Coumarin and Moracin Derivatives from Mulberry Leaves (Morus alba L.) with Soluble Epoxide Hydrolase Inhibitory Activity

Abstract

This study identified three coumarins (1–3), and six moracin derivatives (4–9). The structures of these natural compounds were determined by the spectroscopic methods, including 1D and 2D NMR methods, and comparison with previous reported data. All of the isolated compounds were assessed for the effects on the soluble epoxide hydrolase (sEH) inhibitory activity. Among them, compounds 1–7 exhibited significant inhibitory effect with 100% inhibitory, with IC50 values of 6.9, 0.2, 15.9, 1.1, 1.2, 9.9, and 7.7 µM, respectively. A kinetic study revealed that compounds 1–4, and 6 were competitive types of inhibitors, compounds 5 and 7 were mixed types of inhibitors. These results suggest that moracin and coumarin derivatives from mulberry leaves are significant sEH inhibitors.

Small Molecule Soluble Epoxide Hydrolase Inhibitors in Multitarget and Combination Therapies for Inflammation and Cancer

“…Interestingly, very few natural products bear the urea or carbamate groups that form the mainstay of synthetic sEHIs. Moracin and coumarin derivatives from mulberry leaves have been identified as significant sEHIs [ 120 ]. Sun and coworkers collected protostane-type triterpenoids from Alisma orientale and reported their potential sEH inhibitory activities [ 121 ].…”

Paving the way towards effective plant-based inhibitors of hyaluronidase and tyrosinase: a critical review on a structure–activity relationship

“…The IC 50 for 3-feruloyl-4′,6′-diacetyl sucrose, 3-feruloyl-6′-acetylsucrose 3,6-diferuloylsucrose was >400 µM. None of the isolated compounds inhibited the enzyme more strongly than the positive control, kojic acid (IC 50 =28.60 µM) 143 .…”

Screening and Identification of Novel Soluble Epoxide Hydrolase Inhibitors from Corn Gluten Peptides

“…The effects of the concentrations of the enzyme, substrate, and the hydrolysis time of sEH on PHOME were determined according to the methods reported previously [ 11 , 23 ]. Briefly, 130 µL of 12.5 or 62.5 ng/mL human sEH solution (final concentration, dissolved in 25 mM bis-Tris-HCl containing 0.1% BSA, pH 7.0) and 20 µL of 10% methanol were added to a 96-well plate and incubated at room temperature for 15 min.…”