The essential oil of turpentine and its major volatile fraction (α- and β-pinenes): a review

Mercier, B.; Prost, Josiane; Prost, Michel

doi:10.2478/v10001-009-0032-5

Cited by 153 publications

(124 citation statements)

References 76 publications

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“…The highly lipophilic and volatile essential oils of conifer trees, such as pinenes and other bicyclic monoterpenes, may cause toxicity upon inhalation, cutaneous exposure, or massive oral ingestion (Mercier et al, 2009). By contrast, the toxicity of the resiniferous ingredients in larch turpentines, including larixol or larixyl acetate has not been reported in detail.…”

Section: Larixyl Acetate Is a Trpc6 Inhibitormentioning

confidence: 94%

Identification and Validation of Larixyl Acetate as a Potent TRPC6 Inhibitor

et al. 2015

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Classical or canonical transient receptor potential 6 (TRPC6), a nonselective and Ca 21 -permeable cation channel, mediates pathophysiological responses within pulmonary and renal diseases that are still poorly controlled by current medication. Thus, controlling TRPC6 activity may provide a promising and challenging pharmacological approach. Recently identified chemical entities have demonstrated that TRPC6 is pharmacologically targetable. However, isotype-selectivity with regard to its closest relative, TRPC3, is difficult to achieve. Reasoning that balsams, essential oils, or incense materials that are traditionally used for inhalation may contain biologic activities to block TRPC6 activity, we embarked on a natural compound strategy to identify new TRPC6-blocking chemical entities. Within several preparations of plant extracts, a strong TRPC6-inhibitory activity was found in conifer balsams. The biologic activity was associated with nonvolatile resins, but not with essential oils. Of various conifers, the larch balsam was unique in displaying a marked TRPC6-prevalent mode of action. By testing the main constituents of larch resin, we identified larixol and larixyl acetate as blockers of Ca 21 entry and ionic currents through diacylglycerol-or receptor-activated recombinant TRPC6 channels, exhibiting approximately 12-and 5-fold selectivity compared with its closest relatives TRPC3 and TRPC7, respectively. No significant inhibition of more distantly related TRPV or TRPM channels was seen. The potent inhibition of recombinant TRPC6 by larixyl acetate (IC 50 5 0.1-0.6 mM) was confirmed for native TRPC6-like [Ca 21 ] i signals in diacylglycerol-stimulated rat pulmonary artery smooth muscle cells. In isolated mouse lungs, larix-6-yl monoacetate (CAS 4608-49-5; larixyl acetate; 5 mM) prevented acute hypoxiainduced vasoconstriction. We conclude that larch-derived labdane-type diterpenes are TRPC6-selective inhibitors and may represent a starting point for pharmacological TRPC6 modulation within experimental therapies.

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Section: Larixyl Acetate Is a Trpc6 Inhibitormentioning

confidence: 94%

Identification and Validation of Larixyl Acetate as a Potent TRPC6 Inhibitor

et al. 2015

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“…Both α-and β-pinene have been reported as sedatives (Mercier et al, 2009) and analgesics (Erazo et al, 2006). Kasanen et al (1998) also reported that all pinenes induced sedation followed by signs of anesthesia in mice.…”

Section: Transportation Experimentmentioning

confidence: 99%

Anesthesia and transport of fat snook Centropomus parallelus with the essential oil of Nectandra megapotamica(Spreng.) Mez

