Search

Indian meal moth, Plodia interpunctella (Lepidoptera: Pyralidae), is a worldwide omnivorous pest. It is the primary insect pest in many economically important stored crops. The insecticidal activity of essential oils (EOs) extracted from Ajania potaninii and Ajania fruticulosa were evaluated against Plodia interpunctella. EOs obtained by hydro-distillation were analyzed by GC–MS. Fumigant toxicity testing indicated that both EOs and their main components were toxic to P. interpunctella adults. 1,8-Cineole exhibited the strongest activity, having an LC50 of 0.86 mg/L air and being twice as active as camphor. Myrtenol was also strongly toxic to P. interpunctella adults (LC50 0.99 mg/L air), while camphor, verbenol, borneol, and the two complete EOs exhibited lower toxicity. None of the EOs or main components exhibited significant toxicity against the larvae of P. interpunctella. This study provides evidence of the individual active substances accounting for the insecticidal activity of EOs from A. potaninii and A. fruticulosa. These EOs have potential as biological insecticides for controlling insect pest damage in stored crops.

Acinetobacter baumannii (AB) is rising as a human pathogen of critical priority worldwide as it is the leading cause of chronic opportunistic infections in healthcare settings and the condition is ineradicable with antibiotic therapy. AB possesses the ability to form biofilm on abiotic as well as biotic surfaces which plays a major role in its pathogenesis and resistance in clinical settings. Hence, the demand for an alternative therapy to combat the biofilm-associated infections is increasing. The present study explored the antibiofilm potential of myrtenol, a bicyclic monoterpene present in various plants against reference and clinical strains of AB. Myrtenol (200 μg/mL) exhibited a strong antibiofilm activity without exerting any harmful effect on growth and metabolic viability of AB strains. Microscopic analyses confirmed the reduction in the biofilm thickness and surface coverage upon myrtenol treatment. Especially, myrtenol was found to be effective in disrupting the mature biofilms of tested AB strains. Furthermore, myrtenol inhibited the biofilm-associated virulence factors of AB strains such as extracellular polysaccharide, cell surface hydrophobicity, oxidant resistance, swarming and twitching motility. Transcriptional analysis unveiled the suppression of the biofilm-associated genes such as bfmR, csuA/B, bap, ompA, pgaA, pgaC, and katE by myrtenol. Notably, myrtenol improved the susceptibility of AB strains towards conventional antibiotics such as amikacin, ciprofloxacin, gentamicin and trimethoprim. Thus, the present study demonstrates the therapeutic potential of myrtenol against biofilm-associated infections of AB.

This article describes the design and biological properties of a BODIPY FL-labeled monoterpenoid BF2-meso-(4-((1″R)-6″,6″-dimethylbicyclo[3.1.1]hept-2″-ene-2″)yl-methoxycarbonylpropyl)-3,3′,5,5′-te...

The search for renewable fuels or components which may improve or replace fossil fuels is an important step towards a sustainable future. In particular, the pine oleoresin produced by conifer trees, which is composed by turpentine oil and non-volatile rosin, may be transformed into alternative fuels. In this work, combustion of six molecules which can be obtained from oleoresin either by distillation (i.e., α- and β-pinene) or by further oxyfunctionalization (nopol, terpineol, myrtenol, and borneol) was studied to assess the potential of pine oleoresin as raw material for biofuels. Emission indices of the main pollutants (carbon monoxide-CO, unburned hydrocarbons-UHC, and nitrogen oxides-NOx) were obtained in non-premixed co-flow laminar flames of the oleoresin-derived molecules blended with n-heptane. The main characteristics of the flames (i.e., temperature and height) were also determined. Significant increase in flame temperature and reduction in CO and UHC emissions with respect to n-heptane were observed with nopol, terpineol, and myrtenol, along an increase in NOx emissions, suggesting an improvement in combustion performance. In addition, differences in emission indices, evidenced for these molecules (even between α- and β-pinene), suggest the importance of the molecular structure in the combustion reaction.

In this study, a gas chromatography-type electronic nose (GC E-nose) was used to identify the chemical components of blue ginger (Dichorisandra thyrsiflora) essential oil (DTEO) and to rapidly screen the antioxidant and radical scavenging activities of these components through combined with the chemical methodology. The results showed that most of the compounds in DTEO had certain scavenging abilities to 1,1-diphenyl-2- picrylhydrazine (DPPH), 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonate) (ABTS) and hydroxyl (OH) radicals, but the radical scavenging abilities were quite different. α-Terpineol, eucalyptol, β-elemene, and epicurzerenone showed the strongest DPPH radical scavenging abilities and scavenging rates were 82.5%, 81.4%, 72.4%, and 60.4%, respectively. Eucalyptol, 2-nonanol, myrtenol, and α-terpineol showed the strongest ABTS radical scavenging abilities and scavenging rates were 82.9%, 81.7%, 81.7%, and 78.6%, respectively. Myrtenol and camphor showed the strongest OH radical scavenging abilities and scavenging rates were 55.0% and 53.2%, respectively. Furthermore, the mechanisms of radical scavenging and the structure-activity relationship between the structure and radical scavenging activity were elucidated.

The reaction mechanism of the isomerization of α and β-pinene epoxides with Fe species as catalysts was studied with density functional theory (DFT) calculations and an experimental methodology. β-pinene epoxide can be isomerized into myrtanal and myrtenol in four steps, while in the case of perillyl alcohol, two additional steps are necessary. On the other hand, high selectivity to myrtanal obtained experimentally can be explained by the number of steps and the kind of the hydrogen transference that is easier for this compound in comparison with myrtenol and perillyl alcohol. A thermodynamic analysis showed that transformation into myrtenol, myrtanal, and perillyl alcohol is spontaneous but transformation into myrtanal is the most favorable. In the case of α-pinene epoxide rearrangement, a mechanistic study was carried out toward the optimization of the possible intermediates. Synthesis of campholenic aldehyde and carveol from α-pinene epoxide was carried out through three steps after the coordination of oxygen to iron, showing that in contrast to carveol formation, campholenic aldehyde synthesis is spontaneous. Analysis of ∇2ρ, the total energy density (H = V + G), and the |V|/G ratio evaluated at the bond critical point of the Fe-O bond showed for both epoxides that such interaction is closed shell instead of covalent. Apparently, α-pinene epoxide can be isomerized faster that β-pinene epoxide with Fe3+, which is in agreement with previous experimental results. This is the first report where a reaction mechanism of isomerization of monoterpenes epoxides is studied based on very detailed experimental and computational methodologies.

A natural zeolite presents in rocks of volcanic origin located in Colombia was characterized and tested for the isomerization of β-pinene epoxide. The material was characterized by TPD-NH3, BET, SEM, FRX, FTIR of adsorption-desorption of pyridine, TPD-CO2 and TPR-H2. It was found that 65% of the acidity was strong and 75% was Lewis type; the material also had strong basicity (57%), and a surface area of 34.9 m2 g−1. The effect of different parameters such as kind of solvent (ethanol, THF, dioxane, acetone and toluene), concentration of catalyst, temperature and time on catalysts activity was evaluated in the ring-opening reaction of β-pinene epoxide. The maximum conversion (97%), selectivities to perillyl alcohol (47%), myrtanal (23%) and myrtenol (12%) were obtained with toluene (70 °C, 2.5 h). A reaction mechanism was proposed based on the experimental and theoretical results for explaining the formation of the products synthetized from the catalytic reaction over Bronsted and Lewis acid sites. The catalyst was reused five times without apparent loss of conversion, but with a slight decreasing of selectivity to perillyl alcohol and increase of selectivity to myrtanal and myrtenol.

Cyclic oxyterpenes are natural products that are mostly used as fragrances, flavours and drugs by the cosmetic, food and pharmaceutical industries. However, only a few cyclic oxyterpenes are accessible via chemical syntheses, which are far from being ecofriendly. We report here the synthesis of six cyclic oxyterpenes derived from ß-pinene while respecting the principles of green and sustainable chemistry. Only natural or biosourced catalysts were used in mild conditions that were optimised for each synthesis. A new generation of ecocatalysts, derived from Mn-rich water lettuce, was prepared via green processes, characterised by MP-AES, XRPD and TEM analyses, and tested in catalysis. The epoxidation of ß-pinene led to the platform molecule, ß-pinene oxide, with a good yield, illustrating the efficacy of the new generation of ecocatalysts. The opening ß-pinene oxide was investigated in green conditions and led to new and regioselective syntheses of myrtenol, 7-hydroxy-α-terpineol and perillyl alcohol. Successive oxidations of perillyl alcohol could be performed using no hazardous oxidant and were controlled using the new generation of ecocatalysts generating perillaldehyde and cuminaldehyde.

