(-)-beta-Pinene

The heartwoods of Pinus armandii Franch

Protective Effect of the Hexanic Extract of Eryngium carlinae Inflorescences In Vitro, in Yeast, and in Streptozotocin-Induced Diabetic Male Rats.[Pubmed:30917540]

Antioxidants (Basel). 2019 Mar 26;8(3). pii: antiox8030073.

In the present study, we investigated the composition and antioxidant activity of the hexanic extract of Eryngium carlinae inflorescences by employing in vitro assays to measure antioxidant capacity and 2,2-diphenyl-1-picrylhydrazyl scavenging activity. We also applied the hexanic extract to Saccharomyces cerevisiae, under hydrogen peroxide-induced stress. Finally, we tested the extract in male Wistar rats with and without streptozotocin-induced diabetes. The compounds in the hexanic extract were analyzed by gas-chromatography-mass spectrometry, which revealed mainly terpenes and sesquiterpenes, including (Z)beta-farnesene (38.79%), beta-pinene (17.53%), calamene (13.3%), and alpha-farnesene (10.38%). In vitro and in S. cerevisiae, the extract possessed antioxidant activity at different concentrations, compared to ascorbic acid (positive control). In normoglycemic and hyperglycemic rats, oral administration of 30 mg/kg of the extract reduced blood glucose levels; lipid peroxidation in liver, kidney and brain; protein carbonylation; and reactive oxygen species (ROS) production. It also increased catalase activity in the brain, kidneys and liver. These findings show that this hexanic extract of E. carlinae inflorescences possessed antioxidant properties.

Chemical composition, antioxidant, antimicrobial and anticancer activities of the essential oil from the rhizomes of Zingiber striolatum Diels.[Pubmed:30908095]

Nat Prod Res. 2019 Mar 25:1-5.

The chemical composition and biological activities of the essential oil (EO) from the rhizomes of Zingiber striolatum Diels were reported for the first time. Forty-five compounds were identified, and represented 95.7% of the total composition of the EO. The predominant components of the EO were beta-phellandrene (24.0%), sabinene (17.3%), beta-pinene (11.4%), geranyl linalool (8.6%), terpinen-4-ol (8.3%), alpha-pinene (5.6%) and crypton (4.5%). The EO revealed a weak DPPH and ABTS radical-scavenging activity. The EO exhibited significant antimicrobial activity with the inhibition zones (12.86-24.62 mm) and MIC (0.78-3.12 mg/mL) against Enterococcus faecalis, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Candida albicans. The EO showed significant cytotoxicity against human leukemic (K562), lung cancer (A549) and prostatic carcinoma (PC-3) cell lines with the IC50 values of 29.67, 48.87 and 86.05 mug/mL, respectively. Thus, the EO could be regarded as a bioactive natural product with potential for utilization in the cosmetic and pharmaceutical industry.

Influence of Monoterpenes in Biological Activities of Nectandra megapotamica (Spreng.) Mez Essential Oils.[Pubmed:30901829]

Biomolecules. 2019 Mar 21;9(3). pii: biom9030112.

Investigating the influence of seasonal variations on biological activities is important for pharmacological studies and metabolic engineering. Therefore, this study was conducted to determine the variation of the chemical composition of essential oils obtained from Nectandra megapotamica leaves, collected at different stages of plant development, as well as its influence on the biological activities. A total of 38 compounds were identified that accounted for 97(-)99.2% of the chemical composition of the oils. Major differences were observed in the monoterpenic fraction, representing 5.1% of the compounds identified in the productive rest phase to 37.1% in the blooming phase. Bicyclogermacrene and germacrene D were the predominant compounds identified in the oil of all collections. Furthermore, limonene, beta-pinene, and spathulenol were identified predominantly in the samples of blooming and fruiting phases. The oils exhibited significant antichemotactic activity and different effects in scavenging the radical 2,2-diphenyl-1-picrylhydrazyl. Variations were also observed in the antifungal activity, with the minimum inhibitory concentrations ranging from 125 to 500 mug/mL. These results demonstrate the influence of monoterpenes, primarily limonene, alpha-pinene, and beta-pinene, on the bioactivities of the oil. Studies investigating the variations in the chemical composition of essential oil may offer a strategy to produce a compound or a group of compounds of interest to industries with a specific pharmacological focus.

Simultaneous GC-FID Quantification of Main Components of Rosmarinus officinalis L. and Lavandula dentata Essential Oils in Polymeric Nanocapsules for Antioxidant Application.[Pubmed:30881726]

J Anal Methods Chem. 2019 Feb 10;2019:2837406.

