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Evaluation of the leishmanicidal activity of different mixtures of β-caryophyllene oxide and lupenone against Old and New World Leishmania spp. showed that both the pure β-caryophyllene oxide and the 1:4 mixture of lupenone and β-caryophyllene oxide are similarly active against promastigotes of L. amazonensis, L. braziliensis, L. mexicana, L. tropica, and L. aethiopica, with IC50 values ranging from 14 to 39.3 μg/ml, and reduce the infectivity of macrophages by L. mexicana and L. tropica. However, the 1:4 mixture of lupenone and β-caryophyllene oxide showed a better selectivity index than the pure sesquiterpene and increased production of NO, H2O2, and cytokines; these results suggest that the 1:4 mixture of terpenoids has both leishmanicidal activity and an immunomodulator effect, without affecting cell viability.

To predict important secondary organic aerosol (SOA) properties, information on viscosity or diffusion rates within SOA is needed. Ozonolysis of β-caryophyllene is an important SOA source; however,...

Objective: To research the biological impact on the endocannabinoid system (ECS) from dietary sources of [Formula: see text]-caryophyllene (BCP). This will encompass pre-clinical and clinical research for BCP. The bioavailability of BCP will be explored, focusing on bioavailability improvement. This research will establish if there is justification to warrant the development of a medical food for supporting the ECS through dietetic supplementation of BCP. Methods: Research and review papers were identified through the search engines Google Scholar, PubMed, and ScienceDirect. Main keywords included [Formula: see text]-caryophyllene, endocannabinoid system, dietary cannabinoids, cannabinoid type-2 receptor, and bioavailability. Results: The human body is limited in the digestion of BCP from food. This is because BCP is poorly absorbed in the gut. Everyone has different underlying endocannabinoid efficiency and most people do not have the full potential of supporting their ECS through diet. Conclusion: A medical food can be developed to use BCP with a delivery system, so that the bioactive food cannabinoid is readily absorbed. This will deliver dietary support to the ECS, that otherwise would be available from food. This review provides insight into the efficacy of using BCP in medical foods as dietary support for the ECS. Supporting the ECS can assist in maintaining homeostasis, regulating immune function, pain intensity, inflammatory markers, sleep patterns, mood, appetite, and stress susceptibility.

The experimental vapor–liquid equilibrium (VLE) data for a ternary system of β-caryophyllene + dipentene + α-pinene and two binary systems composed of β-caryophyllene (1) + dipentene (2) and dipent...

The aim of this study was to examine whether the process of initial colonization and the formation of mature biofilm structure of foodborne bacterial pathogens Listeria monocytogenes and Salmonella typhimurium can be impeded by active essential oil components β-caryophyllene, cinnamaldehyde and eugenol at their individual and combined effects. Among the essential oil components tested, cinnamaldehyde and eugenol at their individual effect showed >50% degradation in biofilm biomass against preformed (matured) biofilms of both the studied bacteria, whereas β-caryophyllene failed to do so. In combination, cinnamaldehyde/eugenol blend showed synergistic antibiofilm efficacy against preformed biofilms of both the studied bacteria L. monocytogenes (FICI: 0·24) and S. typhimurium (FICI: 0·40), whereas other tested combinations showed additive antibiofilm efficacy with FICI ranged from 2·02 to 2·35. Essential oil components alone and in combination also showed much higher inhibition effect on biofilm formation at the initial stage compared to their inhibition effect on preformed biofilms. The results provide evidence that cinnamaldehyde/eugenol combination may help in designing a more potent novel, natural antibiofilm blend at sufficiently low concentrations in the food and pharmaceutical industries. SIGNIFICANCE AND IMPACT OF THE STUDY: In the present work, synergistic antibiofilm efficacy of cinnamaldehyde/eugenol combination against established biofilms of foodborne bacterial pathogens Listeria monocytogenes and Salmonella typhimurium has been reported. These synergistic interactions may help in designing a more potent, safe and effective novel natural antibiofilm agent in food and pharmaceutical industries. Besides, this combination will also be helpful in reducing concentration of individual components, thereby minimizing the undesirable impact on sensory properties of food. To our knowledge, this is the first time, synergistic antibiofilm efficacy of cinnamaldehyde/eugenol blend against established biofilms of foodborne bacterial pathogens has been reported.