The aim of this study was to examine the effects of (-)-myrtenol alone and combined with antifungal agents against Candida spp. The Minimum Inhibitory Concentration (MIC) and Minimum Fungicidal Concentration of (-)-myrtenol and fluconazole against C. albicans and C. parapsilosis strains was obtained using CLSI guidelines. Combination of (-)-myrtenol with antifungal drugs was determined by checkboard test. The (-) myrtenol showed MIC ranging from 256 to 512 µg/mL against both species assay. And the MFC was 512 µg/mL, demonstrated nature fungicidal (MFC/MIC < 4). In addition, combination of antifungal agents (amphotericin B and fluconazole) and (-) myrtenol showed synergistic and additive effects on strains assays. Based on these results, the present study demonstrates that (-) myrtenol showed strong fungicide activity against Candida spp. In addition, Combination of antifungal agents and (-) myrtenol reduces the effective concentrations of both the agents with synergistic to additive effects. Therefore, (-) myrtenol has potential to be developed into an antifungal agent. El objetivo de este estudio fue analizar los efectos del (-) - myrtenol solo y combinado con agentes antifúngicos contra Candida spp. La Concentración Inhibitoria Mínima (MIC) y la Concentración Fungicida Mínima de (-) - myrtenol y fluconazol contra cepas de C. albicans y C. parapsilosis se obtuvieron utilizando las pautas de CLSI. La combinación de (-) - myrtenol con fármacos antimicóticos se determinó mediante la prueba del tablero de ajedrez. El (-) myrtenol mostró una CIM que varió de 256 a 512 µg / mL contra ambas especies. Y la MFC fue de 512 µg / mL, demostró naturaleza fungicida (MFC / MIC

Gestational diabetes mellitus (GDM) is a special kind of diabetes that arises only during pregnancy. A woman with GDM has a higher risk of developing type-2 diabetes and other metabolic diseases. In this exploration, we intended to scrutinize the therapeutic actions of Myrtenol against the streptozotocin (STZ)-provoked GDM in rats. GDM was provoked in the pregnant rats via injecting the 1% of STZ (25 mg/kg) and then treated with the 50 mg/kg of myrtenol. The glucose level and bodyweight of animals were noted. The lipid profile, that is, total cholesterol, triglycerides, low-density lipoprotein, and high-density lipoprotein (HDL) was determined by respective kits. The lipid peroxidation and antioxidants status were examined using assay kits. The status of proinflammatory markers was investigated by assay kits. The messenger RNA (mRNA) expressions of TLR4/MyD88/NF-κB signaling proteins were studied by reverse transcription polymerase chain reaction analysis. The hepatic and pancreatic tissues were examined microscopically. Myrtenol treatment notably decreased the status of blood glucose and lipid profile and improved the HDL in the GDM rats. The status of lipid peroxidation and inflammatory markers were substantially reduced by the myrtenol and it enhanced the antioxidants status of GDM animals. Myrtenol treatment remarkably downregulated the mRNA expressions of TLR4/MyD88/NF-κB signaling proteins. The histological findings also proved the therapeutic actions of myrtenol. Altogether, the findings of this investigation unveiled the therapeutic actions of the myrtenol against the STZ-provoked GDM in rats. Myrtenol could be a promising therapeutic agent to treat GDM in the future.

The spotted wing drosophila, Drosophila suzukii, is an invasive pest species from Southeast Asia that was recently introduced in Europe and North America. As this fruit fly lays its eggs in ripening soft-skinned fruit, it causes great damage to a variety of crops, including cherries, blueberries, blackberries, raspberries, grapes, plums and strawberries. Consequently, there is a great demand for an effective and species-specific lure, which requires the development of successful attractants. Until now, there is no lure available that is species-specific and can detect the presence of D. suzukii before infestation. As blackberry (Rubus fruticosus) is one of the preferred host crops of D. suzukii, the volatile compounds of R. fruticosus berries are here identified and quantified using multiple headspace SPME (solid phase micro extraction) GC-MS (gas chromatography–mass spectrometry). Subsequently, the attractivity of 33 of the identified compounds was tested with a two-choice laboratory bioassay. Acetaldehyde, hexyl acetate, linalool, myrtenol, L-limonene and camphene came out as significantly attractive to D. suzukii. The first four attractive compounds induced the strongest effect and therefore provided the best prospects to be implemented in a potential lure. These findings could contribute towards the development of more effective attractants for monitoring and mass trapping D. suzukii. ispartof: Insects vol:12 issue:5 ispartof: location:Switzerland status: published

The chemical profile, antiproliferative, antioxidant and antiphytoviral activities of the species Hypericum perforatum ssp. veronense (Schrank) H. Lindb. (Clusiaceae) were investigated. Free volatiles were isolated and the chemical composition was determined in the lipophilic fraction (essential oil) and for the first time in the water fraction (hydrosol). The aim is to provide phytochemical data for H. perforatum ssp. veronense useful for distinguishing ssp. veronense from ssp. angustifolium, as there are taxonomic disagreements between them and the composition of the secretory products may be helpful in this respect. In the essential oil, the most abundant compounds identified were α-pinene and n-nonane, while in the hydrosol, myrtenol, carvacrol and α-pinene were the most abundant. Overall, the class of monoterpenes and oxygenated monoterpenes dominated in the EO and hydrosol samples. The essential oil showed high antioxidant activity, in contrast to the antiproliferative activity, where the hydrosol showed exceptional activity against three cancer cell lines: Hela (cervical cancer cell line), HCT116 (human colon cancer cell line) and U2OS (human osteosarcoma cell line). Both the essential oil and hydrosol showed antiphytoviral activity against tobacco mosaic virus infection on the local host plants. This is the first report dealing with biological activities of hydrosol of H. perforatum ssp. veronense, and the obtained results suggest that this traditional medicinal plant is a valuable source of volatiles with promising antiproliferative, antioxidant and antiphytoviral activities.

Made available in DSpace on 2021-06-25T10:29:32Z (GMT). No. of bitstreams: 0 Previous issue date: 2021-04-16 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Lippia alba (Mill.) N. E. Br. (Verbenaceae) is an aromatic shrub whose essential oils have stood out as a promising source for application in several industrial fields. In this study, the essential oils chemical characterization of eight new L. alba genotypes was performed. The selected materials were collected from the Active Germplasm Bank of the Agronomic Institute and the essential oils were extracted by hydrodistillation. Flow-modulated comprehensive two-dimensional gas chromatography coupled to mass spectrometry (GC×GC-MS) was employed for chemical characterization and evaluation of possible co-eluted compounds. In addition, the chemical analyses were submitted to multivariate statistical analyses. From this investigation, 73 metabolites were identified in the essential oils of the genotypes, from which α-pinene, β-myrcene, 1,8-cineole, linalool, neral, geranial, and caryophyllene oxide were the most abundant compounds among the accessions. This is the first report disclosing α-pinene in higher amounts in L. alba (19.69%). In addition, sabinene, trans-verbenol, myrtenol, (E)-caryophyllene, α-guaiene, germacrene D, and α-bulnesene were also found in relevant quantities in some of the genotypes, and myrtenal and myrtenol could be well separated through the second dimension. Such results contributed to the understanding of the chemical composition of those new genotypes, being important to drive a future industrial applicability and studies in genetic breeding. Vegetable Genetic Resources Center Agronomic Institute School of Agriculture São Paulo State University (Unesp) Institute of Chemistry University of Campinas (Unicamp) School of Agriculture São Paulo State University (Unesp) FAPESP: 2018/26066-1

One-pot bio-based myrtenol amination was studied in the presence of alumina supported Au, Au–Pd and Pd nanoparticles subjected to the thermal treatment under oxidizing or reducing atmosphere. Myrtenol amination with aniline was carried out under nitrogen atmosphere (9 bar) at 453 K using toluene as a solvent. The effect of the active metal along with the influence of redox pre-treatment on the catalytic behavior in the hydrogen borrowing reaction was explored. The catalyst characterization was done by transmission electron microscopy, X-ray photoelectron spectroscopy, inductively coupled plasma optical emission spectroscopy, nitrogen adsorption. The active metal and the catalysts redox pretreatment affected more noticeably selectivity to the reaction products rather than myrtenol conversion. Monometallic Au/Al2O3 catalyst promoted predominantly formation of the target secondary amine and the corresponding imine without a significant impact of the side reaction of C=C bond hydrogenation in myrtenol, whereas monometallic Pd catalyst activated C=C bond resulting in its hydrogenation. At the same time in the presence of Au–Pd simultaneous hydrogenation of both C=C and C=N bond occurred. Au–Pd catalysts activated in oxygen and hydrogen showed different catalytic activity determined by the composition of surface active sites. Monometallic gold catalyst was more effective in the hydrogen transfer in the case of substrates with competitive unsaturated functional groups.

