Β-caryophyllene Oxide Research Articles

Antibiofilm Activity of Invasive Plants against Candida albicans: Focus on Baccharis halimifolia Essential Oil and Its Compounds.

The extracts of five invasive plants were investigated for antifungal and antibiofilm activities against Candida albicans, C. glabrata, C. krusei, and C. parapsilosis. The antifungal activity was evaluated using the microdilution assay and the antibiofilm effect by measurement of the metabolic activity. Ethanol and ethanol-water extracts of Reynoutria japonica leaves inhibited 50 % of planktonic cells at 250 μg mL-1 and 15.6 μg mL-1 , respectively. Ethanol and ethanol-water extracts of Baccharis halimifolia inhibited >75 % of the mature biofilm of C. albicans at 500 μg mL-1 . The essential oil (EO) of B. halimifolia leaves was the most active (50 % inhibition (IC50 ) at 4 and 74 μg mL-1 against the maturation phase and 24 h old-biofilms of C. albicans, respectively). Oxygenated sesquiterpenes were the primary contents in this EO (62.02 %), with β-caryophyllene oxide as the major component (37 %). Aromadendrene oxide-(2), β-caryophyllene oxide, and (±)-β-pinene displayed significant activities against the maturation phase (IC50 =9-310 μ mol l-1 ) and preformed 24 h-biofilm (IC50 =38-630 μ mol l-1 ) of C. albicans with very low cytotoxicity for the first two compounds. C. albicans remained the most susceptible species to this EO and its components. This study highlighted for the first time the antibiofilm potential of B. halimifolia, its EO and some of its components.

β­caryophyllene oxide induces apoptosis and inhibits proliferation of A549 lung cancer cells

One of the most common cancers that result in death is lung cancer. There is new hope in the fight against lung cancer thanks to the chemopreventive properties of natural dietary substances like β-caryophyllene oxide (CPO), and research is currently being done to test this theory. CPO, a sesquiterpene isolated from medicinal plant essential oils, inhibits carcinogenesis and has been effective in treating many cancers. This study examined how CPO affected proliferation of human lung cancer A549 cells. CPO was found to have an inhibitory concentration (IC50) of 124.1 g/ml. The proliferative markers Ki67 and PCNA were significantly inhibited after cells were treated with CPO at a concentration of 50 g/ml compared to controls. CPO-treated cells expressed more P21, P53, and DNA strand breaks than controls. This was accompanied by a significant cell cycle arrest in the S and G2/M phases. In treated A549 cells, this was also associated with a significant induction of apoptosis, as shown by the upregulation of the expression of caspases 3, 7, and 9, as well as Bax, and the downregulation of Bcl-2. Furthermore, the redox status of treated A549 cells revealed a marked rise in GSH and GPx activity levels and a decline in 4-HNE levels, indicating low oxidative stress following CPO treatment of A549 cells. In conclusion, cell cycle arrest and apoptosis, which are unrelated to oxidative stress, were the mechanisms by which CPO reduced cancer lung cell growth. This finding might be a potential therapeutic target for the treatment of lung cancer.Graphical abstractHypothetical scheme of CPO anticancer effects (mechanism of signaling) in A549 cells; in vitro. CPO treatment increases expression of p21, p53 and DNA fragmentation. These events cause arrest of cell cycle which was associated with significant induction in apoptosis via increase expression of caspases (-3,-7,-9), and Bax and downregulation of Bcl-2.

Extinction Risk Assessment and Chemical Composition of Aerial Parts Essential Oils from Two Endangered Endemic Malagasy Salvia Species.

Seven essential oil samples of two endemic species of Malagasy sage, Salvia sessilifolia Baker and Salvia leucodermis Baker, were investigated via GC(RI), GC-MS and 13C NMR spectrometry. In total, 81compounds were identified accounting for 93.5% to 98.7% of the total composition. The main constituents for the both species were (E)-β-caryophyllene (29.2% to 60.1%), myrcene (1.2% to 21.7%), α-humulene (5.2% to 19.7%), (E)-nerolidol (0.8% to 15.5%) and caryophyllene oxide (1.4% to 10.8%). Ethnobotanical survey of 46 informants revealed that decoctions of leafy twigs and chewed leaves were usually used. Due to the repeated fires, over-harvesting and grazing, the populations of S. sessilifolia and S. leucodermis are drastically fragmented. These risk factors led to threats to the habitats of the target species. Salvia sessilifolia Baker and Salvia leucodermis Baker are proposed to be classified as endangered species.

