A New Sesquiterpene Essential Oil from the Native Andean Species Jungia rugosa Less (Asteraceae): Chemical Analysis, Enantiomeric Evaluation, and Cholinergic Activity.

As part of a project devoted to the phytochemical study of Ecuadorian biodiversity, new essential oils are systematically distilled and analysed. In the present work, Jungia rugosa Less (Asteraceae) has been selected and some wild specimens collected to investigate the volatile fraction. The essential oil, obtained from fresh leaves, was analysed for the first time in the present study. The chemical composition was determined by gas chromatography, coupled to mass spectrometry (GC-MS) for qualitative analysis, and to flame ionization detector (GC-FID) for quantitation. The calculation of relative response factors (RRF), based on combustion enthalpy, was carried out for each quantified component. Fifty-six compounds were identified and quantified in a 5% phenyl-polydimethylsiloxane non-polar column and 53 compounds in a polyethylene glycol polar column, including four undetermined compounds. The main feature of this essential oil was the exclusive sesquiterpenes content, both hydrocarbons (74.7% and 80.4%) and oxygenated (8.3% and 9.6%). Major constituents were: γ-curcumene (47.1% and 49.7%) and ß-sesquiphellandrene (17.0% and 17.9%), together with two abundant undetermined oxygenated sesquiterpenes, whose abundance was 6.7-7.2% and 4.7-3.3%, respectively. In addition, the essential oil was submitted to enantioselective evaluation in two ß-cyclodextrin-based enantioselective columns, determining the enantiomeric purity of a minor component (1S,2R,6R,7R,8R)-(+)-α-copaene. Finally, the AChE inhibition activity of the EO was evaluated in vitro. In conclusion, this volatile fraction is suitable for further investigation, according to two main lines: (a) the purification and structure elucidation of the major undetermined compounds, (b) a bio-guided fractionation, intended to investigate the presence of new sesquiterpene AChE inhibitors among the minor components.

A Novel Chemical Profile of a Selective In Vitro Cholinergic Essential Oil from Clinopodium taxifolium (Kunth) Govaerts (Lamiaceae), a Native Andean Species of Ecuador.

A novel chemical profile essential oil, distilled from the aerial parts of Clinopodium taxifolium (Kunth) Govaerts (Lamiaceae), was analysed by Gas Chromatography-Mass Spectrometry (GC-MS, qualitative analysis) and Gas Chromatography with Flame Ionization Detector (GC-FID, quantitative analysis), with both polar and non-polar stationary phase columns. The chemical composition mostly consisted of sesquiterpenes and sesquiterpenoids (>70%), the main ones being (E)-ß-caryophyllene (17.8%), α-copaene (10.5%), ß-bourbonene (9.9%), δ-cadinene (6.6%), cis-cadina-1(6),4-diene (6.4%) and germacrene D (4.9%), with the non-polar column. The essential oil was then submitted to enantioselective GC analysis, with a diethyl-tert-butyldimethylsilyl-ß-cyclodextrin diluted in PS-086 chiral selector, resulting in the following enantiomeric excesses for the chiral components: (1R,5S)-(-)-α-thujene (67.8%), (1R,5R)-(+)-α-pinene (85.5%), (1S,5S)-(-)-ß-pinene (90.0%), (1S,5S)-(-)-sabinene (12.3%), (S)-(-)-limonene (88.1%), (S)-(+)-linalool (32.7%), (R)-(-)-terpinen-4-ol (9.3%), (S)-(-)-α-terpineol (71.2%) and (S)-(-)-germacrene D (89.0%). The inhibition activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) of C. taxifolium essential oil was then tested, resulting in selective activity against BChE with an IC50 value of 31.3 ± 3.0 µg/mL (positive control: donepezil, IC50 = 3.6 µg/mL).

Chemical, Enantioselective, and Sensory Analysis of a Cholinesterase Inhibitor Essential Oil from Coreopsis triloba S.F. Blake (Asteraceae).

The fresh leaves of Coreopsis triloba S.F. Blake, collected at Cerro Villonaco in Loja, Ecuador, were investigated with respect to their essential oil (EO). The chemical composition was determined qualitatively through gas chromatography coupled with mass spectrometry (GC-MS) and quantitatively by gas chromatography coupled with flame ionization (GC-FID), using relative response factors (RRF) based on the enthalpy of combustion. The essential oil contained between 92.5% and 93.4% of monoterpene hydrocarbons, with (E)-ß-ocimene being the main component (35.2-35.9%), followed by ß-phellandrene (24.6-25.0%), α-pinene (15.3-15.9%), myrcene (10.9-11.0%), sabinene (2.2-2.4%), (Z)-ß-ocimene (1.5%), and germacrene D (1.2-1.3%). The enantiomeric distribution of α-pinene, ß-pinene, limonene, and germacrene D was also determined. The main components responsible for the aroma were identified through aroma extract dilution analysis (AEDA), a gas chromatography-olfactometry (GC-O) based technique, being α-pinene, ß-pinene (0.6%), terpinolene (0.1%), α-copaene (0.1-0.3%), ß-phellandrene, and (E)-4,8-dimethyl-1,3,7-nonatriene (0.1-0.2%) the main olfactory constituents according to the decreasing factor of dilution (FD) order. The biological tests showed IC50 inhibition values of 42.2 and 6.8 µg/mL for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively.