New Essential Oils from Ecuadorian Gynoxys cuicochensis Cuatrec. and Gynoxys sancti-antonii Cuatrec. Chemical Compositions and Enantioselective Analyses.

The present study belonged to an unfunded project, dealing on the systematic description of unprecedented essential oils (EOs), distilled from 12 species of genus Gynoxys Cuatrec. In this very case, the aim was the first chemical and enantiomeric analyses of two volatile fractions, obtained from the leaves of Gynoxys cuicochensis Cuatrec. and Gynoxys sancti-antonii Cuatrec. These EOs were analyzed by GC-MS (qualitatively) and GC-FID (quantitatively), detecting 89 and 60 components from G. cuicochensis and G. sancti-antonii, respectively. Major components for G. cuicochensis EO, on a nonpolar and polar stationary phase, were α-pinene (29.4-29.6%), p -vinylguaiacol (3.3-3.6%), and germacrene D (20.8-19.9%). In G. sancti-antonii EO, the main compounds were α-pinene (3.0-2.9%), β-pinene (12.9-12.1%), γ-curcumene (19.7-18.3%), germacrene D (9.0% on the polar phase), ar -curcumene (5.3% on the polar phase), δ-cadinene (4.1-4.6%), α-muurolol (3.3-2.4%), α-cadinol (3.0% on both columns), and an undetermined compound, of molecular weight 220. In addition to chemical composition, the enantioselective analysis of the main chiral compounds was carried out on two different chiral selectors. In G. cuicochensis EO, (1 R ,5 R )-(+)-α-pinene, ( S )-(+)-β-phellandrene, ( R )-(-)-piperitone, and ( S )-(-)-germacrene D were enantiomerically pure, whereas β-pinene, sabinene, α-phellandrene, limonene, linalool, and terpinen-4-ol were observed as scalemic mixtures. On the other hand, in G. sancti-antonii EO, the pure enantiomers were (1 S ,5 S )-(-)-α-pinene, (1 R ,5 R )-(+)-sabinene, ( R )-(-)-β-phellandrene, ( S )-(-)-limonene, (1 S ,2 R ,6 R ,7 R ,8 R )-(+)-α-copaene, ( R )-(-)-terpinen-4-ol, and ( S )-(-)-germacrene D, whereas β-pinene, linalool, and α-terpineol were present as scalemic mixtures. The principal component analysis demonstrated that G. cuicochensis volatile fraction was quite similar to many of the other EOs of the same genus, whereas G. sancti-antonii produced the most dissimilar EO. Furthermore, the enantioselective analyses showed the usual variable enantiomeric distribution, with a greater presence of enantiomerically pure compounds in G. sancti-antonii EO.