The essential oils (EO) of R. officinalis and L. dentata have been widely used due to their antioxidant activity. However, due to their high volatility, the loading of EO into polymeric nanocapsules (NC) represents an efficient way of retaining their effect in future topical administration. In this way, the quantitative determination of EO incorporated into NC is necessary for simultaneous monitoring of the main components of the EO during the nanoencapsulation process as well as for precise and exact dosing of the components used during the performance of in vitro and in vivo biological tests. In this study, EO were isolated by hydrodistillation in a Clevenger-type apparatus and characterized by GC-MS and GC-FID analyses. The major constituents of EO-R. officinalis were camphor (39.46%) and 1,8-cineole (14.63%), and for EO-L. dentata were 1,8-cineole (68.59%) and beta-pinene (11.53%). A new analytical method based on GC-FID for quantification of free and encapsulated EO was developed and validated according to ICH. Linearity, limit of detection and quantification, and intra- and interday precision parameters were determined. The methods were linear and precise for the quantification of the main components of EO. The EO were encapsulated by nanoprecipitation and were analyzed by the GC-FID method validated for their direct quantification. The NC size was 200 nm with homogeneous size distribution. The quantification of the incorporated EO within a NC is an important step in NC characterization. In this way, an encapsulation efficiency of at least 59.03% and 41.15% of total EO-R. officinalis and EO-L. dentata, respectively, was obtained. Simple, repeatable, and reproducible methods were developed as an analytical tool for the simultaneous quantification of the main components of EO loaded in polymeric nanocapsules as well as their monitoring in biological assays.

Essential Oil Composition and Biological Activity of "Pompia", a Sardinian Citrus Ecotype.[Pubmed:30841559]

Molecules. 2019 Mar 5;24(5). pii: molecules24050908.

Pompia is a Sardinian citrus ecotype whose botanical classification is still being debated. In the present study, the composition of Pompia peel essential oil (EO) is reported for the first time, along with that of the leaf EO, as a phytochemical contribution to the classification of this ecotype. The peel EO was tested for its antioxidant ability (with both the 2,2-diphenyl-1-picarylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays). Moreover, its antimicrobial activities were tested for the first time on dermatophytes (Microsporum canis, Microsporum gypseum, and Trichophyton mentagrophytes), on potentially toxigenic fungi (Fusarium solani, Aspergillus flavus, and Aspergillus niger) as well on bacteria (Escherichia coli, Staphylococcus aureus, and Staphylococcus pseudointermedius). The dominant abundance of limonene in the peel EO seems to distinguish Pompia from the Citrus spp. to which it had previously been associated. It lacks gamma-terpinene, relevant in Citrus medica EO. Its relative content of alpha- and beta-pinene is lower than 0.5%, in contrast to Citrus limon peel EO. Pompia peel and leaf EOs did not show significant amounts of linalool and linalyl acetate, which are typically found in Citrus aurantium. Pompia peel EO antioxidant activity was weak, possibly because of its lack of gamma-terpinene. Moreover, it did not exert any antimicrobial effects either towards the tested bacteria strains, or to dermatophytes and environmental fungi.

Compartment specific chiral pinene emissions identified in a Maritime pine forest.[Pubmed:30841390]

Sci Total Environ. 2019 Mar 1;654:1158-1166.

To track unknown sources and sinks of volatile organic compounds (VOCs) inside forest canopies we measured diel cycles of VOC exchanges in a temperate maritime forest at the branch, stem and ground level with special focus on the chiral signatures of pinenes. All compartments released day and night alpha- and beta-pinene as major compounds. In addition, strong light dependent emissions of ocimene and linalool from branches occurred during hot summer days. In all compartments the overall emission strength of pinenes varied from day to day spanning 1 to 2 orders of magnitude. The highest pinene emissions from ground and stem were observed during high moisture conditions. Despite this variability stem emissions consistently expressed a different chiral composition than branch emissions, the former containing a much larger fraction of (-)-enantiomers than the latter. Pinene emissions from dead needle litter and soil were mostly enriched in (-)-enantiomers, while the chiral signatures of the ambient air inside the forest showed mostly intermediate levels compared to the emission signatures. These findings suggest that different organ-specific pinene producing enzymes exist in Maritime pine, and indicate that emissions from ground and stem compartments essentially contribute to the canopy VOC flux. Overall the results open new perspectives to explore chirality as a possible marker to recognize shifts in the contributions of different VOC sources present within forest ecosystems and to explain observed temporal changes in the chiral signature of pinenes in the atmosphere.

Chemical Composition and Antimicrobial Activity of Laurus nobilis L. Essential Oils from Bulgaria.[Pubmed:30813368]

Molecules. 2019 Feb 22;24(4). pii: molecules24040804.

