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

Abstract

Pinus species are important in traditional medicine throughout their ranges, and pine essential oils are of interest in aromatherapy and as topical treatments. In this work, the leaf (needle) essential oils of Pinus ponderosa var. ponderosa and Pinus contorta subsp. contorta from Oregon and Pinus flexilis growing in Idaho, have been obtained by hydrodistillation and analyzed by gas chromatographic techniques. The leaf essential oil of P. ponderosa was dominated by β-pinene (21.5–55.3%), methyl chavicol (8.5–41.5%), α-pinene (3.6–9.6%), δ-3-carene (3.6–6.2%), and α-terpineol (1.4–5.3%). The major components of P. contorta essential oil were β-phellandrene (23.8%), terpinen-4-ol (11.0%). The essential oil of P. flexilis was dominated by α-pinene (37.1%), β-pinene (21.9%), bornyl acetate (12.8%), and camphene (8.5%). Chiral gas chromatography revealed the enantiomeric ratios of α-pinene and limonene to be variable, but (−)-β-pinene predominated in Pinus essential oils.

Limonene Enantiomeric Ratios from Anthropogenic and Biogenic Emission Sources

“…If these results are representative of emissions from fragranced VCPs, atmospheric measurements of (−)-limonene in urban spaces would provide a lower bound for the contribution of limonene from biogenic sources or, alternatively, the (+)-limonene would provide an upper bound for the contribution from fragranced VCPs. It is possible that some household products could have a different limonene enantiomeric fingerprint, particularly for products that use essential oils sourced from non-citrus plants, such as pines . However, citrus essential oils account for the largest proportion of commercial natural flavors and fragrances, so we believe the anthropogenic fragrance signature is likely consistent with the results shown in this study.…”

Gymnosperms of Idaho: Chemical Compositions and Enantiomeric Distributions of Essential Oils of Abies lasiocarpa, Picea engelmannii, Pinus contorta, Pseudotsuga menziesii, and Thuja plicata

“…Consistent with these findings, the (−)-enantiomers predominate for camphene, β-pinene, limonene, β-phellandrene, and α-terpineol in the Pinaceae essential oils of Abies concolor , Abies balsamea [ 47 ], Picea pungens [ 48 ], Pinus ponderosa , Pinus contorta , and Pinus flexilis [ 11 ]. Likewise, while (+)-α-thujene was the exclusive enantiomer in T. plicata , (−)-α-thujene was dominant in A. concolor and A. balsamea [ 47 ].…”

“…murrayana from Oregon [ 10 ], and P. contorta subsp. contorta from Oregon [ 11 ], an AHC analysis was carried out ( Figure 12 ). The three P. contorta subsp.…”

“…Engelm. (the Sierra lodgepole pine), which ranges in the Cascade Range in Washington and Oregon, south into northern California and the Sierra Nevada Range ( Figure 5 ) [ 10 , 11 ]. The gray-brown bark of P. contorta subsp.…”

Silver Nanoparticles Synthesized from Abies alba and Pinus sylvestris Bark Extracts: Characterization, Antioxidant, Cytotoxic, and Antibacterial Effects

“…Coumaroylquinic acids have been previously identified in the bark of other Pinus species such as Pinus nigra [ 29 ] and Pinus densiflora [ 77 ]. Mentha-2,8-dien-1-ol, menthane-3,8-diol, menth-2-en-1-ol, and cymen-8-ol are volatile monoterpenoids present in the essential oils isolated from various coniferous species [ 78 , 79 , 80 , 81 , 82 , 83 ]. On the basis of mass spectral data ( Supplementary Table S1 ), previous investigations on MS/MS fragmentation of monoterpene glycosides [ 84 , 85 ], and the KNApSacK database [ 71 ], seven glycosides of the previously mentioned volatile monoterpenoids were tentatively identified in both bark extracts.…”