Ods rp c18

NMR spectra were carried out on a Bruker Avance Neo at 400 MHz and 800 MHz (Bruker BioSpin, Fällanden, Switzerland) using tetramethylsilane (TMS) as internal standard. Optical rotations (ORs) were recorded on an Autopol III automatic polarimeter (Rudolph Research Analytical). A Chirascan spectrometer was used to obtain the UV and experimental CD spectra. HRESIMS data were obtained on a LC-30A + TripleTOF5600+ (AB Sciex Pte. Ltd., Framingham, MA, USA). Separations and purifications of the samples were conducted on silica gel (200–300 and 300–400 mesh, Qingdao Marine Chemical Ltd., Qingdao, China), ODS RP-C₁₈ (50 μm, YMC Co., Ltd., Kyoto, Japan), and Sephadex LH-20 (40–70 μm, Amersham Pharmacia Biotech AB, Stockholm, Sweden). A shimadzu LC-20AP liquid chromatography system equipped with a reversed-phase (RP) C-18 column (10 mm × 250 mm, 5 μm) was applied to complete sample purification.

One-dimensional- and two-dimensional-NMR spectra were obtained from a Bruker Avance III 600 MHz spectrometer (Bruker BioSpin Inc., Zurich, Switzerland). Optical rotations were measured with an MCP 200 Modular Circular Polarimeter (Anton Paar, Graz, Austria). HRESIMS spectrum was obtained from a MicrOTOF-Q II ESI mass spectrometer (Bruker, Bremen, Germany). UV spectrum was obtained from a Hitachi U-3900 UV-visible spectrophotometer (Hitachi High-Tech Science Corporation, Tokyo, Japan). ECD spectra were recorded by a MOS-500 Circular Dichroism spectropolarimeter (Bio-Logic, Grenoble, France). Semi-preparative HPLC was performed on an LC-6A (Shimadzu, Kyoto, Japan) equipped with preparative YMC Pack ODS-A column (250 × 20 mm, 5 μm, YMC, Kyoto, Japan). A Daicel Chiralpak AD-H (250 × 4.6 mm, 5 μm, Daicel, Tokyo, Japan) was used for the chiral separations. Column chromatography (CC) was carried out over silica gel (100–200 and 200–300 mesh, Qingdao Haiyang Chemical Co., Ltd., Qingdao, China), Sephadex LH-20 (Amersham Pharmacia Biotech AB, Uppsala, Sweden), and ODS RP-C18 (40–63 μm, YMC, Kyoto, Japan). Thin Layer Chromatography (TLC) was performed on pre-coated silica gel GF-254 (Qingdao Marine Chemical Factory, Qingdao, China).