Specific rotations were measured using a DIP-360 digital polarimeter (JASCO, Easton, PA, USA). Nuclear magnetic resonance (NMR) spectra were recorded on a JEOL ECX 400 FT-NMR spectrometer (JEOL, Tokyo, Japan) at room temperature. Electrospray ionization time-of-flight mass spectrometry (ESI-TOF-MS) experiments were performed using a Waters Xevo G2-XS Q-TOF mass spectrometer (Waters, Milford, MA, USA). Column chromatography was performed on Silica Gel 60 (Nacalai Tesque, Kyoto, Japan, 230–400 mesh) and YMC ODS-A gel (YMC Co. Ltd., Kyoto, Japan, 50 µm). Thin-layer chromatography (TLC) was performed on TLC Silica Gel 60F254 (Merck, Damstadt, Germany) and TLC Silica Gel 60 RP-18 F254S (Merck, Damstadt, Germany) plates. The spots were visualized by spraying with 10% aq. sulfuric acid followed by heating. High-performance liquid chromatography (HPLC) was performed using a UV-8020 UV-VIS detector (Tosoh Corp., Tokyo, Japan), DP-8020 pump (Tosoh Corp., Tokyo, Japan), and DP-8020 degasser (Tosoh Corp., Tokyo, Japan). An XBridge BEH C18 Column (Waters, Milford, MA, USA, 130 Å, 3.5 µm, 10 mm × 250 mm) was used for preparative purposes.
Gel ods a
Manufactured by YMC
Sourced in Japan, Sweden, China
YMC Gel ODS-A is a reversed-phase chromatography gel designed for the separation of a wide range of organic compounds. It features a chemically bonded octadecyl (C18) stationary phase on a high-purity, spherical silica gel matrix.
Automatically generated - may contain errors
Lab products found in correlation
Kieselgel 60 f254, by Merck Group (3 mentions)
Av 600 spectrometer, by Bruker (3 mentions)
Biotek synergy h1, by Agilent Technologies (3 mentions)
Sephadex lh 20, by GE Healthcare (3 mentions)
Sephadex lh 20, by Cytiva (3 mentions)
Tensor 27 ftir spectrometer, by Bruker (3 mentions)
Chirascan circular dichroism spectrometer, by Applied Photophysics (3 mentions)
343 polarimeter, by PerkinElmer (3 mentions)
Jnm eca 500 mhz nmr instrument, by JEOL (3 mentions)
Silica gel 60, by Nacalai Tesque (2 mentions)
Tlc silica gel 60 rp 18 f254s, by Merck Group (2 mentions)
Uv 2550 spectrophotometer, by Shimadzu (2 mentions)
Rid 10a refractive index detector, by Shimadzu (2 mentions)
Pack ods a 250 10 mm column, by YMC (2 mentions)
Silica gel, by GE Healthcare (2 mentions)
Agilent 1100 series system, by Agilent Technologies (2 mentions)
P 2200 polarimeter, by Jasco (2 mentions)
Varian xl 400 spectrometer, by Agilent Technologies (2 mentions)
Silica gel, by Merck Group (2 mentions)
Xevo g2 xs qtof mass spectrometer, by Waters Corporation (1 mentions)
24 protocols using gel ods a
1
Analytical Methods for Structural Characterization
2
Analytical Techniques for Carbohydrate Characterization
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Optical rotations were obtained using a P-1020 digital polarimeter (JASCO, Easton, USA). NMR spectra were recorded on a JEOL ECX 400 NMR spectrometer (JEOL, Tokyo, Japan). High-resolution electrospray ionization (HR-ESI) time-of-flight mass spectrometry (MS) experiments utilized a JEOL AccuTOF™ LC 1100 mass spectrometer (JEOL, Tokyo, Japan). High-performance liquid chromatography (HPLC) analysis of sugar was run on an Agilent 1100 Series HPLC system (Agilent, Santa Clara, CA, USA) equipped with a YMC-Pack NH2 column (250 mm × 4.6 mm i.d., NH12S05-2546WT, YMC Co. Ltd., Kyoto, Japan) and an optical rotation detector JASCO OR-2090 (JASCO, Easton, USA). Column chromatography was performed on silica gel 60 (230–400 mesh, Nacalai Tesque Inc., Kyoto, Japan) and YMC ODS-A gel (50 μm, YMC Co. Ltd., Kyoto, Japan). Thin-layer chromatography (TLC) was performed on Kieselgel 60 F254 and TLC silica gel 60 RP-18 F254S(Merck, Darmstadt, Germany) plates. Spots were visualized by spraying with 1% Ce(SO4)2-10% aqueous H2SO4 solution, followed by heating.
