The 1H (600 MHz/800 MHz) and 13C (600 MHz/800 MHz) NMR spectra were recorded using a Bruker AVANCE III 600 MHz Spectrometer (1H NMR spectra parameter configuration: NS = 4, DS = 2, DW = 41.6 usec. 13C NMR spectra parameter configuration: NS = 4/1024, DS = 2/4, DW = 41.6/13.8 usec.) and Bruker AV 800MHz Spectrometer (1H NMR spectra parameter configuration: NS = 4, DS = 0, DW = 31.2 usec. 2D NMR spectra parameter configuration: NS = 8/16, DS = 16/16, DW = 56.8/59.4 usec) (Bruker, Billerica, MA, USA) in a deuterated solvent. HR-ESI-MS and ESI-MS analyses were performed using a Shimadzu Corporation UPLC-IT-TOF spectrometer (Shimadzu, Kyoto, Japan). Preparative high-performance liquid chromatography was performed on a DAC-HB50 separation module combined with a UV detector at 535 and 280 nm (Hanbon, Huai’an, China). A C18-ODS-A (300 mm × 50 mm, 5 μm, YMC, Kyoto, Japan) and XAqua C18 semi-preparative column (4.6 × 250 mm, 5 μm, Acchrom, Wenling, China) were used for separation. UV spectra were acquired using a T6 New Century spectrophotometer (Persee, Beijing, China). Microscopic observation and photographs were taken using a SZX7 dissecting microscope (Olympus, Tokyo, Japan) and a CCD camera (VertA1, Shanghai, China). All chemicals and solvents were of chromatographic grade.
C18 ods a
Manufactured by YMC
Sourced in China, Japan
The C18 ODS-A is a type of chromatographic column used for liquid chromatography analysis. It is designed with a stationary phase consisting of octadecylsilane (ODS) bonded to a silica support, which is commonly referred to as a reverse phase column.
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Lab products found in correlation
Av600 nmr spectrometer, by Bruker (4 mentions)
Ftir 8400s spectrometer, by Shimadzu (4 mentions)
Q tof spectrometer, by Waters Corporation (3 mentions)
Uv 2550, by Shimadzu (2 mentions)
J 815 spectropolarimeter, by Jasco (2 mentions)
Uv 2550 spectrophotometer, by Shimadzu (2 mentions)
Silica gel column, by Qingdao Marine Chemical (2 mentions)
Uplc it tof spectrometer, by Shimadzu (1 mentions)
Av800 mhz spectrometer, by Bruker (1 mentions)
Szx7 dissecting microscope, by Olympus (1 mentions)
Ccd camera, by Olympus (1 mentions)
Avance 3 600 mhz spectrometer, by Bruker (1 mentions)
Silica gel, by Qingdao Marine Chemical (1 mentions)
Artemisinin standard, by Merck Group (1 mentions)
Model ultimate 3000, by Thermo Fisher Scientific (1 mentions)
Hplc system, by Shimadzu (1 mentions)
Spd m20a, by Shimadzu (1 mentions)
Lc 20ad pump, by Shimadzu (1 mentions)
Uv 2600 uv visible spectrometer, by Shimadzu (1 mentions)
Avance neo 500 spectrometer, by Bruker (1 mentions)
10 protocols using c18 ods a
1
Multi-Spectroscopic Characterization of Compounds
2
Spectroscopic Characterization of Compounds
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1D and 2D NMR spectra were obtained with a Bruker AV 600 NMR spectrometer(chemical shifts are presented asδ values with TMS as the internal standard) (Bruker, Billerica, Germany). HR-ESI-MS were performed on a Q-tof spectrometer (Waters, Milford, MA, USA). UV and IR data were done using a Shimadzu UV2550 and FTIR-8400Sspectrometer (Shimadzu, Kyoto, Japan), respectively. Thin-layer chromatography (TLC) was performed on pre-coated silica gel GF254 (Zhi Fu Huang Wu Pilot Plant of Silica Gel Development, Yantai, China). Semi-preparative HPLCwas conducted on an analytic LC equipped with a pump of P230, a DAD detector of 230+ (Ellte, Dalian, China) with a C18 ODS-A (5 µm, YMC, Kyoto, Japan). Column chromatography with silica gel was used (100-200 and 200-300 mesh, Qingdao Marine Chemical plant, Qingdao, China). All solvents used were of analytical grade (Beijing Chemical Plant, China).