Artemisia argyi H.Lév. & Vaniot essential oil induces ferroptosis in pancreatic cancer cells via up-regulation of TFR1 and depletion of γ-glutamyl cycle

Artemisia argyi H.Lév. & Vaniot, a traditional Chinese medicine with a history spanning over two millennia, has been extensively used in folk medicine to treat dysmenorrhea, uterine bleeding and inflammation. Recent studies have demonstrated that the essential oil extracted from Artemisia argyi H.Lév. & Vaniot, known as AAEO, exhibits significant anti-tumor properties against liver and lung cancers. There is a scarcity of research on the potential impact of AAEO on pancreatic cancer (PC) cells. In this study, UPLC-MS/MS-based metabolomics method was established to evaluate the effect of AAEO on the proliferation of PC cells. The differential compounds included 5-oxoproline, glutamate, γ-glutamylcysteine, glutathione, arachidonic acid, adrenal acid and linoleic acid were detected by metabolomics, enriching in the γ-glutamyl cycle and polyunsaturated fatty acid metabolism, which were closely related to ferroptosis. Meanwhile, AAEO dramatically increased the levels of intracellular iron ion via up-regulation of TFR1, augmented reactive oxygen species and malondialdehyde in a dose-dependent manner by down-regulation of γ-glutamyl cycle through decreasing expressions of SLC7A11. Additionally, β-caryophyllene oxide, one of the main components of AAEO, could covalently bind to Cys in SW1990 cells to form a conjugate Cpo-Cys, resulting in the inhibition of glutathione synthesis. Importantly, the ferroptosis inhibitor deferoxamine significantly blocked the inhibitory effect of AAEO on SW1990 cells. Meanwhile, β-caryophyllene oxide, dihydro-β-ionone and α-bisabolol had strong binding force with GPX4, SLC7A11 and TFR1, respectively. These findings showed that AAEO induced ferroptosis via regulation of γ-glutamyl cycle by SLC7A11 and iron disorders by TFR1. Our study discovered AAEO as a potential therapeutic approach to induce ferroptosis to prevent or treat PC.

Essential oil composition, antimicrobial and antioxidant properties of Pluchea eupatorioides Kurz collected from Vietnam

Pluchea eupatorioides Kurz, which belongs to the family Asteraceae, is known for its medicinal properties and has been traditionally used to treat various diseases. This study aimed to investigate the chemical composition of the essential oil extracted from the aerial parts of P. eupatorioides and evaluate its antimicrobial and antioxidant activities. The essential oil was isolated by hydrodistillation and analysed by gas chromatography/ mass spectrometry (GC/MS). Thirty-three volatile compounds were identified in P. eupatorioides essential oil, including β-caryophyllene (29.36%), 2,5-dimethoxy-p-cymene (18.41%), α-isocomene (15.74%), and caryophyllene oxide (9.77%) as the major compounds. The antimicrobial activity of P. eupatorioides essential oil was investigated using a broth microdilution assay to determine the minimum inhibitory concentration (MIC). The results indicated that P. eupatorioides essential oil demonstrated effectiveness against Staphylococcus aureus ATCC 25923 and Candida albicans ATCC 10231 with a MIC of 100 µg/mL. Moreover, the essential oil was also found to be effective against Bacillus cereus ATCC 14579 and Escherichia coli ATCC 25922, but with a slightly higher MIC of 200 µg/mL. Furthermore, the antioxidant activity of P. eupatorioides essential oil was determined using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) scavenging assays. The IC50 values calculated using the DPPH and ABTS assays were 164.2 and 136.1 µg/ mL, respectively. These findings demonstrate that the P. eupatorioides essential oil could be used as a potential source of antimicrobial and antioxidant agents for the food and pharmaceutical industries. This is the first report describing the chemical compositions, antimicrobial and antioxidant activities of P. eupatorioides essential oil.

