si3 [M − 2H]2−: 791.8737, found: 791.8740.
6
Characterization of Natural Products
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Optical rotations were determined with a Perkin-Elmer 41 polarimeter equipped with a sodium lamp (589 nm). UV, CD, and FT-IR spectra were performed on a Varian Cary 50, a JASCO-810 CD spectrometer, and a Bruker Vertex 70 instruments, respectively. 1D and 2D NMR spectra were recorded on a Bruker AM-400 spectrometer, and the 1H and 13C NMR chemical shifts were referenced with respect to the solvent or solvent impurity peaks. HRESIMS were carried out in the positive ion mode on a Thermo Fisher LC-LTQ-Orbitrap XL spectrometer. X-ray data were collected using a Bruker APEX DUO instrument. Column chromatography was conducted with silica gel (200–300 and 300–400 mesh; Qingdao Marine Chemical Inc., China), Sephadex LH-20 (GE Healthcare Bio-Sciences AB, Sweden), and MCI gel (75–150 μm, Mitsubishi Chemical Corporation, Tokyo, Japan). Semi-preparative HPLC was carried out on a Dionex quaternary system with a diode array detector at a flow rate of 2.5 mL/min using a reversed-phased C18 column (5 μm, 10 × 250 mm, YMC-pack ODS-A).Thin-layer chromatography (TLC) was performed with silica gel 60 F254 (Yantai Chemical Industry Research Institute) and RP-C18 F254 plates (Merck, Germany).
7
Analytical Profiling of Organic Compounds
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Perkin Elmer (Waltham, MA, USA) system 2000 FT-IR spectrophotometer was used for IR spectrum measurement. JASCO (Tokyo, Japan) P-1020 digital polarimeter was utilized for optical rotation measurement. UV and ECD spectra were recorded on JASCO V-530 UV/VIS spectrophotometer and JASCO J-815 CD spectrometer, respectively. Electrospray ionization (ESI) mass data were obtained from Waters (Milford, MA, USA) 2695 separations module and Bruker (Billerica, MA, USA) APEX II spectrometer (high resolution). NMR spectra were obtained by Bruker AVIII HD 700 MHz FT-NMR and AVAN CEIII 600 MHz FT-NMR. Merck (Darmstadt, Germany) silica gel 60 and GE Healthcare (Chicago, IL, USA) Sephadex LH-20 were used for column chromatography. The instrumentation for HPLC was composed of a Shimadzu (Kyoto, Japan) LC-20AD pump and a Shimadzu SPD-M20A PDA detector.
8
Column Chromatography Purification Techniques
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Diaion HP20SS (63−150 µm) and MCI-gel CHP20P (75−100 μm) (Mitsubishi Chemical Co., Tokyo, Japan), Sephadex LH-20 (25−100 μm) and TSK gel Toyopearl HW-40F (37−70 μm) (GE Healthcare Bio-Science AB, Uppsala, Sweden), and RP-18 (40−60 μm, Merck, Darmstadt, Germany) were used as the padding of column chromatography (CC). Thin-layer chromatography (TLC) was carried out using precasted silica gel F254 plates (Qingdao Haiyang Chemical Co., Ltd. Qingdao, China) using methylbenzene:ethyl formate:formic acid (Shanghai Titan Scientific Co., Ltd., Shanghai, China) (1:7:2, 1:7:1, 2:7:1, 3:6:1, 4:5:1, v/v/v) as the eluents. UV radiation was used to locate the spots by soaking with a sulfuric acid:ethanol (1:9, v/v) solution followed by heating. The deionized water and redistilled organic solvents such as acetone, chloroform (CHCl3), methanol (MeOH), ethyl acetate (EtOAc), ethanol (EtOH), and n-butanol (n-BuOH) were used for column chromatography. The chromatographic-grade acetonitrile (MeCN), formic acid (HCOOH), and deionized water (H2O) were used for HPLC.
9
Structural Analysis of Carbohydrate Compounds
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Optical rotations were measured on a Perkin-Elmer 241 MC digital polarimeter (German PerkinElmer Corporation, Boelingen, Germany). 1D and 2D-NMR spectral experiments were measured in CD3OD on a Bruker AVANCE-500 and a Bruksmer AVANCE-800 spectrometer (Bruker Corporation, Karlsruhe, Germany) with TMS as an internal standard. The IR spectra were recorded on a Shimadzu IRPrestige-21 spectrophotometer (Shimadzu Corporation, Tokyo, Japan). The ESI-MS and HR-ESI-MS spectra were carried out on a Waters Micromass Quattro mass spectrometer (Waters, Shanghai, China). Column chromatographies (CC) were operated on a Sephadex LH-20 (GE-Healthcare, Uppsala, Sweden), ODS silica gel (Lichroprep RP-18, 40–63 µm, Merck Inc., Darmstadt, Germany), and silica gel H (10−40 µm, Qingdao Marine Chemical Inc., Qingdao, China). The GC analysis was performed on an Agilent 6890N apparatus using an HP-5 capillary column (30 m × 0.32 mm, 0.5 µm) and an FID detector with an initial temperature of 120 °C for 2 min and then temperature programming to 280 °C at the rate of 10 °C/min. Standards for D-xylopyranose (D-Xyl), L-arabopyranose (L-Ara), and L-rhamnose (L-Rha) were purchased from Sigma Chemical Co. (St. Louis, MO, USA), and D-apiose (D-Api) was purchased from Herbest Bio-Tech Co. (St. Baoguo, Baoji, China).
10
Structural Elucidation of Natural Products
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Optical rotations were measured on a JASCO P-2000 polarimeter (JASCO International Co. Ltd., Tokyo, Japan). IR data were collected using a Nicolet 6700 FT-IR spectrometer (Thermo Electron Corp., Waltham, MA, USA). ECD spectra were recorded using Chirascan Plus (Applied Photophysics Ltd., Surrey, UK). UHPLC systems (Ultimate 3000, Thermo Scientific, Milan, Italy) coupled to a Waters Xevo G2 QTOF MS spectrometer (Waters, Co., Milford, MA, USA) were used to generate HRESIMS values and perform LC-MS/MS analysis. Semipreparative HPLC was performed using a Gilson HPLC system with a UV/VIS-155 detector and a 321 pump. An RS Tech Optima Pak C18 column (10 × 250 mm, 10 μm) was used as the HPLC column. All solvents employed for extraction and isolation were of analytical grade. The 1D (1H and 13C) and 2D (HSQC, HMBC and 1H-1H COSY) NMR spectra were collected using JEOL 400 MHz (JEOL Ltd., Tokyo, Japan), Bruker Avance 500 MHz and Bruker Avance 800 MHz NMR spectrometers (Bruker, Billerica, MA, USA). DiaionTM HP-20 ion exchange resin and GE Healthcare SephadexTM LH-20 (18–111 μm) were employed for column chromatography. Thin layer chromatography was performed with silica gel 60 F254 and RP-18 F254 plates.
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