The detailed molecular composition of laboratory-generated secondary organic aerosols (SOA) during the high-NO photooxidation of β-pinene (βP) was investigated using a novel thermal desorption dichloromethane-assisted low-pressure photoionization mass spectrometry (TD-CH2Cl2-assisted LPPI-MS) technique. We found that protonated norpinone gave the highest signal intensity, which supported that assumption that this compound was the key oxidation species responsible for promoting βP-SOA formation. In addition to the previously identified monomers (i.e., 2,2-dimethylcyclobutyl-1,3-dicarboxaldehyde (m/z 140), pinene aldehyde (m/z 150), myrtenol (m/z 152), (2,2-dimethyl-3-acetyl)-cyclobutylformate (m/z 156), pinene acid (m/z 166), and isomers of pinalic-3-acid (m/z 170)), two additional nitrogen-containing species (i.e., C10 hydroxy nitrate and C10 carbonyl nitrate) were also observed at m/z values of 214 and 216 in the mass spectrum of βP-SOA. Furthermore, the losses of 18 (H2O), 46 (NO2), and 64 (H2O + NO2) were attributed to the typical fragmentation pathways of the two nitrogen-containing species. Overall, these results not only contribute to an improved understanding of βP-SOA formation, but they also indicate that TD-CH2Cl2-assisted LPPI-MS can be used as a novel detection means to study SOA formation.

The gastroprotective property of (−)-myrtenol, a monoterpenoid, has been demonstrated previously against acute gastric ulceration induced by ethanol. However, the healing property of (−)-myrtenol in a chronic gastric ulcer model remains to be verified. This study evaluated its healing efficacy and the mechanism involved using the rat model of chronic gastric ulcer induced by serosal injection of 80% acetic acid in vivo, and human gastric adenocarcinoma cells (AGS) in vitro. The results showed that compared to vehicle-treated ulcer controls, oral administration of (−)-myrtenol (50 and 100 mg/kg/day) for 7 days promoted ulcer healing, as indicated by significant decreases in ulcer area and volume. The macroscopic and microscopic findings confirmed the healing potential of (−)-myrtenol. The ulcer healing activity was also associated with significant increases in gastric mucin content, collagen deposition, number of cells with positive marking for proliferating cell nuclear antigen (PCNA), and by changes in the expression of the inflammatory parameters tumor necrosis factor (TNF)-α, interleukin (IL)-1β and cyclooxygenase (COX)-2, as well as a decrease of metalloproteinases (MMP-9 and MMP-2) activity. Furthermore, in vitro assays using the AGS cultures revealed that (−)-myrtenol favors wound healing activity via stimulation of cell proliferation and migration without altering the cell viability. Taken together, these findings indicate that (−)-myrtenol has gastro-cytoprotective and ulcer healing properties that can be further explored to develop a new therapeutic agent from a natural source for the treatment of gastric ulcer.

Aroma is one of the most important aspects to determine the wine quality and its market value. Changes of volatile profiles and terpenoid precursors were monitored for blueberry wines made from two different southern high bush cultivars (Misty and O'Neal) during the alcoholic fermentation using solid phase microextraction-gas chromatography-quadrupole time of flight-mass spectrometry (SPME-GC-QTOF-MS). Volatile profile of the wine significantly changed as a function of time during fermentation, which was due to the gradual reduction of C6 compounds, extraction and hydrolysis of terpenoids precursors, and generation of esters and alcohols. Misty samples contained higher amount of terpenoids compared to the O'Neal samples during the whole fermentation process. E-asarone and methyl isoeugenol were only detected in O'Neal samples. Myrtenol, E-carveol and borneol were presented mainly as bound form, while other terpenoids mainly as free form in the final wines, indicating the different resistance of the glycoside to acid hydrolysis during fermentation.

The hydroformylation of the naturally occurring hydroxyolefins (1R)-(–)-myrtenol (1) and (1R)-(–)-nopol (2) was performed employing a rhodium(I)/bulky phosphite catalytic system. Both substrates demonstrated to be quite reluctant to hydroformylation and revealed a strong tendency to form isomeric saturated aldehydes under hydroformylation conditions. In spite of these challenges, catalytic systems and conditions were found to allow the synthesis of corresponding hydroxyaldehydes. The products, either isolated or as a mixture, presented a pleasant smell and are potentially useful as fragrances. In addition, it was possible to perform the reactions in eco-friendly solvents.

In the current work gold catalysts supported on both commercial oxides and oxides synthesized by the sol-gel method were used for the one-pot alcohol amination of myrtenol. In general, utilization of metal oxides synthesized by the sol-gel method as the gold catalyst support enhanced the knowledge regarding key parameters determining catalytic behavior. Synthesized alumina was characterized by stronger acid sites favoring primary amine accumulation on the catalyst surface, as compared to the commercial oxide. Utilization of mixed metal oxides synthesized by the sol-gel method resulted in the non-additive behavior of different oxides enhancing the catalytic activity. Introduction of ceria into alumina modified the support basicity resulting in more efficient alcohol activation.

A library of pinane-based 2-amino-1,3-diols, analogues of biologically active sphingosine, was synthesised in a stereoselective manner. Isopinocarveol prepared from (–)-α-pinene was converted to condensed oxazolidin-2-one in two steps by carbamate formation followed by a stereoselective aminohydroxylation process. The relative stereochemistry of the pinane-fused oxazolidin-2-one was determined by 2D NMR and X-ray technics. The regioisomeric spiro-oxazolidin-2-one was prepared in a similar way starting from commercially available (1R)-(–)-myrtenol. Reduction or alkaline hydrolysis of oxazolidines followed by reductive alkylation resulted in primary and secondary 2-amino-1,3-diols, which underwent regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3.

In recent years, there has been a growing interest in the screening of natural active ingredients from Eucalyptus essential oils because of their evident importance in practical utility and their undeniable therapeutic properties. Based on this, the aim of the present study was to investigate the chemical profile of the essential oils of the trunk bark of Eucalyptus torquata Luehm. (ETEO), and E. salmonophloia F. Muell. (ESEO), growing in Tunisia. The in vitro cytotoxic properties of the extracted EOs were also evaluated against two human cancer cell lines: breast carcinoma cell lines MDA-MB-231 and colorectal cancer cell lines SW620. The analysis by gas chromatography coupled with mass spectrometry (GC/MS) led to the identification of 32 compounds from the ETEO, with the dominant constituents being the monoterpenes trans-myrtanol (73.4 %) and myrtenol (4.7 %), and the apocarotene (E)-β-ionone (3.9 %). In the case of ESEO, 29 compounds were identified with trans-myrtanol (25.0 %), decanoic acid (22.1 %), nonanoic acid (9.8 %), γ-elemene (6.5 %), γ-maaliene (5.5 %), and α-terpineol (5.3 %) as the main components. The cytotoxicity of EOs against the two chosen cell lines was tested using Crystal Violet Staining (CVS) assay and 5-fluorouracil as a reference drug. The two EOs exhibited a significant dose-dependent inhibition against the viability of the used cell lines. Their inhibitory effects were particularly observed towards SW620 colon carcinoma cells with IC50 values of 26.71±1.22 and 22.21±0.85 μg/mL, respectively, indicating that both oils were more cytotoxic for SW620 cells compared to MDA-MB-231 one.

