The IR spectra (KBr pellets) were run on a 380 FT-IR instrument from Nicolet (Thermo, Pittsburgh, PA, USA). The HRMS were recorded with an API QSTAR Pulsar mass spectrometer (Bruker, Bremen, Germany). The UV spectra were obtained from a DU-800 spectrometer (Beckman, Brea, CA, USA). Optical rotations were measured on an Autopol III polarimeter (Rudolph, Hackettstown, NJ, USA). CD spectra were recorded with a J-815 spectrometer (JASCO, Tokyo, Japan). The NMR spectra were recorded on an AV-500 spectrometer (500 MHz for 1H-NMR and 125 MHz for 13C-NMR; Bruker), using the solvent residue signal as the internal standard. Column chromatography was performed with ODS gel (20–45 mm, Fuji Silysia Chemical Co. Ltd., Durham, NC, USA), Sephadex LH-20 (Merck, Darmstadt, Germany) and silica gel (60–80, 200–300 mesh, Qingdao Haiyang Chemical Co. Ltd., Qingdao, China). TLC was carried out on silica gel G precoated plates (Qingdao Haiyang Chemical Co. Ltd.), and spots were detected by spraying with 5% H2SO4 in EtOH followed by heating.
Lh 20
Manufactured by Merck Group
Sourced in Germany, United States
LH-20 is a size exclusion chromatography column used for the separation and purification of molecules based on their size and molecular weight. It is composed of a cross-linked dextran resin and is suitable for the fractionation of proteins, peptides, nucleic acids, and other macromolecules.
Automatically generated - may contain errors
Lab products found in correlation
Silica gel g precoated plates, by Qingdao Haiyang Chemical (3 mentions)
Gf254, by Qingdao Haiyang Chemical (3 mentions)
Silica gel 60, by Merck Group (3 mentions)
Av 500 spectrometer, by Bruker (2 mentions)
Kieselgel 60 gf254, by Merck Group (2 mentions)
Kieselgel 60, by Merck Group (2 mentions)
Sephadex g 50, by Merck Group (2 mentions)
1 6 diphenyl 1 3 5 hexatriene dph, by Merck Group (2 mentions)
Calcein, by Merck Group (2 mentions)
Du 800 spectrometer, by Beckman Coulter (1 mentions)
Api qstar pulsar mass spectrometer, by Bruker (1 mentions)
J 815 spectrometer, by Jasco (1 mentions)
Silica gel, by Qingdao Haiyang Chemical (1 mentions)
Precoated silica gel 60 f254 plates, by Merck Group (1 mentions)
241 mc polarimeter, by PerkinElmer (1 mentions)
Fthrms orbitrap, by Thermo Fisher Scientific (1 mentions)
Mn silica gel 60 m, by Merck Group (1 mentions)
Dip 3600, by Jasco (1 mentions)
Avance 600, by Bruker (1 mentions)
Supernova diffractometer, by Rigaku (1 mentions)
20 protocols using lh 20
1
Characterization of Novel Compounds
2
Spectroscopic Analysis of Natural Products
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Optical rotations were measured using a PerkinElmer-241 MC polarimeter (Waltham, MA, USA). Bruker AVANCE DMX 300 or 600 NMR spectrometers (Karlsruhe, Germany) were employed to record 1H, 13C and 2D NMR spectra. A Thermo Finnigan LCQ Deca LC-MS system (San Jose, CA, USA) was used to analysis the crude extract. ESI-HRMS data were obtained by a FT-HRMS-Orbitrap (Thermo Finnigan, San Jose, CA, USA) mass spectrometer. A Dionex P580 system (Germering, Germany) coupled to a photodiode array detector (UVD340S) was used to perform HPLC analysis. A Europhere 10 C18 (125 × 4 mm, L × ID, Knauer, Germany) was used for analytical separation. HPLC separation was carried out with a Lachrom-Merck Hitachi semi-preparative HPLC system (Darmstadt, Germany) (Pump L7100; UV detector L7400; column: Europhere 100 C18, 300 × 8 mm, Knauer, Germany). Merck MN silica gel 60 M (0.04–0.063 mm, Dueren, Germany) or Sephadex LH-20 (Darmstadt, Germany) were applied for column chromatography as stationary phases. Pre-coated silica gel 60 F254 plates (Merck) were used for TLC (Thin layer chromatography) analysis under detection at 254 and 366 nm and/or using anisaldehyde as spray-reagent. Spectral grade solvents were used for spectroscopic measurements while distilled solvents were used for column chromatographic separations. ECD spectra were recorded on a J-810 spectropolarimeter.
