Chemical and Enantioselective Analysis of the Essential Oils from Different Morphological Structures of Ocotea quixos (Lam.) Kosterm

The traditional Ecuadorian spice Ishpingo, characterized by a strong cinnamon-like aroma, is constituted by the dry cupules of Amazonian species Ocotea quixos. Nevertheless, bark and leaves also present aromatic properties and are sometimes used as substitutes. In the present study, the essential oils, distilled from these morphological structures, are comparatively analyzed for their chemical and enantiomeric compositions. A total of 88 components were identified with 2 orthogonal GC columns, whereas 79, corresponding to more than 94%, were also quantified with at least 1 column. Major compounds were (E)-methyl cinnamate in cupules (35.9–34.2%), (E)-cinnamaldehyde in bark (44.7–47.0%), and (E)-cinnamyl acetate (46.0–50.4%) in leaves. For what concerns the enantioselective analysis, 10 chiral terpenes and terpenoids were detected, of which 6 were present as enantiomeric pairs in at least 1 essential oil, the others being enantiomerically pure. Both quantitative and enantioselective analyses were submitted to Principal Component Analysis (PCA) and Hierarchical Cluster Analysis (HCA), where their results confirmed significative difference among the three products.

Enantioselective Analysis of Mexiletine Using Chromatographic Techniques: A Review

Background: Mexiletine belongs to the β-amino-aryl-ether group of pharmaceutical and applied in the diagnosis of antiarrhythmics, allodynia, and myotonic disorders. In its chemical structure, it possesses a chiral center and practiced in the form of the racemic mixture. The production and accessibility of mexiletine have accompanied with a meaningful development in awareness of its pharmacologic actions. But in clinical arrhythmias and binding experiments on cardiac sodium channels, the (R)-enantiomer of mexiletine is more potent than the (S)-enantiomer. Also, (S)-enantiomer is further active in the diagnosis of allodynia than the (R)-enantiomer. Methods: During the last two decades, chromatographic techniques such as HPLC, and GC coupled with mass spectrometry or field ionization detector was used for the stereoselective analysis of MEX enantiomers. Results: The direct enantioresolution deal with the use of chiral stationary phases (CSPs) with or no pre-derivatization which depend on a chromophoric entity in the racemates whereas indirect HPLC process involved the use of chiral derivatization reagents (CDR) for the synthesis of diastereomeric derivatives of racemates. Different techniques have their strengths and weaknesses. Conclusion: Regulation of enantiomeric purity and estimation of particular enantiomers of drug molecules stays an essential topic for therapeutic, diagnostic, and regulatory uses and to promote a precise assessment of the hazards to human health by false enantiomers. This review aims to offer a systematic survey of the analytical methods (chromatography based) used in the enantioselective analysis of MEX developed in the last two decades (the year 2000 onwards).

Chemical and Enantioselective Analysis of the Leaf Essential Oil from Piper coruscans Kunth (Piperaceae), a Costal and Amazonian Native Species of Ecuador

In the present study, an essential oil was distilled from the leaves of Piper coruscans Kunth, a native Amazonian species belonging to the family Piperaceae and quite common in Ecuador. The chemical analysis was performed by GC-MS (qualitative) and GC-FID (quantitative), on polar and non-polar columns, detecting a total of 58 compounds of which 52 were identified. All the identified compounds were quantified. The essential oil was mainly constituted of sesquiterpenes (54.1–55.0%) and oxygenated sesquiterpenoids (32.5–33.6%), the major constituents being: (E)-β-caryophyllene (24.1–25.0%), α-humulene (11.6–12.0%), caryophyllene oxide (9.3–10.9%), linalool (4.5–5.2%), humulene epoxide II (3.6–4.1%), (E)-nerolidol (3.7–4.0%), α-copaene (3.7–3.9%), α-muurolol (3.4–3.7%), α-selinene (3.4–3.5%), β-selinene (3.1–3.3%), and one undetermined oxygenated sesquiterpenoid (3.1–3.3%). The aqueous phase (hydrolate) of the distillation process was also submitted to chemical analysis, showing linalool as the main organic compound in solution, with a concentration of 12.3–15.7 mg/100 mL. The essential oil was than analyzed for the enantiomeric distribution of its monoterpene constituents, affording the following enantiomeric excesses in two β-cyclodextrin-based enantioselective columns: (1S,5S)-(-)-α-pinene (60.0–69.6%), (1S,5S)-(-)-β-pinene (5.2–7.2%), (R)-(-)-α-phellandrene (72.5–78.2%), (R)-(+)-limonene (28.6%) and (R)-(-)-linalool (1.8–3.1%).