Sonchus erzincanicus (Asteraceae) is an endemic species in Turkey, where six Sonchus species grow. In this study, a phytochemical study was performed on the aerial parts of the plant. The study describes the isolation and structure elucidation of five flavonoids and two α-ionone glycosides from S. erzincanicus. The compounds were isolated using several and repeated chromatographic techniques from ethyl acetate and aqueous phases that were partitioned from a methanol extract obtained from the plant. 5,7,3′,4′-Tetrahydroxy-3-methoxyflavone (1) and quercetin 3-O-β-D-glucoside (2) were isolated from the ethyl acetate phase, while corchoionoside C 6’-O-sulfate (3), corchoionoside C (4), luteolin 7-O-glucuronide (5) and luteolin 7-O-β-D-glucoside (6), apigenin 7-O-glucuronide (7) were isolated from the aqueous phase. Corchoionoside C 6’-O-sulfate (3), isolated for the first time from a natural source, was a new compound. The structures of the compounds were elucidated by means of 1H-NMR, 13C-NMR, 2D-NMR (COSY, HMQC, HMBC) and ESI-MS.
The aim of this study was to design new molecules and evaluate their anticholinesterase and amyloid beta (Aβ) inhibition activities as multifunctional drug candidates for the treatment of Alzheimer's disease (AD). A series of 5,6-dimethoxy-1H-indene-2-carboxamides (1-22) was synthesized; cholinesterase inhibitory activities of the compounds were measured according to Ellman's colorimetric assay, while the thioflavin T assay was used for measuring the inhibition of Aβ aggregation. The results revealed that most compounds showed higher inhibitory activity against BuChE than AChE. Compounds 20 and 21 were found to be the most potent BuChE inhibitors with respective IC values of 1.08 and 1.09 μM. Compounds 16, 20, 21 and 22 exhibited remarkable inhibition of Aβ aggregation. Kinetic analysis showed that the most potent BuChE inhibitor (20) acted as a noncompetitive inhibitor. Docking studies suggested that inhibitor 20 displayed many potential hydrogen-bondings with the PAS of BuChE. These results suggest that compound 20 may be an especially promising multifunctional drug for the prevention and treatment of AD.
Abstract:The essential oil was obtained by hydrodistillation from the aerial parts of Origanum rotundifolium Boiss. Its chemical content and composition were analyzed by using a gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Total phenolic content of the essential oil was determined as 132.39 µg gallic acid equivalent by Folin-Ciocalteu's method and the major component was identified as carvacrol (56.8 %) along with p-cymene (13.1 %), (Z)--ocimene (5.4 %), -caryophyllene (3.9 %), borneol (3.4 %) and thymol (3.2 %). After chemical characterization, the essential oil was evaluated for its antioxidant activity by DPPH free radical, superoxide anion radical and hydrogen peroxide scavenging activities as well as ferrous ion-chelating power test, ABTS radical cation decolorization assay and ferric thiocyanate methods. Besides antioxidant activity, acetylcholinesterase and butyrylcholinesterase inhibitory activities of the essential oil were also evaluated by Ellman's method. It demonstrated inhibitory activities on AChE and BuChE, key enzymes in the pathogenesis of Alzheimer's disease (AD), in addition to significant antioxidant activity.
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