Metabolomic Profiling, Antioxidant and Enzyme Inhibition Properties and Molecular Docking Analysis of Antarctic Lichens

Abstract

The lichen species Lecania brialmontii, Pseudephebe pubescens, and Sphaerophorus globosus are part of the prominent lichenoflora of the Antarctic territory. In this work, we report the metabolomic identification of ethanolic extracts of these species, their antioxidant and cholinesterase enzyme inhibitory activity, and conduct a molecular docking analysis with typical compounds. Eighteen compounds were identified by UHPLC-ESI-QTOF-MS in L. brialmontii, 18 compounds in P. pubescens, and 14 compounds in S. globosus. The content of phenolic compounds was variable among the species, ranging from 0.279 to 2.821 mg AG/g, and all three species showed high inhibition potential on the cholinesterase enzymes. Molecular docking showed important interactions between AChE and BChE with the selected compounds. This study evidences the chemical fingerprint of three species of the order Lecanorales that support the continuation of the study of other biological activities and their potential for medical research.

Liquid chromatography-electrospray ionization-mass spectrometry/mass spectrometry characterization of depsides and depsidones from the Chilean lichen Parmotrema perlatum

“…31–33 In the licheńs research, LC-MS has been applied to characterization, untargeted/targeted screening, quantification and dereplication of licheńs substances based on the structure fragmentation. 16,34 Analysis of lichens based on LC-ESI/MS/MS including species of the genus Cetraria , 35 Cladonia , 36,37 Evernia , 38 Lecania , Pseudephebe , 39 Ramalina , 40 Sphaerophorus , 39 Sticta , 19 Umbilicaria , 41 Usnea , 29 Xanthoparmelia , 42 and Parmotrema , 6,7 have been reported.…”

“…[31][32][33] In the lichen ́s research, LC-MS has been applied to characterization, untargeted/targeted screening, quantification and dereplication of lichen ́s substances based on the structure fragmentation. 16,34 Analysis of lichens based on LC-ESI/MS/MS including species of the genus Cetraria, 35 Cladonia, 36,37 Evernia, 38 Lecania, Pseudephebe, 39 Ramalina, 40 Sphaerophorus, 39 Sticta, 19 Umbilicaria, 41 Usnea, 29 Xanthoparmelia, 42 and Parmotrema, 6,7 have been reported. According to previous chemical studies of the Parmotrema genus, 6,7,18,20,[24][25][26]30,43 we show the chemistry of this genus based on characteristic lichen compounds, such as depsidone, depsidone, and diphenylether found in P Perlatum, as shown in Table 2.…”

Phytochemical Characterization and In Vitro and In Silico Biological Studies from Ferns of Genus Blechnum (Blechnaceae, Polypodiales)

“…Molecular docking was performed using the respective rigid crystallographic enzyme structures and the flexible ligands whose torsion angles were identified (for 10 independent urns per ligand). Targeted coupling was performed using the UCSF Chimera program [ 28 , 29 ] taking the reference inhibitor galantamine for acetylcholinesterase and butyrylcholinesterase as the catalytic site. Polar hydrogens and Gasteiger partial charges were added for the docking process; a grid chart was created using the Autodock Vina tools in the UCSF Chimera software.…”

Antioxidant and antidiabetic activity and phytoconstituents of lichen extracts with temperate and polar distribution

“…The two-dimensional structures of the phytochemicals that did not present any violation of Lipinsk's relation as well as any risk of toxicity (2.5DHA, cyperine, diospyrol, hypoxyphenone, lecanoric acid, orsellinic acid, prephenic acid, SDA, O4BBA) were prepared using the ChemDraw 8.0 program (PerkinElmer Informatics, Waltham, MA, United States). Subsequently, the chemical structures of the ligands were imported into the Avogadro program (https://avogadro.cc, accessed on 06 June 2023) to optimize the geometry of the ligands using the MMFF94 force field function (Torres-Benítez et al, 2022;Torres-Benítez et al, 2023a). All the optimized compounds were saved in the mol2 format to carry out the molecular docking studies with the enzymes αamylase, α-glucosidase, and human pancreatic lipase.…”

“…Enzyme optimization was performed using UCSF Chimera software (v1.16, San Francisco, California, United States); water molecules were removed, and ligands were removed from the active site of crystallographic enzymes. All polar hydrogen atoms aggregated at pH = 7.4, considering the appropriate ionization states for basic and acidic amino acid residues (Silman et al, 1994;Torres-Benítez et al, 2022).…”