A COMPREHENSIVE REVIEW ON LEMONGRASS (CYMBOPOGON CITRATUS) OIL EXTRACTION AND ITS APPLICATIONS

This article presents a comprehensive review of methods of extraction, properties, compositions and industrial application of lemongrass essential oil. Lemongrass (Cymbopogon citratus) essential oil has been used traditionally since ancient days in medicine as remedy to improve blood circulation, treat fever and malaria, promote digestion and as well used to increase immune system of the human body. Essential Oils of lemongrass are used in various industries. Some of the industries in which they are used extensively include Aromatherapy, Food and drink industry, Pharmaceuticals industry, Fragrance and Flavour industry, Agriculture and Livestock industry, Cosmetic and Soaps industry, House hold and Domestic. The quality of the essential oil from lemongrass strongly depends on the extraction method and operating conditions. Basically lemongrass essential oil can be obtained by various extraction methods, such as steam distillation, conventional solvent extraction, Soxhlet extraction, ultrasound-assisted extraction (UAE), hydrodistillation (HD), microwave-assisted hydrodistillation (MAHD), Simultaneous-distillation-extraction technique (SDE), Solvent-Free-Microwave-Extraction Technique (SFME) and supercritical fluid extraction (SFE) with CO2. The composition of essential oil of Cympobogon citratus contains α-pinene, β-pinene, delta-3-catrene, myrcene dipentene, β-phellandrene, β-cymene , methyl heptanene, citronellal, β-elemene, β-caryophyllene, citronellyl acetate, geranyl acetate , citral A , citral B, geraniol, elemol , and β-caryophyllene oxide, etc. In addition, lemongrass oil also contains essential minerals such as Fe, Zn, Mg, Na, K, Ca, Mn, P etc. The most important physicochemical properties of lemongrass oil includes specific gravity, Optical rotation, refractive index, percentage of citral, freezing point, moisture content, acid value, ester value, carbonyl value and phenol content . Nevertheless, the chemical composition of the essential oil of Lemongrass also varies with the geographical origin, cultivation practices, plant age, photoperiod, harvest period, cultivars, and extraction methods. However, for extraction of lemongrass oil, green technology such SFE, SDE, SFME and MAHD that are consumer and environmental friendly in industrial-scale essential oil production should be considered as a method to overcome the limitations of traditional distillation methods. KEYWORDS: Essential Oil, Lemongrass, Microwave-Assisted-Hydrodistillation. Solvent Extraction, Steam Distillation, Supercritical Fluid Extraction

Preparation, physicochemical characterization and computational studies of Plectranthus ornatus codd essential oil/β-cyclodextrin inclusion complex

This study aims to prepare and chemically characterize inclusion complexes (IC) between β-cyclodextrin (β-CD) and Plectranthus ornatus essential oil (OEPO). Samples were evaluated by gas chromatography coupled with mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (FTIR). Moreover, a theoretical study concerning inclusion complexes of β-CD with the four main compounds of OEPO through Molecular Dynamics (MD) simulations, Density Functional Theory (DFT) and Parametric Method-6 (PM6) calculations was performed. The GC-MS analysis of OEPO resulted in the identification of 36 volatile compounds, with the four main components of this essential oil being: β-caryophyllene (21.52%), terpinen-4-ol (6.89%), phytol (4.00%) and caryophyllene oxide (3.32%). The GC-MS results indicated the presence of OEPO volatile compounds in the ICs prepared by the water/ethanol kneading (KWE) and water kneading (KW) method. More specific, β-CD inclusion complexes with β-butoxyethanol (1.15%), 1,3,8-ρ-menthatriene (0.45%), β-caryophyllene (0.20%), phytol (0.41%) and δ-cadinol (0.20%) prepared by the KWE method were detected, while the KW inclusion method resulted in the encapsulation of β-butoxyethanol (3.98%) only. The higher inclusion content of OEPO molecules in KWE was also confirmed by FTIR, with the KWE complex showing more OEPO absorption bands than KW. The PM6 study showed that hydrogen bonds are important, but hydrophobic interactions are the main driving force for triggering the complex formation of the main OEPO volatile compounds with β-CD. The intermolecular host-guest interactions and the investigation for the most suitable inclusion mode were examined by conducting several Molecular dynamics simulations. Moreover, PM6 and DFT approaches revealed the most stable cyclodextrin inclusion complex structures. These findings are in accordance with the experimental data from GC-MS analysis. The effect of solvent on the interaction energy was also studied through simulations and the results showed that the most stable structures are characterized by the formation of hydrogen bonds between guests and cyclodextrin hosts. The developing of such preparation methods that results in ICs like OEPO/β-CD may be useful in the optimization of existing formulations and therefore, be adopted by the pharmaceutical industry

