1260 quadrupole

Low-resolution LC/MS measurements were performed using an Agilent Technologies 1260 quadrupole (Agilent Technologies, Santa Clara, CA, USA) and a Waters micro mass ZQ LC/MS system (Waters Corp, Milford, MA, USA) with a reverse-phase column (Phenomenex Luna C18 (2) 100 Å, 50 mm × 4.6 mm, 5 µm, Torrance, CA, USA). The flow rate was 1.0 mL/min, the duration was 18.0 min, and the solvent gradient ranged from 5% to 100% acetonitrile (CH₃CN, Samchun, Seoul, Republic of Korea) in water. LC/MS was performed at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University (Seodaemun, Seoul, Republic of Korea).

Low-resolution LC/MS measurements were performed using the Agilent Technologies 1260 quadrupole (Agilent Technologies, Santa Clara, CA, USA) and Waters Micromass ZQ LC/MS system (Waters Corp, Milford, MA, USA) using a reversed-phase column (Phenomenex, Torrance, CA, USA) (Phenomenex Luna C18 (2) 100 Å, 50 mm × 4.6 mm, 5 µm) at a flow rate of 1.0 mL/min at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University. The NMR spectra were obtained using an Agilent NMR spectrometer (Agilent, Santa Clara, CA, USA) at 400 MHz for ¹H and at 100 MHz for ¹³C using the signals of the residual solvent as internal references (δ_H 7.24 ppm and δ_C 77.2 ppm for deuterated chloroform [CDCl₃]). High-resolution EI-MS spectra were acquired using a JEOL JMS-AX505WA mass spectrometer (JEOL Ltd., Tokyo, Japan) at Seoul National University.

Low-resolution LC/MS measurements were carried out using an Agilent Technologies 1260 quadrupole (Agilent Technologies, Santa Clara, CA, USA) and Waters Micromass-ZQ 2000 MS system (Waters Corp, East Lyme, CT, USA) using a reversed-phase column (Phenomenex Luna C-18 (2), 50 mm × 4.6 mm, 5 µm, 100 Å) at a flow rate of 1.0 mL/min at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University. A solvent signal as an internal standard on Varian Inova spectrometers (Bruker, Billerica, MA, USA) was used to collect 1H and 2D NMR spectra at 400 MHz in CDCl3. Also using the Varian Inova spectrometer, the 13C NMR spectrum was acquired at 100 MHz. Open-column chromatography was performed on C-18 resin (40–63 μm, ZEO prep 90) with a gradient solvent of water (H₂O) and methanol (MeOH). The fractions acquired from open-column chromatography were subsequently purified by reverse-phase high-performance liquid chromatography (HPLC) using a Phenomenex Luna C-18 (2), 100 Å, 250 nm × 10 mm, 5 μm column with a mixture of acetonitrile (CH₃CN) and H₂O at a flow rate of 2.0 mL min⁻¹.