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1

Analytical Techniques for Compound Characterization

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Various NMR spectra were obtained using the NMR System 400 MHz spectrometer (Agilent Technologies, Santa Clara, CA, USA) and 600 MHz spectrometer (Bruker, Karlsruhe, Germany). MS analysis was performed using the AccuTOF LC-plus JMS-T100LP system (JEOL, Tokyo, Japan). Optical rotations were measured using a digital polarimeter (DIP-1000; JASCO, Tokyo, Japan). UV spectra were recorded on a spectrophotometer (8453 UV-visible spectrophotometer; Agilent Technologies). IR spectra were recorded on a Fourier transform IR spectrometer (FT-710; Horiba Ltd., Kyoto, Japan).
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2

Spectroscopic Characterization of Compounds

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Various NMR spectra were obtained using an INOVA 600 MHz spectrometer (Agilent Technologies, Santa Clara, CA, USA). FAB-MS spectra were recorded on a mass spectrometer (JMS-700 Mstation; JEOL, Tokyo, Japan). UV spectra were recorded on a spectrophotometer (Beckman DU640 spectrophotometer; Beckman Coulter, Inc., Fullerton, CA, USA). IR spectra were recorded on a Fourier transform infrared spectrometer (FT-710; Horiba Ltd, Kyoto, Japan).
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3

Characterization Methods for Bioactive Compounds

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General Experimental Procedures EI-MS and FAB-MS were measured on a JMS-MS 700 mass spectrometer (JEOL, Tokyo, Japan). 1 (link) H-and 13 C-NMR spectra were recorded on a JNM-AL-400 NMR spectrometer (JEOL) at 400 MHz for 1 H and 100 MHz for 13 (link) C in CDCl 3 (δ H 7.24, δ C 77.0). Specific rotations were obtained with the digital polarimeter P-2300 (JASCO, Tokyo, Japan). UV spectra were measured on the UV-visible (Vis) spectrophotometer U-3310 (Hitachi High Technologies Co., Ltd., Tokyo, Japan). ECD spectra were measured with a JASCO J-720 spectropolarimeter. IR spectra were recorded on the Fourier transform infrared spectrometer FT-710 (Horiba Ltd., Kyoto, Japan). Preparative HPLC was performed using an L-6200 HPLC system (Hitachi High Technologies Co., Ltd.).
Materials PTP1B was purchased from Enzo Life Sciences (Farmingdale, NY, U.S.A.). p-Nitrophenyl phosphate (pNPP) was purchased from Sigma-Aldrich (St. Louis, MO, U.S.A.). Oleanolic acid was purchased from Tokyo Chemical Industry (Tokyo, Japan). Plastic plates (96-well) were purchased from Corning Inc. (Corning, NY, U.S.A.). All other chemicals including organic solvents were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan).
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