Av 600 nmr spectrometers

Optical rotations were recorded on an Anton Paar MCP 200 polarimeter. UV spectra were measured on a Shimadzu UV-2201 spectrometer. ECD spectra were obtained on a Bio-Logic MOS 450 spectrometer. IR spectra were measured on a Bruker IFS-55 spectrometer. 1D and 2D NMR spectra were acquired on Bruker AV-400 or AV-600 NMR spectrometers. Mass spectra were measured on Bruker micrOTOFQ-Q mass spectrometer. Single-crystal X-ray diffraction data was collected on a Rigaku Saturn 724 CCD diffractometer. Column chromatography (CC) were performed with D101 macroporous adsorption resin (D101 MAR), silica gel, ODS, and Sephadex LH-20. Semipreparative HPLC was performed with YMC ODS column, and the HPLC system was equipped with a Shimadzu SPD-20A UV–vis detector and LC-6AD pump.

Optical rotations were performed on a PerkinElmer model 341 polarimeter. The UV spectra were obtained with a JASCO V-730BIO spectrophotometer. The ECD spectra were carried out on a Bio-Logic Science MOS-450 circular dichroism spectrometer. The IR spectra were run on a JASCO FT/IR-4100 Fourier transform infrared spectrometer using the KBr disk method. The NMR spectra were recorded on Bruker AV-600 NMR spectrometers with the deuterated solvent used as the internal reference (¹H NMR residual proton signal: methanol-d₄ δ 3.31; ¹³C NMR methanol-d₄ δ 49.0). The ¹H NMR spectra were run at 600 MHz, and the ¹³C NMR spectra were produced at 150 MHz. Chemical shifts were expressed in δ (ppm) and reported as s (singlet), d (doublet), t (triplet), dd (doublet of doublets), dt (doublet of triplets), td (triplet of doublets), br (broad), and m (multiplet), respectively. HRESIMS were measured on a Q-Exactive Hybrid Quadrupole Orbitrap mass spectrometer. Column chromatography was performed with D101 macroporous resin (Hebei Cangzhou Baoen Chemical Co., Ltd.), silica gel (Qingdao Marine Chemical Co., Ltd.), and ODS (50 μm, YMC Co., Ltd.). Preparative HPLC was conducted on a YMC ODS column (5 μm, 10 mm × 250 mm) with an LC-10AD pump system and an SPD-20A UV detector (Shimadzu).