Changes in the essential oil content and composition of pelargonium graveolens l’hér with different drying methods

In this study, the effect of various drying methods (fresh plant, shade-drying, sun-drying, and oven-drying at 30 and 60 °C) on the essential oil (EO) composition of rose-scented geranium were determined. Essential oil samples were extracted by hydrodistillation and analyzed by GC and GC-MS systems. The highest EO contents were obtained in the fresh plant (1.98%), followed by shade-drying (1.34 %) and oven-drying at 30 °C (1.20 %). The main components were citronellol (23.99-39.87%), geraniol (4.15-17.09%), menthone (4.48-8.34%), linalool (1.96-7.42%), β-caryophyllene (2.63-4.32%), geranyl tiglate (0.99-4.52%), citronellyl butyrate (0.53-5.31%) and cis-rose oxide (0.71-3.15%). The drying methods showed a marked impact on the constituents of the EO samples. The results demonstrated that drying the aerial parts of fresh geranium, and shade-drying and oven-drying at 30 °C were the best optimal methods to obtain the highest oil yield, and citronellol, geraniol, and linalool contents in the oil.

Essential Oils of Alpinia monopleura and Their Antibacterial and Antioxidant Activity

Alpinia monopleura is an endemic plant which widespread and abundant in Sulawesi. Nevertheless, previous studies have not studied the chemical compound and biological activity. This study describes the chemical compounds and antibacterial and antioxidant properties of the essential oils isolated from A. monopleura. The essential oil was obtained by the hydro distillation method and interpreted by GCMS. Antibacterial properties were determined by the agar diffusion method, while DPPH and ABTS determined antioxidant activity. The most important components are α-caryophyllene, β-pinene, limonene, α-pinene, β-caryophyllene and caryophyllene oxide. Essential oils of leaves and fruit showed excellent antibacterial properties with a MIC strength of 31.3 μg/mL against Staphylococcus aureus ATCC 25023 and Escherichia coli ATCC 35218. The highest antioxidant effect was also shown by inhibiting ABTS and DPPH radicals, with IC50 strength ​​of essential oil obtained from the leaf being 15.60 and 19.42 μg/mL, respectively, while from the fruit were 10.44 and 11.93 μg/mL. These antibacterial and antioxidant properties indicate that essential oils have advantages in their use in the food and pharmaceutical industries.

Chemistry and Bioactivity of Croton Essential Oils: Literature Survey and Croton hirtus from Vietnam.

