Caryophyllene Oxide Research Articles

Applicability of NMR in combination with chemometrics for the characterization and differentiation of oil-resin extracted from Copaifera langsdorffii and Copaifera spp.

Copaiba oil-resin is a natural product widely used in popular medicine and as raw material for pharmaceutical and cosmetic industry. Differences between species or extraction sites can cause changes in the product composition, which highlights the importance of its quality control regarding purity and identification of the Copaifera species from which the oil-resin was extracted. Thus, this work proposes to use the NMR technique associated with chemometric to differentiate and characterize samples of copaiba oil-resin obtained from different species and regions of Brazil. For this, 1H and 13C NMR spectra of 26 samples of copaiba oil-resin were acquired and submitted to chemometric analysis, which allows the recognition of patterns between the samples, as well as indicate the main variables responsible for the clustering. Based on these results, two-dimensional NMR experiments were carried out to identify the structure of the molecules that can be used as chemical markers to differentiate the oil-resin extracted from the Copaifera langsdorffii from other Copaifera species (Copaifera spp.). The structural elucidation of three terpenes (hardwickic acid, caryophyllene oxide, and kaurenoic acid) was successfully achieved, thus showing a decisive role in distinguishing the Copaifera langsdorffii samples.

Phytochemical profile and antimicrobial activity of essential oils from two Syzygium species against selected oral pathogens

BackgroundThe genus Syzygium (Myrtaceae) comprises several essential oil-rich species that are utilized traditionally for treating tooth infections and toothache. The current study aimed to extract essential oils (EOs) from the leaves of Syzygium samarangense and Syzygium malaccense cultivated in Egypt for the first time and screen their antimicrobial potential against oral-related pathogens.MethodsThe intended EOs were extracted using hydrodistillation (HD) by boiling fresh leaves with distilled water; supercritical fluid (SF) by extracting the dried leaves using supercritical CO2 at 40 °C and 150 bar; and the headspace (HS) in which the fresh leaves were heated in a glass vial and the vaporized aroma were analyzed. The volatile constituents were analyzed using GC/MS and identified by comparing the experimental Kovats' retention indices with the literature. The antimicrobial activity was assessed against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Candida albicans using agar diffusion, microwell dilution, and biofilm formation assays. Statistical significance (p < 0.05) was determined by applying one-way ANOVA and Duncan's post hoc test.ResultsThe yield of the extracted EOs differs between the applied methods, and the SF approach harvested the maximum (0.52–0.46%). The GC–MS analysis of SF EOs revealed a discrepancy between the two species. Since S. malaccense showed an abundance of hydrocarbons represented mainly by squalene (60.60%), S. samarangense was deemed to have oxygenated sesquiterpenes exemplified in globulol (52.09%). On the other side, the HD and HS EOs were sequentially comparable, while differed in the percentage of their majors. γ-terpinene (33.06%) pioneered the HS-derived aroma of S. malaccense, while S. samarangense was abundant with α-pinene (30.18%). Concurrently, the HD EOs of S. malaccense and S. samarangense were commonly denoted by caryophyllene oxide (8.19%-18.48%), p-cymene (16.02%- 19.50%), and γ-terpinene (12.20%-17.84). Ultimately, both species EOs exhibited broad-spectrum antimicrobial potential, although the HD EO was more potent than the SF EO. The HD EOs of both species potently inhibited the growth of E. coli (MIC 3.75 µL/mL) and suppressed C. albicans biofilm formation by 83.43 and 87.27%, respectively. The SF-EOs efficiently suppressed the biofilm formation of Gram-positive bacteria by 76.45%-82.95%.ConclusionEOs extracted from both species by different methods possessed a unique blend of volatile components with broad-spectrum antimicrobial activity. They were promoted as bioactive hits for controlling oral infections, however further investigations concerning their safety in clinical settings are needed.