3
HPLC-QTOF-MS and NMR Analysis Protocol
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HPLC system (Agilent, USA) consisted of a model G1276A pump, model G1367B Autosampler and model G1316A UV detector. The chromatograph was equipped with a reversed-phase C18 column of Grace Alltima (250 mm × 4.6 mm, 5 μm). The QTOF-MS system (Bruker, Germany) with an ESI source was performed. HPLC separations were performed on a Hitachi 655-15 series pumping system equipped with a Hitachi L-2490 refractive index detector using a YMC-Park ODS-A column (250 × 10 mm I.D, S-5 μm, and 12 nm). NMR spectra were performed on a Bruker ARX-300, ARX-400, and ARX-600 spectrometer using trimethylchlorosilane as the internal standard. Column chromatography was performed on a 200–300 mesh silica gel (Qingdao Marine Chemical Factory, People's Republic of China). Column chromatography was performed using YMC ODS-A gel (12 nm S-75 μm, YMC Co., Ltd., Japan) and D-101 macroporous adsorption resin (Shanghai Hualing Resin Factory, People's Republic of China). TLC was performed with precoated silica gel GF254 plates (Qingdao Marine Chemical Factory, People's Republic of China). Microplate reader (Thermofisher Scientific, Finland) was used to test the activities. Acetylthiocholine iodide, S-butyrylthiocholine iodide, AChE, and BuChE were bought from Sigma Company.
4
Comprehensive Analytical Characterization of Compounds
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Optical rotations were obtained using an Anton Paar MCP 200 polarimeter. Ultraviolet spectra were obtained with a Beckman Coulter DU 730 nucleic acid/protein analyzer. CD spectra were measured on a Biologic MOS-450 spectra polarimeter (Biologic Science, Claix, France). IR spectra were performed on a Bruker Tensor 27 FT-IR spectrophotometer (film). NMR spectra were recorded on a Bruker AV-600 spectrometer using tetramethylsilane as an internal standard, and the chemical shifts were recorded in δ values. HRESIMS were measured using a Bruker micro TOF-Q mass instrument (Bruker Daltonics, Billerica, MA, USA). ESIMS were performed on an Agilent 1290-6420 Triple Quadrupole LC-MS spectrometer. Silica gel (300–400 mesh, and 1200–1500 mesh, Qingdao Marine Chemical Ltd., Qingdao, China), Sephadex LH-20 (GE Healthcare Biosciences AB, Uppsala, Sweden), YMC*GEL ODS-A (S-50 μm, 12 nm) (YMC Co., Ltd., Kyoto, Japan), and MCI gel (CHP-20P, Mitsubishi Chemical Corp., Tokyo, Japan) were utilized for column chromatography. Semipreparative HPLC was performed using a ODS column (250 mm × 10 mm, 5 μm, YMC-ODS-A). Unless otherwise specified, all chemicals and solvents were purchased from Sinopharm Chemical Reagent Co., Ltd. (Shenyang, China). Biological assays were analyzed using a microplate reader (BioTek Synergy H1, BioTek Instruments, Inc., Vermont, USA).
