Detection of the Previously Unobserved Stereoisomers of Thujone in the Essential Oil and Consumable Products of Sage (Salvia officinalis L.) Using Headspace Solid-Phase Microextraction–Gas Chromatography–Mass Spectrometry

Abstract

The discovery of the (+)-α-thujone and (-)-β-thujone stereoisomers in the essential oil of sage (Salvia officinalis L.) and dietary supplements is documented for the first time. The detection was accomplished using a chiral resolution protocol of racemic α-/β-thujone on headspace solid-phase microextraction-gas chromatography-mass spectrometry. Because the previously unreported stereoisomers, (+)-α-thujone and (-)-β-thujone, are not commercially available, a three-step synthesis of racemic thujone from commercially available starting materials was developed. Thermolysis studies demonstrated that no racemization at the cyclopropane stereocenters occurs, corroborating that the detection is not an artifact from the hydrodistillation process. The developed chiral resolution of thujone was also used to provide evidence for the absence of the (+)-α-thujone and (-)-β-thujone enantiomers in other common thujone-containing essential oils.

A GC–MS method validation for quantitative investigation of some chemical markers inSalvia hypargeiaFisch. & C.A. Mey. of Turkey: Enzyme inhibitory potential of ferruginol

“…Plant secondary metabolites having the potential to treat a variety of diseases are divided into many classes such as flavonoids, phenolic acids, phenolic glycosides, unsaturated lactones, phenylpropanoids, lignins, terpenoids, and steroids. These valuable compounds have many applications in the cosmetic, food, and pharmaceutical industries (Banerjee & Bonde, 2011;Williams, Yazarians, Almeyda, Anderson, & Boyce, 2016).…”

Thymus mastichina L. essential oils from Murcia (Spain): Composition and antioxidant, antienzymatic and antimicrobial bioactivities

“…Moreover, no chiral characterization of above mentioned TmEOs has been reported [ 2 – 11 ]. However, such data are important for quality assurance, since they help to assess either the genuineness or possible adulteration of the EOs, as well as their origin [ 12 ]. Furthermore, the information is required to use TmEOs as a natural source of pure enantiomers [ 13 ].…”

Salvia officinalis L. Essential Oils from Spain: Determination of Composition, Antioxidant Capacity, Antienzymatic, and Antimicrobial Bioactivities

“…As regards the chiral characterization of SoEOs, only a few studies have reported the enantiomeric distribution of the principal components . The chiral distribution of the main compounds counts as a quality assurance marker to determine both the authenticity and the applicability of a given EO.…”

“…As regards the chiral characterization of SoEOs, only a few studies have reported the enantiomeric distribution of the principal components. [26] [27] The chiral distribution of the main compounds counts as a quality assurance marker to determine both the authenticity and the applicability of a given EO. An adulterated EO may contain racemic mixtures of the main compounds, obtained by chemical synthesis, making it cheaper than the corresponding EOs with their chiral natural compounds.…”