3
Spectroscopic Analysis of Bioactive Compounds
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Optical rotations were obtained on a Perkin-Elmer 341 digital polarimeter (PerkinElmer, Norwalk, Waltham, MA, USA). UV and IR spectra were recorded on Shimadzu UV2550 and FTIR-8400S spectrometer (Shimadzu, Kyoto, Japan), respectively. ECD spectra were obtained using a JASCO J-815 spectro polarimeter. NMR spectra were obtained with a Bruker AV 600 NMR spectrometer (chemical shift are presented as δ values with TMS as the internal standard) (Bruker, Billerica, Germany). HR-ESI-MS were performed on a Q-tof spectrometer (Waters, Milford, MA, USA). Preparative HPLC was performed on an analytic LC equipped with a pump of P230, a DAD detector of 230+ (Ellte, Dalian, China), semi-preparative column. C18 ODS-A (50 μm, YMC, Kyoto, Japan) and Silica gel (100–200 and 200–300 mesh, Qingdao Marine Chemical Plant, Qingdao, China) was used for column chromatography. TLC analyses were carried out on Silica gel GF254 pre-coated plates (Zhi Fu Huang Wu Pilot Plant of Silica gel Development, Yantai, China) with detection accomplished by spraying with 5% H2SO4 followed by heating at 100 °C. HUVECs cell was purchased at Shanghai cell bank of Chinese academy of sciences. All solvents used were of analytical grade (Beijing Chemical Works, Beijing, China).
4
NMR and Mass Spectrometry Analysis Protocol
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NMR spectra were obtained with a Bruker AV 600 NMR spectrometer (chemical shift are presented as δ values with TMS as the internal standard) (Bruker, Billerica, Germany). Abbreviations are as follows: s (singlet), d (doublet), dd (doublet of doublet) t (triplet), q (quartet), m (multiplet), bs (broad singlet). Chemical shifts (δ) are given in ppm relative to solvent residual peak (CD3OD, δ = 3.3 ppm, DMSO-d6, δ = 2.5 ppm) as external standard. High resolution mass spectra (HR-ESI-MS) was conducted with ThermoFisher Scientific LTQ-Orbitrap XL spectrometer (Waters, Milford, MA, USA). UV and IR data were obtained using a Shimadzu UV2550 spectrophotometer and a FTIR-8400S spectrometer (Shimadzu, Kyoto, Japan), respectively. Precoated silica gel GF254 plates (Zhi Fu Huang Wu Pilot Plant of Silica Gel Development, Yantai, China) were needed for TLC. Semi-preparative HPLC was conducted on an analytic LC equipped with a pump of P230 and a DAD detector of 230+ (Ellte, Dalian, China) with a C18 ODS-A (5 µm, YMC, Kyoto, Japan). Column chromatography used silica gel columns (200–300 mesh, Qingdao Marine Chemical plant, Qingdao, China). All solvents used were of analytical grade (Beijing Chemical Plant, Beijing, China).
5
Comprehensive Analytical Characterization
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1D and 2D-NMR spectra were obtained with a Bruker AV 600 NMR spectrometer (chemical shift are presented as δ values with TMS as the internal standard) (Bruker, Billerica, Germany). HRESIMS was performed on a Q-tof spectrometer (Waters, Milford, MA, USA). UV and IR data were obtained using a Shimadzu UV2550 spectrophotometer and a FTIR-8400S spectrometer (Shimadzu, Kyoto, Japan), respectively. CD spectra were obtained using a JASCO J-815 spectropolarimeter (Tokyo, Japan). Thin-layer chromatography (TLC) was performed on pre-coated silica gel GF254 (Zhi Fu Huang Wu Pilot Plant of Silica Gel Development, Yantai, China). Semi-preparative HPLC was conducted on an analytic LC equipped with a pump of P230 and a DAD detector of 230+ (Ellte, Dalian, China) with a C18 ODS-A (5 µm, YMC, Kyoto, Japan). Column chromatography used silica gel columns (200–300 mesh, Qingdao Marine Chemical plant, Qingdao, China). All solvents used were of analytical grade (Beijing Chemical Plant, China).
6
Quantifying Artemisinin in Artemisia annua
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Quantification of artemisinin was performed as described previously (Zhang et al., 2009 (link)). Leaves from 3 month-old A. annua were collected, dried for 48 h at 50°C and pulverized into powder. 0.1 g dried-leaf powder was used for the ultrasonic extraction with 1 mL methanol for 30 min. Then the mixture was centrifuged at 12, 000 rpm for 5 min. The supernatants were filtered using filters (0.22 μm). The samples were analyzed by the HITACHI 2695 HPLC system coupled with a SANCO ELSD180 detector. The conditions were as follows: mobile phase, water/methanol (20:80, v/v); column, YMC-Pack ODS-A C18; flowrate, 1 ml/min. Artemisinin was set at 5.577 for artemisinin. The artemisinin standard was purchased from Sigma. Three biological repeats were measured for each sample.