Chemical profile of essential oils of the Costa Rican native tree Myrcianthes storkii (Myrtaceae)

Introduction: The genus Myrcianthes ranges from southern Florida to Chile, including the Caribbean, and the species Myrcianthes storkii is a shrub or tree found in Costa Rica and western Panama, in wet to very rainy, cloud, and oak forests (altitude 1300-3150m). Objective: To identify the chemical composition of essential oils from leaves, floral buds, and twigs of M. storkii of Costa Rica. Methods: We obtained the essential oils through hydrodistillation in a Clevenger-type apparatus. The chemical composition of the oils was done by GC/FID and GC/MS, using the retention indices on DB-5 and Carbowax types of capillary columns in addition to mass spectra. Results: The oils consisted mainly of terpenoids (55,45-87,75%). A total of 281 compounds accounted for 91,27-74,56% of the total amount of oils. The major constituents from the leaf oil were myrcene (17,44%), cis-calamenene (12,60%), α-pinene (5,48%), (E)-caryophyllene (5,16%), limonene (3,91%), p-cymene (3,71%), 1,8-cineole (2,80%), and α-humulene (2,80%). The floral bud essential oil consisted mainly of α-pinene (15,23%), cis-calamenene (12,70%), myrcene (8,59%), 1,8-cineole (4,26%), germacrene B (3,65%), α-humulene (3,55%), and (E)-caryophyllene oxide (2,93%). The major components of twig oil were cis-calamenene (11,31%), palmitic acid (7,99%), (E)-caryophyllene (4,68%), -cadinene (3,28%), cubenol (3,24%), and (Z)-caryophyllene oxide (2,94%). Conclusion: The presence of a significant quantity of myrcene and cis-calamenene seems to be characteristic of this species.

Chemical composition and content of essential oil from cultivated bald cypress (Taxodium distichum L.)

The essential oils extracted from the cone scale (CS), seed (SE), and thin branch with leaf (BL) of Taxodium distichum harvested during the winter season were analyzed by gas chromatography-mass spectrometry. Up to 37 components were identified, accounting for more than 96% of the total oil volume in all samples. Monoterpenes (CS 93.4%, SE 85.2%, and BL 72.8%) represented the major constituents of the essential oils, followed by smaller quantities of sesquiterpenoids. Monoterpene hydrocarbons (MH) dominated, with limonene (CS 56.5%, SE 50.5%, and BL 43.8%) and α-pinene (CS 31.7%, SE 26.1%, and BL 16.2%) being the main constituents. Representative minor constituents in the CS oil are camphene (1.3%) and bornyl acetate (2.6%); in the SE oil, β-myrcene (1.7%) and bornyl acetate (5.1%) were found; and in BL essential oil, β-myrcene (3.1%) and bornyl acetate (6%). Sesquiterpene hydrocarbons (CS 4.6%, SE 7.8%, and BL 12.9%) were the other major subclasses of components, with caryophyllene (CS 4.1%, SE 6.8%, and BL 9.3%) as the main constituent. The only oxygen-containing sesquiterpene found was caryophyllene oxide (CS 1.5%, SE 5.5%, and BL 8.3%). The compounds could be of great interest in food, cosmetics, and pharmaceutical applications.

The gut microbiome and metabolites are altered and interrelated in patients with functional constipation.

Gut microbiota and metabolites have been identified to contribute to the pathogenesis of functional constipation (FC); however, the underlying mechanism(s) have not been elucidated, and the relationship between the gut microbiota and metabolites in FC has received limited attention in the literature. 16S rDNA sequencing and non-targeted metabolomic detection based on liquid chromatography-mass spectrometry (LC-MS/MS) technologies were combined to analyze the altered gut microbiome and metabolic profile of fecal samples from FC patients and healthy individuals (healthy control; HC). The richness and diversity of gut microbiota significantly (p < 0.01) increased in FC patients. Compared to the HC group, 18 genera, including Intestinibacter, Klebsiella, and Akkermansia, exhibited statistically significant changes (p < 0.05). Metabolic analysis showed that metabolic profiles were also markedly altered with 79 metabolites, such as (-)-caryophyllene oxide, chenodeoxycholic acid, and biliverdin, indicating significant inter-group differences (p < 0.05). Besides, the primary bile acid biosynthesis, as well as the metabolic profile of porphyrin and chlorophyll, were the most dominant enriched pathways (FDR < 0.01), in which chenodeoxycholic acid and biliverdin were significantly enriched, respectively. Correlation analysis demonstrated a strong relationship between 10 genera and 19 metabolites (r > 0.6, FDR < 0.05), and notably, Intestinibacter showed a negative correlation with biliverdin (FDR < 0.001), which highlighted the interplay of the gut microbiota and metabolites in the pathogenesis of FC. Our research describes the characteristics of the gut microbiota and metabolic profiles and the correlation between the gut microbiota and metabolites in FC patients. This may contribute to the understanding of the underlying mechanisms involved in FC pathogenesis and may provide novel insights into therapeutic interventions.