Aging is associated with detrimental cellular and cognitive changes, making it an important public health concern; yet, many of these changes may be influenced by nutritional interventions. The natural sesquiterpene β-caryophyllene (BCP) has anti-inflammatory and antioxidant effects that are mediated by cannabinoid type-2 receptor activation, and these actions promote neuroprotection in different animal models that involve a cognitive damage. Consequently, whether chronic administration of BCP might prevent the age-related cellular and cognitive damage in a model of aging induced by chronic d-galactose (GAL) consumption was assessed here. Male BALB/c mice were administered BCP (10 mg/kg, oral), GAL (300 mg/kg, intraperitoneal), or GAL+BCP, and long-term memory and cognitive flexibility were evaluated in the normal and the reverse phases of Morris water maze test. In addition, immunohistochemistry was performed on prefrontal and hippocampal brain slices to detect glial acidic fibrillary protein and DNA oxidation. Although GAL administration reduced cognitive flexibility (

Epilobium angustifolium L. is a plant widely used in folk medicine. It is rich in biologically active compounds including phenols, flavonoids, terpenes, aliphatic acids and sterols; however, until now, little attention has been paid to its volatile components. This research demonstrated that Epilobium angustifolium L. is rich in β-caryophyllene that is possibly responsible for its unique therapeutic properties. The leaves of Epilobium angustifolium L. are traditionally used as a tea. On the other hand, β-caryophyllene is soluble in oils, thus an extract of Epilobium angustifolium L. in edible oils should also demonstrate a healing effect. Therefore, quick and reliable methods of β-caryophyllene determination in edible oils and in water solutions are required. In this work, headspace gas chromatography is suggested to determine β-caryophyllene. At the optimized chromatographic conditions for β-caryophyllene solutions in coconut oil the calibration curve was linear up to 10 mg g–1, the detection limit was 60 µg kg–1, for β-caryophyllene solutions in water the calibration curve was linear up to 40 µg l–1, and the detection limit was 6 µg l–1. The methods were applied for the β-caryophyllene determination in the extract of Epilobium angustifolium L. in sunflower oil and in Epilobium angustifolium L. tea.

The purpose of this study is to check the effectiveness of the analysis method that separates and quantifies β-caryophyllene among clove extracts and validate according to current ICH guidelines. The beta caryophyllene was active constituent of clove buds. The developed method gave a good detection response. In the specificity test, the standard solution was detected at about 17.316 minutes, and the test solution was detected at 17.317 minutes. The linearity of β-caryophyllen was confirmed, and at this time, the correlation coefficient (R 2 ) of the calibration curve showed a high linearity of 0.999 or more in the concentration range. The levels of LOD and LOQ were 1.28 ug/mL and 3.89 ug/mL, respectively. The accuracy was confirmed to be 101.6 ~ 102.2% and RSD 0.95 ~ 1.31%. As a result of checking the repeatability and inter-tester reproducibility to confirm the precision, the RSD was found to be 1.34 ~ 2.69%. This validated GC method was successfully applied to a soft capsule containing clove extract and other materials for clinical trials. Therefore, this method can be used as an analytical tool for quality control of various samples including clove extracts and their products for food and pharmaceutical uses.

Cinnamomum porrectum (Roxb.) Kosterm is an important plant which produces natural essential oil. In this study, essential oil was hydro-distilled from leaves of five different samples of C. porrect...

We examine synthesized standards of structurally related β-caryophyllene ozonolysis products at the air/water and air/ammonium sulfate (aq) interfaces using polarization-resolved standard- and high...

Chemical composition of the essential oils (16 samples) obtained by hydro-distillation from inflorescences and leaves of Helichrysum arenarium L. plants growing in Lithuanian forests is reported. F...

Lantana camara species is generally seen only as a detriment to plantations but it also possess medicinal potential. This work aimed to analyse the essential oil (EO) yield and chemical com...

Five novel formyl-phloroglucinol-β-caryophyllene meroterpenoids, namely littordials A–E (1–5), were isolated from the leaves of Psidium littorale. Their structures were established by spectroscopic data and computational methods, and the structure of 1 was confirmed by X-ray crystallography. Littordials A–E feature unusual acyl phloroglucinol units, and 5 possesses a rare 6/7/9/4-fused tetracyclic ring system. Compounds 2, 3 and 5 exhibited cytotoxic activities on two cancer cell lines (MDA-MB-231 and B16) with IC50 values from 6.6 ± 1.5 to 9.2 ± 1.7 μM.

By integrating organic synthesis, secondary organic aerosol synthesis and collection, density functional theory (DFT) calculations, and vibrational sum frequency generation (SFG) spectroscopy, we identify close spectral matches between the surface vibrational spectra of β-caryophyllene-derived secondary organic material (SOM) and those of β-caryophyllene aldehyde and β-caryophyllonic acid at various interfaces. Combined with the record high surface tension depression described previously for these same oxidation products, we discuss possibilities for an intrinsically chemical origin for cloud activation by terpene-derived surfactants. Although the present study does not unequivocally identify the synthesized and analyzed oxidation products on the β-caryophyllene-derived SOM surfaces, these two compounds appear to be the most surface active out of the series and have also been foci of previous β-caryophyllene field and laboratory studies. An orientation analysis by phase-resolved SFG spectroscopy reveals a...