The present study aimed to experimentally identify the essential oil of Algerian Cyperus rotundus L. and to model the interaction of some known anti-inflammatory molecules with two key enzymes involved in inflammation, 5-Lypoxygenase (5-LO) and leukotriene A4 hydrolase (LTA4H). Gas chromatography/gas chromatography–mass spectrometry (GC/GC-MS) revealed that 92.7% of the essential oil contains 35 compounds, including oxygenated sesquiterpenes (44.2%), oxygenated monoterpenes (30.2%), monoterpene hydrocarbons (11.8%) and sesquiterpene hydrocarbons (6.5%). The major identified oxygenated terpenes are humulene oxide II, caryophyllene oxide, khusinol, agarospirol, spathulinol and trans-pinocarveol Myrtenol and α-terpineol are known to exhibit anti-inflammatory activities. Several complexes obtained after docking the natural terpenes with 5-LO and LTA4H have shown strong hydrogen bonding interactions. The best docking energies were found with α-terpineol, Myrtenol and khusinol. The interaction between the natural products and amino-acid residues HIS367, ILE673 and GLN363 appears to be critical for 5-LO inhibition, while the interaction with residues GLU271, HIS295, TYR383, TYR378, GLU318, GLU296 and ASP375 is critical for LTA4H inhibition. Molecular dynamics (MD) trajectories of the selected docked complexes showed stable backbone root mean square deviation (RMSD), supporting the stability of the natural product–enzyme interaction. Communicated by Ramaswamy H. Sarma

The increase in Staphylococcus aureus resistance to conventional antibacterials and persistent infections related to biofilms, as well as the low availability of new antibacterial drugs, has made the development of new therapeutic alternatives necessary. Medicinal plants are one of the main sources of bioactive molecules and myrtenol is a natural product with several biological activities, although its antimicrobial activity is little explored. Based on this, the objective of this study was to evaluate the antibacterial activity of myrtenol against S. aureus, determining the minimum inhibitory and bactericidal concentrations (MIC and MBC), investigating the possible molecular target through the analysis of molecular docking. It also aimed to evaluate the effect of its combination with antibacterial drugs and its activity against S. aureus biofilms, in addition to performing an in silico analysis of its pharmacokinetic parameters. Myrtenol showed MIC and MBC of 128 &micro, g/mL (bactericidal action) and probably acts by interfering with the synthesis of the bacterial cell wall. The effects of the association with antibacterials demonstrate favorable results. Myrtenol has remarkable antibiofilm activity and in silico results indicate a good pharmacokinetic profile, which make myrtenol a potential drug candidate for the treatment of infections caused by S. aureus.

Myrtenol has gained wide interest because of its pharmacological profiles, mainly for treatment of chronic diseases. To improve the solubility of myrtenol, the formation of inclusion complexes with β-cyclodextrin was performed by physical mixture, kneading process or slurry complexation (SC) methods and characterized using thermal analysis, XRD, SEM and NMR. From these results, myrtenol complexed by SC was successfully complexed into β-cyclodextrin cavity. The interaction between myrtenol and β-cyclodextrin was confirmed by molecular docking. Hence, the SC β-cyclodextrin-myrtenol complex was evaluate for its anti-hyperalgesic, anxiolytic and antioxidant activity in a fibromyalgia model. Results show that myrtenol and β-cyclodextrin form a stable complex and have anti-hyperalgesic effect, improve the cognitive impairment caused and have an anxiolytic-like effect. Furthermore, the β-cyclodextrin/myrtenol complex decrease lipoperoxidation, increased catalase activity and a reduce SOD/CAT ratio. Therefore, β-cyclodextrin/myrtenol complex reduce painful behavior, improves motor skills and emotional behavior and decreases oxidative stress in a fibromyalgia model.

Tetra-substituted zinc(II) and copper(II) phthalocyanines bearing peripheral alkoxy-monoterpene groups were prepared by conventional vs. non-conventional synthetic approaches (ultrasound and microwave irradiation). The synthesis of (1[Formula: see text]-(–)-myrtenol (a) and (1[Formula: see text],2[Formula: see text],5[Formula: see text]-([Formula: see text]-menthol (b) derived phthalonitrile precursors was performed through ipso-nitro aromatic substitution reactions, with optimal conditions being obtained using ultrasound irradiation, which allowed us to achieve full conversions in 4.5 h, with isolated yields up to 74%. The subsequent cyclotetramerization of monoterpene-based phthalonitriles was carried out using Zn(II) or Cu(II) salts as metal templates, and also using conventional and non-conventional heating methods. Microwave-assisted synthesis was shown to be the most efficient approach, providing complete conversions in 1 h, yielding the target monoterpene-based metallophthalocyanines in up to 70% isolated yields. Furthermore, photophysical and photochemical studies revealed that Zn(II) phthalocyanines possess fluorescence quantum yields in the range of [Formula: see text] 0.27–0.29, while Cu(II) phthalocyanines exhibited room temperature phosphorescence. In addition, the monoterpene-based Zn(II) phthalocyanines led to high singlet oxygen quantum yields ([Formula: see text] 0.55–0.69).

One-pot amination of natural monoterpene alcohols was studied over Au/ZrO2 catalyst, focusing on the structure effect of substrates selected based on their pharmaceutical relevance. Bicyclic (myrtenol and nopol, bearing an unconjugated –OH group) and monocyclic (perillyl) alcohols were chosen for aniline amination under comparable conditions. Utilization of nopol resulted in a tenfold decrease in the reaction rate from that for myrtenol, increasing selectivity to the amine. The influence of secondary transformation was more noticeable for monocyclic perillyl alcohol with a conjugated –OH group. Myrtenol amination was explored with a range of aliphatic and aromatic amines, showing that the primary amine structure affected both the initial dehydrogenation rate and the selectivity to the desired amine. A good correlation was found between substrate structure and reactivity using the Hammett equation. The myrtenol consumption rate was tentatively proposed to be affected by the Auδ+ availability required for alcohol dehydrogenation. Propanol-2, introduced as a hydrogen donor, improved the yield of the target amine.

Myrtenol is a bicyclic monoterpene with anti-in fl ammatory properties. However, the mechanisms involved are partially unknown. Here, we investigated the effect of myrtenol during experimental chronic arthritis and the possible modulating activity of oxidative stress and neutrophil migration. Complete Freund's Adjuvant (CFA)-sensitized rats were treated with vehicle (1 mL/kg, po), myrtenol (12.5, 25 or 50 mg/kg, po), indomethacin (10 mg/kg, po) or dexamethasone (0.4 mg/kg) followed by intra-articular injection of CFA (0.5 mg/mL, 50 m L per joint). Then, paw edema and articular incapaci- tation (paw elevation time) were evaluated for 14 days. On the last day, a blood concentration superoxide dismutase (SOD) and nitrite was determined. In another experimental setting, human neutrophils were incubated with vehicle (sterile saline, 1 mL) or myrtenol (10 e 100 ng/mL) and the in vitro chemotaxis to N-formylmethionine-leucyl-phenylalanine (fMLP) (10 7 M/well) was evaluated. In addition, antiin- fl ammatory effect of myrtenol was investigated in carrageenan-induced peritonitis. We found that CFA induced a prominent paw swelling and incapacitation of the joint, which were signi fi cantly prevented by myrtenol ( P < 0.05). In addition, blood accumulation nitrite was attenuated by myrtenol when compared with vehicle-treated CFA group ( P < 0.05). Furthermore, plasma levels of SOD were signi fi cantly increased by myrtenol versus vehicle-treated CFA group ( P < 0.05). Moreover, fMLP-triggered neutrophil chemotaxis and carrageenan-induced peritonitis were markedly prevented by myrtenol ( P < 0.05). Therefore, myrtenol showed anti-in fl ammatory and antinociceptive effects on experimental chronic arthritis, which seems to be related to the direct modulation of neutrophil migration and antioxidant activity

The family of succulent plants, Crassulaceae, is known for many benefits, as well for the limited distribution of aromatic representatives. It is also observed the deficiency of data on content and distribution of volatile compounds within the genus Hylotelephium. Accordingly, this is the first report on volatiles from roots of three Hylotelephium taxa: H. telephium, H. maximum and H. spectabile x telephium. Two types of volatiles were isolated: headspace (HS) volatiles and solvent extract volatiles from the distillation water (SE), further analyzed by GC–MS/FID. The obtained results contribute to the knowledge that some of the genera of Crassulaceae family “hides” unexplored sources of aromaticity and fragrance. All three SEs are characterized by low yields and the high content of monoterpene alcohol – myrtenol. The differences are mostly reflected in content of some myrtenol analogs (cis-myrtanol, trans-myrtanol and myrtenoic acid) and aliphatic alcohol oct-1-en-3-ol. HS volatiles of H. telephium and H. spectabile x telephium contain myrtenol and oct-1-en-3-ol, while H. maximum beside them contain 3-octanol in significant amount. Additionally, characteristic distribution pattern of the SE volatiles could be used for chemotaxonomic purposes, while the distribution pattern of HS volatiles is practically inapplicable in that manner. Due to high content of myrtenol in root volatiles, it could be used in traditional medicine, as supplement, flavouring or aroma agent.