et al. 2013

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This study analyzed the chemical composition and anesthetic potential of essential oil (EO) of Nectandra megapotamica in fat snook (Centropomus parallelus). For the extraction of EO by hydrodistillation, leaves were separated in young (EO-Y) or old (EO-O), and the chemical composition of the EOs was determined by CG-MS. The anesthetic potential was assessed by the evaluation of induction and recovery time of anesthesia and stress response from anesthesia and transport. Three experiments were carried out: i) four different concentrations of each EO were tested to evaluate anesthesia induction and recovery time; ii) two concentrations of EO-O were tested for the evaluation of its effects on stress parameters (glucose, lactate, and Na + and K + plasma levels) caused by anesthesia; and iii) fish were transported in plastic bags, supplied with two concentrations of EO-O for the evaluation of water quality and mortality. All experiments were performed on fish acclimated to 0 and 33 ppt salinity. The main constituents of the Y and O-EOs were bicyclogermacrene (46.5/34.6%), α-pinene (26.8/26.2%), β-pinene (7.9/12.3%), and germacrene D (9.6/9.1%). Mild sedation was achieved at 30 µL L -1 (1.3-3.2 min) and deep anesthesia at 150 µL L -1 (5.6-8.0 min) with both EOs. The recovery time ranged from 1-10 min. The EO-O was not able to avoid the stress of anesthesia evidenced by elevated glucose and lactate plasma levels observed in all groups. Plasma levels of Na + and K + were not significantly affected by treatments. During transport, the use of EO-O did not prevent deterioration in water quality and the post-transport mortality. In conclusion, the EO of N. megapotamica has anesthetic activity in fat snook, but it was not able to prevent the stress of anesthesia and transport.Este estudo analisou a composição química e o potencial anestésico do óleo essencial (OE) de Nectandra megapotamica em robalos-peva (Centropomus parallelus). Para a extração do OE por hidrodestilação, as folhas foram separadas em jovens (OE-J) ou velhas (OE-V) e a composição química foi determinada por CG-EM. O potencial anestésico foi acessado através da avaliação do tempo de indução e recuperação da anestesia e resposta ao estresse do procedimento anestésico e transporte. Foram realizados três experimentos: em primeiro lugar, quatro concentrações diferentes de cada OE foram testadas para avaliar o tempo de indução à anestesia e de recuperação; em segundo lugar, duas concentrações do OE-V foram testadas para avaliar os efeitos sobre os parâmetros de estresse (níveis plasmáticos de glicose, lactato, Na + e K + ) causados pelo procedimento anestésico; em terceiro lugar, os peixes foram transportados em sacos plásticos com duas concentrações do OE-V para avaliação da qualidade da água e mortalidade. Todos os experimentos foram realizados em peixes aclimatados à salinidade zero e 33. Os constituintes majoritários do OE-J e OE-V foram: biciclogermacreno (46,5/34,6%), α-pineno (26,8/26,2%), β-pineno (7,9/12,3%) e germacreno D (9,6/9,1%). Sedação leve foi alca...

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“…To date, a crystal structure of CYP2A6 with environmentally important monoterpenes and a direct structural comparison of CYP2B and 2A enzymes in the presence of such hydrocarbons have been lacking. Sabinene is a major olefinic monoterpene derived from the volatile oils found in plants and is often used as an odorant and perfume additive and as an important constituent of plant oils in alternative medicine (Karp et al, 1987;Mercier et al, 2009;Harrison et al, 2013). In the current study, we sought to determine the first crystal structure of human CYP2A6 in complex with sabinene and compare it with the CYP2B6 complex.…”

Section: Introductionmentioning

confidence: 99%

Structural and Biophysical Characterization of Human Cytochromes P450 2B6 and 2A6 Bound to Volatile Hydrocarbons: Analysis and Comparison

et al. 2015

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X-ray crystal structures of complexes of cytochromes CYP2B6 and CYP2A6 with the monoterpene sabinene revealed two distinct binding modes in the active sites. In CYP2B6, sabinene positioned itself with the putative oxidation site located closer to the heme iron. In contrast, sabinene was found in an alternate conformation in the more compact CYP2A6, where the larger hydrophobic side chains resulted in a significantly reduced activesite cavity. Furthermore, results from isothermal titration calorimetry indicated a much more substantial contribution of favorable enthalpy to sabinene binding to CYP2B6 as opposed to CYP2A6, consistent with the previous observations with (1)-a-pinene. Structural analysis of CYP2B6 complexes with sabinene and the structurally similar (3)-carene and comparison with previously solved structures revealed how the movement of the F206 side chain influences the volume of the binding pocket. In addition, retrospective analysis of prior structures revealed that ligands containing -Cl and -NH functional groups adopted a distinct orientation in the CYP2B active site compared with other ligands. This binding mode may reflect the formation of Cl-p or NH-p bonds with aromatic rings in the active site, which serve as important contributors to protein-ligand binding affinity and specificity. Overall, the findings from multiple techniques illustrate how drugs metabolizing CYP2B6 and CYP2A6 handle a common hydrocarbon found in the environment. The study also provides insight into the role of specific functional groups of the ligand that may influence the binding to CYP2B6.

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The essential oil of turpentine and its major volatile fraction (α- and β-pinenes): a review

Cited by 153 publications

References 76 publications

Identification and Validation of Larixyl Acetate as a Potent TRPC6 Inhibitor

Identification and Validation of Larixyl Acetate as a Potent TRPC6 Inhibitor

Anesthesia and transport of fat snook Centropomus parallelus with the essential oil of Nectandra megapotamica(Spreng.) Mez

Structural and Biophysical Characterization of Human Cytochromes P450 2B6 and 2A6 Bound to Volatile Hydrocarbons: Analysis and Comparison

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