Background: The β-caryophyllene (BCP), a phytocannabinoid present in various essential oils, demonstrated selective action on the CB2 endocannabinoid receptor and attracted considerable attention because of its several pharmacological activities. Despite this recognized potential, this hydrophobic compound is a volatile and acid-sensitive sesquiterpene that readily oxidizes when exposed to air, and has low bioavailability in oral formulations. Thus, the development of formulations that guarantee its stability and increase its bioavailability is a challenge for its use in the pharmaceutical field. Methods: The present review brings for the first time a comprehensive overview of the controlled and vectorized release formulations tested for BCP administration. Among these, we have addressed nanoemulsions, inclusion complexes with cyclodextrins, liposomes, wound dressings, nanocomposites and nanoparticles. A literature search was performed on Pubmed, Web of Science and Science direct, and patents documents were also searched on European Patent Office, World Intellectual Property Organization and Brazilian National Institute of Industrial Property. Results: The systems presented here may represent an interesting approach to overcome the limitations already mentioned for this terpene. These systems proved to be promising for improving solubility, stability and controlled release of this pharmacological relevant sesquiterpene. In the industrial field, some companies have filed patent applications for the commercial use of the BCP, however, the use of pharmaceutical formulations still appeared moderate. Conclusion: This prospective study evidenced the new perspectives related to BCP vectorization systems in the pharmaceutical and industrial marketing field and may serve as a basis for further research and pharmaceutical use of this powerful cannabinoid.

Eupatorium fortunei Turcz. is a widely used Chinese herbal medicine in China. In this study, a gas chromatography-triple quadrupole mass spectrometry (GC-MS/MS) method was developed and validated to simultaneously determine the contents of p-cymene, thymol, neryl acetate, and β-caryophyllene in roots, stems, and leaves of Eupatorium fortunei Turcz. harvested at different growth periods. All four constituents could be detected in leaves, three could be detected in stems except β-caryophyllene, and only thymol could be detected in roots. The order of the total contents of four constituents in different parts was leaves > stems > roots. It indicated that the leaves could be the proper medicinal parts of Eupatorium fortunei Turcz. The content of four constituents in leaves varied a lot among different growth periods and showed an M-shaped change trend with the growth of Eupatorium fortunei Turcz. The four constituents accumulated to the highest values in early July followed by mid-September. Accordingly, the best harvest time of Eupatorium fortunei Turcz. is early July and mid-September.

The activity of β-caryophyllene oxide as either a contact or noncontact repellent was evaluated against two laboratory strains (Aedes albopictus and Anopheles dirus) using an excito-repellency test system. N, N-Diethyl-3-methylbenzamide (DEET) was used as a standard reference baseline for comparative purposes. β-Caryophyllene oxide and DEET were tested at concentrations of 0.1, 0.25, 0.5 and 1.0% (v/v). In addition, the phototoxic and genotoxic effects of β-caryophyllene oxide were investigated on Balb/c 3T3 mouse fibroblasts (3T3-L1) and Chinese hamster ovary cell line (CHO-K1). The results demonstrated that the higher concentrations of test compounds (0.5 and 1.0%) produced greater behavioral responses. Aedes albopictus was more sensitive to β-caryophyllene oxide than An. dirus. Moderate avoidance response rates (25-56% escape) of Ae. albopictus at 0.5% and 1.0% β-caryophyllene oxide were observed in contact and noncontact trials compared with low response rates from An. dirus (26-31% escape). DEET at ≤1% displayed lower irritancy and repellency (1-38%) than β-caryophyllene oxide when tested against the two mosquito species. Knockdown responses (37%) were only observed in An. dirus exposed to 1% β-caryophyllene oxide in the contact trial. β-Caryophyllene oxide did not show any phototoxic potential (PIF= 0.38) nor was there any significant genotoxic response as indicated by no increase in micro-nucleated cells with or without metabolic activation. β-Caryophyllene oxide could be considered as a safe repellent, effective against mosquitoes.

(E)-&beta, caryophyllene (BCP) is a natural sesquiterpene hydrocarbon present in hundreds of plant species. BCP possesses several important pharmacological activities, ranging from pain treatment to neurological and metabolic disorders. These are mainly due to its ability to interact with the cannabinoid receptor 2 (CB2) and the complete lack of interaction with the brain CB1. A systematic analysis of plant species with essential oils containing a BCP percentage &gt, 10% provided almost 300 entries with species belonging to 51 families. The essential oils were found to be extracted from 13 plant parts and samples originated from 56 countries worldwide. Statistical analyses included the evaluation of variability in BCP% and yield% as well as the statistical linkage between families, plant parts and countries of origin by cluster analysis. Identified species were also grouped according to their presence in the Belfrit list. The survey evidences the importance of essential oil yield evaluation in support of the chemical analysis. The results provide a comprehensive picture of the species with the highest BCP and yield percentages.

The first semisynthetic route toward rumphellaones B (2) and C (3) and their C-8 epimers as well as the shortest synthesis of rumphellaone A (1) and its C-8 epimer from the most accessible sesquite...

