C. longa was harvested from the Jindo-country, Jeonnam-province, Korea. The plant was identified by comparing with a specimen (voucher No. MPS004295) from the National Institute of Horticultural and Herbal Science (NIHHS), Eumseong, Korea. Reagent-grade solvent was used for extraction and column chromatography (CC). CC was performed using YMC ODS-A (C18) (YMC, Kyoto, Japan), Cytiva Sephadex™ LH-20 (Cytiva, Marlborough, MA, USA), and silica gel (Merck, Darmstadt, Germany). Subsequently, 1D and 2D NMR spectra were recorded in chloroform-d, acetone-d6 and dimethyl sulfoxide (DMSO)-d6 using a JEOL JNM ECP-400 spectrometer (400 MHz 1H and 100 MHz 13C).
Sephadex lh 20
Manufactured by Cytiva
Sourced in China, Sweden, Japan, Germany, United States, United Kingdom
Sephadex LH-20 is a size-exclusion chromatography medium used for the separation and purification of a wide range of molecules, including proteins, peptides, and small organic compounds. It is a hydrophilic, cross-linked dextran polymer with a porous structure that allows for size-based separation. Sephadex LH-20 is commonly used in various applications, such as desalting, fractionation, and purification of samples.
Automatically generated - may contain errors
Lab products found in correlation
Silica gel, by Qingdao Marine Chemical (41 mentions)
P 1020, by Jasco (18 mentions)
Drx 500, by Bruker (16 mentions)
Silica gel, by Qingdao Haiyang Chemical (15 mentions)
Mci gel chp 20p, by Mitsubishi (11 mentions)
P 1020 digital polarimeter, by Jasco (11 mentions)
P 1020 polarimeter, by Jasco (10 mentions)
Chirascan circular dichroism spectrometer, by Applied Photophysics (9 mentions)
Gf254 plates, by Qingdao Haiyang Chemical (9 mentions)
Tensor 27 ftir spectrometer, by Bruker (8 mentions)
Pack ods a, by YMC (8 mentions)
Silica gel, by Merck Group (7 mentions)
Ir affinity 1 spectrometer, by Shimadzu (7 mentions)
341 polarimeter, by PerkinElmer (7 mentions)
Sepa 300 polarimeter, by Horiba (7 mentions)
J 810 spectropolarimeter, by Jasco (7 mentions)
Uv 2401 pc spectrophotometer, by Shimadzu (7 mentions)
Rp 18 f254, by Merck Group (7 mentions)
Avance 3 600, by Bruker (7 mentions)
Gf254, by Qingdao Marine Chemical (6 mentions)
240 protocols using sephadex lh 20
1
Isolation and Characterization of Curcuma longa Compounds
2
Flash Column Chromatography Separations
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Flash column chromatography separations were performed by using silica gel (80 mesh and 300 mesh; Fuji silysia Co. (Aichi, Japan)) or Biotage IsoleraTM (Uppsala, Sweden) equipped with Biotage SNAP Ultra Silica Cartridges (10 g, 25 g, 50 g, 100 g, and 340 g) (Uppsala, Sweden) or Biotage Sfär Silica HC D Cartridges (10 g, 25 g, 100 g, 200 g, and 350 g) (Uppsala, Sweden). The quantity of silica gel was typically 100 to 200 times the weight of the crude sample. Cytiva Sephadex LH-20 (Tokyo, Japan) was used for size-exclusion chromatography. Solvent systems for chromatography are specified as v/v ratios.
3
Characterization of Natural Compounds
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The optical rotation values were measured on a 241 polarimeter (Perkin-Elmer). The infrared spectra were measured by a FTS 165-IR instrument (Bio-Rad, USA). A Varian INOVA-400 FT-NMR spectrometer (USA) and a Bruker APEX II spectrometer were used to record the NMR and HRESIMS data, respectively. Different types of chromatographic materials were used for the fractionation of natural compounds, including Sephadex LH-20 (Amersham Biosciences), silica gel (200– 300 mesh, Qingdao Haiyang Chemical Co., Ltd), and ODS (YMC Co., Ltd). Prep-HPLC separation was performed on a prep-HPLC manufactured by Hanbon Sci & Tech of China using a Megres C18 column (250 mm × 20 mm).