3
Characterization of Novel Organic Compounds
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The optical rotations were determined with a Jasco DIP-3600 digital polarimeter (Jasco, Tokyo, Japan) using a 10 mm cell. The high-resolution mass spectra were recorded using a Micromass-Q-TOF-MS (Waters, Milford, MA, USA). For the DMSO-d6, MeOD, CDCl3, and Acetone-d6, the 1H NMR and 13C NMR spectra were recorded using Bruker DRX (1H NMR, 500 MHz and 13C NMR, 125 MHz) and Bruker Avance 600 (1H NMR, 600 MHz, and 13C NMR, 150 MHz) spectrometers (Bruker, Rheinstetten, Germany), respectively. X-ray crystallography data were collected with a Rigaku Supernova diffractometer using Cu Kα (λ = 1.54184 Å) radiation. Column chromatography (CC) readings were carried out using silica gel (63–200 μm, Merck, Darmstadt, Germany), and Sephadex LH-20. A TLC analysis was performed using percolated aluminum plates backed with silica gel 60 F254 sheets. The TLC plate was visualized under UV light (254 and 365 nm), sprayed with H2SO4 (10%), and then heated.
4
Purification and Characterization of Natural Compounds
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Thin-layer chromatography (TLC) was performed on silica gel GF254 (Qingdao Haiyang Chemical Co., Ltd, China) and column chromatography was performed with silica gel (60–80, 200–300 mesh, Qingdao Haiyang Chemical Co.). Sephadex LH-20 (Merck, Germany). The ESI-MS spectra were measured with a VG Auto-3000 Spectrometer, Sephadex LH-20 (Merck, Germany) and MS-C18 column (3.5 μm, 4.6 by 150 mm, Waters). Nuclear Magnetic Resonance (NMR) spectra were obtained on a Bruker AV-500 spectrometer with tetramethylsilane (TMS) as an internal standard. Infrared Spectroscopy (IR) spectra were recorded on a Nicolet 380 FT-IR instrument, as KBr pellets (Thermo, Pittsburgh, PA, USA). UV spectra were obtained on a Shimadzu UV-2550 spectrometer (Beckman, Brea, CA, USA).
5
Chromatographic Characterization of Extracts
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TLC (Kieselgel 60 GF254, Merck, Darmstadt, Germany) was performed in heptane/EtOAc mixtures (9:1; 7:3 and 1:1 v/v), and spots were visualized by spraying plates with H2SO4-MeOH (5:95, v/v) and heating to 120 °C. Silica gel (Kieselgel 60, Merck 0.063–0.200 mm) and Sephadex (LH-20, Merck) were used for column chromatography (CC). Ethyl lactate was purchased from Sigma Aldrich (Saint Louis, MO, USA). Purified water (TOC < 5 µg/L) was obtained from a reverse osmosis system (Arium 126 61316-RO and Arium 611 UV unit (Sartorius, Goettingen, Germany)). Methanol (HPLC grade) and formic acid (for mass spectrometry, puriss. p.a.) were purchased from J.T. Baker (Phillipsburg, NJ, USA). Folin–Ciocalteu (FC) reagent, 2,2-diphenyl-1-picrylhydrazyl (DPPH), ferric chloride hexahydrate, 2,4,6-tris(2-pyridyl)-s-triazine, Trolox, quercetin, gallic acid, di-methyl sulfoxide (DMSO), and trichloroacetic acid were purchased from Merck (Darmstadt, Germany).
6
Multistep Synthesis and Characterization
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CUR and all reagents were purchased from Merck (Kenilworth, USA), and solvents and catalysts from Synth (Diadema, Brazil). Reactions were monitored using thin-layer chromatography (TLC) (Merck, Kenilworth, USA). Silica-gel (200-300 mesh) and LH-20 (Sephadex) (Merck, Kenilworth, USA) were used for column chromatography separations. Melting points (MP) were determined in Tecnopon PFM-IIV apparatus (MS Tecnopon Instrumentação, Piracicaba, Brazil) and were uncorrected. Nuclear magnetic resonance spectra ( 1 H and 13 C NMR) were carried out on Bruker Avance III 14.1 T (600 MHz) and Bruker Avance III 9.4 T (400 MHz) spectrometers (Bruker, Billerica, USA), using CDCl 3 or DMSO-d 6 as solvents and TMS (tetramethylsilane) as internal reference (Merck, Kenilworth, USA). Chemical shifts (δ) and coupling constants (J) were expressed in ppm and Hz, respectively. Multiplicities were reported as singlet (s), doublet (d) and doublet of doublet (dd). High resolution mass spectrum of MAC 4 was performed on ESI-QqTOF-MS spectrometer (Xevo G2 Xs, Waters, Massachusetts, USA).
