Α-terpineol Research Articles

TG-FTIR-QMS analysis of more environmentally friendly poly(geranyl methacrylate)-co-poly(cyclohexyl methacrylate) copolymers

The pyrolysis and thermal oxidation course of new, more environmentally friendly copolymers, not described in the literature so far, was systematically investigated by the TG/FTIR/QMS technique. New materials were obtained in the UV polymerization process of geranyl methacrylate, a monomer synthesized on the basis of natural, terpene alcohol (geraniol), and cyclohexyl methacrylate using a variable percentage of individual monomers. As confirmed, the copolymers were characterized by excellent resistance to solvents and chemical environment as well as Tg in the range 34.5–53.8 ⁰C. The TG/DTG analyses proved their high thermal stability in an inert atmosphere and satisfactory thermal resistance in an oxidizing atmosphere. The thermal resistances of the copolymers were directly dependent on the percentage of individual monomers. The simultaneous TG/DTG coupled with the FTIR and QMS analyses confirmed that the decomposition course of the tested materials was complex, in both atmospheres. The pyrolysis process included two main stages. In the first stage, depolymerization, random cleavage of the CC and CO bonds and decarboxylation were the main processes. These led to the emission of methacrylate monomers, myrcene, geraniol, citral, propene, methacrylic acid and other structure low molecular saturated and unsaturated compounds, as the main products of pyrolysis. In the second stage, the secondary reactions between intermediate volatiles and the formed residues were expected. Under oxidative conditions, the decomposition mechanism was more complicated. The depolymerization, random cleavage of the CC and CO bonds, decarboxylation and additional reactions of the intermediates with oxygen led to the emission of methacrylate monomers, myrcene, geraniol, citral, propene, methacrylic acid and other structure low molecular saturated and unsaturated compounds and more oxidized gaseous products.

Solvent-free dehydration, cyclization, and hydrogenation of linalool with a dual heterogeneous catalyst system to generate a high-performance sustainable aviation fuel

The development of efficient catalytic methods for the synthesis of bio-based, full-performance jet fuels is critical for limiting the impacts of climate change while enabling a thriving modern society. To help address this need, here, linalool, a terpene alcohol that can be produced via fermentation of biomass sugars, was dehydrated, cyclized, and hydrogenated in a one-pot reaction under moderate reaction conditions. This sequence produced a biosynthetic fuel mixture primarily composed of 1-methyl-4-isopropylcyclohexane (p-menthane) and 2,6-dimethyloctane (DMO). The reaction was promoted by a catalyst composed of commercial Amberlyst-15, H+ form, and 10% Pd/C. Two other terpenoid substrates (1,8-cineole and 1,4-cineole) were subjected to the same conditions and excellent conversion to high purity p-menthane was observed. The fuel mixture derived from linalool exhibits a 1.7% higher gravimetric heat of combustion and 66% lower kinematic viscosity at −20 °C compared to the limits for conventional jet fuel. These properties suggest that isomerized hydrogenated linalool (IHL) can be blended with conventional jet fuel or synthetic paraffinic kerosenes to deliver high-performance sustainable aviation fuels for commercial and military applications.

Linalool attenuated ischemic injury in PC12 cells through inhibition of caspase-3 and caspase-9 during apoptosis.

Numerous studies have indicated the pharmacological properties of linalool, a volatile terpene alcohol found in many flowers and spice plants, including anti-nociceptive, anti-inflammatory, and neuroprotective activities. The aim of this study was to explore the mechanisms of neuroprotection provided by (±) linalool and its enantiomer, (R)-(-) linalool against oxygen, and glucose deprivation/reoxygenation (OGD/R) in PC12 cells. PC12 cells were treated with (±) linalool and (R)-(-) linalool before exposure to OGD/R condition. Cell viability, reactive oxygen species (ROS) production, malondialdehyde (MDA) level, DNA damage, and the levels of proteins related to apoptosis were evaluated using MTT, comet assay, and western blot analysis, respectively. IC50 values for the PC12 cells incubated with (±) linalool and (R)-(-) linalool were 2700 and 2600 μM after 14 h, as well as 5440 and 3040 μM after 18 h, respectively. Survival of the ischemic cells pre-incubated with (±) linalool and (R)-(-) linalool (100 μM of both) increased compared to the cells subjected to the OGD/R alone (p < .001). ROS and MDA formation were also decreased following incubation with (±) linalool and (R)-(-) linalool compared to the OGD/R group (p < .01). In the same way, pre-treatment with (±) linalool and (R)-(-) linalool significantly reduced OGD/R-induced DNA injury compared to that seen in OGD/R group (p < .001). (±) Linalool and (R)-(-) linalool also restored Bax/Bcl-2 ratio and cleaved caspase-3 and caspase-9 (p < .001, p < .01) following ischemic injury. The neuroprotective effect of linalool against ischemic insult might be mediated by alleviation of oxidative stress and apoptosis.

