Rotavapor r 3000r

Chemicals and reagents were from Merck (Darmstadt, Germany). Evaporation of solvents was performed on a vacuum rotary evaporator (Rotavapor R-3000r, Buchi, Switzerland). FCPC was carried out on a Kromaton instrument equipped with a 1000-ml column, adjustable rotation of 200–2000 rpm and a preparative Laboratory Alliance pump with a pressure safety limit of 50 bar. NMR spectra in MeOD were recorded at 400 and 600 MHz (Bruker Advance III 600 MHz and DRX 400). 2D NMR experiments, including correlation spectroscopy (COSY), heteronuclear single-quantum correlation (HSQC) and heteronuclear multiple-bond correlation (HMBC) were performed using standard Bruker microprograms. Electrospray ionisation mass spectrometry (ESI-MS) experiments were performed on a LTQ-Orbitrap XL hybrid mass spectrometer (Thermo-Scientific, Bremen, Germany). Analytical TLC was performed on Merck Kieselgel 60 F₂₅₄ or RP-8 F₂₅₄ plates. Spots were visualized by UV light (254 and 365 nm) or by spraying with sulfuric vanillin. The plates were then heated for 2 min at 110°C. Preparative TLC was conducted on PLC Silica gel 60 F254 plates (1 mm). The selected zones were scraped and extracted with ethyl acetate to separate the corresponding compounds. Column chromatography was performed on silica gel 70–230 mesh (63–200 μm). Size exclusion chromatography was performed on Sephadex LH-20.

Chemicals and reagents were from Merck (Darmstadt, Germany). Evaporation of solvents was performed on a vacuum rotary evaporator (Rotavapor R-3000r, Buchi, Switzerland). Fast Centrifugal Partition Chromatography (FCPC) was carried out on a Kromaton FCPC instrument equipped with a 1,000-mL column, adjustable rotation of 200–2,000 rpm and a preparative Laboratory Alliance pump with a pressure safety limit of 50 bar. NMR spectra in CDCl₃ were recorded at 400 and 600 MHz (Bruker Advance III 600 MHz and DRX 400). 2D NMR experiments, including COSY, HSQC, and HMBC were performed using standard Bruker microprograms. Analytical TLC was performed on Merck Kieselgel 60 F254 or RP-8 F254 plates. Spots were visualized by UV light (254 and 365 nm) or by spraying with sulfuric vanillin. Preparative TLC was conducted on TLC Silica gel 60 F254 plates (1 mm). The selected zones were scraped and extracted with ethyl acetate to separate the corresponding compounds. Column chromatography was performed on silica gel 70–230 mesh (63–200 μm). Size exclusion chromatography was performed on Sephadex LH-20.

¹H and ¹³C NMR spectra were obtained at 500 MHz, using a Bruker Avance III 500 MHz spectrometer (500 MHz and 125 MHz for ¹H and ¹³C NMR respectively) equipped with a low volume 1.7 mm inverse detection microcryoprobe. HRESIMS and LC-UV–MS data were measured using a Bruker maXis QTOF mass spectrometer coupled to an Agilent 1200 HPLC system and on an Agilent 1100 single quadrupole LC–MS system, as previously described^{35 (link)}. Preparative HPLC was performed on a Gilson 322 System using a Xbridge™ C18 (19 × 250 mm, 5 μm) column at a flow rate of 14 mL/min. Semipreparative HPLC was performed on the same system using a Xbridge™ C18 (10 × 150 mm, 5 μm) column or a Xbridge Prep Phenyl, (10 × 150 mm, 5 μm) column at a flowrate of 3.6 mL/min. Evaporation of solvents was performed on a vacuum rotary evaporator (Rotavapor R-3000r, Buchi, Postfach, Switzerland). The acetone employed for extraction, as well as the solvents used for isolation were of analytical and HPLC grade, respectively.