New Facts on the Antimicrobial Essential Oil of Satureja kitaibelii.

The objective of the present study was to assess the difference in antimicrobial activity of Satureja kitaibelii Wierzb. ex Heuff. essential oil at three growth stages. In addition, using statistical and chemometric tools, we tried to explain why the essential oil from a certain vegetation stage shows the highest antimicrobial activity. S. kitaibelii essential oils demonstrated minimum inhibitory concentration values from 160 to 10000 μg mL-1 , and minimum microbicidal concentration values from 630 to 20000 μg mL-1 . Geraniol, borneol, limonene and p-cymene are the dominant compounds of S. kitaibelii essential oil. The most abundant compound, geraniol, possesses antimicrobial activity in a range of MIC values from 40 to 5000 μg mL-1 and MMC values from 80 to 10000 μg mL-1 . The highest activity of essential oil for all tested strains of microorganisms was recorded in November. Results of statistical analysis indicate that the percentage of dominant compounds of essential oils does not affect the antibacterial activity of essential oils. Chemometric analyses leads to the conclusion that borneol, spathulenol, caryophyllene oxide and limonene can be the main contributors to the antibacterial activity of essential oil from November and that their mutual ratio is important. These results may represent a new methodological approach for future research on essential oils.

Essential Oils From the Trunks and Leaves of Paramignya scandens (Griff.) Craib From Vietnam: Phytochemical Composition, In Vitro α-Amylase and Tyrosinase Inhibitory Activities and In Silico Molecular Docking Studies

Objective/Background: This work aims to evaluate the chemical composition of Paramignya scandens essential oils (EOs), their in vitro α-amylase, tyrosinase inhibitory activities, and in silico molecular docking study. Methods: The EOs of P scandens trunks and leaves were extracted by hydrodistillation process and the chemical compositions were determined by gas chromatography-mass spectrometry. These EOs were also tested for in vitro α-amylase and tyrosinase inhibitory activities. Additionally, in silico molecular docking simulations on the main components of the EOs were performed. Results: The EO profiles of P scandens trunks and leaves included 21 (98.8%) and 34 (89.7%) components, respectively. The main compounds in the trunk EO were ( E)- β-caryophyllene (60.8%), α-humulene (13.0%), and germacrene D (7.4%). The predominant compounds of the leaf EO were caryophyllene oxide (16.7%), ( E) -β-caryophyllene (14.6%), spathulenol (12.2%), germacrene D (6.5%), and α-humulene (5.0%). Moreover, their α-amylase and tyrosinase inhibitory effects were demonstrated for the first time. In molecular docking results, ( E)- β-caryophyllene was the potential compound in EOs with the best binding affinity against the α-amylase enzyme, whereas spathulenol revealed the strongest binding ability with the tyrosinase enzyme. Furthermore, the assessment of potential interactions between the main components of the EOs and the selected proteins was elucidated. Conclusions: The results of this work revealed that EOs of P scandens trunks and leaves had α-amylase and tyrosinase inhibition properties and potential applications in nutraceuticals, medicine, and cosmetics.

Influence of distillation time and distillation apparatus on the chemical composition and quality of Lavandula angustifolia Mill. essential oil

Abstract In the study, the influence of distillation time as well as distillation apparatus on the chemical composition and quality of lavender (Lavandula angustifolia Mill.) essential oil were investigated. Two different types of distillation apparatuses: Deryng (popular in Poland) and Clevenger-type (recommended by European Pharmacopoeia) were used for the isolation of the essential oil from dried lavender flowers (Lavandulae flos). Moreover, different distillation times (2, 3 and 4 hours) were also applied. The chemical composition of the isolated oils, determined by gas chromatography coupled with mass spectrometry (GC-MS), revealed the dominance of linalool (11.55–17.19%) and linalyl acetate (12.84–16.78%) in the all analyzed samples. Other important constituents were: caryophyllene oxide (5.66–7.35%), lavandulyl acetate (4.64–5.40%) and borneol (4.62–5.51%). On the basis of the obtained data it was proved that the distillation time and distillation apparatus affect the amounts of some constituents in the lavender oil.