Menthol nanoliposomes enhanced anti-tumor immunotherapy by increasing lymph node homing of dendritic cell vaccines

Menthol, a cyclic terpene alcohol, plays a critical role in overcoming the blood-brain barrier and stratum corneum barrier. Herein, we innovatively propose a menthol nanoliposome (Men-nanoLips) that can dramatically increase lymph node accumulation of the dendritic cell (DC)-based anti-tumor vaccines. Specifically, Men-nanoLips efficiently enhanced lymphatic endothelial cell (EC) barrier permeability by reducing the expression of tight junction proteins. And interestingly, Men-nanoLips not only up-regulated the expression of CCR7 in DCs but also increased the secretion of CCL21 in lymphatic ECs. Moreover, Men-nanoLips promoted DC vaccine maturation as evidenced by increasing the expression of costimulatory molecules and up-regulating the pseudopodia-like protein. With those complementary mechanisms provided by Men-nanoLips, the number of the B16 whole-tumor cell lysate-loaded DCs that target the draining LN enhanced remarkably and significantly boosted the treatment efficacy of DC anti-tumor vaccines. Therefore, we concluded that Men-nanoLips could be instructive for increasing LN homing of DC vaccines.

Effect of Drying Methods on Volatile Compounds of Citrus reticulata Ponkan and Chachi Peels as Characterized by GC-MS and GC-IMS

To reflect the volatile differences of dried citrus peel as affected by cultivars and drying methods, the volatile compounds of dried citrus peel of two cultivars (Citrus reticulata “Chachi” and Citrus reticulata “Ponkan”), prepared under three drying methods (sun-drying (SD), hot-air-drying (AD), and freeze-drying (FD)), were analyzed by GC-MS, odor activity values (OAVs), and GC-IMS. GC-MS data indicated that SD was favorable to preserve terpenic alcohols (linalool, α-terpineol and terpinene-4-ol), β-cymene, methyl methanthranilate, and monoterpenes; while AD was favorable to preserve aliphatic aldehydes and sesquiterpenes; and SD was more similar with AD in GC-MS analysis of volatile profile (of higher MW) for both cultivars from the PCA outcome. Furthermore, significant difference in volatile isomeric composition of different samples was also clearly demonstrated through extracted ion chromatogram (EIC) by GC-MS analysis. GC-IMS analysis showed the favorability of FD to preserve ketones, phenols, esters, and aromatic aldehydes; and SD was more similar with FD in GC-IMS analysis of volatile profile (of smaller MW) for both cultivars from the PCA outcome. Moreover, the OAVs indicate that 2-methoxy-4-vinylphenol contributed much to the flavor of dried Ponkan peel, while 2-methoxy-4-vinylphenol, methyl methanthranilate, and methyl anthranilate played an important role in the flavor of dried Chachi peel; and the highest OAVs for monoterpenes were observed at SD for both cultivars. Thus, the combination of GC-MS and GC-IMS analyses with PCA in this paper suggested the superiority of SD to preserve volatiles and characteristic aroma in dried citrus peel, and that SD contributed much to the quality of dried Chachi peel.