Laurel, Laurus nobilis L. is an evergreen plant belonging to the Lauraceae family, native to Southern Europe and the Mediterranean area. This is the first report on the composition and bioactivity of laurel essential oil (EO) from Bulgaria. The oil yield was 0.78%, 0.80%, and 3.25% in the fruits, twigs, and leaves, respectively. The main constituents in the fruit EO were 1,8-cineole (33.3%), alpha-terpinyl acetate (10.3%), alpha-pinene (11.0%), beta-elemene (7.5%), sabinene (6.3%), beta-phellandrene (5.2%), bornyl acetate (4.4%), and camphene (4.3%); those in the twig EO were 1,8-cineole (48.5%), alpha-terpinyl acetate (13.1%), methyl eugenol (6.6%), beta-linalool (3.8%), beta-pinene (3.4%), sabinene (3.3%) and terpinene-4-ol (3.3%); and the ones in the leaf EO were 1,8-cineole (41.0%), alpha-terpinyl acetate (14.4%), sabinene (8.8%), methyl eugenole (6.0%), beta-linalool (4.9%), and alpha-terpineol (3.1%). The antibacterial and antifungal properties of laurel EOs were examined according to the agar well diffusion method. The leaf EO showed antibacterial and antifungal activities against almost all strains of the microorganisms tested, whereas the twig EO was only able to inhibit Staphylococcus aureus. Pseudomonas aeruginosa ATCC 9027 and Escherichia coli ATCC 8739 were the bacterial strains that showed the highest resistance to the laurel EO. The results can benefit the EO industry and biopesticide development.

Partially (resp. fully) reversible adsorption of monoterpenes (resp. alkanes and cycloalkanes) to fused silica.[Pubmed:30795661]

J Chem Phys. 2019 Feb 21;150(7):074701.

This work compares the extent of reversibility and the thermodynamics of adsorption (Kads, DeltaG degrees ads) of room-temperature vapors of common environmentally relevant monoterpenes (alpha-pinene, beta-pinene, limonene, and 3-carene) and industrially relevant cyclic and acyclic non-terpene hydrocarbons (cyclohexane, hexane, octane, and cyclooctane) to fused silica surfaces. Vibrational sum frequency generation spectroscopy carried out in the C-H stretching region shows negligible surface coverage-dependent changes in the molecular orientation of all species surveyed except for cyclohexane. The group of monoterpenes studied here distinctly exhibits partially reversible adsorption to fused silica surfaces compared to the group of non-terpene hydrocarbons, demonstrating a link between molecular structure and adsorption thermodynamics. The standard Gibbs free energy of adsorption is nonlinearly correlated with the equilibrium vapor pressure of the compounds surveyed.

Molecular Docking Studies of Coumarins Isolated from Extracts and Essential Oils of Zosima absinthifolia Link as Potential Inhibitors for Alzheimer's Disease.[Pubmed:30781573]

Molecules. 2019 Feb 17;24(4). pii: molecules24040722.

Coumarins and essential oils are the major components of the Apiaceae family and the Zosima genus. The present study reports anticholinesterase and antioxidant activities of extracts and essential oils from aerial parts, roots, flowers, fruits and coumarins-bergapten (1); imperatorin (2), pimpinellin (3) and umbelliferone (4)-isolated of the roots from Zosima absinthifolia. The investigation by light and scanning electron microscopy of the structures of secretory canals found different chemical compositions in the various types of secretory canals which present in the aerial parts, fruits and flowers. The canals, present in the aerial parts, are characterized by terpene hydrocarbons, while the secretory canals of roots, flowers and fruits include esters. Novel data of a comparative study on essential oils constituents of aerial parts, roots, flowers and fruits of Z. absinthfolia has been presented. The roots and fruits extract showed a high content of total phenolics and antioxidant activity. The GC-FID and GC-MS analysis revealed that the main components of the aerial parts, roots, flowers and fruits extracts were octanol (8.8%), octyl octanoate (7.6%), octyl acetate (7.3%); trans-pinocarvyl acetate (26.7%), beta-pinene (8.9%); octyl acetate (19.9%), trans-p-menth-2-en-1-ol (4.6%); octyl acetate (81.6%), and (Z)-4-octenyl acetate (5.1%). The dichloromethane fraction of fruit and flower essential oil was characterized by the highest phenolics level and antioxidant activity. The dichloromethane fraction of fruit had the best inhibition against butyrylcholinesterase enzyme (82.27 +/- 1.97%) which was higher then acetylcholinesterase inhibition (61.09 +/- 4.46%) of umbelliferone. This study shows that the flowers and fruit of Z. absinthifolia can be a new potential resource of natural antioxidant and anticholinesterase compounds.