Comparative Study of Essential Oils from Different Organs of Syzygium cumini (Pamposia) Based on GC/MS Chemical Profiling and In Vitro Antiaging Activity

Syzygium cumini L. is an evergreen tree belonging to family Myrtaceae, employed for different traditional uses like diabetes, inflammation, and fever. The current study aimed to compare the chemical compositions of the essential oils (EOs) isolated from different organs of Syzygium cumini (leaves (Scl), fruits (Scf), seeds (Scs), and bark (Scb)) using a GC/MS analysis. Also, a chemometric analysis was applied to explore the main similarities and differences among different organs using a Principal Component Analysis (PCA) and a hierarchal cluster analysis (HCA). Furthermore, in vitro antiaging activities were investigated via anti-collagenase, anti-elastase, and anti-hyaluronidase assays. The GC-MS analysis revealed 82 compounds representing 92.13%, 99.42%, 100%, and 92.97% in Scl, Scf, Scs, and Scb, respectively. The predominant components were α-pinene, β-pinene, (E)-β-caryophyllene, α-caryophyllene, caryophyllene oxide, and α-humulene epoxide II with variable percentages. All EOs were positioned on positive PC1, except for Scs, which was positioned on the negative side in a separate quadrant. The HCA dendrogram displayed the closeness of Scl and Scb, which was not clearly recognized in the PCA score plot. Moreover, the Scs oils were totally discriminated from other parts. The Scl and Scs oils showed superior anti-collagenase, anti-elastase, and anti-hyaluronidase activities. Thus, S. cumini oils should be considered for cosmetic preparations to retard skin aging manifestations.

Chemical Composition and Antimicrobial Activity against the Listeria monocytogenes of Essential Oils from Seven Salvia Species.

In recent years, essential oils (EOs) have received interest due to their antibacterial properties. Accordingly, the present study aimed to investigate the effectiveness of the EOs obtained from seven species of Salvia on three strains of Listeria monocytogenes (two serotyped wild strains and one ATCC strain), a bacterium able to contaminate food products and cause foodborne disease in humans. The Salvia species analysed in the present study were cultivated at the Botanic Garden and Museum of the University of Pisa, and their air-dried aerial parts were subjected to hydrodistillation using a Clevenger apparatus. The obtained EOs were analysed via gas chromatography coupled with mass spectrometry for the evaluation of their chemical composition, and they were tested for their inhibitory and bactericidal activities by means of MIC and MBC. The tested Eos showed promising results, and the best outcomes were reached by S. chamaedryoides EO, showing an MIC of 1:256 and an MBC of 1:64. The predominant compounds of this EO were the sesquiterpenes caryophyllene oxide and β-caryophyllene, together with the monoterpenes bornyl acetate and borneol. These results suggest that these EOs may possibly be used in the food industry as preservatives of natural origins.

Identification of Anti-Neuroinflammatory Bioactive Compounds in Essential Oils and Aqueous Distillation Residues Obtained from Commercial Varieties of Cannabis sativa L.

Neuroinflammation, which is mainly triggered by microglia, is a key contributor to multiple neurodegenerative diseases. Natural products, and in particular Cannabis sativa L., due to its richness in phytochemical components, represent ideal candidates to counteract neuroinflammation. We previously characterized different C. sativa commercial varieties which showed significantly different chemical profiles. On these bases, the aim of this study was to evaluate essential oils and aqueous distillation residues from the inflorescences of three different hemp varieties for their anti-neuroinflammatory activity in BV-2 microglial cells. Cells were pretreated with aqueous residues or essential oils and then activated with LPS. Unlike essential oils, aqueous residues showed negligible effects in terms of anti-inflammatory activity. Among the essential oils, the one obtained from ‘Gorilla Glue’ was the most effective in inhibiting pro-inflammatory mediators and in upregulating anti-inflammatory ones through the modulation of the p38 MAPK/NF-κB pathway. Moreover, the sesquiterpenes (E)-caryophyllene, α-humulene, and caryophyllene oxide were identified as the main contributors to the essential oils’ anti-inflammatory activity. To our knowledge, the anti-neuroinflammatory activity of α-humulene has not been previously described. In conclusion, our work shows that C. sativa essential oils characterized by high levels of sesquiterpenes can be promising candidates in the prevention/counteraction of neuroinflammation.