Photodynamic inactivation of multidrug-resistant bacteria in wastewater effluent using green phytochemicals as a natural photosensitizer

The control of multidrug-resistant bacteria (MDRB) is a great challenge in the 21st century. Photodynamic treatment (PDT) is one of the promising approaches to control MDRB. In the process, powerful oxidants such as reactive oxygen species (ROS) are produced, which cause cytotoxic damage and cell death of bacteria. This study examined a new and environment-friendly strategy for the photodynamic inactivation of two MDRB (Escherichia coli and Staphylococcus aureus) and total coliform (TC) in wastewater effluent using two phytochemicals, pyrogallol (PGL) and terpinolene (TPN), along with white and blue light-emitting diode (LED) light. Fourier-transform infrared spectroscopy (FTIR) of the phytochemicals confirmed the presence of different phenolic and aromatic compounds, which can enhance the generation of ROS alongside inactivating the bacterial cells. In the PDT process, white LED light was more active in controlling MDRB than blue LED light. After 80 min irradiation with white LED light (17 mW/cm2), the MDRB bacteria were eradicated completely at a minimum inhibitory concentration (MIC) dose (0.156 mg/mL for E. coli and 0.078 mg/mL for S. aureus) of PGL. In addition, light intensity was an important parameter in photodynamic disinfection. The TC in the secondary effluent was inactivated completely by both phytochemicals after 60 min of exposure to white LED light with an intensity of 80 mW/cm2. The photosensitizing activity of phytochemicals was analyzed by a bactericidal and imidazole-RNO assay. These assays showed that PGL contributed to the generation of •OH radicals, whereas TPN produced 1O2 in the PDT process. Transmission electron microscopy (TEM) confirmed bacterial cell disruption after treatment. Overall, PDT using the phytochemicals as PS is a sustainable approach to control the MDRB and TC in wastewater successfully.

Effect of Czech Hop Varieties on Aroma of Dry-Hopped Lager Beer.

The hoppy aroma in beer is characterized by an overall pleasant profile. The impacts of five Czech hop cultivars, Rubin, Saaz, Vital, Harmonie, and Kazbek, were tested on the hop aroma of the resulting beers, compared with a control beer sample, which was hopped with a commercial hop extract during wort boiling. GC-MS analysis was used for the identification and quantification of aroma-active compounds in the hops and beer. Dry hopping was successful in terms of improving the hoppy aroma in beer. Odorants such as β-myrcene, linalool, geraniol, β-citronellol, humulene epoxide I, and 2-methylbutyl-2-methylpropanoate were found at higher concentrations than the control in all dry-hopped beers. To quantify the success of dry hopping, the transfer rates of hop odorants were calculated. Those of linalool, geraniol and humulene epoxide I were adequate, whereas the transfer rates of polar compounds, e.g., β-myrcene, were relatively low, mostly due to their polarity. Changes in hop oil constituents were clearly notable, with the generation of β-citronellol, the release of other terpene alcohols from their glycosides or oxidation of α-humulene. Yeast metabolism also played an important role in these changes.

Evolution-Guided Biosynthesis of Terpenoid Inhibitors.

Terpenoids, the largest and most structurally diverse group of natural products, include a striking variety of biologically active compounds, from flavors to medicines. Despite their well-documented biochemical versatility, the evolutionary processes that generate new functional terpenoids are poorly understood and difficult to recapitulate in engineered systems. This study uses a synthetic biochemical objective─a transcriptional system that links the inhibition of protein tyrosine phosphatase 1B (PTP1B), a human drug target, to the expression of a gene for antibiotic resistance in Escherichia coli (E. coli)─to evolve a terpene synthase to produce enzyme inhibitors. Site saturation mutagenesis of poorly conserved residues on γ-humulene synthase (GHS), a promicuous enzyme, yielded mutants that improved fitness (i.e., the antibiotic resistance of E. coli) by reducing GHS toxicity and/or by increasing inhibitor production. Intriguingly, a combination of two mutations enhanced the titer of a minority product─a terpene alcohol that inhibits PTP1B─by over 50-fold, and a comparison of similar mutants enabled the identification of a site where mutations permit efficient hydroxylation. Findings suggest that the plasticity of terpene synthases enables an efficient sampling of structurally distinct starting points for building new functional molecules and provide an experimental framework for exploiting this plasticity in activity-guided screens.

Metabolite Profiling, Stability Testing, Pharmacokinetics, and In Vivo Pattern Recognition Analysis of Arq-e-Keora: A Traditional Unani Formulation.

