UHPLC-MS Chemical Fingerprinting and Antioxidant, Enzyme Inhibition, Anti-Inflammatory In Silico and Cytoprotective Activities of Cladonia chlorophaea and C. gracilis (Cladoniaceae) from Antarctica

Abstract

The lichen species Cladonia chlorophaea and C. gracilis (Cladoniaceae) are widely distributed in the island archipelago of maritime Antarctica and represent a natural resource of scientific interest. In this work, the metabolomic characterization of the ethanolic extracts of these species and the determination of the antioxidant activity, enzymatic inhibition and anti-inflammatory potential of selected compounds on the 5-lipoxygenase enzyme by molecular docking and cytoprotective activity in the SH-SY5Y cell line were carried out. Nineteen compounds were identified by liquid chromatography coupled with quadrupole-time-of-flight mass spectrometry (UHPLC-ESI-QTOF-MS) in each of the species. The contents of phenolic compounds, antioxidant activity, the inhibition of cholinesterases (acetylcholinesterase and butyrylcholinesterase) and digestive enzymes (α-glucosidase and pancreatic lipase) were variable among species, with better results in C. chlorophaea. Molecular docking evidenced significant binding affinities of some compounds for the 5-lipoxygenase enzyme, together with outstanding pharmacokinetic properties. Both extracts were shown to promote cell viability and a reduction in reactive oxygen species production in an H2O2-induced oxidative stress model. This study contributes to the chemical knowledge of the Cladonia species and demonstrates the biological potential for the prevention and promising treatment of central nervous system pathologies, inflammatory disorders and metabolic alterations.

Phytochemical analyses by LC‐HRMS, FTIR spectral analysis, antioxidant, antidiabetic and antityrosinase activity of Crataegus orientalis Pall. ex M. Bieb fruit extracted with various solvents

“…Torres‐Benítez et al . showed that ethanol extracts of Cladonia chlorophaea and Cladonia gracilis (Cladoniaceae) had higher inhibition of α‐glucosidase compared to reference acarbose 67 . Aanachi et al .…”

“…66 Torres-Benítez et al showed that ethanol extracts of Cladonia chlorophaea and Cladonia gracilis (Cladoniaceae) had higher inhibition of ⊍-glucosidase compared to reference acarbose. 67 Aanachi et al reported that methanol extract showed the best inhibition against tyrosinase among Pelargonium graveolens methanol, dichloromethane and hexane extracts. 68 Tlili and Sarikurkcu studied ⊍-amylase and ⊍-glucosidase inhibition in water extracts of the five medicinal species (Camellia sinensis L., Erica arborea L., Ilex paraguariensis A. St. Hilaire, Rosmarinus officinalis L., and Thymus vulgaris L.).…”

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.…”

“…The results obtained from molecular docking were analyzed and visualized in the Discovery Studio Visualizer software [ 30 ]. Once the molecular docking was done, the best conformation at the catalytic site was analyzed by evaluating the best hydrogen bonding interactions or π interactions, including the free ligand binding energy (kcal/mol) [ 29 , 31 ].…”

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

“…[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.…”