Effect of essential oil from Ageratum fastigiatum on beta-integrin (CD18) expression on human lymphocytes stimulated with phorbol myristate acetate in vitro.[Pubmed:30758988]

Nat Prod Res. 2019 Feb 13:1-5.

Agareratum fastigiatum is a Brazilian medicinal plant used as anti-inflammaroty and for wound healing by the folk medicine. In vitro and in vivo studies involving A. fastigiatum essential oil (EOAF) showed indications of anti-inflammatory activity, however, its effect on membrane integrins involved on cell migration is still unclear. Hence, it was evaluated in the present study the effect of EOAF on CD18 frequency on human lymphocytes. By using gas chromatography/mass spectrometry it was identified 9 compounds on EOAF: alpha-pinene; beta-pinene; beta-myrcene; d-limonene; beta-ocimene; sesquiterpenes; alpha-copaene; 4,8-beta-epoxi-caryophyllene; germacrene and bicyclogermacrene. On in vitro tests, 6.25 x 10(-3) and 12.5 x 10(-3) microL/mL EOAF reduced CD18 frequency on phorbol-12-myristate-13-acetate (PMA)-stimulated lymphocytes. Such cells were obtained from peripheral blood of healthy volunteers, and were treated or not with EOAF. They were stained with fluorescent anti-CD18 monoclonal antibodies, after 24 hours incubation. Our data corroborates previous findings, indicating a possible anti-inflammatory activity of EOAF.

Gas Chromatography-Mass Spectrometry (GC-MS) Analysis of Essential Oils from AgNPs and AuNPs Elicited Lavandula angustifolia in vitro Cultures.[Pubmed:30744099]

Molecules. 2019 Feb 9;24(3). pii: molecules24030606.

The aim of this study was to determine how the addition of gold and silver nanoparticles to culture media affects the composition of essential oils extracted from Lavandula angustifolia propagated on MS media with the addition of 10 and 50 mg*dm-3 of gold (24.2 +/- 2.4 nm) and silver (27.5 +/- 4.8 nm) nanocolloids. The oil extracted from the lavender tissues propagated on the medium with 10 mg*dm-3 AgNPs (silver nanoparticles) differed the most with respect to the control; oil-10 compounds were not found at all, and 13 others were detected which were not present in the control oil. The addition of AuNPs (gold nanoparticles) and AgNPs to the media resulted in a decrease of lower molecular weight compounds (e.g., alpha- and beta-pinene, camphene, delta-3-carene, p-cymene, 1,8-cineole, trans-pinocarveol, camphoriborneol), which were replaced by those of a higher molecular weight (tau- and alpha-cadinol 9-cedranone, cadalene, alpha-bisabolol, cis-14-nor-muurol-5-en-4-one, (E,E)-farnesol).

Towards green drugs against cestodes: Effectiveness of Pelargonium roseum and Ferula gummosa essential oils and their main component on Echinococcus granulosus protoscoleces.[Pubmed:30736953]

Vet Parasitol. 2019 Feb;266:84-87.

Cystic echinococcosis is of great public health importance. Surgery is the efficient treatment for this infection. To minimize the risk of cyst intraoperative leakage, using scolicidals is crucial. To date, any efficacious scolicidal without side effect has not been introduced. Since essential oils of Pelargonium roseum and Ferula gummosa have shown several bioactivities, we evaluated their potential against protoscoleces of E. granulosus using albendazole as positive control. Furthermore, chemical composition of both essential oils was analyzed by gas chromatography-mass spectrometry (GC-MS) analyses, and their main constituents were also evaluated for scolicidal activity. Different concentrations of essential oils and their two main constituents were tested for scolicidal activity. Mortality rate was measured by eosin staining. Results of GC-MS revealed citronellol and beta-pinene as the main constituents of P. roseum and F. gummosa essential oils, respectively. After 60 min of exposure to 50 mug/mL of P. roseum and F. gummosa, mean mortality rate of protoscoleces was 100%. However, beta-pinene and citronellol at the same time point with only 10 mug/mL concentrations resulted in approximately higher than 80% mortality. Essential oils of P. roseum and F. gummosa showed significant toxic effect on E. granulosus with 50% lethal concentration (LC50) values of 8.52 and 17.18 mug/mL, respectively. Based on the LC50 values, beta-pinene (2.20 mug/mL) was the most potent scolicidal agent in the present study. The overall toxicity of beta-pinene and citronellol was significantly higher than the whole essential oils of F. gummosa and P. roseum. Based on these results, beta-pinene and citronellol can be considered as candidate ingredients for the development of green scolicidals.