Using essential oils to control vectors, intermediate hosts, and disease-causing microorganisms is a promising approach. The genus Croton in the family Euphorbiaceae is a large genus, with many species containing large amounts of essential oils, however, essential oil studies are limited in terms of the number of Croton species investigated. In this work, the aerial parts of C. hirtus growing wild in Vietnam were collected and analyzed by gas chromatography/mass spectrometry (GC/MS). A total of 141 compounds were identified in C. hirtus essential oil, in which sesquiterpenoids dominated, comprising 95.4%, including the main components β-caryophyllene (32.8%), germacrene D (11.6%), β-elemene (9.1%), α-humulene (8.5%), and caryophyllene oxide (5.0%). The essential oil of C. hirtus showed very strong biological activities against the larvae of four mosquito species with 24 h LC50 values in the range of 15.38-78.27 μg/mL, against Physella acuta adults with a 48 h LC50 value of 10.09 μg/mL, and against ATCC microorganisms with MIC values in the range of 8-16 μg/mL. In order to provide a comparison with previous works, a literature survey on the chemical composition, mosquito larvicidal, molluscicidal, antiparasitic, and antimicrobial activities of essential oils of Croton species was conducted. Seventy-two references (seventy articles and one book) out of a total of two hundred and forty-four references related to the chemical composition and bioactivity of essential oils of Croton species were used for this paper. The essential oils of some Croton species were characterized by their phenylpropanoid compounds. The experimental results of this research and the survey of the literature showed that Croton essential oils have the potential to be used to control mosquito-borne and mollusk-borne diseases, as well as microbial infections. Research on unstudied Croton species is needed to search for species with high essential oil contents and excellent biological activities.

Chemical compositions of Litsea umbellata and inhibition activities

Abstract Litsea umbellata (Lour.) Merr. is a plant commonly grown in Vietnam and some Asian countries. The plant is used in traditional medicines and exhibits significant biological activities. However, the sesquiterpenes’ extraction in the essential oil (EO) of L. umbellata harvested from the northern region of Vietnam has been limitedly known. Therefore, in the present study, the L. umbellata leaves and stem EOs were obtained by hydrodistillation method, then determined for the phytochemical profile by using gas chromatography–mass spectrometry system, and investigated the cytotoxicity activities against five cancer cell lines. Results have identified a total of 21 and 26 compounds in the EOs of L. umbellata leaves and stem, respectively, with the main sesquiterpene compounds being β-caryophyllene (16.87–11.04%), (+)-spathulenol (9.74–6.57%), β-caryophyllene oxide (26.12–18.34%), and (−)-spatulenol (11.08–8.8%). L. umbellata leaves exhibit significant anti-cancer activity with IC50 values ranging from 29.58 to 62.96 µg/ml. Otherwise, L. umbellata EOs also exhibited the good inhibition activities against DPPH free radical and three bacteria strains. The chemical constituents and cytotoxicity activity of L. umbellata EO stems have been reported for the first time and provided the future applications of this plant.

Study of Plant Growth and Essential Oil of Nepeta cataria L. in Kazakhstan

The genus Nepeta exhibits a wide spectrum of biological activity in medicine, agriculture, and the food industry. The purpose of the research is to develop the optimal agricultural technology for plantation cultivation of Nepeta cataria L. with the preservation of useful properties and to increase the content of essential oil in the conditions of Northern Kazakhstan. The objects of research are annual plants N. cataria L. growing on a plantation in the Akmola region. It has been reliably proven that the increase in the growth of N. cataria L., the biomass, and the yield is positively affected by the application of complex fertilizer N100P80K120. The essential oil yield was 0.52% in the experiment without fertilizers and 0.57% in the experiment with fertilizers. The main components of the essential oil of N. cataria L. grown in the experimental plots (plot #1 and plot #2) were 4aα7α7aα-Nepetalactone (76.5612 and 79.3200%), β-caryophyllene (4.0001 and 4.0351%) and caryophyllene oxide (1.9789 and 2.5969%). The remaining components were contained in the essential oil in small quantities. The composition of the essential oil of plants from Kazakhstan was similar to the composition of the essential oil of plants from central Iran, Egypt, and Korea, because the main substance was nepetalactone. The conducted studies prove the success of growing catnip in the conditions of Northern Kazakhstan.

