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3 protocols using semipreparative xdb c18 column

1

Analytical Characterization of Compounds

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IR spectrum was recorded on a Nicolet 6700 spectrometer (Thermo Scientific, Waltham, MA, USA). Optical rotation was measured on a PerkinElmer 241 MC polarimeter (PerkinElmer, Fremont, CA, USA). 1H and 13C NMR spectra were acquired on a Bruker DRX-500 spectrometer (Bruker Biospin AG, Fällanden, Germany). Chemical shifts (δ) are reported in ppm with reference to the solvent signals, and coupling constants (J) are in Hz. ESIMS spectra were recorded on a Finngan-MAT-95 mass spectrometer and HRESIMS spectra were recorded on an Agilent 1290–6545 UHPLC-QTOF mass spectrometer. Commercial silica gel (Qingdao Haiyang Chemical Co., Ltd., Qingdao, China, 200–300 and 300–400 mesh) and Sephadex LH-20 gel (Amersham Biosciences, Little Chalfont, UK) were used for column chromatography (CC). Precoated silica gel GF-254 plates (Sinopharm Chemical Reagent Co., Shanghai, China) were used for analytical TLC. Reversed-phase (RP) HPLC was performed on an Agilent 1260 series liquid chromatograph equipped with a DAD G1315D detector at 210 nm (Agilent, Santa Clara, CA, USA). An Agilent semipreparative XDB-C18 column (5 μm, 250 × 9.4 mm) was employed for the purification. All solvents used for CC and HPLC were of analytical grade (Shanghai Chemical Reagents Co., Ltd., Shanghai, China) and chromatographic grade (Dikma Technologies Inc., Lake Forest, CA, USA), respectively.
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2

Spectroscopic Analysis of Organic Compounds

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1D and 2D NMR spectra
were acquired in CDCl3 with a Bruker AVANCE III 400, Bruker
AVANCE III 500, or Bruker AVANCE III 600 spectrometer (Bruker Biospin
AG, Fällanden, Germany) with residual CDCl3H 7.26 ppm, δC 77.16 ppm) as the internal
standard. HRESIMS spectra were measured using an Agilent G6520 Q-TOF
mass spectrometer. A Nicolet 6700 spectrometer (Thermo Scientific,
Waltham, MA, USA) was used to obtain the IR spectra. Circular dichroism
spectra
were measured using a JASCO 810 spectrometer. UV spectra were acquired
using a Varian Cary 50 Bio spectrophotometer. Optical rotations were
obtained on a PerkinElmer 241MC polarimeter. Column chromatography
(CC) was performed using commercial silica gel (Sinopharm Chemical
Reagent Co., Ltd., 200–300 and 300–400 mesh) and Sephadex
LH-20 gel (GE Healthcare). Thin-layer chromatography was performed
on precoated silica gel plates [Merck Chemicals (Shanghai) Co., Ltd.,
G60 F-254]. RP-HPLC was performed on an Agilent 1260 series liquid
chromatography system (Agilent, Santa Clara, CA, USA) equipped with
a DAD G1315D detector at 210 nm and an Agilent semi-preparative XDB-C18
column (5 μm, 250 × 9.4 mm). All solvents used for CC were
of analytical grade (Shanghai Chemical Reagent Co., Ltd.) and for
HPLC were of chromatographic grade (Dikma Technologies Inc).
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3

Characterization of Chemical Compounds

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The IR spectrum was recorded on a Nicolet iS50 spectrometer (Thermo Fisher Scientific, Madison, WI, USA). Optical rotations were measured on a PerkinElmer 241MC polarimeter. 1H and 13C NMR spectra were acquired on a Bruker AVANCE III 600 MHz spectrometer. Chemical shifts are reported with the residual CHCl3 (δH 7.26 ppm; δC 77.16 ppm) as the internal standard for 1H and 13C NMR spectra. HRESIMS spectra were recorded on Agilent G6250 Q-TOF (Agilent, Santa Clara, CA, USA). Commercial silica gel (Qingdao Haiyang Chemical Co., Ltd., Qingdao, China, 200–300 mesh, 300–400 mesh) was used for column chromatography, and precoated silica gel GF254 plates (Sinopharm Chemical Reagent Co., Shanghai, China) were used for analytical TLC. Sephadex LH-20 (Amersham Biosciences, Piscataway, NJ, USA) was also used for column chromatography. Reverse-phase (RP) HPLC was performed on an Agilent 1260 series liquid chromatography equipped with a DAD G1315D detector at 210 nm (Agilent, Santa Clara, CA, USA). An Agilent semi-preparative XDB-C18 column (5 μm, 250 × 9.4 mm) was employed for the purification. All solvents used for column chromatography and HPLC were of analytical grade (Shanghai Chemical Reagents Co., Ltd., Shanghai, China) and chromatographic grade (Dikma Technologies Inc., Foothill Ranch, CA, USA), respectively.
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