Arq-e-Keora is a liquid formulation of the Unani system of medicine and used since long for the management of weakness of heart, palpitations, etc. The study was carried out to generate a scientific data for its metabolite profiling, stability testing, pharmacokinetics, and pattern recognition analysis of Arq-e-Keora. Arq-e-Keora has been prepared as water distillate of male wpadix of Pandanus odoratissimus L.f. TLC profiling of Arq-e-Keora was performed using hexane and acetone (7:3, v/v) as a solvent system. The metabolic profiling of volatile compounds was carried out using GC-MS. Pharmacokinetic analysis was performed through GC-MS to evaluate how quickly it absorbs and distributes in plasma. The pattern recognition analysis was performed in order to recognize the pattern and fate of metabolites in rat plasma up to 24 h after single oral administration of Arq-e-Keora. TLC and GC-MS analysis resulted in profiling of 11 and 21 metabolites, respectively. GC-MS analysis revealed that phenethyl alcohol, alpha-terpinolene, beta terpinene, alpha terpinene, beta fenchyl alcohol, hexadecanoic acid, and octadecanoic acid are the major metabolites found in Arq-e-Keora. The stability analysis showed that most of the compounds are stable at refrigerator temperature during their consumption. Pharmacokinetics data of phenethyl alcohol showed its absorption was rapid, with Tmax occurring within 1 h after oral administration of Arq-e-Keora. In vivo pattern recognition analysis suggests that some metabolite expression was altered after its oral administration. As a result, our model could be used for quality, stability, and pharmacokinetic evaluation of various Unani formulations mentioned in Unani Pharmacopoeia of India. This is the first study of pharmacokinetic analysis and metabolite pattern of traditional Unani formulation after its oral administration in Wistar rats.

Mammalian derived lipocalin and secretoglobin respiratory allergens strongly bind ligands with potentially immune modulating properties.

Allergens from furry animals frequently cause sensitization and respiratory allergic diseases. Most relevant mammalian respiratory allergens belong either to the protein family of lipocalins or secretoglobins. Their mechanism of sensitization remains largely unresolved. Mammalian lipocalin and secretoglobin allergens are associated with a function in chemical communication that involves abundant secretion into the environment, high stability and the ability to transport small volatile compounds. These properties are likely to contribute concomitantly to their allergenic potential. In this study, we aim to further elucidate the physiological function of lipocalin and secretoglobin allergens and link it to their sensitizing capacity, by analyzing their ligand-binding characteristics. We produced eight major mammalian respiratory allergens from four pet species in E.coli and compared their ligand-binding affinities to forty-nine ligands of different chemical classes by using a fluorescence-quenching assay. Furthermore, we solved the crystal-structure of the major guinea pig allergen Cav p 1, a typical lipocalin. Recombinant lipocalin and secretoglobin allergens are of high thermal stability with melting temperatures ranging from 65 to 90°C and strongly bind ligands with dissociation constants in the low micromolar range, particularly fatty acids, fatty alcohols and the terpene alcohol farnesol, that are associated with potential semiochemical and/or immune-modulating functions. Through the systematic screening of respiratory mammalian lipocalin and secretoglobin allergens with a large panel of potential ligands, we observed that total amino acid composition, as well as cavity shape and volume direct affinities to ligands of different chemical classes. Therefore, we were able to categorize lipocalin allergens over their ligand-binding profile into three sub-groups of a lipocalin clade that is associated with functions in chemical communication, thus strengthening the function of major mammalian respiratory allergens as semiochemical carriers. The promiscuous binding capability of hydrophobic ligands from environmental sources warrants further investigation regarding their impact on a molecule's allergenicity.