Isolation and Characterization of One New Natural Compound with Other Potential Bioactive Secondary Metabolites from Glycosmis cyanocarpa (Blume) Spreng. (Family: Rutaceae)

Glycosmis cyanocarpa (Blume) Spreng is a plant in the Rutaceae family and a species in the Glycosmis genus that has received little attention. Therefore, this research aimed to report the chemical and biological analysis of Glycosmis cyanocarpa (Blume) Spreng. The chemical analysis involved the isolation and characterization of secondary metabolites through an extensive chromatographic study, and the structures of these metabolites were elucidated on the basis of a detailed analysis of NMR and HRESIMS spectroscopic data and by comparison with those of related compounds reported in the literature. Different partitions of the crude ethyl acetate (EtOAc) extract were evaluated for antioxidant, cytotoxic, and thrombolytic potentials. In chemical analysis, one new phenyl acetate derivative, namely 3,7,11,15-tetramethylhexadec-2-en-1-yl 2-phenylacetate (1), along with four known compounds N-methyl-3-(methylthio)-N-(2-phenylacetyl) acrylamide (2), penangin (3), β-Caryophyllene oxide (4), and acyclic diterpene-phytol (5) were isolated for the first time from the stem and leaf of the plant. The ethyl acetate fraction showed significant free radical scavenging activity with an IC50 value of 11.536 µg/mL compared to standard ascorbic acid (4.816 µg/mL). In the thrombolytic assay, the dichloromethane fraction showed the maximum thrombolytic activity of 16.42% but was still insignificant compared to the standard streptokinase (65.98%). Finally, in a brine shrimp lethality bioassay, the LC50 values of dichloromethane, ethyl acetate, and aqueous fractions were found to be 0.687 µg/mL, 0.805 µg/mL, and 0.982 µg/mL which are significant compared to the standard vincristine sulfate of 0.272 µg/mL.

Duguetia lanceolata A. St.-Hil. (Annonaceae) Essential Oil: Toxicity against Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae) and Selectivity for the Parasitoid Trichogramma pretiosum Riley (Hymenoptera: Trichogrammatidae)

The fall armyworm (FAW) Spodoptera frugiperda is a polyphagous pest that is difficult to control due to populations resistant to various active ingredients. Thus, the objective of this study was to evaluate the toxicity of essential oils (EOs) from the organs of Annona neolaurifolia, Duguetia lanceolata, and Xylopia brasiliensis, against the FAW and its natural enemy, Trichogramma pretiosum. The most active EOs were those from the leaves and stem bark of D. lanceolata, which presented LD90 to S. frugiperda equal to 70.76 and 127.14 µg of EO/larvae, respectively. The major compounds in the EO of D. lanceolata (leaves) were β-caryophyllene and caryophyllene oxide. Although individually inactive against the FAW, when combined, those compounds reduced the insect’s probability of survival. However, the mortality was lower than that caused by EO. This result suggests that other components of EO contribute to the activity against FAW. Furthermore, the EO of the leaves from D. lanceolata presented low toxicity to the egg-larva stage of T. pretiosum, but was toxic to other phases. Thus, EO from D. lanceolata is potentially useful for developing new products to control S. frugiperda.

Chemical composition and antimicrobial activity of essential oils from leaves and rhizomes of Curcuma zedoaria obtained via supercritical fluid extraction

Supercritical fluid extraction is a rapid, selective, and environmentally friendly method of particular interest in the extraction of essential oils from plants and herbs. Curcuma zedoaria is a member of the Zingiberaceae family widely cultivated in India, China, and Southeast Asia, including Vietnam. This study examined the chemical composition and antimicrobial activity of essential oils from the leaves and rhizomes of C. zedoaria from Vietnam obtained via supercritical fluid extraction. The main compounds of leaf essential oil were iso-borneol (31.2%), β-elemene (14.7%), β-caryophyllene (11.4%), 1,8-cineole (9.7%), and caryophyllene oxide (5.9%). In rhizome essential oil, 1,8-cineole (41.7%), β-elemene (13.6%), curzerenone (12.3%), camphor (10.2%), and germacrene B (5.2%) comprised the main compounds. The essential oils from C. zedoaria leaves and rhizomes displayed antimicrobial activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus cereus, and Candida albicans, with minimum inhibitory concentration values ranging from 100–400 µg/mL. Thus, our results support the need for further investigation of C. zedoaria essential oils as a potential source of antimicrobial agents.