A trial was conducted to evaluate the antiviral activity and immunomodulatory effect of B-Caryophyllene (BCP) using NDV as a viral model. First, an in ovo experiment was conducted to estimate the antiviral mechanism of BCP. Next, an in vivo experiment was designed to confirm its antiviral efficacy as well as its immunomodulatory and growth promoting ability. According to the in ovo experiment, BCP possesses antiviral influence up to 61.7% when treated before or during NDV infection. Oral supplementation of chickens with two doses of BCP (200 and 400 μg/bird) resulted in a significant increase in the NDV HI-Ab responses and a significant increase in interferon-α signaling cytokines. These obvious immunomodulatory effects improved the bird clinical protection against virulent NDV challenge. To conclude, we introduced a new compound for the poultry industry sector that has antiviral and immunostimulant properties when supplemented orally before or during NDV infection.

Simple Summary Caryophyllane sesquiterpenes are unique natural compounds widely occurring in nature, especially in plant essential oils, that are characterized by multiple properties of pharmacological interest. Although β-caryophyllene is the most investigated compound, its metabolite β-caryophyllene oxide and the analogues α-humulene and isocaryophyllene have been evaluated, too. Previous studies showed a polypharmacological profile of these compounds and a possible interest in cancer research; however, emerging evidence have highlighted a complex pool of healing properties, including a block of carcinogen-mediated DNA damage and cytoprotection against anticancer drug toxicity in noncancerous cells, along with antiproliferative and chemosensitizing activitives in cancer cells, thus suggesting their promising role as chemopreventive agents. In line with this evidence, the present review provides the pharmacological basis to support a further therapeutic interest for caryophyllane sesquiterpenes as chemopreventive agents. Moreover, possible structure–activity relationships and future research directions have been highlighted. Abstract Chemoprevention is referred to as a strategy to inhibit, suppress, or reverse tumor development and progression in healthy people along with high-risk subjects and oncologic patients through using pharmacological or natural substances. Numerous phytochemicals have been widely described in the literature to possess chemopreventive properties, although their clinical usefulness remains to be defined. Among them, caryophyllane sesquiterpenes are natural compounds widely occurring in nature kingdoms, especially in plants, fungi, and marine environments. Several structures, characterized by a common caryophyllane skeleton with further rearrangements, have been identified, but those isolated from plant essential oils, including β-caryophyllene, β-caryophyllene oxide, α-humulene, and isocaryophyllene, have attracted the greatest pharmacological attention. Emerging evidence has outlined a complex polypharmacological profile of caryophyllane sesquiterpenes characterized by blocking, suppressing, chemosensitizing, and cytoprotective properties, which suggests a possible usefulness of these natural substances in cancer chemoprevention for both preventive and adjuvant purposes. In the present review, the scientific knowledge about the chemopreventive properties of caryophyllane sesquiterpenes and the mechanisms involved have been collected and discussed; moreover, possible structure–activity relationships have been highlighted. Although further high-quality studies are required, the promising preclinical findings and the safe pharmacological profile encourage further studies to define a clinical usefulness of caryophyllane sesquiterpenes in primary, secondary, or tertiary chemoprevention.

Cannabinoids help in pain treatment through their action on CB1 and CB2 receptors. β-caryophyllene (BCP), an ancient remedy to treat pain, is a sesquiterpene found in large amounts in the essential oils of various spice and food plants such as oregano, cinnamon, and black pepper. It binds to the CB2 receptor, acting as a full agonist. Sex differences in the BCP-induced analgesic effect were studied by exposing male and female rats to a persistent/repeated painful stimulation. To simulate treatment of a repeated inflammatory condition, after the first formalin injection (FT1; 50 μl, 2.5%), rats received BCP per os for 7 days at two dosages: 5 and 10 mg/kg dissolved in olive oil (OIL). The control group was treated with OIL for 7 days. On day 8, the formalin test was repeated (FT2) with a lower formalin concentration (50 μl, 1%). During the first and second formalin tests, pain-induced responses (licking, flexing, and paw jerk) and spontaneous behaviors were recorded and analyzed. In the FT1 (before the beginning of treatment with BCP), females displayed higher pain responses than did males in terms of flexing duration during the first part of the test (I phase and interphase), while during the second part (II phase early and late) males showed higher levels than did females in licking duration. In the FT2, the pain responses generally decreased in the BCP groups in a dose-dependent manner (i.e., greater effect of BCP10), with a more pronounced reduction in males than in females; moreover, the pain responses remained high in the OIL groups and in the female BCP5 group. In conclusion, long-term intake of BCP appears to be able to decrease pain behaviors in a model of repeated inflammatory pain in both sexes, but to a greater degree in males.

