Avance neo 600 spectrometer

Room temperature FT-IR spectra of synthetic samples were determined on a Perkin Elmer Spectrum RX I spectrophotometer using KBr pellets. ¹HNMR spectra were carried out on a Bruker Avance NEO-600 spectrometer at room temperature using DMSO-d6.

Optical rotations were measured with a JASCO P-2000 automatic polarimeter in MeOH at 20 °C. The CD spectra were recorded on a JASCO P-1500 spectropolarimeter. NMR spectra were recorded in CDCl₃ using residual solvents as internal standards with a Bruker AVANCE NEO 600 spectrometer with a 5 mm inverse detection triple resonance (H-C/N/D) cryoprobe having z-gradients. The chemical shift values are given in parts per million (ppm) relative to TMS at 0.0 ppm, and the coupling constants are in Hertz. High-resolution electrospray ionization mass spectra (HRESIMS) were measured on an Agilent (Santa Clara, CA, USA) 6545 Q-TOF instrument. Reversed-phase HPLC purification was carried out on a Waters HPLC equipped with a 1525 binary pump, and a Thermo Scientific (Waltham, MA, USA) ODS-2 Hypersil column (5 µm, 250 × 10 mm). Normal phase column chromatography and thin-layer chromatography were performed using silica gel (200–300 mesh) and GF254 (10–20 mm) (Qingdao Marine Chemical Company, Qingdao, China). YMC*GEL ODS-A (AA12S50; YMC Co., Ltd., Japan) was used for reverse phase column chromatography. Sephadex LH-20 was a product from GE Biotechnology, USA.

Curcumol was isolated from the oil of Oleum curcumae (purchased from local commercial sources) [18 (link)]. Reagents and solvents were purchased from Adamas, JK chemical, and local commercial sources. The reagents and the solvents were purified according to the guidelines in Purification of Laboratory Chemicals. ¹ H and ¹³ C NMR spectra were recorded on a Bruker Avance NEO 600 spectrometer with TMS as the internal standard. ESI-MS data were carried out on an Agilent 1100 instrument and Thermo ultimate 3000/Q EXACTIVE FOCUS mass spectrometers. Column chromatography was obtained on silica gel (40–80, 200–300, 300–400, mesh; Qingdao Marine Chemical Co. Ltd., Qingdao, China). Fractions were monitored by TLC (GF₂₅₄, Qingdao Marine Chemical Co., Ltd., Qingdao, China), and spots were detected with a UV254 lamp via heating SiO₂ plates sprayed with 7% H₂SO₄ in EtOH.

Optical rotations were measured on a Jasco P-1010 Polarimeter (JASCO, Tokyo, Japan) in MeOH at 20 °C and UV spectra were measured on a ThermoFisher Evolution 201/220 spectrophotometer (Thermo Scientific, Waltham, MA, USA). NMR spectra were recorded on a Bruker AVANCE NEO 600 spectrometer (BrukerBiospin AG, Fällanden, Germany). ¹H chemical shifts were referenced to the residual CDCl₃ (7.26 ppm) and ¹³C chemical shifts were referenced to the CDCl₃ (77.2 ppm) solvent peaks. High-resolution electrospray ionization mass spectra (HRESIMS) were performed on an Agilent 6230 TOF LC/MS system (Agilent Technologies Inc., Palo Alto, CA, USA) and Thermo Scientific TM Q Exactive PlusTM (Thermo Scientific, Waltham, MA, USA). Reversed-phase HPLC purifications were performed on a Waters 1525 binary HPLC pump attached to a Waters 2998 photodiode array detector (Waters) using a preparative Cosmosil ODS column (250 mm × 20.0 mm i.d., 5 µm, Cosmosil, Nakalai Tesque Co. Ltd., Kyoto, Japan). Column chromatography was performed on silica gel (Qingdao Haiyang Chemical Co. Ltd., Qingdao, China) and YMC reversed-phase silica gel (50 μm, YMC Co. Ltd., Kyoto, Japan). Precoated silica gel plates (HSGF-254, Qingdao Haiyang Chemical Co. Ltd., Qingdao, China) were used for analytical thin-layer chromatography (TLC). Spots were detected on TLC by heating after spraying with a sulfuric acid reagent.

A ThermoFisher Evolution 201/220 spectrophotometer (Thermo Scientific, Waltham, MA, USA) was used for UV spectroscopy measurements. Optical rotations were measured using a Jasco P-1010 Polarimeter (JASCO, Tokyo, Japan) with sodium light (589 nm). NMR spectra were recorded on a Bruker AVANCE NEO 600 spectrometer (BrukerBiospin AG, Fällanden, Germany). ¹H chemical shifts were referenced to the residual CDCl₃ (7.26 ppm), and ¹³C chemical shifts were referenced to the CDCl₃ (77.2 ppm) solvent peaks. High-resolution electrospray ionization mass spectra (HRESIMS) were performed on an ultra-high-performance liquid chromatograph (UPLC) and TIMS-QTOF high-resolution mass spectrometry (Waters, Milford, MA, USA). The purification was performed by reversed-phase high-performance liquid chromatography using a Shimadzu LC-20AT system (Shimadzu Corporation, Tokyo, Japan). The solvents used for HPLC were all Fisher HPLC grade. A Cosmosil C₁₈-MS-II column (250 mm × 20.0 mm, id, 5 μm, Cosmosil, Nakalai Tesque Co., Ltd., Kyoto, Japan) was used for the preparative HPLC separation. Column chromatography was performed using silica gel (300–400 mesh, Qingdao Ocean Chemical Co. Ltd., Qingdao, China) and C₁₈ reversed-phase silica gel (75 µm, Nakalai Tesque Co., Ltd., Kyoto, Japan).