ФОРМУВАННЯ АРОМАТУ ПЛОДОВО-ЯГІДНИХ ВИНОМАТЕРІАЛІВ

One of the important indicators of wine quality is the bouquet, which directly depends on the aroma of the constituents. Aromatic substances of wines can be represented by all classes of organic compounds in order to detect the effect of substances on the aroma and determine the activity of volatile components of the aroma (OAV) by dividing the concentration of the substance on its threshold concentration. If OAV&gt; 1, means that the component already contributes to the flavor. For analysis, we took the results of studies of 25 samples of fruit and berry wine materials, in which the concentrations of volatile aromatic components were defined by chromatographic method. Threshold concentrations of components were detected from the literature and relevant databases. The activity of volatile aromatic components was calculated and analyzed, also the aroma of wine materials was determined. According to the activity of aroma components (OAV), apple wine materials have a fruity aroma, which may be accompanied by shades of pear associated with isoamyl acetate activity; pineapple – ethyl butyrate; roses and honey - phenylethyl alcohol; lilac - α -terpineol; exotic fruits - β-damascenone. The aroma of apple juice is influenced by aromatic aldehyde - trans-2-hexenal, β-damaskenone and vanillin. Pear wine materials are close to apple in terms of aroma activity and are characterized by fruit tones with strong pear tones due to the activity of isoamyl acetate and pineapple – ethyl butyrate. Gooseberry unfortified wine material from fruit species Krasen has a light red color and a clean fresh aroma with hints of fruit and pineapple. The aroma of blackcurrant wines was defined by the activity of volatile components that predetermine the fruit aroma as well as the activity of terpene alcohol α-terpineol. Wine materials contain 3-oxy-β-damascone (2.45-4.34 mg / dm3), 3-oxo-α-ionol (2.98-3.58 mg / dm3), linaloxide (0.90) and dehydro -3-oxo-α-ionol (1.05 mg / dm3), which obviously define their species flavor. Unfortified jostaberry wine materials have a red color and a distinctive delicate aroma reminiscent of pomegranate. In addition to α-terpineol, jostaberry wine material contains terpene alcohol cineole (0.84 mg / dm3), terpinene-4-ol (0.18 mg / dm3), these components may, together with α-terpineol, determine the species aroma of jostaberry wine materials. Butyrolactone gives tenderness to jostaberry and gooseberry wine materials in concentrations of 16.86 and 4.70 mg / dm3, respectively. Raspberry wine materials have an extremely pleasant aroma and bouquet, which is formed due to the activity of minor volatile components: β-ionone, linalool, α-terpineol. The nobility of the aroma is determined by the activity of δ-decalactone. Raspberry ketone (1.75 mg / dm3) is found in the wine material, which is contained in raspberries and definitely participates in the formation of the aroma of wine material. The aroma of elderberry juice is due to the activity of aromatic aldehyde trans-2-hexenal, vanillin, β-ion, β-damaskenone, linalool and α-terpineol, the activity of which is respectively 359, 300, 254, 107, 40 and 1.8. In wine materials it can be observed much higher activity of volatile components from elderberry: isoamyl and phenylethyl alcohols, as well as isoamyl acetate, which affects their aroma. Minor components of juice retain activity in wine materials: linalool and β-damaskenone. Wine materials from black elderberry are recommended for use in blended wines.

ALLELOPATIC EFFECTS OF SOME ESSENTIAL OIL COMPONENTS OF THYME AND ROSE ON GERMINATION: CASE STUDY OF BARLEY

The study was carried out to determine whether different concentrations of essential oil components (geraniol, carvacrol, thymol, and alpha terpinene) and essential oil of thyme (Thymus vulgare) have any allelopathic effects on the germination of barley seeds. The study was carried out in the laboratory environment according to the divided plots experimental design in random plots. At the end of the experiment, the effects of allelochemical types of carvacrol, thymol and geraniol doses on germination rate and seedling dry weight were found to be statistically significant (p&lt;0.01). It was determined that geraniol (0.00245 g), carvacrol (0.01790 g) and thymol (0.02590 g) had the most negative effects on seedling dry weight, respectively. As a result, it was determined that some of the herbal allelochemicals used were effective on the germination of barley seed and seedling growth, and the effect rate increased as the dose increased. Thymol, geraniol and carvacrol showed the most negative effects on the germination rate of barley seed at all doses. On the other hand, adverse effects were determined at high doses of alpha terpinene. All doses of thyme essential oil and low doses of alpha terpinene showed similar effects with the control. As a result; It is thought that essential oil components, which have a negative effect on the germination of barley seed, can be used in the production of plant-based bio-herbicides.

Investigation on structural, spectroscopic, DFT, biological activity and molecular docking simulation of essential oil Gamma-Terpinene