5
Structural Elucidation of Natural Products
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Optical rotations were acquired with a Perkin-Elmer 341 polarimeter. The UV spectra were acquired using a Varian Cary Eclipse 300 spectrophotometer, while the IR spectra were recorded on a Bruker Vector 22 spectrometer with KBr pellets. The NMR spectra were recorded on a Bruker Avance 600 NMR spectrometer with TMS as an internal standard. The HRESIMS measurements were obtained with a Q-TOF Micromass spectrometer (Waters, USA). X-ray crystallographic analysis was performed with a Bruker SMART APEX (II)-CCD diffractometer with Cu Kα radiation (λ = 1.54178 Å). The materials for the CC were silica gel (100–200 mesh; Huiyou Silical Gel Development Co. Ltd., Yantai, China), silica gel H (10–40 μm; Yantai), Sephadex LH-20 (40–70 μm; Amersham Pharmacia Biotech AB, Uppsala, Sweden), and YMC-GEL ODS-A (50 μm; YMC, Milford, MA). Semi-preparative HPLC was conducted on an Agilent 1200 instrument using an Eclipse XDB-C18 column (5 μm, 9.4 × 250 mm). Preparative TLC (0.4–0.5 mm) was conducted on glass plates precoated with silica gel GF254 (Yantai).
6
Spectroscopic Characterization of Compounds
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Optical rotations were determined using a PerkinElmer 341 automatic polarimeter. Ultraviolet (UV) spectra were measured with a UV-2550 spectrophotometer (Shimadzu Corporation, Tokyo, Japan). IR spectra were measured on a Bruker Tensor 27 FT-IR spectrometer (film). 1H and 13C NMR, DEPT, and 2D NMR spectra were carried out on a Bruker AV-600 spectrometer using TMS as internal standard, δ in ppm rel. HRESIMS (including ESIMS) were recorded on a Bruker maXis TOF-QII mass spectrometer (Bruker Fällanden, Switzerland). Column chromatography (CC) were performed on silica gel (100–200 mesh, 300–400 mesh, Qingdao Marine Chemical Ltd., Qingdao, China), Sephadex LH-20 (GE Healthcare Bio-sciences AB, Sweden), YMC GEL ODS-A (S-50 μm, 12 nm) (YMC Co., Ltd, Kyoto, Japan). Semi-preparative HPLC separations were performed using an ODS column (YMC-ODS-A, 250 × 20 mm, 5 μm). Circular dichroism (CD) spectra were recorded on a Chirascan circular dichroism spectrometer (Applied Photophysics).
7
Characterization of Organic Compounds by Spectroscopic Techniques
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Optical rotations were measured using a PerkinElmer 343 polarimeter (Waltham, MA, USA). ECD spectra were recorded with an Chirascan Plus spectropolarimeter (Applied Photophysics , Leatherhead, UK). The 1H and 13C NMR spectra were obtained using Bruker Avance III-700 spectrometer (Bruker, Ettlingen, Germany). Chemical shifts were referenced to the corresponding residual solvent signal (δH 3.31/δC 49.0 for CD3OD). HRESIMS were measured using Bruker maXis Impact II mass spectrometer (Bruker Daltonics, Bremen, Germany). Low-pressure column liquid chromatography was performed using YMC*Gel ODS-A (YMC Co., Ltd., Kyoto, Japan). HPLC was performed using Shimadzu Instrument equipped with RID-10A refractive index detector (Shimadzu Corporation, Kyoto, Japan) and YMC-Pack ODS-A (250 × 10 mm) column (YMC Co., Ltd., Kyoto, Japan).