The one-pot myrtenol amination with aniline was performed over Au (3 wt.%)/ZrO2 catalyst using methanol, 2-propanol or formic acid as hydrogen donors with the aim to enhance the target amine yield. It was found that addition of small amounts of 2-propanol or formic acid (additive/myrtenol ratio equals to 0.5 and 0.25, respectively) led to the increase of the target amine yield up to 68 and 65%, respectively, compared with 52% amine yield in the absence of additives. However, further increase of additive amount decreased amine formation: 2-propanol interacted with aniline competing with myrtenol; formic acid introduction into the reaction mixture suppressed activity of Au/ZrO2 catalyst due to strong adsorption of formic acid and decomposition products on the support basic sites strongly required for the initial alcohol activation. Methanol was found not to be effective as a hydrogen donor for one-pot alcohol amination.

The one-pot myrtenol amination was studied over Au (3 wt.%)/ZrO2 catalyst under mixed N2/H2 atmosphere (9 bar). The effect of hydrogen addition was explored with the aim to increase selectivity to the target amines. Hydrogen addition timing depending on myrtenol conversion and hydrogenation temperature affected selectivity to the reaction products. Hydrogen addition (1 bar) after almost complete myrtenol conversion at 100 °C increased the yield to amine up to 68% preserving C C bond in the initial myrtenol structure. Hydrogen addition at 180 °C irrespective of the myrtenol conversion level provoked reduction of both C C and C N bonds with formation of two diastereomers (yield up to 93%), with trans-isomer formation being preferred when hydrogen was added at almost complete myrtenol conversion. It was shown, that in the presence of a gold catalyst controlled hydrogenation of competitive C C and C N groups can be performed during one-pot alcohol amination by regulation of the reaction conditions.

The effect of the gold catalysts redox treatment on the formation of active catalysts for one-pot myrtenol amination with aniline was studied. A series of nanosized gold catalysts over metal oxides such as ZrO2, CeO2, La2O3 different in their basicity were synthesized by the deposition–precipitation method and characterized using TEM, XPS and TPR-, TPO-MS. One-pot myrtenol amination was carried out in a batch reactor at 180 °C under nitrogen pressure 9 bar. The catalytic activity and selectivity were shown to depend on the catalyst redox treatment. Pre-reduced gold catalysts supported on zirconium or cerium oxides were shown to be more effective in alcohol activation while once pre-oxidized catalysts promoted formation of the target amine with high selectivity. It was shown that thermal activation of catalysts in oxygen resulted in higher efficiency of ammonia removal compared to treatment in hydrogen. Difference in activity and selectivity for pre-reduced and pre-oxidized catalysts was proposed to be mainly related to the different degree of the support basic properties modification by residual ammonia.

Methicillin-resistant Staphylococcus aureus (MRSA) is a deleterious human pathogen responsible for severe morbidity and mortality worldwide. The pathogen has attained high priority in the World Health Organization (WHO) – Multidrug-resistant (MDR) pathogens list. Emerging MDR strains of S. aureus are clinically challenging due to failure in conventional antibiotic therapy. Biofilm formation is one of the underlying mechanisms behind the antibiotic resistance. Hence, attenuating biofilm formation has become an alternative strategy to control persistent infections. The current study is probably the first that focuses on the antibiofilm and antivirulence potential of myrtenol against MRSA and its clinical isolates. Myrtenol exhibited a concentration-dependent biofilm inhibition without causing any harmful effect on cell growth and viability. Further, microscopic analysis validated the biofilm inhibitory efficacy of myrtenol against MRSA. In addition, myrtenol inhibited the synthesis of major virulence factors including slime, lipase, α-hemolysin, staphyloxanthin and autolysin. Inhibition of staphyloxanthin in turn sensitized the MRSA cells to healthy human blood and hydrogen peroxide (H2O2). Notably, myrtenol treated cells were deficient in extracellular DNA (eDNA) mediated autoaggregation as eDNA releasing autolysis was impaired by myrtenol. Biofilm disruptive activity on preformed biofilms was observed at concentrations higher than minimum biofilm inhibitory concentration (MBIC) of myrtenol. Also, the non-cytotoxic effect of myrtenol on human peripheral blood mononuclear cell (PBMC) was evidenced by trypan blue and Alamar blue assays. Transcriptional analysis unveiled the down-regulation of global regulator sarA and sarA mediated virulence genes upon myrtenol treatment, which is well correlated with results of phenotypic assays. Thus, the results of the present study revealed the sarA mediated antibiofilm and antivirulence potential of myrtenol against MRSA.

Research Highlights: We found that the initial attack location together with the aggregation pheromones played an important role in mediating the aggressive behavior of T. brevipilosus on P. kesiya. Background and Objectives: T. brevipilosus was identified as an aggressive species, which possesses the ability to kill live, healthy P. kesiya. In this scenario, we study the top-down attack pattern of T. brevipilosus on P. kesiya during the entirety of the reproductive period. Materials and Methods: We investigated the phenology of trunk attack on P. kesiya over a period of three years in Pu&rsquo, er City, China. The hindguts extracts of the females and males T. brevipilosus were analyzed by coupled gas chromatography-mass spectrometry (GC-MS). The candidate aggregation pheromone compounds of T. brevipilosus were determined through electrophysiology experiments (electroantennographic detection, EAD and electroantennography, EAG), laboratory olfactometer bioassays, and field trapping. Results: we found that the pioneer beetles preferentially infested the crown of P. kesiya at the early stage of attack following spring flight with the later arriving beetles selectively attacking the lower area of the trunk to avoid intraspecific competition and better utilize limited resources, which exhibits a top-down attack pattern. During gallery initiation, the beetles release aggregation pheromones to attract conspecifics to conduct a mass attack. The chemical analyses indicated that the hindgut extracts of gallery-initiating beetles contained a larger amount of myrtenol, cis-verbenol, trans-verbenol, and verbenone. Myrtenol and trans-verbenol were identified as candidate aggregation pheromone compounds. In addition, a blend of these two components with S-(&minus, )-&alpha, pinene and S-(&minus, )-&beta, pinene attracted more T. brevipilosus individuals in a field bioassay. Conclusions: We concluded that the preference for the initial attack location together with the aggregation pheromones played an important role in mediating the top-down attack pattern of T. brevipilosus on P. kesiya.

Sideritis plants and their extracts have been used in traditional medicine as sedatives, anxiolytics and anticonvulsant agents. Pinenes are the most prevalent of the volatile aroma components in Siderites extracts and the pinene metabolites myrtenol and verbenol have been identified as the most potent positive allosteric modulators of synaptic GABAA receptors composed of α1β2 and α1β2γ2 subunits. In view of their therapeutic spectrum, we wondered whether these two terpenoids would also augment tonic GABA currents mediated by extrasynaptic GABAA receptors containing the δ subunit. When we expressed α4β2δ receptors in HEK293 cells, we found that co-application of myrtenol or verbenol enhanced whole-cell current responses to GABA by up to 100%. Consistent with their effects on heterologous α1β2γ2 receptors, we found that myrtenol and verbenol, when co-applied with GABA via local perfusion, increased the amplitude and area of miniature inhibitory postsynaptic potentials (mIPSCs) recorded in whole-cell voltage-clamp recordings from granule cells in the dentate gyrus of mouse hippocampal brain slices. In addition, co-application of terpenoids with GABA was also able to enhance tonic GABA current, measured from the change in baseline current and current noise, compared to GABA perfusion alone. Our results suggest that myrtenol and verbenol act as positive allosteric modulators at synaptic and extrasynaptic GABAA receptors, thereby augmenting phasic and tonic GABAergic inhibition. Thus, our study reveals an important pharmacological and therapeutic target of bicyclic monoterpenoids.

The insecticidal activity and chemical constituents of the essential oil from Ajania fruticulosa were investigated. Twelve constituents representing 91.0% of the essential oil were identified, and the main constituents were 1,8-cineole (41.40%), (+)-camphor (32.10%), and myrtenol (8.15%). The essential oil exhibited contact toxicity against Tribolium castaneum and Liposcelis bostrychophila adults with LD50 values of 105.67 μg/adult and 89.85 μg/cm(2) , respectively. The essential oil also showed fumigant toxicity against two species of insect with LC50 values of 11.52 and 0.65 mg/l, respectively. 1,8-Cineole exhibited excellent fumigant toxicity (LC50 = 5.47 mg/l) against T. castaneum. (+)-Camphor showed obvious fumigant toxicity (LC50 = 0.43 mg/l) against L. bostrychophila. Myrtenol showed contact toxicity (LD50 = 29.40 μg/cm(2) ) and fumigant toxicity (LC50 = 0.50 mg/l) against L. bostrychophila. 1,8-Cineole and (+)-camphor showed strong insecticidal activity to some important insects, and they are main constituents of A. fruticulosa essential oil. The two compounds may be related to insecticidal activity of A. fruticulosa essential oil against T. castaneum and L. bostrychophila.

