Silica gel plate

All chemical reagents were purchased from Energy Reagent Co., Ltd. (Anqing, China) or Shanghai Huangdi Chemical Co., Ltd. (Shanghai, China). Unless otherwise noted, all commercially available reagents were used directly after they were received. In order to monitor the reaction, thin-layer chromatography (TLC) was performed on silica gel plate (Qingdao Haiyang Chemical Co., Ltd., Qingdao, China) and visualized by UV light. All melting points were determined on a digital X4 melting point analyzer (Henan Ruike Medical Instrument Co., Ltd., Xinxiang, China) using open capillary tubes and were uncorrected. HRMS were obtained with a ESI-Brucker APEX Ⅱ49e mass spectrometer (Bruker, Billerica, MA, USA). ¹H-NMR and ¹³C-NMR spectra were recorded with JNM-ECS (JEOL Co., Ltd., Tokyo, Japan) and Bruke AM-400 spectrometer (Bruker, Billerica, MA, USA), respectively. The solvents used were deuterated reagents (DMSO-d₆ and CDCl₃). Unless otherwise noted, further purification of products was performed via column chromatography on silica gel (200–300 mesh, Gansu Yihua chemical Glass Instrument Co., Lanzhou, China) and the products were eluted in an appropriate solvent mixture under air pressure. The crystal of the typical compound was obtained by solvent evaporation method and determined by Super Nova single crystal diffractometer (Agilent, Santa Clara, CA, USA).

The main instruments and materials used in this study were run following standard protocols including automatic tissue homogenizer, ultraviolet/visible spectrophotometer, ultra high speed refrigerated centrifuge, high-speed countercurrent chromatography, high-performance liquid chromatography, gas chromatography, nucleic acid extractor, fluorescent PCR instrument, ¹H NMR (provided by Kunming Institute of Botany), ¹³C NMR (provided by Kunming Institute of Botany), Macroporous adsorption resin D101 (Dalian Elite Co., Ltd.), D201 (Dalian Elite Co., Ltd.), Sephadex LH-20 (Amersham Biotechnology, Switzerland), MCI (Mitsubishi Chemical, Japan), column chromatography silica gel, thin-layer chromatography silica gel, silica-gel plate (second branch of Qingdao Haiyang Chemical Co., Ltd.), RP18 (Dalian Elite Co., Ltd.), and EYELA rotary evaporator (Japan Chemical Co., Ltd).