4
Spectroscopic Analysis of Organic Compounds
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Optical rotations were recorded with a JASCO P-1020 digital polarimeter. UV spectra were recorded on a 2489 detector of Waters. ECD spectra were measured on JASCO J-815 spectrometer. IR spectra were obtained on a Nicolet Nexus 470 spectrophotometer in KBr discs. NMR spectra were recorded on a Varian System 500 spectrometer, JEOL JNM-ECP 600 spectrometer, Bruker AVANCE NEO 400 spectrometer, or Bruker AVANCE III 600 spectrometer, and chemical shifts were referenced to the corresponding residual solvent signals (δH/C 3.31/49.00 for methanol-d4, δH/C 2.50/39.52 for DMSO-d6). HRESIMS were measured on a Q-TOF Ultima Global GAA076 LC mass spectrometer. LC-MS data were obtained on a Waters ACQUITY SQD 2 UPLC/MS system with a reversed-phase C18 column (ACQUITY UPLC BEH C18, 2.1 × 50 mm, 1.7 μm) at a flow rate of 0.4 mL/min. Semipreparative HPLC was performed using a C18-PFP column (ACE C18-PFP, 10 × 250 mm, 5 μm), Phenyl column (YMC-Pack Ph, 10 × 250 mm, 5 μm), or π-NAP column (COSIMOSIL π-NAP, 10 × 250 mm, 5 μm). Analytical thin layer chromatography (TLC) was carried out on plates pre-coated with silica gel GF254 (10–40 μm). Column chromatography (CC) were performed using silica gel (200–300 mesh, Qingdao Marine Chemical Factory) and Sephadex LH-20 (Amersham Biosciences).
5
Spectroscopic Analysis of Natural Compounds
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The melting points were tested by a Putiantongchuang WRX-5A apparatus. Optical rotations were measured on a Jasco-P-1020 polarimeter. IR spectra were obtained by using a Bruker Tensor 27 FT-IR spectrometer with KBr pellets. NMR spectra were acquired with instrument of a Bruker DRX-500. HSESIMS was measured on an API QSTAR Pulsar spectrometer. Silica gel (200–300 mesh, Qingdao Marine Chemical Inc., China) and Sephadex LH-20 (Amersham Biosciences, Sweden) were used for column chromatography (CC). Fractions were monitored by TLC (Qingdao Marine Chemical Inc., China) and spots were visualized by heating silica gel plates immersed in vanillin–H2SO4 in EtOH, in combination with Agilent 1200 series HPLC system (Eclipse XDB-C18 column, 5 μm, 4.6 × 150 mm). Preparative HPLC was performed on an Agilent 1100 series with a Zorbax SB-C18 (5 μm, 9.4 × 150 mm) column.
6
Analytical Techniques for Compound Characterization
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The NMR spectra were acquired using a Bruker Avance 500 MHz MHz NMR spectrometer with TMS as an internal standard (Bruker, Fallanden, Switzerland). ESIMS data were collected on an Agilent Technologies 1290-6430A Triple Quad LC/MS (Agilent Technologies, Palo Alto, CA, USA). Preparative HPLC separations were carried out using a YMC-pack ODS-A column (250 × 20 mm, 5 µm, and 12 nm, YMC Co., Ltd., Kyoto, Japan). Semi-preparative HPLC separations were performed utilizing a YMC-pack ODS-A/AQ column (250 × 10 mm, 5 µm, and 12 nm, YMC Co., Ltd., Kyoto, Japan) and a YMC-pack Cellulose-SB column (250 × 10 mm, 5 µm, and 12 nm, YMC Co., Ltd., Kyoto, Japan). Column chromatography were performed with silica gel (200–300 mesh, Qingdao Marine Chemical Inc., Qingdao, China) and Sephadex LH-20 (Amersham Biosciences, Uppsala, Sweden), respectively. Thin-layer chromatography (TLC) was conducted with precoated glass plates GF-254 (Merck KGaA, Darmastadt, Germany).