Agathis robusta (C. Moore ex F. Muell.) F.M. Bailey, commonly known as Queensland Kauri or smooth-barked Kauri, is a coniferous tree in the family Araucariaceae. This study aimed to investigate the chemical composition and antibacterial activity of the essential oil of A. robusta from India. The hydrodistilled resin and leaf essential oils were analyzed using GC-FID and GC-MS. Altogether, 34 constituents (forming 98.2% of the resin oil) and 43 constituents (forming 91.2% of the leaf oil composition) were identified. Major constituents of the resin oil were isobornyl acetate (37.9%), limonene (12.3%), bornyl acetate (7.4%), and myrtenol (5.8%), while the leaf oil contained β-selinene (18.1%), rimuene (14.2%), caryophyllene oxide (11.5%), spathulenol (10.5%), α-selinene (9.8%), and γ-muurolene (5.8%) as main constituents. The resin essential oil showed minimum inhibitory concentration (MIC) in the range of 250–500 μg/mL and minimum bactericidal concentration (MBC) in the range of 500 to >1000 μg/mL against ...

The chemical composition of essential oil isolated from the needles of Juniperus commuis L. (Cupressaceae) by hydrodistillation was analyzed by capillary GC-FID and GC/MS. A total of seventy-four compounds representing 93.35% of the oil were identified, the main components from oil were α-pinene (14.2%) followed by sabinene (12.4%), terpinene 4-ol (14.1%), γ-terpinene (5.9%), (2Z,6E) farnesol (5.4%) and manoyl oxide (4.1%). The enantiomeric distribution of α-pinene, sabinene, camphene, β-pinene, limonene, terpinen-4-ol, borneol and myrtenol were successfully determined in essential oil of J. communis.

Myrtenol and myrtanal find their utilization as fine chemicals or intermediates for the synthesis of food additive myrtanol. β-Pinene oxide rearrangement was studied using homogeneous Lewis and Bronsted acids as catalysts for the production of these compounds. The composition of reaction products depended on the type of active sites. Lewis active sites favoured the formation of myrtanal while in presence of Bronsted active sites undesirable perillyl aldehyde and perillyl alcohol were formed to a high extent. Optimal reaction conditions for myrtenol and myrtanal preparation were found. With 5 mol.% of anhydrous SnCl2 as Lewis acid catalysts and 1,4-dioxane as the solvent β-pinene oxide achieved total conversion with 95% selectivity to desired products.

Meliboeus ohbayashii primoriensis (Coleoptera: Buprestidae) is an important pest of the walnut tree Juglans regia (Juglandaceae), but the volatiles mediating this plant-herbivore interaction are unknown. In this study, volatiles emitted by healthy J. regia and by plants infested with M. ohbayashii primoriensis (Coleoptera: Buprestidae) were obtained by a dynamic headspace method and analyzed by gas chromatography-mass spectrometry. We identified 26 major compounds and compared the volatile composition of healthy and buprestid-infected J. regia. Green leaf volatiles were detected in all damaged plants, including the monoterpenoids β-phellandrene and (E)-β-ocimene, the sesquiterpenoids (-)-β-bourbonene, β-ylangene, and (E,E)-α-farnesene, the alcohols linalool, myrtenol, and (E)-(-)-pinocarveol, the ketones (E)-pinocamphone and (Z)-pinocamphone, and the ester methyl salicylate. The major volatiles detected in healthy plants were β-pinene (36.26 %), α-pinene (23.81 %), D-limonene (12.03 %), sabinene (8.63 %), and β-myrcene (4.35 %). The main volatiles from M. ohbayashii primoriensis larva-infested plants were β-pinene (37.82 %), α-pinene (20.36 %), D-limonene (14.71 %), germacrene D (5.24 %), sabinene (4.52 %), and β-phellandrene (3.80 %). These results enrich our understanding of volatiles of healthy plants and plants infested with M. ohbayashii primoriensis. Furthermore, they provide a theoretical basis and scientific foundation for integrated pest management and for effective ecologically sustainable pest control strategies. Resumen Meliboeus ohbayashii primoriensis (Coleoptera: Buprestidae) es una plaga importante del nogal Juglans regia (Juglandaceae), pero se desconocen los compuestos volátiles que median esta interacción planta-herbívoro. En este estudio, se obtuvieron los volátiles emitidos por plantas de J. regia tanto sanas como infestadas con M. ohbayashii primoriensis (Coleoptera: Buprestidae), mediante un método de espacio de cabeza dinámico y se analizaron por cromatografía de gases-espectrometría de masas. Se identificaron 26 compuestos principales y se comparó la composición volátil de J. regia sana e infectada con bupréstido. Se detectaron volátiles de hojas verdes en todas las plantas dañadas, incluidos los monoterpenoides β-felandreno y (E)-β-ocimeno, los sesquiterpenoides (-)-β-bourboneno, β-ylangeno y (E,E)-α-farnesano, los alcoholes linalool, mirtenol y (E)-(-)-pinocarveol, las cetonas (E)-pinocamfono y (Z)-pinocamfono, y el éster salicilato de metilo. Los principales volátiles detectados en plantas sanas fueron β-pineno (36,26 %), α-pineno (23,81 %), D-limoneno (12,03 %), sabineno (8,63 %) y β-mirceno (4,35 %). Los principales volátiles de las plantas infestadas de larvas de M. ohbayashii primoriensis fueron β-pineno (37,82 %), α-pineno (20,36 %), D-limoneno (14,71 %), germacreno D (5,24 %), sabineno (4,52 %), y β-felandreno (3,80 %). Estos resultados enriquecen nuestra comprensión de los volátiles de plantas sanas e infestadas con M. ohbayashii primoriensis. Además, proporcionan una base teórica y una científica para el manejo integrado de plagas y para estrategias efectivas, ecológicamente sostenibles, para el control de plagas.

GABAA receptors are ligand-gated anion channels that form pentameric arrangements of various subunits. Positive allosteric modulators of GABAA receptors have been reported as being isolated either from plants or synthesized analogs of known GABAA receptor targeting drugs. Recently, we identified monoterpenes, e.g. myrtenol as a positive allosteric modulator at α1β2 GABAA receptors. Here, along with pharmacophore-based virtual screening studies, we demonstrate that scaffold modifications of myrtenol resulted in the loss of modulatory activity. Two independent approaches, fluorescence-based compound analysis and electrophysiological recordings in whole-cell configurations were used for analysis of transfected cells. C-atoms 1 and 2 of the myrtenol backbone were identified as crucial to preserve positive allosteric potential. A modification at C-atom 2 and lack of the hydroxyl group at C-atom 1 exhibited significantly reduced GABAergic currents at α1β2, α1β2γ, α2β3, α2β3γ and α4β3δ receptors. This effect was independent of the γ2 subunit. A sub-screen with side chain length and volume differences at the C-atom 1 identified two compounds that inhibited GABAergic responses but without receptor subtype specificity. Our combined approach of pharmacophore-based virtual screening and functional readouts reveals that side chain modifications of the bridged six-membered ring structure of myrtenol are crucial for its modulatory potential at GABAA receptors.

Two white rot fungi, Ceriporia sp. ZLY-2010 (CER) and Stereum hirsutum (STH) were used as biocatalysts for the biotransformation of (-)-α-pinene. After 96 hr, CER converted the bicyclic monoterpene hydrocarbon (-)-α-pinene into α-terpineol (yield, 0.05 g/L), a monocyclic monoterpene alcohol, in addition to, other minor products. Using STH, verbenone was identified as the major biotransformed product, and minor products were myrtenol, camphor, and isopinocarveol. We did not observe any inhibitory effects of substrate or transformed products on mycelial growth of the fungi. The activities of fungal manganese-dependent peroxidase and laccase were monitored for 15 days to determine the enzymatic pathways related to the biotransformation of (-)-α-pinene. We concluded that a complex of enzymes, including intra- and extracellular enzymes, were involved in terpenoid biotransformation by white rot fungi.