The existing information supports the use of this material as described in this safety assessment. β-Caryophyllene was evaluated for genotoxicity, repeated dose toxicity, reproductive toxicity, local respiratory toxicity, phototoxicity/photoallergenicity, skin sensitization, and environmental safety. Data show that β-caryophyllene is not genotoxic. Data on β-caryophyllene provided a calculated Margin of Exposure (MOE) > 100 for the repeated dose toxicity and fertility endpoints. The developmental and local respiratory toxicity endpoints were evaluated using the Threshold of Toxicological Concern (TTC) for a Cramer Class I material, and the exposure to β-caryophyllene is below the TTC (0.03 mg/kg/day and 1.4 mg/day, respectively. Data show that there are no safety concerns for β-caryophyllene for skin sensitization under the current declared levels of use. The phototoxicity/photoallergenicity endpoints were evaluated based on data and ultraviolet/visible (UV/Vis) spectra; β-caryophyllene is not expected to be phototoxic/photoallergenic. The environmental endpoints were evaluated; β-caryophyllene was found not to be Persistent, Bioaccumulative, and Toxic (PBT) as per the International Fragrance Association (IFRA) Environmental Standards, and its risk quotients, based on its current volume of use in Europe and North America (i.e., Predicted Environmental Concentration/Predicted No Effect Concentration [PEC/PNEC]), are

Introduction: The effects of the grinding procedure on the supercritical fluid extraction (SFE) yields of eugenol, β-caryophyllene, α-humulene, and eugenyl acetate from clove are discussed in detail in this paper. Methods: For this purpose, five grinding procedures were employed: 1) continuous 1-min grinding, 2) continuous 2-min grinding, 3) two 1-min grinding periods with 6-min stop in between 4) continuous 4-min grinding, and 5) four 1-min grinding periods with 6-min stops in between. After that, the extractor was filled with 12 g of milled clove obtained using one of the grinding procedures while the other SFE parameters were kept constant (pressure of 150 bar, temperature of 40 °C, supercritical CO2 flow rate of 1.03×10−4 kg/s, static time of 20 min, and dynamic extraction time of 15 min). Then, the composition of the extract was evaluated by gas chromatography (GC). Conclusion: It was found that the grinding procedure has considerable effects on the recoveries of eugenol, β-caryophyllene, α-humulene, and eugenyl acetate from clove, and employing four 1-min grinding periods with 6-min stops in between as the grinding procedure gave the highest content of the aforementioned components in the extract.

A nature-inspired bioorthogonal reaction has been developed, hinging on an inverse-electron-demand Diels-Alder reaction of tetrazine with β-caryophyllene. Readily accessible from the cheap starting material through a scalable synthesis, the newly developed β-caryophyllene chemical reporter displays appealing reaction kinetics and excellent biocompatibility, which renders it applicable to both in vitro protein labeling and live cell imaging. Moreover, it can be used orthogonally to the strain-promoted alkyne-azide cycloaddition for dual protein labeling. This work not only provides an alternative to the existing bioorthogonal reaction toolbox, but also opens a new avenue to utilize naturally occurring scaffolds as bioorthogonal chemical reporters.

In this study, the chemical composition and antibacterial and antiproliferative potential of the essential oil obtained from fresh leaves of Psidium myrtoides (PM-EO) against oral pathogens and hum...

β-caryophyllene is a food additive that is found in food plants and has broad pharmacological potential. However, little toxicological information has been reported and its use is based on the fact that this bicyclic sesquiterpene is daily consumed as a plant food in much larger quantities than as a food additive. Thus, this study evaluated acute (14-day) and repeated-dose (28 days) oral β-caryophyllene toxicity in female Swiss mice analyzing changes in body weight, food intake, water intake, hematological and biochemical parameters, organ weight after necropsy, oxidative stress markers and histopathology of various tissues. Acute (300 and 2000 mg/kg) and repeated-dose (300 and 2000 mg/kg) toxicity studies were performed according to the Organization for Economic Cooperation and Development (OECD) guideline 423 and 407, respectively. There was absence of adverse clinical signs and mortality in any animal subjected to acute and repeated-dose toxicity study. In addition, no significant changes in body weight, food and water intake, oxidative stress biomarkers, hematological and biochemical parameters were observed when compared to control group from single-dose and repeated-dose toxicity study. Therefore, the results of this study provide an understanding of the toxicity profile of β-caryophyllene which can be considered a compound with toxicity at doses higher than 2000 mg/kg body weight.

Copaiba oleoresin presents several compounds with known biologic activity and physiologic effects, including analgesic and insecticide properties. Among them are the terpenoids (mainly dite...

Essential oils from the stems and leaves of Croton rhamnifolioides Pax and Hoffm from three locations in the semiarid region of the state of Pernambuco, Brazil, were investigated. Seventy constituents were identified by gas chromatography-mass spectrometry (GC-MS) of the oils from the municipalities of Serra Talhada (ST), Buique (BU) and Floresta (FL), representing 97.99±1.03% and 97.12±0.94% of the leaf and stem oils in ST, 97.42±0.77% and 97.50±0.68% in BU and 98.30±0.84% and 97.10±0.80% in FL. Sesquiterpenes were predominant in the oils. β-caryophyllene was the main constituent in all locations (ST: 22.45±0.70% in leaf oil and 25.80±0.63% in stem oil; BU: 33.34±0.56% in leaf oil and 38.45±0.95% in stem oil; FL: 26.67±0.53% in leaf oil and 29.50±0.86% in stem oil). Bicyclogermacrene (ST: 11.65±0.75% in leaf oil and 9.34±0.55% in stem oil; FL: 10.58±0.38% in leaf oil and 9.90±0.66% in stem oil) and 1,8-cineole (BU: 10.45±0.56% in leaf oil and 6.50±0.26% in stem oil) were also found in significant...