8
Spectroscopic Analysis of Compounds
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Optical rotations were determined using an MCP200 automatic polarimeter (Anton Paar, Graz, Austria). Ultraviolet spectra were recorded on a DU 730 nucleic acid/protein analyzer (Beckman Coulter, Brea, CA, USA). IR spectra (film) were measured with a Tensor 27 FT-IR spectrometer (Bruker, Ettlingen, Germany). 1D and 2D NMR spectra were recorded on a Bruker AV-600 spectrometer, δ in ppm rel. to TMS, J in Hz. ESIMS were recorded using an 1290-6420 Triple Quadrupole LC-MS spectrometer (Agilent, Santa Clara, CA, USA). HRESIMS were recorded with an Agilent G6230 TOF mass spectrometer. Silica gel (100–200 mesh, 300–400 mesh, Qingdao Marine Chemical Ltd., Qingdao, China), Sephadex LH-20 (GE Healthcare Bio-sciences AB, Uppsala, Sweden), YMC*GEL ODS-A (S-50 μm, 12 nm) (YMC Co., Ltd., Kyoto, Japan), and reversed-phase HPLC (Rohm and Hass Shanghai Chemical Industry Co., Ltd., Shanghai, China) were used for column chromatography. Biological assays were analyzed using a microplate reader (BioTek Synergy H1, BioTek Instruments, Winooski, VT, USA).
9
Spectroscopic Characterization of Compounds
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The NMR experiments were performed using a JNM-ECA 500 MHz NMR instrument (JEOL Ltd., Tokyo, Japan). HRESIMS was carried out on a JMS-700 MStation Mass Spectrometer (JEOL Ltd., Tokyo, Japan). UV spectra were recorded on an Evolution 260 Bio UV–Visible spectrophotometer (Thermo Fischer Scientific, Waltham, MA, USA). Thin-layer chromatographic (TLC) analysis was performed on Kieselgel 60 F254 (Merck, Darmstadt, Germany) and Kieselgel 60 RP-18 F254S (Merck), with visualization performed under UV light (254 and 365 nm) and 10% (v/v) sulfuric acid spray followed by heating (200 °C, 2 min). YMC Gel ODS-A (12 nm, S-150 μm; YMC Co., Kyoto, Japan) was used for column chromatography (CC). Preparative HPLC was performed using a Gilson Preparative HPLC system (Gilson Inc., Middleton, WI, USA) equipped with YMC Pack Pro C18 (5 μm, 250 × 20 mm, YMC Co.). Analytical HPLC was performed using an Agilent 1100 series system (Agilent Technologies, Palo Alto, CA, USA) equipped with YMC-Triart C18 (5 μm, 250 × 4.6 mm, YMC Co.). A [60Co] γ-irradiator (150 TBq capacity; AECL, Ottawa, Canada) was used for gamma irradiation. All other chemicals and solvents used in this study were of analytical grade.
10
Comprehensive Analytical Techniques for Natural Products
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Optical rotations were measured with an AntonPaar MCP 200 automatic polarimeter. Ultraviolet (UV) spectra were obtained on a UV-2550 spectrophotometer (Shimadzu Corporation, Tokyo, Japan). IR spectra were recorded on a Bruker Tensor 27 FT-IR spectrometer (film). 1D and 2D-NMR spectra were carried out on a Bruker AM-400 and an Avance-500 spectrometer, δ in ppm rel. to TMS, J in Hz. ESIMS and HRESIMS were measured with a Bruker miXis TOF-QII mass spectrometer (Bruker, Fällanden, Switzerland), respectively. Silica gel (100–200 mesh, 300–400 mesh, Qingdao Marine Chemical Ltd., Qingdao, China), Sephadex LH-20 (GE Healthcare Bio-sciences AB, Uppsala, Sweden), and YMC GEL ODS-A (S-50 μm, 12 nm) (YMC Co., Ltd., Kyoto, Japan) were used for column chromatography. Semipreparative HPLC analyses were performed using an ODS column (YMC-ODS-A, 250 × 20 mm, 5 μm). Circular dichroism (CD) spectra were measured on a Chirascan circular dichroism spectrometer (Applied Photophysics Ltd., Leatherhead, UK). MTT assays were analyzed using a microplate reader (BioTek Synergy H1, BioTek Instruments, Inc., Vermont, USA).
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