Hydrolats from Humulus lupulus and Their Potential Activity as an Organic Control for Varroa destructor

Varroa destructor is a parasitic mite, which is considered a severe pest for honey bees causing serious losses to beekeeping. Residual hydrolats from steam extraction of hop essential oils, generally considered as a waste product, were tested for their potential use as acaricides on V. destructor. Four hop varieties, namely Cascade, Spalt, Victoria, and Mapuche, showed an interesting performance as feasible products to be used in the beekeeping industry. Some volatile oxidized terpenoids were found in the hydrolats, mainly β-caryophyllene oxide, β-linalool, and isogeraniol. These compounds, together with the presence of polyphenols, flavonoids, and saponins, were probably responsible for the promissory LC50 values obtained for mites after hydrolat exposition. Victoria hydrolat was the most toxic for mites (LC50: 16.1 µL/mL), followed by Mapuche (LC50 value equal to 30.1 µL/mL), Spalt (LC50 value equal to 114.3 µL/mL), and finally Cascade (LC50: 117.9 µL/mL). Likewise, Spalt had the highest larval survival, followed by Victoria and Mapuche. Cascade was the variety with the highest larval mortality. In addition, none of the extracts showed mortality higher than 20% in adult bees. The Victoria hydrolat presented the best results, which makes it a good compound with the prospect of an acaricide treatment against V. destructor.

Quantitative Determination of Cannabis Terpenes Using Gas Chromatography-Flame Ionization Detector.

Background: Cannabis has a long history of being credited with centuries of healing powers for millennia. The cannabis plant is a rich source of cannabinoids and terpenes. Each cannabis chemovar exhibits a different flavor and aroma, which are determined by its terpene content. Methods: In this study, a gas chromatography-flame ionization detector method was developed and validated for the determination of the 10 major terpenes in the main three chemovars of Cannabis sativa L. with n-tridecane used as the internal standard following the standard addition method. The 10 major terpenes (monoterpenes and sesquiterpenes) are α-pinene, β-pinene, β-myrcene, limonene, terpinolene, linalool, α-terpineol, β-caryophyllene, α-humulene, and caryophyllene oxide. The method was validated according to Association of Official Analytical Chemists guidelines. Spike recovery studies for all terpenes were carried out on placebo cannabis material and indoor-growing high THC chemovar with authentic standards. Results: The method was linear over the calibration range of 1-100 μg/mL with r2>0.99 for all terpenes. The limit of detection and limit of quantification were calculated to be 0.3 and 1.0 μg/mL, respectively, for all terpenes. The accuracy (%recovery) at all levels ranged from 89% to 104% and 90% to 111% for placebo and indoor-growing high THC chemovar, respectively. The repeatability and intermediate precision of the method were evaluated by the quantification of target terpenes in the three different C. sativa chemovars, resulting in acceptable relative standard deviations (less than 10%). Conclusions: The developed method is simple, sensitive, reproducible, and suitable for the detection and quantification of monoterpenes and sesquiterpenes in C. sativa biomass.

β-Caryophyllene oxide inhibits metastasis by downregulating MMP-2, p-p38 and p-ERK in human fibrosarcoma cells.

When cancer cells transform into malignant tumors, they gain the ability to ignore growth-inhibiting signals, have endless reproduction potential, resist apoptosis, and induce angiogenesis and invade other tissues. Matrix metalloproteinases (MMPs) allow tumor cells to move into surrounding tissues in many malignancies, but metastasis is blocked by MMPs inhibitors. Therefore, the effect of β-caryophyllene oxide (CPO) contained in Piper nigrum on Mitogen-activated protein kinase (MAPKs) related to MMPs signaling pathways in human fibrosarcoma was examined in HT1080 cells. The effect of CPO on cell viability was performed using the MTT assay. Cytotoxicity was observed in the presence of CPO above 16 μM. Next, gelatin zymography was performed in the cells activated with phorbol-12-myristate-13-acetate (PMA). It was found that CPO at 32 μM reduced MMP-9 activity by 28% and MMP-2 activity by 60%. To confirm the effect of CPO on MMPs, Western blot analyses for MMP-2, MAPKs were carried out in this study. The expression level of MMP-2 was reduced by 45% in the presence of CPO at 32 μM, but those of p-p38 and p-ERK were reduced by 50% and 40%, respectively. CPO decreased the expression levels of MMP-2 and MMP-9 in the immunofluorescence staining assay. Finally, an invasion assay was performed in PMA-treated human fibrosarcoma cells. It was demonstrated that CPO reduced cell invasion of HT1080 cells in a dose-dependent manner starting at a concentration of 2μM. The above results suggest that CPO could be used as a potential candidate for the treatment of metastasis by inhibiting MMP-2, p-p38 and p-ERK. PRACTICAL APPLICATIONS: Cancer makes it easier for cells to spread to other tissue via blood and lymph systems. Tumor cells deplete nutrients and induce angiogenesis, which penetrates and spreads to other parts of the body. As a result, the effect of CPO against cell invasion was evaluated in this study. CPO reduced cancer cell invasion by inactivating p-ERK and p-p38, according to the findings. MMP-2 and MMP-9 activation and protein expression were also decreased by CPO. As a result, CPO might be used as an alternate treatment agent for preventing metastasis.