Sexual maturation of male Bactrocera correcta (Bezzi) and age-related responses to β-caryophyllene (CP) and methyl eugenol (ME) were examined to identify effective attractants for sexually immature males of the species. Sexual maturation rates (100 × number of cages containing males which attained sexual maturity/total number of cages at a given day) over different ages were 0.0%, 6.7%, and 100.0% for 5-, 6-, and 13-day-old, respectively, and at all the different ages, more males were captured with CP than with ME. The capture rate (the predicted probability by logistic regression) with CP was 29.7% (30.6%) for 5-day-old males, which were still sexually immature, and 52.7% (38.2%) for 6-day-old males, for which the earliest sexual maturation was observed. In contrast, no 5-day-old males responded to ME (the probability was 12.6%), and the capture rate (the probability) of 6-day-old males was merely 0.3% (14.5%), while the rate gradually increased later. The present study revealed that certain males of B. correcta responded to CP prior to sexual maturation but not to ME under the laboratory conditions. These results imply that CP could be an effective attractant used in male annihilation techniques for B. correcta and that ME may not be useful.

Pseudomonas fluorescens are able to cause the biodeterioration process of fresh-cut lettuce via the indole-3-acetic acid (IAA)-dependent type III secretion system (TTSS). The application of pepper EOs of proven of anti-IAA and anti-TTSS activities into salad dressing can reduce the organoleptic deterioration of fresh-cut leafy vegetables during storage. In this work, the influence of black and white pepper EOs on IAA production and on TTSS gene expression in P. fluorescens KM06 was examined. The black and white pepper EOs and β-caryophyllene at concentrations below the sub-MICs altered (i.e., 78%, 94%, and 90%, respectively) the IAA production in a 72 h old culture of P. fluorescens KM06. All the test agents significantly reduced the mRNA levels of the TTSS gene (−0.106, −0.428, and −0.448 for black pepper EO, white pepper EO and β-caryophyllene, respectively) (p

Spiranthera odoratissima A. St.-Hil. (Rutaceae), "manacá", is popularly used for head, muscle aches, rheumatism and, stomach, uterine, renal and liver disorders. The aims of this study were to investigate the physico-chemical and morphological properties of microencapsulated powder of volatile oil from S. odoratissima leaves, optimize the drying process and verify the influence of drying parameters on microencapsulation by spray-drying. The volatile oils from leaves were extracting by hydrodistillation in a Clevenger type apparatus and analyzed by GC/MS. The emulsions were prepared and spray-dried. Box-Behnken experimental model was used for optimize the effects of drying parameters on the encapsulation responses. The β-caryophyllene content in the microcapsules was determined by HPLC. The results suggest that the best operational conditions for the atomization drying of S. odoratissima volatile oil were inlet temperature of 158°C, feed flow of 0.25L/h and drying nozzle diameter of 0.7mm. These results reveal the technological potential of the microcapsules obtained from S. odoratissima volatile oils. Spiranthera odoratissima A. St.-Hil. (Rutaceae), "manacá", se usa popularmente para dolores de cabeza, musculares, reumatismo, estomago, útero, renales y trastornos hepáticos. Los objetivos de este estudio fueron investigar las propiedades físico-químicas y morfológicas del polvo microencapsulado de aceite volátil de hojas de S. odoratissima, optimizar el proceso de secado y verificar la influencia de los parámetros de secado en la microencapsulación por atomización. Los aceites volátiles de las hojas se extrajeron por hidrodestilación en un aparato tipo Clevenger y se analizaron por GC / MS. Las emulsiones se prepararon y se secaron por pulverización. Se utilizó el modelo experimental Box-Behnken para optimizar los efectos de los parámetros de secado en las respuestas de encapsulación. El contenido de β-cariofileno en las microcápsulas se determinó mediante HPLC. Los resultados sugieren que las mejores condiciones operativas para el secado por atomización del aceite volátil de S. odoratissima fueron una temperatura de entrada de 158 °C, un flujo de alimentación de 0,25 L / h, un diámetro de boquilla de secado de 0,7 mm. Estos resultados revelan el potencial tecnológico de las microcápsulas obtenidas a partir de aceites volátiles de S. odoratissima. Spiranthera odoratissima A. St.-Hil. (Rutaceae), "manacá", é utilizada popularmente para tratar dores de cabeça, de estômago, doenças musculares, reumatismo, disordens do útero, rins e fígado. Os objetivos deste estudo foram investigar as propriedades físico-químicas e morfológicas do pó microencapsulado do óleo volátil das folhas de S. odoratissima, otimizar o processo de secagem e verificar a influência dos parâmetros de secagem na microencapsulação por spray-dry. Os óleos voláteis das folhas foram extraídos por hidrodestilação em aparelho tipo Clevenger e analisados por CG / EM. As emulsões foram preparadas e secas por pulverização. O modelo experimental Box-Behnken foi utilizado para otimizar os efeitos dos parâmetros de secagem nas respostas de encapsulamento. O conteúdo de β-cariofileno nas microcápsulas foi determinado por HPLC. Os resultados sugerem que as melhores condições operacionais para a secagem por atomização do óleo volátil de S. odoratissima foram temperatura de entrada de 158 °C, vazão de alimentação de 0,25L/ h, diâmetro do bico de secagem de 0,7mm. Esses resultados revelam o potencial tecnológico das microcápsulas obtidas a partir de óleos voláteis de S. odoratissima.

