Abstract

The phytochemical investigation of both volatile and fixed metabolites of Clinopodium taxifolium (Kunth) Govaerts (Lamiaceae) was performed for the first time. It allowed the isolation and characterization of the essential oil and six known compounds: carvacrol (1), squalane (2), uvaol (3), erythrodiol (4), ursolic acid (5), and salvigenin (6). Their structures were identified and characterized by Nuclear Magnetic Resonance (NMR) and Gas Chromatography coupled to Mass Spectroscopy (GC-MS), and corroborated by literature. The essential oil of the leaves was obtained by hydrodistillation in two different periods and analyzed by GC-MS and GC coupled to Flame Ionization Detector (GC-FID). A total of 54 compounds were detected, of which 42 were identified (including trace constituents). The major constituents were carvacrol methyl ether (18.9–23.2%), carvacrol (13.8–16.3%) and, carvacryl acetate (11.4–4.8%). The antibacterial activities were determined as Minimum Inhibition Concentration (MIC) against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Pseudomonas aeruginosa and Micrococcus luteus. The hexane and methanol extracts exhibited activity only against Klebsiella pneumoniae (250 and 500 μg/mL respectively), while the ethyl acetate extract was inactive. The hypoglycemic activity was evaluated by the in vitro inhibition of α-glucosidase. The ethyl acetate (EtOAc) extract showed strong inhibitory activity with IC50 = 24.88 µg/mL, however methanolic and hexanic extracts showed weak activity. As a pure compound, only ursolic acid showed a strong inhibitory activity, with IC50 = 72.71 μM.

Highlights

  • Since ancient times plants have generated great interest in every civilization, due to their potential as drugs

  • A bio-guided fractionation of the ethyl acetate (EtOAc) extract of C. taxifolium led to the isolation of ursolic acid (5), as the compound responsible for the α-glucosidase inhibition activity

  • All molecules were characterized by spectroscopic techniques such as MS, Nuclear Magnetic Resonance (NMR) (1 H and 13 C) in one and 2D dimension experiments, and further comparison with literature data

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Summary

Introduction

Since ancient times plants have generated great interest in every civilization, due to their potential as drugs. Today, they are still a very rich source of inspiration for the discovery of new active principles or for the study of biological activities [1,2]. Many methods are known to identify bioactive molecules from plant extracts. A very common approach is the so-called bioguided fractionation. It consists of setting up a fractionation scheme, and to screen fractions for the presence of the desired bioactive properties. Active fractions are further sub-fractionated and tested, until pure molecules responsible for the bioactivity can be identified

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