Authenticity control of pine sylvestris essential oil by chiral gas chromatographic analysis of α-pinene

Abstract

Numerous terpenes present in essential oils (EOs) display one or more chiral centers. Within the same genus the enantiomeric ratio of these compounds can be different. Thus, the determination of enantiomers is a valuable tool to evaluate authenticity and quality of EOs. In here, the terpene profile of primary and commercial pine EOs was analyzed by conventional and chiral gas chromatography coupled to a flame ionization detector. The enantiomeric excess of ( ±)-α-pinene was determined and significant differences between primary and commercially available EOs were observed. Primary EOs of Pinus sylvestris L. showed a positive enantiomeric excess of (+)-α-pinene whereas commercial EOs labeled as P. sylvestris L. exhibited an enantiomeric excess of (−)-α-pinene. Thus, chiral analysis provides useful information on the authenticity of pine EOs and allows to uncover possible mislabeling, the use of the wrong herbal substance and sources of adulteration in pine oil.

Essential Oil Compositions of Pinus Species (P. contorta Subsp. contorta, P. ponderosa var. ponderosa, and P. flexilis); Enantiomeric Distribution of Terpenoids in Pinus Species

“…A perusal of Table 5 reveals that the enantiomeric distribution of α-pinene and limonene in Pinus species is variable both between species and within species. Allenspach and co-workers found that (+)-α-pinene generally predominated in primary essential oils of P. sylvestris and P. cembra , but that P. mugo and P. nigra were generally dominated by (−)-α-pinene [ 25 ]. The enantiomeric distribution in β-pinene in Pinus species, however, is consistently dominated by (−)-β-pinene.…”

The pinene scaffold: its occurrence, chemistry, synthetic utility, and pharmacological importance

“…Steuer and co-workers have demonstrated the value of chiral analysis in authenticating essential oils from different pine species and have recently shown that the dominant pinene enantiomer in Pinus sylvestris is (+)-α-pinene whereas (−)-α-pinene predominates in Pinus nigra and Pinus mugo . 1 α-Pinene is a major component of essential oils from conifers, Cannabis sativa , and Piper . α-Pinene is a significant component of turpentine, and it is responsible for the strong smell of pine trees.…”

Variations in Essential Oils from South Siberian Conifers of the Pinaceae Family: New Data towards Identification and Quality Control

“…In addition, many essential oils are the object of falsification [7] . Recent data on authenticity control of essential oils have stated that ‘Primary EOs of Pinus sylvestris L. showed a positive enantiomeric excess of (+)‐α‐pinene whereas commercial EOs labeled as P. sylvestris L. exhibited an enantiomeric excess of (−)‐α‐pinene [8] . So, determination of the enantiomeric composition of the key components is an important tool in determining the authenticity of essential oils used in medical practice.…”

“…[7] Recent data on authenticity control of essential oils have stated that 'Primary EOs of Pinus sylvestris L. showed a positive enantiomeric excess of (+)-α-pinene whereas commercial EOs labeled as P. sylvestris L. exhibited an enantiomeric excess of (À )-α-pinene. [8] So, determination of the enantiomeric composition of the key components is an important tool in determining the authenticity of essential oils used in medical practice. For coniferous essential oils, a set of characteristic components indicating the range of their content can be considered as a chromatographic profile in the WHO definition, [9] and the enantiomer ratios of the chiral components of the essential oil are specific analytical markers.…”

“…Sabine ex Trautv., (6) Larix sukaczewii Dylis, (7) Pinus larix L. var. russica Endl., (8) Pinus ledebourii (Rupr.) Endl.…”