Density functional theory (DFT) quantum chemical computations were used to explore the structural and spectroscopic characteristics of the Gamma terpinene molecule in this study. The inhibitory nature of the title chemical was revealed via molecular docking research. The optimization was conducted out through the DFT/B3LYP approach with the basis set 6-311++G(d,p). Molecular docking research was used to assess the anticancer activity of the Gamma terpinene molecule. The vibrational frequencies were allocated and compared to the empirically measured vibrational frequencies using the optimized molecular structure. The ultraviolet-visible spectrum was modeled and experimentally validated. Simulated computations of the molecular electrostatic potential surface were also performed to analyze the reactive behavior of the Gamma terpinene molecule. The stability and molecular reactivity of the molecule were computed using the HOMO-LUMO energies, energy gap, chemical potential (μ), electronegativity (χ), hardness (η), and softness (S) values. Natural bond orbital analysis has been used to obtain the molecule's second order perturbation energy E(2) values, which show the bioactivity of the Gamma terpinene molecule. The molecule's reactive site is confirmed by the Mulliken atomic charge distribution and total electron density plotted with the molecular electrostatic potential surface analysis. The in vitro investigation through disc diffusion method was used to assess gamma-terpinene's antibacterial and antifungal activity, while in silico analysis through molecular docking and pharmacokinetic evaluation was used to assess its anti-cancer activity and drug-likeness property. In anti-bacterial and anti-fungal analysis zones of clearance was observed at different concentrations and the highest binding affinity was observed against the breast cancer target protein ERα with a docking score of -6.6Kcal/mol.

Novel Pesticidal Efficacy of Araucaria heterophylla and Commiphora molmol Extracts against Camel and Cattle Blood-Sucking Ectoparasites.

Botanical insecticides are promising pest control agents. This research investigated the novel pesticidal efficacy of Araucaria heterophylla and Commiphora molmol extracts against four ectoparasites through treated envelopes. Seven days post-treatment (PT) with 25 mg/mL of C. molmol and A. heterophylla, complete mortality of the camel tick, Hyalomma dromedarii and cattle tick, Rhipicephalus (Boophilus) annulatus were reached. Against H. dromedarii, the median lethal concentrations (LC50s) of the methanol extracts were 1.13 and 1.04 mg/mL and those of the hexane extracts were 1.47 and 1.38 mg/mL, respectively. The LC50 values of methanol and hexane extracts against R. annulatus were 1.09 and 1.41 plus 1.55 and 1.08 mg/mL, respectively. Seven days PT with 12.5 mg/mL, extracts completely controlled Haematopinus eurysternus and Hippobosca maculata; LC50 of Ha. eurysternus were 0.56 and 0.62 mg/mL for methanol extracts and 0.55 and 1.00 mg/mL for hexane extracts, respectively, whereas those of Hi. maculata were 0.67 and 0.78 mg/mL for methanol extract and 0.68 and 0.32 mg/mL, respectively, for hexane extracts. C. molmol extracts contained sesquiterpene, fatty acid esters and phenols, whereas those of A. heterophylla possessed monoterpene, sesquiterpene, terpene alcohols, fatty acid, and phenols. Consequently, methanol extracts of C. molmol and A. heterophylla were recommended as ecofriendly pesticides.

Development and In Vitro Validation of Antibacterial Paints Containing Chloroxylenol and Terpineol.

The establishment of self-disinfecting surfaces is an important method to avoid surface contamination. Recently, paints with antimicrobial properties have been developed to be applied on different surfaces, avoiding contamination with pathogens. In this work, self-disinfecting paints containing Chloroxylenol (CLX), Terpineol (TRP), and a mixture of both substances were developed. The goal was to evaluate and validate these paints using international standards for eventual commercialization and application in scenarios where surface contamination represents a problem. The paints were challenged with five different bacteria, Gram-positive and Gram-negative, before and after a scrub resistance test, where the long-term efficacy of the paints was evaluated. The antibacterial activity assessment was performed following ISO 22196 and JIS Z2801. In general, the paints showed very promising results, demonstrating their antibacterial activity, before and after scrub resistance test. The paint incorporating the mixture of CLX and TRP (CLX+TRP) stood out by revealing consistent results of antibacterial activity both before and after the scrub resistance test for most of the tested bacteria. The cytotoxicity of the developed paints was assessed in vitro by performing tests by direct contact with a human skin cell line, HaCaT, and testes on extracts with HaCaT and a pulmonary cell line, A549. The methodologies for cytotoxicity assessment were developed based in ISO 10993. For genotoxicity assessment, alkaline comet assay was conducted on both cell lines. The cytotoxicity assessment revealed promising results with the paints, demonstrating values of cellular viability above 70% and values of lactate dehydrogenase (LDH) leakage below 30%. The genotoxic assessment also revealed acceptable values of primary DNA damage for the developed antibacterial paints. In general, the selected methodologies presented good potential to be applied in the validation of both efficacy and safety of the antimicrobial paints, aiming to be applied in real scenarios.