Óleos essenciais das partes aéreas de quatro espécies of Protium (Burseraceae) – Uma contribuição para a flora aromática da Reserva Florestal Adolpho Ducke, Amazonas, Brasil

The Adolpho Ducke Forest Reserve is a fragment of the Amazon Rainforest that has the highest density of collections deposited in the INPA herbarium, and this characterized, vascular flora has been an important basis for chemical studies. This paper describes the chemical composition of the volatiles of aerial parts of the four species of Protium that occurr in the Ducke Reserve. The essential oils obtained by hydrodistillation were analyzed using GC-FID and GC-MS. P. altsonii showed high percentages of the monoterpenes α-pinene (22.05%) and limonene (17.76%) in the leaves, and linear long-chain fatty alcohols, such as n-tetradecanol (19.93%) and hexadecanol (32.56%), in the branches. The essential oil from leaves of P. laxiflorum provided sesquiterpenes α-copaene (18.98%), epi-α-cadinol (9.17%) and β-caryophyllene (9.04%) as the main compounds. In P. pallidum, the sesquiterpenes caryophyllene oxide (29.72%), α-cadinol (28.82%) and epi-α-cadinol (13.96%) were predominant in the leaves, and α-cadinol (25.50%), α-eudesmol (22.29%) and caryophyllene oxide (12.81%) predominated in the branches. β-Caryophyllene (30.59%) and caryophyllene oxide (20.63%) were the main compounds in the leaves of P. paniculatum var. riedelianum. The results presented herein contribute to the knowledge of the aromatic flora of the Ducke Reserve.

Teucrium scordium L. and Mentha pulegium L. essential oil importance in adaptive response to salinity stress

Plant secondary metabolites, including essential oils, are very important in the adaptive responses to stress conditions. Salt stress is a major element in natural saline habitats. Plants adapted to variations in substrate salinity (such as facultative halophytes) are very suitable for comparative analysis of the adaptive response under saline conditions on natural habitats. Based on their distribution on both saline and non-saline habitats, Teucrium scordium L. and Mentha pulegium L. were selected to determine the potential importance of essential oil components in the adaptive response to salt-induced stress conditions as stress-related metabolites. Quantitative-qualitative analysis of essential oils in plant material of the tested species sampled from two saline habitats was performed and compared with samples from non-saline habitat. The prepared plant material of T. scordium and M. pulegium was hydrodistilled using a Clevenger-type apparatus by standard procedure. Volatile compounds were analyzed by GC/MS. The qualitative composition of the T. scordium and M. pulegium essential oils are related to the substrate salinity. The results obtained for the composition of the essential oils indicate that the adaptive response is specific and can be taxonomically related. Both analyzed plants are characterized by the increased synthesis of individual components of essential oil that are potentially important in the adaptive response to saline stress conditions. The adaptive response to saline stress of the analyzed plants includes increased synthesis of individual components of essential oils. Essential oil components such as α-pinene, β-pinene, β-caryophyllene, limonene and caryophyllene oxide, as well as piperitenone, pulegone, isopulegone are important in the adaptive response on saline habitats for T. scordium and M. pulegium, respectively.