Seh 10011669

ESI–mass spectra were obtained on a Shimadzu LC MS-2020-EV. Nuclear magnetic resonance (NMR) spectra were obtained using a Bruker Fourier 300 (¹H-300 MHz, ¹³C-75 MHz) and Jeol JNM-AL 400 (¹H-400 MHz, ¹³C-100 MHz) spectrometer using TMS as an internal standard; chemical shifts were expressed as δ values. CC was carried out using 230–400 mesh silica gel (Kieselgel 60, Merck, Darmstadt, Germany) and RP-18 (ODS-A, 12nm, S-150 mM, YMC). The thin layer chromatography (TLC) was carried out glass plates pre-coated with silica gel 60 F₂₅₄ and RP-18 F₂₅₄ (20 × 20 cm, Merck). Compounds were visualized by dipping plates into 10% (v/v) H₂SO₄ reagent and then heated at 110 °C for 5–10 min. The solvents used for material separation, MeOH, n-hexane, CHCl₃, EtOAc, n-BuOH, were purchased from SK chemical (Suwon, Gyeonggi-do, Korea). AUDA, sEH (10011669) and PHOME (10009134) were purchased from Cayman (Cayman, MI, USA.).

NMR experiments were conducted on an ECA500 instrument (JEOL, Tokyo, Japan), with the chemical shift referenced to the residual solvent signals, and using methanol-d₄ and DMSO-d₆ as the solvent. Thin-layer chromatography (TLC) analysis was performed on silica-gel 60 F254 and RP-18 F254S plates (both 0.25 mm layer thickness; Merck, Darmstadt, Germany). Compounds were visualised by dipping plates into 10% (v/v) H₂SO₄ reagent, which were then air heat-treated at 300 °C for 15 s. Silica gel (60 A, 70–230 or 230–400 mesh ASTM; Merck) and reversed-phase silica gel (ODS-A 12 nm S-150, S-75 μm; YMC Co., Kyoto, Japan) were used for open column chromatography. sEH (10011669), AUDA (479413–70-2), and PHOME (10009134) were purchased from Cayman (Ann Arbour, Michigan, MO).