Potential anti-inflammatory biomarkers from Myrtaceae essential oils revealed by untargeted metabolomics

Many species from Myrtaceae have traditionally been used in traditional medicine as anti-inflammatory, antimicrobial, antidiarrheal, antioxidant and antirheumatic, besides in blood cholesterol reduction. In the present work, the anti-inflammatory activity of essential oils from eighteen Myrtaceae spp. were evaluated according to their ex-vivo anti-inflammatory activity in human blood, and the corresponding biomarkers were determined using untargeted metabolomics data and multivariate data analysis. From these studied species, six displayed anti-inflammatory activity with percentage rates of inhibition of PGE2 release above 70%. Caryophyllene oxide (1), humulene epoxide II (2), β-selinene (3), α-amorphene (4), α-selinene (5), germacrene A (6), β-bisabolene (7), α-muurolene (8), α-humulene (9), β-gurjunene (10), myrcene (11), β-elemene (12), α-cadinol (13), α-copaene (14), E-nerolidol (15) and ledol (16) were annotated as potential anti-inflammatory biomarkers. The results obtained in this study point to essential oils from species of the Myrtaceae family as a rich source of anti-inflammatory agents.

Chemical components and antifungal and anti-mycotoxigenic (aflatoxin b1 and fumonisin b1) activity of star anise (Illicium verum) essential oils in Yen Bai Province, Vietnam

In Vietnam, star anise is grown in the provinces of Yen Bai, Ha Giang, Lao Cai, Lang Son, Bac Kan, and Cao Bang. The study aimed to analyze the chemical components, and antifungal and anti-mycotoxigenic (aflatoxin B1 and fumonisin B1) activity of star anise essential oils. By the gas chromatography mass spectrometry (GC-MS) method, 15 chemical components were predicted in the star anise essential oils. The major components were trans-anethole (67.05%), caryophyllene oxide (12.73%), limonene (4.27%), α-terpineol (2.43%), and myrcene (2.39%). The antifungal activity at 100 ppm recorded 85.24±0.05%, 76.73±0.06%, 69.37±0.02%, and 67.96±0.04% inhibition for Aspergillus flavus, Aspergillus parasiticus, Fusarium verticillioides, and Penicillium, respectively. Complete inhibition of 100% was observed at 200 ppm and 300 ppm for both A. flavus and A. parasiticus and at 400 ppm for F. verticillioides and Penicillium. Complete aflatoxin B1 inhibition was achieved at 100 and 200 ppm for A. flavus and A. parasiticus.

Essential Oils of Five Syzygium Species Growing Wild in Vietnam: Chemical Compositions and Antimicrobial and Mosquito Larvicidal Potentials.

The essential oils of five Vietnamese Syzygium species (Syzygium levinei, S. acuminatissimum, S. vestitum, S. cumini, and S. buxifolium) were first hydro-distilled and analyzed using GC-FID/MS (gas chromatography-flame ionization detection/mass spectrometry). Monoterpene hydrocarbons, sesquiterpene hydrocarbons, and oxygenated sesquiterpenoids were the main chemical classes in these oils. All these essential oils showed good-excellent antimicrobial activities against Gram-positive bacteria Enterococcus faecalis, Staphylococcus aureus, and Bacillus cereus, and the yeast Candida albicans. S. levinei leaf essential oil, rich in bicyclogermacrene (25.3%), (E)-β-elemene (12.2%), (E)-caryophyllene (8.2%), and β-selinene (7.4%), as well as S. acuminatissimum fruit essential oil containing (E)-caryophyllene (14.2%), α-pinene (12.1%), caryophyllene oxide (10.9%), β-selinene (10.8%), α-selinene (8.0%), and α-humulene (5.7%), established the same MIC value of 8 µg/mL against E. faecalis and B. cereus, which were much better than the positive control streptomycin (MIC 128-256 µg/mL). The studied essential oils showed the potential to defend against mosquitoes since they caused the 24 and 48 h LC50 values of less than 50 µg/mL against the growth of Culex quinquefasciatus and Aedes aegypti larvae. Especially, S. buxifolium leaf essential oil strongly inhibited Ae. aegypti larvae with 24 and 48 h LC50 values of 6.73 and 6.73 µg/mL, respectively, and 24 and 48 h LC90 values of 13.37 and 10.83 µg/mL, respectively. These findings imply that Vietnamese Syzygium essential oils might have potential for use as supplemental antibacterial agents or as "green" alternatives for the control of mosquitoes.

