Multidimensional gas chromatography/mass spectrometry (MDGC/MS): A powerful tool for the direct chiral evaluation of aroma compounds in plant tissues. III. (1S)‐(–‐)‐2‐endo‐Acetoxy‐3‐exo‐hydroxybornane (vulgarole) in mugwort (Artemisia vulgaris L.) herb

Abstract

On‐line coupled multidimensional gas chromatography (DB‐5/Lipodex D)/mass spectrometry (MDGC/MS) revealed the occurrence of (1S)‐(–‐)‐2‐endo‐acetoxy‐3‐exo‐hydroxybornane (vulgarole) with 100% enantiomeric excess in mugwort (Artemisia vulgaris L.) herb. The result was verified by means of synthesized optically pure (1R) and (1S) enantiomers of vulgarole.

Gas-Phase Chiral Differentiation of Amino Acid Guests in Cyclodextrin Hosts

“…Currently, cyclodextrins are used in conjunction with HPLC to separate and quantify enantiomeric mixtures of amino acids. The interaction of amino acids and cyclodextrins produces a host−guest complex that can be chromatographically separated. − Several examples of chiral recognition in mass spectrometry have been reported. − The majority of these studies takes advantage of the excess energy produced during ionization to differentiate enantiomers. For example, the population of complexes formed with FAB have a high metastable component.…”

Composition of the Essential Oil of Wild Growing Artemisia vulgaris from Erie, Pennsylvania

“…While Vulgarole has been suggested as a marker for A. vulgaris L. [15], it was not detected in the aerial parts of Artemisia vulgaris L. from Erie, PA., although it was found in samples from Italy [16] and Germany [17]. The presence of a single enantiomer was elucidated in 1991 [15].…”

“…While Vulgarole has been suggested as a marker for A. vulgaris L. [15], it was not detected in the aerial parts of Artemisia vulgaris L. from Erie, PA., although it was found in samples from Italy [16] and Germany [17]. The presence of a single enantiomer was elucidated in 1991 [15]. Vulgarole has however, been reported in a sample of Capsicol using GC-MS [18] and in a sample of Artemisia moorcroftiana Wall from the Kashmir region of India [19].…”

Chiral Recognition Is Observed in the Deprotonation Reaction of Cytochrome c by (2R)- and (2S)-2-Butylamine

“…Chiral specific reactions are important and when used to probe multiply protonated proteins may provide information regarding the gas-phase protein surface as well as the environment at the sites of protonation. The use of mass spectrometry to differentiate chirality has received increasing attention. − However, there are few examples of chiral recognition in a bimolecular gas-phase reaction. Chu et al .…”