Selenium-functionalized cyclic ethers derived from natural terpenic alcohols – biological in vitro profile

Terpenic alcohols linalool, nerolidol and α-terpineol were subjected to the PhSe-induced cyclization, where corresponding cyclic ethers were obtained. The heterocyclic product derived from α-terpineol is a derivate of the natural product eucalyptol, while linalool cyclization produces precursors of the natural product karahanaenone. All three cyclic ether products have an organoselenium moiety in the side chain, which can represent a significant source of bioactivities. Biological evaluation of obtained products, in vitro cytotoxicity and redox status parameters, was performed on two model systems: HCT-116 – immortalized colon cancer cell line, and MRC-5 – healthy fibroblasts isolated from lung pleura. The results indicate a strong prooxidative character of all compounds on colon cancer HCT-116 and healthy MRC-5 cells in the highest applied concentrations. Selectivity towards cancer cells was not observed, except when nerolidol-derived product was used for longer exposure time. A biological evaluation was conducted to establish the quantitative relationship between enhanced radical species formation and cell viability.

Formulation and evaluation of hair growth enhancing effects of oleogels made from Rosemary and Cedar wood oils

Essential oils are one of the most popular natural products, with broad applications in dermatology. Hair loss is a disorder in which the hair falls out from skin areas where they are usually present, such as the scalp and the body.The aim of the work was to formulate oleogels containing two essential oils (Cedarwood and Rosemary) singly and in combination and evaluate their hair growth enhancing effect on an animal model. Oleogels were formed using beeswax as the organogelator with concentrations of 10 % for the oils when used singly or 5 % each for the oils when formulated in combination. Characterization of oleogels were done using spreadability, oil binding capacity (OBC), gas chromatography (GC) and differential scanning calorimetry (DSC). Hair growth evaluation was carried out in 18 albino rats in six groups of threes. A hair removal cream was applied on the experimental animals and the Oleogel applied for six-weeks.GC analysis of the oils revealed the presence of thujopsene, alpha-pinene, beta-pinene, pentane, alpha cedrenea, beta cedrenea, alpha cedrol, gamma-terpene, acetonitrite, atlantone, terpinolene in cedarwood oil while rosemary oil contained 1-8 cineole, camphor, alpha-pinene, beta-pinene, camphene, p-cymene, alpha-terpinene, gamma terpinene, gamma-humulene, beat-bisabolene, genaniol and terpinolene. DSC thermogram of the oleogel formulations showed varying degrees of amorphicity.Spreadability results showed that the oleogels containing cedarwood oil were more spreadable. Conversely, oil binding capacity values were higher with Rosemary oil than Cedar wood oil with values ranging from 91 % (for the oleogel containing 10 % rosemary oil) to 81 % for the bland oleogel (no essential oil). Hair growth evaluation revealed that the oleogel containing rosemary oil (10 %) had similar effects as the positive control (Minoxidil, 2 %) at the end of the six-week period.Oleogels made from cedar wood and rosemary oils have hair growth enhancing effects.

In silico and in vitro antileishmanial effects of gamma-terpinene: Multifunctional modes of action

IntroductionLeishmaniasis denotes a significant health challenge worldwide with no ultimate treatment. The current study investigated the biological effects of gamma-terpinene (GT) on Leishmania major in putative antileishmanial action, cytotoxicity, apoptosis induction, gene expression alteration, antioxidant activity, hemolysis, and ROS generation. MethodsGT and meglumine antimoniate (MA) were probed alone and in combination (GT/MA) for their anti-leishmanial potentials using the MTT biochemical colorimetric assay and a model macrophage cell. In addition, their immunomodulatory properties were assessed by analyzing their effect on the transcription of cytokines related to Th1 and Th2 responses. GT and MA, alone and in combination, were also assessed for their potential to alter metacaspase gene expression in L. major promastigotes by real-time RT-PCR. The hemolytic potential of GT and MA-treated promastigotes were also measured by routine UV absorbance reading. Electrophoresis on agarose gel was employed to analyze genomic DNA fragmentation. ResultsGT demonstrated notable dose-dependent antileishmanial effects towards promastigotes and amastigotes of L. major. The IC50 values for GT against L. major promastigotes and amastigotes were 46.76 mM and 25.89 mM, respectively. GT was considerably safer towards murine macrophages than L. major amastigotes with an SI value of 3.17. Transcriptional expression of iNOS, JAK-1, Interleukin (IL-10), and TGF-β was meaningfully decreased, while the levels of metacaspase mRNA were increased. Results also confirmed GT antioxidant activities. Also, increased levels of intracellular ROS were observed upon treatment of promastigotes with GT. The gel electrophoresis result indicated slight DNA fragmentation in the treated promastigotes by both drugs. A weak hemolytic effect was also observed for GT. ConclusionThe results demonstrated that GT showed potent activity against L. major stages. It seems that its mechanism of action involves representing an immunomodulatory role towards upregulation of iNOS and JAK-1, while downregulation of IL-10 and TGF- β. Moreover, GT has an antioxidative potential and exerts its action through activating macrophages to kill the organism. Further in vivo and clinical studies are essential to explore its effect in future programs.