7
Phytochemical Analysis by Chromatography and Spectroscopy
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Sephadex (GE healthcare) LH-20 and silica gel 60 (Merck KGaA, Darmstadt, Germany) were used for open-column chromatography (CC). Luna C18, phenyl-hexyl (5 μm, 250 × 10 mm, Phenomenex, Torrance, CA, USA) semi-preparative columns were used for high-performance liquid chromatography (HPLC). HPLC instrument used a Shimadzu LC-10AT pump with an SPD-20A UV-Vis detector. The UV spectra were obtained by using a Jasco UV-530 ultraviolet spectrophotometer (Jasco, Tokyo, Japan), whereas the IR spectra were obtained on a Jasco FT-IR-4600 spectrophotometer (Jasco, Tokyo, Japan). Optical rotations were measured with a Jasco P-1020 digital polarimeter (Jasco, Tokyo, Japan). NMR spectra were obtained using JEOL JNM ECS 400 MHz (JEOL, Tokyo, Japan), Varian 600 MHz NMR (Varian, Palo Alto, CA, USA), and Bruker AVIIIHD700X 700 MHz spectrometers (Bruker, Bremen, Germany). ESI–MS data were collected on a VG Biotech Quattro 5022 mass spectrometer (VG Biotech, Altrincham, UK). High-resolution ESI–MS data were obtained with a Bruker APEX II spectrometer (Bruker, Bremen, Germany). Circular dichroism spectra were recorded on a JASCO J-810 spectrophotometer (Jasco, Tokyo, Japan).
8
NMR and HPLC Analysis of Natural Products
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The 1D-and 2D-1 HNMR measurements and mass spectra (ESI) were determined using Bruker ARX 600 NMR spectrometer in CD3OD and Finnigan LCQ Deca mass spectrometer (column: Eurosphere 100-C18 (5 μM; 227 * 2 mm) respectively. Spectral grade solvents were employed for the spectroscopic determinations. HPLC analysis was carried out using a Dionex UltiMate3400 SD with a P580A LPG Pump coupled to a photodiode array detector (UVD 340S) and detection of compounds done at different wavelengths: 235, 254, 280, and 340 nm. The column (125 mm * 4 mm) used for the HPLC analysis was prefilled with Eurosphere-10 C18 (Knauer, Germany); the solvents used for the gradient includes the following: (MeOH, 0.02% H3PO4 in H2O): 0 min (10% MeOH), 5 min (10% MeOH), 35 min (100% MeOH), 45 min (100% MeOH). The optical rotations were performed using 241 MC, Perkin-Elmerpolarimeter in methanol as solvent. The Semi-preparative HPLC separation was done on a Merck Hitachi HPLC System (UV detector UV-L7400 and Chromaster 5410 (photodiode array detector); Pump L-7100 and Chromaster 5110; Eurosphere 100-C18 (10 μm; 300 * 8 mm), Knauer, Germany). Sephadex LH-20 and Merck MN Silica gel 60 M (0.04-0.063 mm) were used for column chromatography while TLC plates with silica gel F254 (Merck, Darmstadt, Germany) were used for thin-layer chromatography. Gradients of CH2Cl2/MeOH were used in each case.
9
Lipid Membrane Composition Analysis
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Eugenol, amphotericin B, calcein, sephadex G-50, LH-20, ergosterol (Erg-), pentamidine isethionate, propidium iodide (PI), and 1,6-diphenyl-1,3,5-hexatriene (DPH) were obtained from Sigma-Aldrich (Bornem, Belgium). Miltefosine was obtained from Santa Cruz Biotechnology (Heidelberg, Germany). calcein-AM included in a live/dead Viability/Cytotoxicity Kit for mammalian cells, Alamar blue and goat anti-Guinea Pig IgG Secondary Antibody, Alexa Fluor™ 488 were obtained from Thermo Fisher Scientific (Merelbeke, Belgium). The 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE), l -α-phosphatidylinositol (PI—Liver, Bovine), and cholesterol (Chol—Ovine Wool) were purchased from Avanti Polar Lipids Inc. (Alabaster, AL, USA). All organic solvents used were from VWR (Leuven, Belgium).
10
Characterization of Organic Compounds
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The 1D (1H, 13C, and DEPT-135) and 2D NMR (COSY, HSQC, HMBC) spectra were recorded on the Avance 400 MHz NMR spectrometer (Bruker, Rheinstetten, Germany) at 400 (proton, 1H) and 100 (carbon, 13C) MHz. Chemical shifts were reported in parts per million (ppm) and coupling constants (J) in Hz. The 1H and 13C NMR values were relative to the internal standard TMS and were acquired in CD3OD, CDCl3, or DMSO-d6. HRESI-MS were obtained on a Waters Synapt G2 mass spectrometer (Cone Voltage 15 V), which operated in the negative and/or positive ion modes using direct injection. ATR-FTIR (PerkinElmer Spectrum 100, Llantrisant, Wales, UK) at a transmission mode of 400–4000 cm−1 column chromatography was performed using Sephadex (LH-20, Sigma-Aldrich, St. Louis, MO, USA), and normal-phase silica gel 60 (70–230 mesh ASTM, Merck, Readington Township, NJ, USA). TLC was performed on silica gel aluminum sheets (Silica gel 60 F254, Merck) to monitor the fractions. Visualization was achieved with 10% H2SO4 and detection with the vanillin sulfuric acid reagent and heating to 105 °C.
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