Eryngium creticum L.: Chemical Characterization, SARS-CoV-2 Inhibitory Activity, and In Silico Study

Abstract

Phytochemical investigation of Eryngium creticum L. has resulted in isolation of five compounds, including four compounds that are reported from the plant for the first time. Compound 1 was identified as ( E )-rosmarinic acid, meanwhile, compound 2 was isolated as an ( E / Z )-rosmarinic acid mixture. Interestingly, the E / Z -isomeric mixture was about 4 times as active as the single E -isomer toward the severe acute respiratory syndrome coronavirus 2 3-chymotrypsin-like protease (3CL pro ), IC 50 = 6.062 and 25.75 μM, respectively. Utilizing combined molecular docking and molecular dynamics (MD) techniques, the binding affinities and features of the isolated compounds were evaluated against 3CL pro . Compound 2 Z demonstrated a higher binding affinity for 3CL pro than 2 E , with docking scores of −8.9 and −8.5 kcal/mol and MM-GBSA/150 ns MD binding energies of −26.5 and −22.1 kcal/mol, respectively. This justifies the superior activity of the E / Z -isomeric mixture versus the single E -isomer. Structural and energetic analyses revealed the stability of 2 Z and 2 E compared to the reference HIV-1 protease inhibitor, lopinavir. Besides, DFT calculations demonstrated the more energetic stability of 2 E compared to 2 Z , which justifies the difficulty in isolating the Z -isomer in a pure form, where it readily isomerizes to the E -isomer.

Intensification of Polyphenols Extraction from Eryngium creticum Leaves Using Ired-Irrad® and Evaluation of Antibiofilm and Antibacterial Activities

“…Many studies have reported on the presence of different phenolic compounds in Eryngium extracts [ 25 , 26 , 27 , 28 ]. Our results are in agreement with the literature, which reported that among the phenolic compounds, rutin and sinapic acid were determined in E. planum , E. campestre, and E. maritimum extracts [ 25 , 26 ].…”

Exploring the Biological and Phytochemical Potential of Jordan’s Flora: A Review and Update of Eight Selected Genera from Mediterranean Region

“…β -Sitosteryl glucoside ( 106 ) was isolated from A. strigosa [ 113 ]. Furthermore, a recent study reported the isolation of β -sitosterol ( 102 ) from E. criticum [ 149 ]. Figure 3 illustrates the chemical structure of the phytosterols identified in the selected genera.…”

Studies on the Nonalkaloidal Secondary Metabolites of Hippeastrum vittatum (L’Her.) Herb. Bulbs

“…Although the development of some vaccines against SARS-CoV-2 has raised expectations regarding the probable end of such unprecedented pandemic, the use of these vaccines has provoked concerns about some possible side effects and adverse interactions. , Besides, the capability of the said vaccines of complete disease prevention also remains to be witnessed, which underlines the importance of identifying new therapeutic agents with considerable efficacy and safety levels . During that journey, numerous studies have been introduced to stop the replication of SARS-CoV-2, focusing on a group of viral proteins as potential therapeutic targets, e.g., helicases, polymerases, and proteases, among others. ,− A large body of literature has therefore considered the application of virtual screening and molecular docking simulations as reasonable tools to mine for possible anti-SARS-CoV-2 candidates. ,− …”