The cytochrome P450 CYP6DE1 catalyzes the conversion of alpha-pinene into the mountain pine beetle aggregation pheromone trans-verbenol.[Pubmed:30728428]

Sci Rep. 2019 Feb 6;9(1):1477.

The recent outbreak of the mountain pine beetle (Dendroctonus ponderosae; MPB) has affected over 20 M hectares of pine forests in western North America. During the colonization of host trees, female MPB release the aggregation pheromone (-)-trans-verbenol. (-)-trans-Verbenol is thought to be produced from the pine defense compound (-)-alpha-pinene by cytochrome P450 (P450) dependent hydroxylation. MPB may also use P450s for the detoxification of other monoterpenes of the pine defense system. Here we describe the functional characterization of MPB CYP6DE1. CYP6DE1, but not the closely related CYP6DE2, used the bicyclic monoterpenes (-)-alpha-pinene, (+)-alpha-pinene, (-)-beta-Pinene, (+)-beta-pinene and (+)-3-carene as substrates. CYP6DE1 was not active with other monoterpenes or diterpene resin acids that were tested as substrates. trans-Verbenol is the major product of CYP6DE1 activity with (-)-alpha-pinene or (+)-alpha-pinene as substrates. When tested with blends of different ratios of (-)-alpha-pinene and (+)-alpha-pinene, CYP6DE1 produced trans-verbenol with an enantiomeric profile that was similar to that produced by female MPB exposed to the alpha-pinene enantiomers.

Effects of Pistacia atlantica on Oxidative Stress Markers and Antioxidant Enzymes Expression in Diabetic Rats.[Pubmed:30716018]

J Am Coll Nutr. 2019 Mar-Apr;38(3):267-274.

INTRODUCTION: Diabetes mellitus (DM) affects many patients all over the world. It involves different parts of the body, such as brain, eyes, kidneys, vessels, and so on. The lack of balance between free radicals and antioxidants is a possible mechanism involved in the pathogenesis of diabetes. Antioxidant treatment, especially natural forms, can be a beneficial solution. Therefore, we evaluated the effects of Pistacia atlantica oleoresin (PAO) on oxidative stress markers and antioxidant enzymes expression in diabetic rats. METHOD: Fifty adult male Wistar rats were allotted randomly into five groups as follow: control group, diabetic control group, glibenclamide control group, diabetic glibenclamide group, diabetic treated group with 200 mg/kg PAO. Then PAO was prepared and analyzed by gas chromatography/mass spectroscopy (GC/MS). LD50 was also estimated for essential oil. Oxidative stress markers and antioxidant enzyme including malondialdehyde (MDA), glutathione (GSH), glutathione peroxidase (GPx), catalase (CAT), and superoxide dismutase (SOD) were also measured. The expression of GPx, CAT, and SOD genes was investigated using real-time polymerase chain reaction (PCR). RESULTS: The main constituents of essential oil gum were beta-pinene (29.38%), followed by alpha-pinene (18.15%), myrcene (7.36%), trans-pinocarveol (7.15%), and camphene (4.12%). Diabetes induced an increased level of MDA (69.92 +/- 3.92 vs. 43.76 +/- 3.73) and decreased levels of GSH (2.57 +/- 0.40 vs. 7.05 +/- 1.59), GPx (11.66 +/- 2.2 vs. 16.38 +/- 2.1), CAT (12.17 +/- 3.38 vs. 18.7 +/- 2.66), and SOD (0.78 +/- 0.67 vs. 2.41 +/- 0.46). In contrast, PAO treatment significantly decreased MDA (54.59 +/- 12.54 vs. 69.92 +/- 3.92) and increased GSH (4.5 +/- 0.89 vs. 2.57 +/- 0.40), GPx (25.86 +/- 5.37 vs. 11.66 +/- 2.2), CAT (22.69 +/- 0.36 vs. 12.17 +/- 3.38), and SOD (3.65 +/- 1.08 vs. 0.78 +/- 0.67) (p < 0.05). Moreover, our results indicated that both GPx and CAT mRNA levels significantly increased approximately 4.46 and 6.23 times in rats fed with 200 mg/kg of PAO, more than that of the healthy control group, respectively (p < 0.01 and p < 0.001, respectively). Also, the average expression level of SOD was also significantly 1.57 higher in rats fed with 200 mg/kg of PAO in comparison to the diabetic control group (p < 0.05). CONCLUSION: The results indicated that PAO could be propose as an agent that protects the body against diseases that are associated with oxidative stress.

β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity.

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