Infrared 400 spectrophotometer

Optical rotations were measured on a JASCO DIP-370 digital polarimeter at 25 °C at the sodium D line (589 nm). UV spectrum were recorded on a Hitachi 300 spectrometer. IR spectra were measured on a Shimadzu Infrared-400 spectrophotometer (Shimadzu, Kyoto, Japan). 1D and 2D NMR spectra (chemical shifts in ppm, coupling constants in Hz) were recorded on Bruker Avance DRX 600 MHz spectrometers (Bruker, Rheinstetten, Germany) using CDCl₃ and CD₃OD as solvents. NMR spectra were referenced to the residual protonated solvent signals (CHCl₃: 7.26 ppm for ¹H and 77.0 ppm for ¹³C; CH₃OD: 3.30 ppm for ¹H and 49.0 ppm for ¹³C). Positive ion HRESIMS data were obtained with a Micromass Q-ToF equipped with leucine enkaphalin lockspray, using m/z 556.2771 [M + H]⁺ as a reference mass. For column chromatography, silica gel (Merck, 70–230 mesh ASTM, Sigma-Aldrich, Darmstadt, Germany) and Sephadex LH-20 (0.25–0.1 mm, Pharmacia, Piscataway, NJ, USA) were used. Precoated silica gel 60 F-254 plates (Merck) were used for TLC. HPLC purifications were performed on a semi-preparative HPLC column (RP18, 5 μm, ARII Cosmosil, 250 × 10 mm, Waters, Nacalai Inc., San Diego, CA, USA).

Optical rotations were measured on a JASCO DIP-370 digital polarimeter at 25 °C at the sodium D line (589 nm). UV spectra were recorded on a Hitachi 300 spectrometer (Hitachi High-Technologies Corporation, Kyoto, Japan). The ECD spectra were obtained on a JASCO J-810 spectropolarimeter with a 0.5 cm cell in MeOH. IR spectra were measured on a Shimadzu Infrared-400 spectrophotometer (Shimadzu, Kyoto, Japan). 1D and 2D NMR spectra (chemical shifts in ppm, coupling constants in Hz) were recorded on Bruker Avance DRX 600 MHz (600 MHz for ¹H and 150 MHz for ¹³C NMR) (Bruker, Rheinstetten, Germany) and Bruker Ascend™ 850 MHz (850 MHz for ¹H and 213 MHz for ¹³C NMR) (Bruker BioSpin, Billerica, MA, USA) spectrometers using CDCl₃ or DMSO-d₆ as solvent. NMR spectra were referenced to the residual protonated solvent signals (for CHCl₃: 7.26 ppm for ¹H and 77.0 ppm for ¹³C; for DMSO: 2.51 ppm for ¹H and 39.6 ppm for ¹³C). Positive ion HRESIMS data were obtained with a Micromass Q-ToF equipped with leucine enkaphalin lockspray, using m/z 556.2771 [M + H]⁺ as a reference mass. For column chromatography, silica gel (Merck, 70-230 mesh ASTM) and Sephadex LH-20 (0.25–0.1 mm, Pharmacia) were used. Precoated silica gel 60 F-254 plates (Merck) were used for TLC. HPLC purifications were performed on a semi-preparative HPLC column (RP18, 5 μm, ARII Cosmosil, 250 × 10 mm, Waters).

Optical rotation: Perkin-Elmer Model 341 LC polarimeter (Perkin-Elmer, Waltham, MA, USA). UV spectra: in MeOH using a Perkin-Elmer Lambda 25 UV/VIS spectrophotometer (Perkin-Elmer, Waltham, MA, USA). IR spectra: Shimadzu Infrared-400 spectrophotometer (Shimadzu, Kyoto, Japan). ESIMS spectra: Agilent 6320 Ion trap mass spectrometer (Agilent Technologies, Santa Clara, CA, USA) equipped with an electrospray ionization interface. NMR spectra: Bruker DRX 700 spectrometer (Bruker, Rheinstetten, Germany). Column chromatographic separations: silica gel 60 (0.04–0.063 mm, Merck, Darmstadt, Germany). TLC analyses: pre-coated silica gel F254 aluminum sheets (Merck, Darmstadt, Germany).