7
Quantitative Analysis of Fat-Soluble Vitamins
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High‐performance liquid chromatography (HPLC) with a photodiode‐array detector (PDA) (Waters) that was equipped with an isocratic pump, a degasser, and automatic injection system (Model Ultimate 3000, Thermo Science) was used. The column used in this study was a YMC‐Pack ODS‐A C18 (150 mm x 4.6 mm, 5 μm). For the analysis of the β‐carotene, the analytical column was maintained at a temperature of 22 ± 1 ℃. The mobile phase consisted of a mixture of methyl tertiary‐butyl ether (MTBE) with methanol (60:40, v/v). The flow rate was set to 2 ml/min with a UV absorbance of 450 nm. To analyze the retinal acetate, ergocalciferol (D2), cholecalciferol (D3), DL‐alpha‐tocopherol acetate, and phylloquinone (K1), and the temperature of column was maintained at 30 ± 1℃. Acetonitrile (ACN) was used as a mobile phase. The flow rate was maintained at 1 ml/min with a UV absorbance of 280 nm (Fanali, D'Orazio, Fanali, & Gentili, 2017 ). The chromatographic peaks for each vitamin were identified by comparing the retention times of the samples with those of the standard compounds. Quantification was conducted using a standard calibration equation obtained from each external standard.
8
Quantitative HPLC Analysis of Citrus Flavonoids
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The extracts obtained from UAE under optimized conditions and conventional HRE were analyzed by an HPLC system (Shimadzu, Kyoto, Japan), which was equipped with two LC-20AD pumps and a diode array detector (SPD-M20A). All chromatography experiments were performed on a YMC-Pack ODS-A C18 (250 mm × 4.6 mm, 5 μm). The mobile phase was comprised of solvent A (0.1% TFA in water) and solvent B (acetonitrile). The solvent gradient in volume ratios was as follows: 0–60 min, 10–100% B. The system was operated at a flow rate of 0.5 mL/min. Analyses were carried out at room temperature, the detection wavelength was set at 280 nm. The phenolic compounds including hesperetin, hesperidin, naringin, neohesperidin, and eriocitrin were identified by comparison with the retention time and UV spectra of individual standards, and quantified using the external standard method.
9
Characterization of Natural Compounds
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Optical rotations were determined on an Anton Paar MCP 200 automatic polarimeter (Graz, Austria). UV Spectra were recorded on a Shimadzu UV-2600 UV–Visible spectrometer. IR spectra were acquired on a Thermo Scientific Fourier Transform NICOLET iS5 Infrared Spectrometer (Waltham, MA, USA) using KBr disks. HRMS (ESI) was measured on an AB SCIEX X500R QTOF mass spectrometry. 1D and 2D NMR data were recorded on a Bruker AVANCE NEO 500 spectrometer (Bremen, Germany). Chemical shift values were expressed in δ (ppm) relative to tetramethylsilane (TMS) as the internal standard. ECD spectra were measured on a Chirascan spectrometer (England, United Kingdom). Precoated silica gel 60 GF254 plates (Branch of Qingdao Haiyang Chemical Co., Ltd., Qindao, China) was used for TLC. Silica gel (200–300 mesh and 300–400 mesh, Qingdao Haiyang Chemical Co., Ltd., Qingdao, China), silica gel for chromatography C18 MB 100-40/75 (Fuji Chemical industries Co., Ltd., Japan) and D-101 macroporous adsorbent resin (Shanghai Macklin Biochemical Co., Ltd., Shanghai, China) were used for column chromatography (CC). A Waters 1500-Series system was applied to perform HPLC separations. For reversed-phase semipreparative HPLC, a YMC Pack ODS-A C18 (250 × 10 mm, 5 μm) column was applied.
10
Isolation and Purification of Angiotensin-Converting Enzyme Inhibitors
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PFMHs were fractioned using ultrafiltration tubes (3 kDa MWCO), and two fractions (>3 kDa and <3 kDa) were obtained. Following the ACEI activity assay, the fraction with the higher activity was dissolved in distilled water at 100 mg mL−1 and loaded onto a Sephadex G-25 gel filtration column (3.5 × 30 cm, GE Ltd., USA), followed by elution using ultrapure water at a flow rate of 1.0 mL min−1 and evaluated at 220 nm. The eluted fractions were collected and lyophilized, and their ACEI activity was subsequently measured. Afterward, the fractions showing the highest activities were pooled and further purified on a YMC-Pack ODS-A C18 semi-preparative column (250 × 10.0 mm) using linear gradient eluting conditions at a flow rate of 2.0 mL min−1. The mobile phase consisted of eluent A (0.1% v/v trifluoroacetic acid (TFA) in ultrapure water) and eluent B (pure methanol). Following the injection of 100 μL of sample solution into the C18 column, the elution gradient was performed as follows: 99% A (0–5 min), 99–39% A (5–65 min), 39% A (65–70 min), 39–99% A (70–75 min) and 99% A (75–80 min). The eluted fractions were monitored at 220 nm and the fractions that showed the strongest ACEI activities were pooled and sequenced.
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