Mentha longifolia ssp. longifolia Essential Oil Components as Novel Carbonic Anhydrase Isoform i and IX Inhibitors: Biological and Molecular Docking Studies

Karaçelik A. A., Özkat G. Y.

Letters in Drug Design and Discovery, vol.20, no.6, pp.767-778, 2023 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 6
  • Publication Date: 2023
  • Doi Number: 10.2174/1570180819666220510144912
  • Journal Name: Letters in Drug Design and Discovery
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Biotechnology Research Abstracts, Chemical Abstracts Core
  • Page Numbers: pp.767-778
  • Keywords: ADMET, Carbonic anhydrase inhibition, essential oil, inhibitor, Mentha longifolia, molecular docking
  • Recep Tayyip Erdoğan University Affiliated: No


Background: Medicinal plant oils are used in the treatment of various human diseases due to their phytochemical components. Recently, enzyme inhibition studies have been increasing in cosmetics, the food industry, and especialy pharmaceuticals. Objective: The main goal of this study is to focus on a specific interaction between the essential oil components of Mentha longifolia ssp. longifolia and carbonic anhydrase (CA) enzyme in vitro and in silico. Methods: The chemical composition of the essential oil was identified by gas chromatography coupled with mass spectrometry (GC-MS). The CA inhibitory activity of M. longifolia essential oil was investigated by using esterase activity for the first time in this study. Molecular docking was performed separately for two different CA isoforms (CA-i and CA-IX). Results: Among fourteen components identified, piperitone (27.14%), 2-acetylcyclopentanone (21.05%), p-menthan-3-one (13.90%), menthan (6.60%), and piperitone oxide (6.52%) were defined as the major compounds. The essential oil showed remarkable inhibitory activity against CA with an IC50 value of 0.010 mg/mL. According to the molecular docking analysis, caryophylene oxide (-6.5 kcal/mol for CAIX isoform, -6.8 kcal/mol for CA-i isoform) and trans-caryophylene (-6.3 kcal/mol for CA-IX isoform, - 6.7 kcal/mol for CA-i isoform) molecules showed the best inhibitory activity in two different CA isoforms. In this study, it was determined that al molecules are bioavailable by ADMET analyses. Conclusion: The results of this study are valuable for the development of natural and new CA enzyme inhibitors without side effects in the treatment of diseases, such as glaucoma, obesity, and epilepsy.