Greener approach for the isolation of oleanolic acid from Nepeta leucophylla Benth . Its derivatization and their molecular docking as antibacterial and antiviral agents

Heliyon · 7 authors, 6 centres

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TL;DR

The derivative 3-Phthaloyl oleanolic acid showed the highest antioxidant activity and best predicted interactions with bacterial and viral protein targets in molecular docking.

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817 CHARS

The study aimed to isolate and characterize bioactive compounds from Nepeta leucophylla. Oleanolic acid was derivatized using ultrasonication, yielding 3-Acetyl, 3-Phthaloyl, and 3-Oxo oleanolic acid with yields of 91.16%, 93.98%, and 83.6%, respectively. In vitro antioxidant screening via DPPH assay found 3-Phthaloyl oleanolic acid exhibited the highest inhibition at 40.83 ± 1.14%. In silico molecular docking predicted antibacterial activity against E. coli, M. tuberculosis, and S. aureus, and antiviral activity against SARS-CoV-2, HIV, and H1N1 influenza. 3-Phthaloyl oleanolic acid showed the best predicted H-bond interactions with bacterial targets and viral proteins (hemagglutinin, reverse transcriptase), while oleanolic acid showed the best interaction with the SARS-CoV-2 RNA-dependent RNA polymerase.

STUDY TYPE

other

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preclinical research

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AI pipeline

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100% · A

ORIGINAL PAPER

PMC10407133

Greener approach for the isolation of oleanolic acid from Nepeta leucophylla Benth . Its derivatization and their molecular docking as antibacterial and antiviral agents

Heliyon

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ABSTRACT

In the present study bioactive methanolic extract along with chloroform and hexane extracts obtained from shade dried leaves of the Himalayan aromatic medicinal plant Nepeta leucophylla Benth. Were screened for the presence of triterpenoids, especially oleanolic acid (OA). Total three compounds oleanolic acid, squalene and linoleic methyl ester were isolated from methanol extract. The percentage yield of OA was 0.11%. Out of these three, OA is more bioactive and was further subjected to derivatization using greener Ultrasonication method. Total three derivatives (3-Acetyl oleanolic acid, 3-Phthaloyl oleanolic acid and 3-Oxo oleanolic acid) were synthesized with 91.16%, 93.98%, and 83.6% respectively. Further, the antioxidant potential of OA and its derivatives were evaluated using DPPH assay which suggested that the 3-Phthaloyl oleanolic acid exhibits highest antioxidant potential with 40.83 ± 1.14% inhibition. OA and its derivatives were screened in-silico antibacterial potential against three bacterial pathogens ( E-coli , M. tuberculosis and S. aureus ) and antiviral potential against Severe Acute Respiratory Syndrome Coronavirus (SARS-CoV-2), Human immunodeficiency virus (HIV) and H1N1 influenza virus. The in-silico results suggested that 3-phthaloyl oleanolic acid showed best H-bonding with FtsA ( Staphylococcus aureus ), enoyl acyl reductase ( E. coli ) and arabinosyl transferase ( Mycobactrium tuberculosis ). 3-Phthaloyl oleanolic acid also showed best H-Bond interactions with the target proteins hemagglutinin (H1N1) and reverse transcriptase (HIV), whereas, oleanolic acid exhibited the best interactions with RNA dependent RNA polymerase (SARS-CoV-2) and thus could be considered for further in vitro studies.

CITATION EXPORT

Ajay Sharma, Deepika Kathuria, Bhaskor Kolita et al.. Greener approach for the isolation of oleanolic acid from Nepeta leucophylla Benth. Its derivatization and their molecular docking as antibacterial and antiviral agents. Heliyon. (2023). https://doi.org/10.1016/j.heliyon.2023.e18639

AUTHORS

7 · 6 CENTRES

Ajay Sharma, Deepika Kathuria, Bhaskor Kolita, Apurba Gohain, Ashoke Kumar Das, Garima Bhardwaj, Jesus Simal-Gandara

aDepartment of Chemistry, Sant Longowal Institute of Engineering and Technology, Sangrur, Longowal, Punjab, 148106, India
bDepartment of Chemistry, University Centre for Research and Development (UCRD), Chandigarh University, Gharuan, Punjab 140413, India
cDepartment of Botany, Jorhat Kendriya Mahavidylaya, Kenduguri, Jorhat, Assam, 785010, India
dDepartment of Chemistry, Assam University Silchar, Dorgakona, Silchar, Assam, 788011, India
eDepartment of Botany, Abhayapuri College, Abhayapuri, Srijangram, Assam, 783384, India
fUniversity of Vigo, Nutrition and Bromatology Group, Analytical Chemistry and Food Science Department, Faculty of Science, E32004 Ourense, Spain