Terpinen-4-ol inhibits the proliferation and mobility of pancreatic cancer cells by downregulating Rho-associated coiled-coil containing protein kinase 2

ABSTRACT Terpinen-4-ol (T4O), a compound isolated from the seeds of turmeric, has exhibited anti-malignancy, anti-aging, and anti-inflammatory properties in previous studies. However, the specific effects and molecular mechanisms of T4O on pancreatic cancer (PC) cells remain largely unknown. In this study, we demonstrated that T4O markedly suppressed PC cell proliferation and colony formation in vitro and induced apoptosis. Similarly, T4O significantly inhibited the migration and invasion of PC cells in vitro. Through RNA sequencing, 858 differentially expressed genes (DEGs) were identified, which were enriched in the Rhodopsin (RHO)/ Ras homolog family member A (RHOA) signaling pathway. Rho-associated coiled-coil containing protein kinase 2 (ROCK2), a DEG enriched in the RHO/RHOA signaling pathway, was considered as a key target of T4O in PC cells; it was significantly reduced after T4O treatment, highly expressed in PC tissues, and negatively associated with patient outcome. Overexpression of ROCK2 significantly reduced the inhibitory effects of T4O on PC cell proliferation and mobility. Moreover, T4O inhibited cell proliferation in vivo and decreased the Ki-67, cell nuclear antigen, EMT markers, and ROCK2 expression. In conclusion, we consider that T4O can suppress the malignant biological behavior of PC by reducing the expression of ROCK2, thus contributing to PC therapy.

Fabrication and assessment of folic acid conjugated-chitosan modified PLGA nanoparticle for delivery of alpha terpineol in colon cancer

The objective of this study was to fabrication of α-terpineol-PLGA nanoparticles coated with folic acid-chitosan (αT-PCF-NPs) as well as evaluates their anticancer effects. αT-PCF-NPs were synthesized using the nanoprecipitation method and characterized by Dynamic light scattering (DLS), zeta potential (ZP), scanning electron microscope (SEM), Fourier transform infrared spectroscopy (FTIR) analysis. Folic acid (FA) binding rate and entrapment efficiency of α-T were assessed by HPLC method. MTT assay was performed for cytotoxicity assessment. Quantitative polymerase chain reaction (qPCR) analysis, acridine orange and propodium iodide (AO/PI) staining and cell cycle analysis were done to assess the pro-apoptotic properties of αT-PCF-NPs. Molecular analysis for angiogenesis and antioxidant properties and murine colon cancer model for antitumor effects of αT-PCF-NPs were used. The % FA-binding and encapsulation efficiency of α-T in αT-PCF-NPs (particle size of 263.95 nm, polydispersity index (PDI) of 0.25, and surface charge of +38.20 mV) was reported to be 67% and 88.1% respectively. The higher inhibitory effect of αT-PCF-NPs on cancer cells compared to HFF cells was confirmed. The pro-apoptotic effect of αT-PCF-NPs was showed by increased SubG1 phase cells, AO/PI staining results and up and down regulation Bax and Bcl-2 as pro and anti-apoptotic genes in HT-29 cells. Antioxidant (SOD) and angiogenesis genes (VEGF and VEGF-R) were inhibited by αT-PCF-NPs exposure in HT-29 cells and also decreased the size of murine tumors was confirmed in exposure of αT-PCF-NPs. αT-PCF-NPs can be considered as a promising anticancer drug for colon cancer.