7
Comprehensive Structural Elucidation Protocol
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UV and IR spectra were measured on an UV-2401PC spectrometer (Shimadzu, Beijing, China) and IR Affinity-1 spectrometer (Shimadzu, Beijing, China), respectively. Optical rotations were performed on a Perkine Elmer 341 polarimeter, and CD spectra were measured with a chirascan circular dichroism spectrometer (Applied Photophysics, Surrey, UK). HR-ESIMS were determined with a Bruker maXis Q-TOF in positive/negative ion mode. The NMR spectra including (1D and 2D NMR) were recorded on a Bruker AC 500 MHz spectrometer using TMS as standard. All chemical shifts were assigned with δ-values. X-ray diffraction intensity data were collected on Agilent Xcalibur Nova single-crystal diffractometer using Cu Kα radiation. Column chromatography (CC) was performed on silica gel (200–300 mesh, 300–400 mesh), and Sephadex LH-20 (Amersham Biosciences, Sweden), respectively. TLC were carried out on silica gel GF254 (10–40 µm) plates (Qingdao Marine Chemical Factory, China). All solvents used were of analytical grade (Tianjin Fuyu Chemical and Industry Factory). Semipreparative HPLC (Agilent Technologies, 1260 infinity series) was performed using an ODS column (YMC-pack ODS-A, 10 × 250 mm, 5 µm, 1.5 mL/min).
8
Comprehensive Spectroscopic Characterization
9
Analytical Characterization of Natural Products
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Semipreparative HPLC (Agilent Technologies, 1260 Infinity II series) was performed using an ODS column (YMC-pack ODS-A, 10 mm × 250 mm, 5 μm). Column chromatography (CC) was performed over silica gel (200–300 mesh; Qingdao Marine Chemical Group Co., Qingdao, China) and Sephadex LH-20 (Amersham Biosciences Inc., Piscataway, NJ, USA) and octadecylsilyl silica gel (YMC Co., Ltd., Kyoto, Japan; 50 μm), respectively. Spots were detected on TLC (Qingdao Marine Chemical Factory, Qingdao, China) under 254 nm UV light. The NMR spectra were obtained on a Bruker Avance-600 MHz spectrometer (Bruker, Billerica, MA, USA) with tetramethylsilane as an internal standard. HR-ESI-MS spectra were recorded on a Bruker miXis TOF-QII mass spectrometer (Bruker, Billerica, MA, USA). Optical rotations were determined with a Perkin Elmer MPC 500 (Waltham, MA, USA) polarimeter. The UV, IR, and ECD spectra were recorded on a Shimadzu UV-2600 PC spectrometer (Shimadzu, Kyoto, Japan), an IR Affinity-1 spectrometer (Shimadzu, Kyoto, Japan), and a Chirascan circular dichroism spectrometer (Applied Photophysics, Leatherhead Surrey, UK), respectively. The artificial sea salt was a commercial product (Guangzhou Haili Aquarium Technology Company, Guangzhou, China). Cells were disrupted using a high pressure homogenizer NanoGenizer (Genizer LLC, Irvine, CA, USA).
10
Comprehensive Analytical Characterization of Compounds
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The specific optical rotation data were acquired on a Rudolph Autopol III automatic polarimeter (Rudolph Research, Fairfield, NJ, USA). The UV spectra were recorded on a Shimadzu UV-2450 spectrophotometer (Shimadzu Corporation, Kyoto, Japan). IR spectra were recorded on a Thermo Nicolet Nexus 470 FT-IR spectrometer (Thermo Nicolet, Vernon Hills, IL, USA). The ECD data were acquired on a JASCO 810 CD spectrophotometer (Jasco Corporation, Tokyo, Japan). NMR spectra were recorded on a Brucker-400 and 600 NMR spectrometer (Bruker Corp. Billerica, MA, USA), with tetramethylsilane as an internal standard. HRESIMS experiments were measured on a Waters Xevo G2 Q-TOF mass spectrometer (Waters MS Technologies, Manchester, UK). Silica gel (100–200 mesh or 200–300 mesh, Qingdao Marine Chemical Co. Ltd., Qingdao, China) and Sephadex LH-20 (Amersham Biosciences, Uppsala, Sweden) were used for open CC. TLC analyses were carried out on the pre-coated silica gel GF254 plates (Qingdao Marine Chemical Co. Ltd., Qingdao, China). The spots were visualized under the UV lights (254 nm and 365 nm). All of the solvents were distilled prior to use.
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