This study aimed to determine the composition of β-Caryophyllene (BCP) content in patchouli oil from various regions in Aceh. The data from GC-MS analysis can also describe the type of BCP isomer most commonly found in Aceh patchouli. This research used Aceh Pogostemon cablin Benth patchouli oil from 17 different locations. Samples were analyzed using TSQ™ 9000 Triple Quadrupole GC-MS/MS (Thermo Scientific) with TraceGOLD TG-1MS GC Columns. The mean BCP retention time was 14.64 minutes, with a standard deviation (SD) of 0.16. Only one type of BCP compound isomer appeared, namely Bicyclo [7.2.0] undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R- (1R*, 4Z, 9S*)]. The results also showed that the average BCP level was 5.51%. Aceh patchouli contains a much higher BCP level than the minimum commercial target (3.4-3.5%). The MS spectrum data also showed a high similarity between the patchouli oil sample fragmentation and the compound library.

In a subchronic toxicity study, administration of β-caryophyllene (BCP) oil by oral gavage to Wistar rats at dosages of 0, 150, 450, or 700 mg/kg/d for 90 days, including a 21-day recovery period, did not produce any significant toxicologic manifestations. The study design also included a 28-day interim sacrifice in the control and high-dose groups. The BCP oil test article was well tolerated as evidenced by the absence of major treatment-related changes in the general condition and appearance of the rats, neurobehavioral end points, growth, feed and water intake, ophthalmoscopic examinations, routine hematology and clinical chemistry parameters, urinalysis, and necropsy findings. The no observed adverse effect level was the highest dosage level administered of 700 mg/kg body weight/d for both male and female rats. The study was conducted as part of an investigation to examine the safety of BCP oil for its proposed use in medical food products.

Ketoprofen (Ket), widely utilized in treatment of many inflammatory disorders, is found to induce liver toxicity especially with overdose. This study aimed to evaluate the possible protective effects of concomitant β-caryophyllene (Cary) and silymarin (Sily) against Ket-induced hepatotoxicity in rats. Forty adult male albino rats were divided into 5 groups (each n = 8): the control group received distilled water for 6 weeks; the Ket-treated group received distilled water for 5 weeks and Ket in a dose of 8 mg·kg−1·day−1 p.o. for the 6th week; the Cary + Ket treated group received Cary in a dose of 200 mg·kg−1·day−1 orally for 6 weeks and Ket for the 6th week; the Sily + Ket treated group received Sily in the dose of 150 mg·kg−1·day−1 for 6 weeks and Ket for the 6th week; and the Cary + Sily + Ket treated group received Sily and Cary for 6 weeks and Ket for the 6th week. At end of the experiment, serum ALT, AST, and albumin and liver total antioxidant capacity (t.TAC) and malondialdehyde (t.MDA) were measured in all rats. Ket increased serum ALT and AST and t.MDA and decreased t.TAC. Cary and Sily improved these changes. Combined Cary and Sily restored these liver changes to nearly normal. Combined Cary and Sily is hepatoprotective, with the ability to scavenge oxidants against Ket-induced hepatotoxicity in rats.

