Chemical and Enantioselective Analyses of an Unprecedented Essential Oil from Ecuadorian Aiouea montana : A Natural Source of S-Methyl-O-2-phenylethyl Carbonothioate.

Fresh and dry leaves of Aiouea montana (Sw.) R. Rohde (Lauraceae) produced, in a quite high yield (0.88% and 1.60%, respectively), an unpleasantly smelling essential oil. The chemical composition was described in this study for the first time, detecting and quantifying 48 compounds. Major components of fresh and dry leaf essential oils were α-pinene (6.7-10.3%), β-pinene (2.8-3.8%), α-phellandrene (12.6-14.5%), α-copaene (3.1-15.7%), δ-cadinene (0.9-3.3%), and S-methyl-O-2-phenylethyl carbonothioate (58.5-33.3%). The dominant compound was already known in the literature by synthesis; however, it was unprecedented so far in nature. The carbonothioate was identified after purification and structure elucidation, by means of mass spectrometry, NMR spectroscopy, and FTIR spectrophotometry. The spectral results were identical to all data reported in the literature for the same molecule. Furthermore, the enantioselective analysis of the essential oil was conducted on a β-cyclodextrin-based stationary phase. Two chiral constituents, (+)-β-phellandrene and (1 R ,2 S ,6 S ,7 S ,8 S )-(-)-α-copaene, were enantiomerically pure, whereas α-thujene, camphene, β-pinene, α-phellandrene, limonene, linalool, and germacrene D were scalemic mixtures. The different chemical and enantiomeric compositions suggested that enzymatic transformations could occur while drying.