Identification of non-alkaloid natural compounds of Angelica purpurascens (Avé-Lall.) Gilli. (Apiaceae) with cholinesterase and carbonic anhydrase inhibition potential

Abstract

In current study is done antioxidant, anticholinesterase, and carbonic anhydrase isoenzymes I and II inhibition assays, screening of biological active compounds and electronic microscopy analysis of secretory canals of fruits, flowers, roots, and aerial parts extracts and essential oils of Angelica purpurascens. Phenolic constituents, antioxidant, and anti-lipid peroxidation potentials of variants were estimated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and thiobarbituric acid (TBA) processes. Cholinesterase inhibition effect was detected through Ellman’s method. The GC/ Mass Spectrometry (MS) and gas chromatography (GC)-flame Ionization Detector (FID) was used for essential oils analysis. NMR techniques was used for identification of the isolated compounds. The fruit hexane and dichloromethane fractions exhibited a greater antioxidant capacity and total phenolic content. The dichloromethane fraction of fruit demonstrated the most higher acetylcholinesterase inhibition (39.86 ± 2.63%), while the fruit hexane fraction displayed the best inhibition towards butyrylcholinesterase (84.02 ± 1.28%). Cytosolic isoenzymes of human carbonic anhydrase (hCA) I, and II isoenzymes were influentially suppressed by flower and fruit dichloromethane fractions with 1.650 and 2.020 µM IC50 values, respectively. The electronic microscopy analysis of secretory canals found that the small number of secretory canals were at leaf while the largest shape of secretory canals was at the fruit. The secretory canals of roots, aerial parts, and fruits include more monoterpene hydrocarbons, while the canals, existing in the flowers are qualified by a higher presence of sesquiterpenes β-caryophyllene (12.1%), germacrene D (4.5%) and ether octyl acetate (11.9%). The highest level of monoterpene β-phellandrene (47.6%) and limonene (8.2%) were found in the fruit essential oil. The next isolated compounds from fruits of A. purpurascens like stigmasterol, β-sitosterol, bergapten, and oxypeucedanin have shown high anticholinesterase and antioxidant activities.

Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

“…Coumarins constitute another important class of cholinesterase inhibitors as seen in some scientific reports [ 86 , 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 , 95 ]. Compounds 1 – 6 ( Table S3 ) isolated from Angelica archangelica , Caryopteris odorata , and Mutellina purpurea showed low activities, and although with slight structural differences, there is no significant difference in their activities [ 86 , 87 , 88 , 89 ]. Between compounds 6 and 7 , the addition of a prenyl group decreases the percentage inhibition.…”

Oleuropein and Verbascoside - Their Inhibition Effects on Carbonic Anhydrase and Molecular Docking Studies

“…On the other hand, the hydroxyl groups of verbascoside exhibited seven hydrogen bondings with the oxygen atoms of the amino acids His67, Asn69, Gln92, Ser197, and Thr199. 1.008 0.9935 0.222 0.9943 0.734 0.12 0.159 0.04 a) Acetazolamide was used as a standard inhibitor for both hCA I, and II, and taken from reference of the previous study 43) . When hCA II docking results of the compounds were evaluated, it was seen that verbascoside had lower energy score 10.08 kcal/mol than oleuropein 8.58 kcal/mol .…”

Oxypeucedanin: Chemotaxonomy, Isolation, and Bioactivities

“…OP has been isolated from the root EtOAc fraction of A. koreana [ 37 ], as well as from the methanolic and CH 2 Cl 2 soluble partitions of A. pancicii by utilizing flash chromatography (FC) and HPLC [ 38 ]. The fruit part of A. purpurascens has been extracted via various organic solvents, and the NHEX fraction was subsequently subjected to CC on silica gel, leading to OP purification [ 39 ].…”

“…In another study, OP indicated a weak anti-AChE activity, with an IC 50 of 69.3 ± 1.1 µg/mL, while eserine had an IC 50 of 0.51 ± 0.03 µg/mL as the positive control [ 19 ]. Moreover, by utilizing the Ellman method, OP revealed the strongest AChE (19.36 ± 1.87%) and BChE (butyrylcholinesterase enzyme, 36.89 ± 1.23%) inhibitory effects among the compounds isolated from Angelica purpurascens, including stigmasterol, β-sitosterol, and bergapten [ 39 ].…”

“…Recently, Karakaya et al [ 39 ] studied the antilipid peroxidation activity of OP in vitro, and a moderate effect was identified, with an IC 50 of 91.27 µg/mL. Oxypeucedanin also was evaluated for its abilities in molecular docking.…”