This research is aimed at evaluating the potential abilities of the natural acaricide of F. suspense oil against Tyrophagus putrescentiae and Dermatophagoides spp. Based on the LD50 values, in contact bioassay, F. suspense oil (8.19, 3.28, and 4.35 µg/cm 2 ) showed acaricidal effects against T. putrescentiae, D. farinae, and D. pteronyssinus, respectively. Fumigant toxicities of F. suspense oil showed similar patterns as those observed with contact toxicities. GC/MS analysis showed the major components of F. suspense oil to be β-pinene (45.88%), myrtenol (13.86%), (+)-α-pinene (13.09%), (−)-trans-pinocarveol (7.34%), sabinene (6.64%) and pinocarvone (4.13%). These findings indicate that F. suspense oil has potential as a natural acaricide.

The aim of this paper was to investigate biochemical composition of Hyssopus officinalis L. (Lamiaceae) in relation to plant age and phenological growth stage under conditions of Ukrainian Polissia, in order to determine the optimal harvest dates of the herbal material and its application spheres. The raw material samples under analysis were cut at various growth stages: the vegetative, budding, blooming, and ripening stages. To study the hyssop oil composition, areal parts of H. officinalis were used. The composition analysis was aimed at determining absolute dry matter (by drying samples at 105 °C up to the constant mass), «crude» cellulose, amounts of protein, fats, calcium, potassium, phosphorus, ascorbic acid, carotene, discernible sugars and tannins and essential oil. The present study has proved that in the plant ontogenesis the amount of essential oil, obtained from H. officinalis areal parts, does not markedly decrease: volatile oil yield in plants of the first, second and third years of life amounted to 1.007%, 0.75% and 0.71% respectively. The composition of volatile oil in the plants of the first year of life reveals 46 components, of which pinocampone (53.73%), isopinocampone (4.66%), myrtenol (9.35%) and camphor (3.86%) prevailed. In H. officinalis volatile oil of the third year 30 components were identified, the prevailing of which were isopinocampone (44.43%), pinocampone (35.49%), myrtenol (5.26%), germacrene D (3.15%), pulegone (2.93%) and bicyclogermacrene (1.35%). It was observed the change in the quantitative and qualitative composition of H. officinalis volatile oil throughout the entire vegetation period. Thus, in the phase of vegetative growth it was identified 25 compounds, the most predominant being elemol (33.25%), germacren D (21.59%) and bicyclogermacrene (15.78%). In the phase of blossoming 30 components can be identified, a high amount of isopinocampone and pinocampone (44.43% and 35.49%) and lover amount of myrtenol (5.26%), pulegone (2.93%) and bicyclogermacrene (1.35%) can be noted. During the fruit-bearing period 21 compounds with the prevalence of elemol (44.46%), bicyclogermarcren (10.30%), germacren D (5.86%), spatulenol (4.36%), β-eudesmol (4.34%), α-eudesmol (4.04%) and γ-eudesmol (3.92%) can be identified. H. officinalis raw material from one-year-old plants is to be used in food industry, whereas plants collected at the blooming stage are preferable for cosmetics and perfumery., Метою роботи було дослідження біохімічного складу Hyssopus officinalis L. (Lamiaceae) залежно від віку та фенологічних фаз розвитку в умовах Полісся України для встановлення оптимальних термінів збирання та напрямів використання фітосировини. Сировину збирали в різні фази розвитку рослин: вегетативного росту, бутонізації, цвітіння та плодоношення. Для аналізу складу використовували надземну частину рослин. Визначали абсолютно суху речовину шляхом висушування зразків за 105 °С до постійної маси, «сиру» клітковину, вміст протеїну, жирів, кальцію, калію, фосфору, аскорбінової кислоти, каротину, водорозчинних цукрів і дубильних речовин, ефірної олії. Встановлено, що в онтогенезі рослин масова частка ефірної олії, виділена з надземної частини H. officinalis, знижується неістотно: вихід ефірної олії у рослин першого року життя становив 1,007%, другого – 0,78%, третього – 0,71%. У рослин першого року життя у складі ефірної олії виявлено 46 компонентів, серед яких домінували: пінокамфон – 53,73%, ізопінокамфон – 4,66%, міртенол – 9,35%, камфора – 3,86%. В ефірній олії H. officinalis третього року життя ідентифіковано 30 компонентів, серед яких переважали: ізопінокамфон – 44,43%, пінокамфон – 35,49%, міртенол – 5,26%, гермакрен D – 3,15%, пулегон – 2,93%, біциклогермакрен – 1,35%. Відзначено зміну кількісного та якісного складу ефірної олії H. officinalis упродовж вегетаційного періоду. У фазі вегетативного росту ідентифіковано 25 сполук, серед яких домінували елемол – 33,25%, гермакрен D – 21,59%, біциклогермакрен – 15,78%. У фазі цвітіння ідентифіковано 30 компонентів, зафіксовано високий вміст ізопінокамфону та пінокамфону – 44,43% і 35,49%), дещо нижчий – міртенолу – 5,26%, пулегону – 2,93%,біциклогермакрену – 1,35%. Під час плодоношення ідентифіковано 21 сполуку з домінуванням елемолу – 44,46%, біциклогермакрену – 10,30%, гермакрену D – 5,86%, спатуленолу – 4,36%, β-евдесмолу – 4,34%, α-евдесмолу – 4,04%, γ-евдесмолу – 3,92%. Зроблено висновок про доцільність використання рослинної сировини гісопу лікарського першого року життя у харчової промисловості, а у фазі цвітіння – у косметології та парфумерії., Целью работы было исследование биохимического состава Hyssopus officinalis L.(Lamiaceae) в зависимости от возраста и фенологических фаз развития в условиях Полесья Украины для установления оптимальных сроков сбора и направлений использования фитосырья. Сырье собирали в разные фазы развития растений: вегетативного роста, бутонизации, цветения и плодоношения. Для анализа состава использовали надземную часть растений. Определяли абсолютно сухое вещество путем высушивания образцов при 105 °С до постоянной массы, «сырую» клетчатку, содержание протеина, жиров, кальция, калия, фосфора, аскорбиновой кислоты, каротина, водорастворимых сахаров и дубильных веществ, эфирного масла. Установлено, что в онтогенезе растений массовая доля эфирного масла, выделенного из надземной части H. officinalis, снижается незначительно: выход эфирного масла у растений первого года жизни составлял 1,007%,второго – 0,78%, третьего – 0,71%. У растений первого года жизни в составе эфирного масла обнаружено 46 компонентов, среди которых доминировали: пинокамфон – 53,73%, изопинокамфон – 4,66%, миртенол – 9,35%, камфора – 3,86%. В эфирном масле H. Officinalis третьего года жизни идентифицировано 30 компонентов, среди которых преобладали: изопинокамфон – 44,43%, пинокамфон – 35,49%, миртенол – 5,26%, гермакрен D – 3,15%, пулегон – 2,93%, бициклогермакрен – 1,35%. Отмечено изменение количественного и качественного состава эфирного масла H. officinalis в течение вегетационного периода. Во время фазы вегетативного роста идентифицировано 25 соединений, среди которых доминировали элемол – 33,25%, гермакрен D – 21,59%, бициклогермакрен – 5,78%. В течение фазы цветения идентифицировано 30 компонентов, отмечено высокое содержание изопинокамфона и пинокамфона – 44,43% и 35,49%, несколько ниже – миртенола – 5,26%, пулегона (2,93%) и бициклогермакрена – 1,35%. Во время плодоношения идентифицировано 21 соединение с преобладанием элемола – 44,46%, бициклогермакрена – 10,30%, гермакрена D – 5,86%, спатуленола – 4,36%, α-эвдесмола – 4,04%, β-эвдесмола – 4,34% и γ-эвдесмола – 3,92%. Сделан вывод о целесообразности использования растительного сырья иссопа лекарственного первого года жизни в пищевой промышленности, а в фазе цветения – в косметологии и парфюмерии.