Description of the subject. Alginate beads that release semiochemical compounds are interesting biological control devices used to attract the natural enemies of aphids in infested crops. Little information, however, is available about the impact of climatic factors on the release of semiochemicals from this diffusive system. Objectives. The objective of this scoping study was to investigate the impact of temperature, relative humidity and wind speed, on the release of E-β-caryophyllene from alginate beads.Method. The impact of the three climatic factors on the release of E-β-caryophyllene from alginate beads was evaluated using a Box-Behnken experimental design and a laboratory scale volatile collection system. The influence of relative humidity on bead water content and size, with and without this semiochemical, was also investigated using a gravimetric method and an easy-to-use photographic device, respectively.Results. The results showed that an increase in temperature caused a significant increase in the E-β-caryophyllene release rate. Neither relative humidity nor airflow, however, had a significant effect on the release of this semiochemical when relative humidity and wind speed ranged from 33% to 75% and from 6.61 x 10-4 m·s-1 to 2.05 x 10-2 m·s-1, respectively. The isotherm curves obtained were characteristic of food products and biopolymer materials. The isotherm shapes were not modified by the incorporation of the semiochemical into alginate beads, and showed an important increase in water content when relative humidity values exceeded 85%. Fortunately, this water content increase did not affect bead size, which facilitates the calculation of E-β-caryophyllene release.Conclusions. The present study shows for the first time the impact of the three main climatic factors on the release of E-β-caryophyllene from alginate beads. It allows learning more about how these biological control devices operate in order to optimize future field trials., Impact des facteurs climatiques sur la diffusion du E-β-caryophyllène à partir de billes d\'alginateDescription du sujet. Les billes d’alginate libérant des substances sémiochimiques sont des dispositifs de lutte biologique intéressants utilisés pour attirer les ennemis naturels des pucerons dans les cultures infestées. Cependant, peu d’informations sont disponibles quant à l’impact des facteurs climatiques sur l’émission des sémiochimiques à partir de ce système de diffusion. Objectifs. L’objectif de cette étude exploratoire était d’étudier l’impact de la température, de l’humidité relative et de la vitesse du vent sur la diffusion de l’E-β-caryophyllène à partir de billes d’alginate.Méthode. L’impact des trois facteurs climatiques sur la diffusion de l’E-β-caryophyllène à partir de billes d’alginate a été évalué en utilisant un plan d’expérience de type Box-Behnken et un système en laboratoire de collecte des composés volatils. L’influence de l’humidité relative sur la teneur en eau et la taille des billes, avec ou sans le sémiochimique, a également été étudiée en utilisant une méthode gravimétrique et un dispositif photographique facile à concevoir. Résultats. Les résultats ont montré qu’une augmentation de la température provoque une augmentation significative du taux de diffusion de l’E-β-caryophyllène. Par contre, l’humidité relative et la vitesse du vent n’ont aucun effet significatif sur la libération de ce sémiochimique dans la gamme de mesures sélectionnée : allant de 33 % à 75 % pour l’humidité relative et de 6,61 x 10-4 m·s-1 à 2,05 x 10-2 m·s-1 pour la vitesse du vent. Les courbes d’isothermes de sorption obtenues étaient caractéristiques de la plupart des produits alimentaires et des biopolymères. Les formes des isothermes n’ont pas été modifiées par l’incorporation du sémiochimique dans les billes d’alginate et elles ont montré une augmentation importante de leur teneur en eau lorsque l’humidité relative dépassait les 85 %. Heureusement, cette augmentation de la teneur en eau n’a pas affecté la forme des billes, ce qui facilite le calcul du taux de diffusion de ce sémiochimique.Conclusions. Cette étude présente pour la première fois l’impact de trois principaux facteurs climatiques sur la diffusion de l’E-β-caryophyllène à partir des billes d’alginate. Elle permet de mieux comprendre le fonctionnement de ces dispositifs de lutte biologique afin d’optimiser les futurs essais sur le terrain.

The bicyclic sesquiterpene β-caryophyllene (BCP) has diverse biological activities, including antioxidant, anti-inflammatory, antidiabetic, and analgesic effects. This study evaluates anxiolytic, toxicity, and antioxidant effects of BCP using in vitro and in vivo test models. The anxiolytic effects were tested in Swiss albino mice ( Mus musculus) by applying the elevated plus-maze, rota-rod, light and dark, and hiding sphere models, while the toxicity was evaluated by brine shrimp ( Artemia salina) lethality bioassay. Additionally, the antioxidant capacity was tested by using 2,2-diphenyl-1-picrylhydrazyl radical, 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid hydroxyl radical scavenging, and the Saccharomyces cerevisiae test model. The results suggest that BCP exerted a dose-dependent anxiolytic-like effect on the experimental animals. It did not show toxicity in A. salina at 24 hours. BCP showed a concentration-dependent free-radical-scavenging capacity, similar to the standard antioxidant Trolox. It also showed protective and repair capacities against hydrogen peroxide-induced damaging effects in isogenic and wild-type S. cerevisiae strains. Taken together, BCP exerted antioxidant and protective effects, which can be targeted to treat neurological diseases and disorders such as anxiety.

Leaves of Actinodaphne pilosa were collected at 2 different seasons from the Pù Hoạt Nature Reserve, Vietnam. The leaf samples were hydrodistilled to give essential oils, which were analyzed by gas chromatography (GC)–mass spectrometry and GC-flame ionization detection. The major components in the essential oils were α-pinene, ( Z)-β-ocimene, ( E)-β-ocimene, β-caryophyllene, germacrene D, bicyclogermacrene, and spathulenol. The essential oils were screened for antimicrobial activity against Enterococcus faecalis, Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, and Candida albicans, as well as mosquito larvicidal activity against Aedes aegypti, Aedes albopictus, and Culex quinquefasciatus. Actinodaphne pilosa leaf essential oils showed broad antimicrobial activity (minimum inhibitory concentration = 32, 64, 64, 16, and 16 μg/mL against E. faecalis, S. aureus, B. cereus, P. aeruginosa, and C. albicans, respectively) and excellent larvicidal activity (24-hour 50% lethal concentration = 19.0, 24.7, and 48.1 μg/mL against A. aegypti, A. albopictus, and C. quinquefasciatus, respectively).