Chemical components from the seeds of Catalpa bungei and their inhibitions of soluble epoxide hydrolase, cholinesterase and nuclear factor kappa B activities

Abstract

Two new chlorinated iridoids, named bungosides A (1) and B (2), were isolated from the seeds of Catalpa bungei (family Bignoniaceae). Their structures were elucidated on the basis of NMR analysis. Twenty known compounds (3-22) were also characterized, including in one case (6-O-phydroxybenzoylglutinoside, 3) the assignment of the absolute configuration by employing electronic circular dichroism (CD) and time-dependent density functional theory (TDDFT) calculations. Compounds 1-3 were unusual cage-like iridoids with an oxygen bridge between C-3 and C-10. Among the isolates, ursolic acid lactone (14) was the most active soluble epoxide hydrolase (sEH) inhibitor with an IC 50 19.1 AE 0.8 mM. In addition, D-pinoresinol (19) and ladanein (21) displayed selectively inhibitory effects on butyrylcholinesterase (BChE) with IC 50 of 31.5 AE 0.4 mM and 33.0 AE 2.3 mM, respectively, but not acetylcholinesterase (AChE) activity, and only compound 18 suppressed NF-kB activity in HepG2 cells (IC 50 21.53 AE 2.37 mM).

In Vitro and In Silico Studies of Soluble Epoxide Hydrolase Inhibitors from the Roots of Lycopus lucidus

“…In this study is the first report of sEH inhibitory activity of compounds 6 , 7 , 9 and 10 . Compounds 1 , 3 and 8 have previously shown significant sEH inhibitory activity related to cardiovascular disease [ 30 , 31 , 32 ]. These sEH results showed that the phenylpropanoid derivatives exhibited stronger inhibitory activity than the triterpene compounds.…”

Nutraceutical Potential of Phenolics from ′Brava′ and ′Mansa′ Extra-Virgin Olive Oils on the Inhibition of Enzymes Associated to Neurodegenerative Disorders in Comparison with Those of ′Picual′ and ′Cornicabra′

“…Phenolic compounds reported in literature as owners of anticholinesterase activity are p -coumaric acid ( p -Cou) and luteolin (Lut) [ 14 , 16 ] in addition to lignans isolated from plants such as syringaresinol (Syr) (which showed an inhibitory effect against AChE) [ 15 ], and pinoresinol (Pin) (which displayed selective inhibitory effects on BuChE, but not against AChE) [ 17 ]. The content of these compounds were higher in ′Brava′ than in ′Mansa′ olive oils, as mentioned before.…”

“…Some phenolic compounds have already addressed to exhibit several remarkable biological activities on inhibition of the previously described enzymes: p -coumaric acid, luteolin and lignans including pinoresinol and syringaresinol as owners of anticholinesterase activities [ 14 , 15 , 16 , 17 ]; oleocanthal, hydroxytyrosol, p -coumaric acid, and luteolin with inhibitory activity against 5-LOX [ 18 , 19 , 20 ] and flavonoids including apigenin and luteolin as responsible of the inhibition of h- MAOs [ 21 , 22 ].…”

Structurally Diverse Sesquiterpenoid Glycoside Esters from Pittosporum qinlingense with Anti-neuroinflammatory Activity

“…The residue was dissolved in pyridine (0.5 mL), to which l -cysteine methyl ester hydrochloride in pyridine (0.1 M, 0.5 mL) was added. After reacting at 60 °C for 1 h, trimethylsilylimidazole (0.05 mL) was added to the reaction mixture and kept at 4 °C for another 8 h. The mixture was analyzed by GC-MS. By comparison of the retention time of the authentic sample, the monosaccharide of compound 1a was determined to be d -fucose ( t R = 21.040 min) . Other compounds were treated under the same conditions.…”