International audience; The EFSA Panelon Food Contact Materials, Enzymes, Flavourings and Processing Aids was requested to consider evaluations of flavouring substances assessed since 2000 by the Joint FAO/WHO Expert Committee on Food Additives (JECFA), and to decide whether further evaluation is necessary, as laid down in Commission Regulation (EC) No1565/2000. The present revision of FGE.73 concerns the inclusion of four additional flavouring substances (p-mentha-1,8-dien-7-ol [FL-no: 02.060], myrtenol [FL-no: 02.091], p-mentha-1,8-dien-7-yl acetate [FL-no: 09.278] and myrtenyl acetate [FL-no: 09.302]) evaluated by JECFA at the 59th meeting. The substances were evaluated through a stepwise approach integrating information on structure-activity relationships, intake from current uses, toxicological thresholds of concern (TTC), and available data on metabolism and toxicity. In agreement with JECFA, the Panelevaluated 22 and one candidate substances via the A and the B-side of the Procedure, respectively, and concluded for all substances No safety concern at estimated levels of intake as flavouring substances' based on the maximised survey-derived daily intake (MSDI) approach. The specifications for the materials of commerce have also been considered. Adequate specifications, including complete purity criteria and identity data, are available for 22 out of the 23 JECFA substances evaluated in this FGE. For [FL-no: 09.278], the stereoisomeric composition is not specified. For the six substances with [FL-no: 02.060, 02.091, 09.034, 09.278, 09.302 and 09.712] evaluated in this FGE, use levels have become available and the modified theoretical added maximum daily intakes (mTAMDIs) were estimated. For two substances [FL-no: 09.034, and 09.712], the mTAMDI estimates were above the TTC for their structural class and more detailed information is needed to finalise their evaluation. For the remaining 17 substances evaluated through the Procedure, use levels are needed to calculate the mTAMDIs in order to identify those flavouring substances that need more refined exposure assessment in order to finalise the evaluation.

The EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) was requested to evaluate the genotoxic potential of flavouring substances from subgroup 2.2 of FGE.19 in the Flavouring Group Evaluation 208 Revision 2 (FGE.208Rev2). In FGE.208Rev1, the CEF Panel evaluated genotoxicity studies on p‐mentha‐1,8‐dien‐7‐al [FL‐no: 05.117], the representative substance for FGE.19 subgroup 2.2. The Comet assay performed in liver showed a positive result, and therefore, the Panel concluded that p‐mentha‐1,8‐dien‐7‐al [FL‐no: 05.117] is genotoxic in vivo and that, accordingly, there is a safety concern for its use as flavouring substance. Since p‐mentha‐1,8‐dien‐7‐al [FL‐no: 05.117] is representative for the nine remaining substances of subgroup 2.2 (p‐mentha‐1,8‐dien‐7‐ol [FL‐no: 02.060], myrtenol [FL‐no: 02.091], myrtenal [FL‐no: 05.106], 2,6,6‐trimethyl‐1‐cyclohexen‐1‐carboxaldehyde [FL‐no: 05.121], myrtenyl formate [FL‐no: 09.272], p‐mentha‐1,8‐dien‐7‐yl acetate [FL‐no: 09.278], myrtenyl acetate [FL‐no: 09.302], myrtenyl‐2‐methylbutyrate [FL‐no: 09.899] and myrtenyl‐3‐methylbutyrate [FL‐no: 09.900]), the Panel concluded in the previous revision of FGE.208 (FGE.208Rev1) that there is a potential safety concern for these substances. Subsequently, the industry has submitted genotoxicity studies on five substances of FGE.19 subgroup 2.2: p‐mentha‐1,8‐dien‐7‐ol [FL‐no: 02.060], myrtenol [FL‐no: 02.091], myrtenal [FL‐no: 05.106], p‐mentha‐1,8‐dien‐7‐yl acetate [FL‐no: 09.278] and myrtenyl acetate [FL‐no: 09.302], which are evaluated in the present revision of FGE.208 (FGE.208Rev2). The Panel concluded that the concern for genotoxicity could be ruled out for p‐mentha‐1,8‐dien‐7‐ol [FL‐no: 02.060], myrtenol [FL‐no: 02.091], p‐mentha‐1,8‐dien‐7‐yl acetate [FL‐no: 09.278] and myrtenyl acetate [FL‐no: 09.302], which will be evaluated through the Procedure. Genotoxicity data on myrtenal [FL‐no: 05.106] were considered equivocal, therefore, it cannot be evaluated through the Procedure, presently. p‐Mentha‐1,8‐dien‐7‐al [FL‐no: 05.117] and four substances not supported by industry (2,6,6‐trimethyl‐1‐cyclohexen‐1‐carboxaldehyde [FL‐no: 05.121], myrtenyl formate [FL‐no: 09.272], myrtenyl‐2‐methylbutyrate [FL‐no: 09.899] and myrtenyl‐3‐methylbutyrate [FL‐no: 09.900]) have been deleted from the Union List.

This article reports the results concerning the qualitative and quantitative composition of the volatile oil obtained from the aerial parts of Tanacetum vulgare, collected in Lithuania, by supercritical fluid extraction (SFE) with CO2 at 90 bar and 40 °C and by hydrodistillation (HD). GC-MS and GC-FID analysis revealed that the oils mainly consisted of 1,8-cineole, trans-thujone, cis-chrysanthenol, borneol and myrtenol. Oils obtained by HD displayed, with respect to the SFE volatile oil, a higher amount of hydrocarbon monoterpenes. The hydrodistilled oil was particularly active against dermatophyte strains and Cryptococcus neoformans, with MIC values in the range of 0.16-0.64 μL/mL. The oil revealed a significant inhibitory effect on germ tube formation in Candida albicans at sub-inhibitory concentrations. At the concentration of 1/16 MIC, the inhibition of filamentation was more than 80% in comparison to untreated control cells.

The essential oil from fruits, leaves and stem bark of Xylopia aethiopica of Congo-Brazzaville was obtained by steam distillation and analyzed by CG on two columns with different polarities (polar and apolar) and by CG/SM. The essential oil from fruits was characterized by the presence of three constituents at levels of at least 10%. These were pinenes (alpha-+beta-) as major components (17%), 1, 8-cineole (13.3%) and sabinene (10%), all monoterpene hydrocarbons. The three most abundant oxygenated monoterpenes were trans-pinocarveol (8.2%), myrtenal (6.3%) and myrtenol (6.2%). The essential oil from leaves was characterized by the presence of pinenes (alpha-+beta-) as major components (39-60%). Sesquiterpenes came second, with caryophyllene the most abundant (6-18%). Oil from stem bark was made up of pinenes (27-57%), with beta-cubebene (11-14%) in second position and transpinocarveol (6%) and myrtenal (5%) jointly in third position.

Hyssop (Hyssopus officinalis L.), family Lamiaceae is an important perennial culinary and medicinal plant cultivated in temperate regions of Asia, Europe and America. The hydrodistilled volatile oils derived from leaf, flower and stem of H. officinalis, collected from Chamoli, Uttarakhand, India (Western-Himalaya) were investigated by gas chromatography (GC–FID) and GC–mass spectrometry (GC–MS). Essential oil yield varied from 0.22% to 4.4% in the different parts of the plant. Fifty-seven constituents, representing 99.8% of the leaf oil composition; 44 constituents, representing 99.4% of the flower oil composition and 57 constituents, comprising 88.4% of the stem oil composition were identified. Major constituents of the oils were cis-pinocamphone (49.7–57.7%), pinocarvone (5.5–24.9%), β-pinene (5.7–9.3%), 1,8-cineole (2.9–8.0%), β-phellandrene (1.8–3.2%), myrtenyl methyl ether (2.7–3.0%), sabinene (0.8–1.9%), isopimara-9(11),15-diene (

UNLABELLED The essential oils of 2 Cameroonian spices, namely, Xylopia aethiopica and Ocimum canum, were chemically investigated and screened for their antibacterial activity. The essential oils were analyzed by means of GC, GC/MS, and NMR. X. aethiopica oil contained myrtenol (12%), a monoterpenoid in highest concentration. The essential oil of O. canum belonged to the known linalool (44%) rich chemotype. The results of the antibacterial screening against the food spoiling bacteria revealed a significant and broad spectrum of activity for these essential oils. The present material of X. aethiopica, which is having myrtenol in relatively higher concentration, has shown moderate antibacterial activity. The bioassay-guided fractionation of Ocimum canum oil through flash chromatography showed that minor compounds, namely, α-terpineol, chavicol, chavibetol, and trans-p-mentha-2,8-dien-ol, significantly contributed for the overall activity observed. Hence, these results evidenced the possible potential of the essential oil of O. canum as a suitable antibacterial for controlling food-borne pathogens whereas the X. aethiopica oil has moderate possibility. PRACTICAL APPLICATION There is a strong global demand for the microbe-free, safe, and healthy foods. In this study, we showed that the essential oil of O. canum (wild basil) can be used as antibacterial for food items. Also, we showed that a value addition in the antibacterial potential of O. canum oil can be done by processing the essential oil through flash chromatographic separations.