Essential oils from Acronychia pedunculata (L.) Miq. in Vietnam: chemical composition, antimicrobial, cytotoxicity and nitric oxide inhibition activities

The chemical composition, antimicrobial, cytotoxic and anti-inflammatory activities of essential oils from different parts of Acronychia pedunculata, a medicinal plant native to Central Highlands of Vietnam, were investigated. Their chemical constituents were determined using GC-MS. The antimicrobial properties were assessed using a microdilution broth method, while the anti-inflammatory properties were measured based on their capacity to inhibit NO production in macrophage cells. Their cytotoxicity was tested using the sulforhodamine B assay on three human cancer cell lines. The GC-MS analysis revealed the presence mainly of caryophyllene oxide (35.3%) and spathulenol (31.9%) in the stem essential oil, caryophyllene oxide (51.3%), and linalool (21.0%) in the leaf essential oil, and α-pinene (21.4%), (E)-β-ocimene (16.5%), linalool (12.5%), and β-caryophyllene (13.0%) in the fruit essential oil. All three essential oils inhibited the growth of various bacteria and fungi, reduced NO production in LPS-induced RAW264.7 cells, and exhibited cytotoxicity against all three tested cancer cell lines. Notably, the fruit essential oil showed the most potent cytotoxicity among the essential oils, with IC50 values of 5.47 ± 0.21, 7.95 ± 0.35, and 9.22 ± 0.52 g/mL against SK-LU-1, MCF-7, and HepG2 cells, respectively. It also had a strong anti-inflammatory effect that was comparable to that of dexamethasone, with an IC50 value of NO production inhibition of 14.62 ± 0.62 mg/mL. These results suggest the potential of the essential oils from this plant to provide leads for the development of anti-inflammatory and anti-cancer agents.

Investigation of essential oil composition, hypericin content, and antioxidant capacity of different extracts from flowers and leaves of Hypericum perforatum L. growing wild in Turkey

In this study, we analyzed the composition of essential oils obtained through hydrodistillation from the leaves and flowers of Hypericum perforatum L., a wild plant species found in Şile, İstanbul, located in the northwest of Turkey. We employed gas chromatography-mass spectrometry (GC-MS) to identify the constituents. Additionally, we investigated the antioxidant capacity and total phenolic composition of the plant using DPPH (2,2-diphenyl-1-picryl-hydrazyl), CUPRAC (CUPric Reducing Antioxidant Capacity), and Folin-Ciocalteu methods. Furthermore, we determined the total amount of hypericin present in the plant. The analysis of essential oils from the leaves revealed the identification of fifty-nine compounds, with 2-methyloctane (34.93%), cyclotetradecane (9.12%), limonene (7.24%), 3-methylnonane (5.58%), α-pinene (5.55%), n-tetradecanol (3.15%), 2-methyldecane (3.03%), nonane (3.0%), and spathulenol (2.07%) as the primary constituents. On the other hand, the essential oil from the flowers contained fifty-seven compounds, with 2-methyloctane (52.81%), α-pinene (4.65%), cyclotetradecane (4.04%), n-tetradecanol (2.99%), D-verbenone (2.28%), 2-methyl-2-octanol (2.17%), and caryophyllene oxide (2.0%) as the major components. When evaluating the antioxidant capacity of H. perforatum L. extracts, our results indicated that both leaves and flowers exhibited significant antioxidant capacity in DPPH assays. However, the Cu2+ ion reduction capacity was comparatively low in the CUPRAC method. The highest hypericin contents of leaves and flowers were determined in extraction with 60% ethanol/water for 120 minutes at 50°C as 0.122 g/g % and with 80% ethanol/water for 120 minutes at 50°C as 0.360 g/g %.

GC-MS Characterization, in Vitro Antioxidant and Anti-Inflammatory Activities of Essential oil from the Leaves of Litsea balansae Lecomte

Objective: This study aimed to analyze the essential oil obtained from Litsea balansae Lecomte leaves and investigate its potential as an anti-inflammatory and antioxidant agent. Methods: Fresh L balansae leaves were collected in Quangtri, Vietnam, and subjected to hydro-distillation using a Clevenger-type apparatus to extract the essential oil. The essential oil composition was analyzed using gas chromatography–mass spectrometry (GC-MS). Antioxidant capacity was evaluated through the 2,2-Diphenyl-1-picrylhydrazyl assay, while the inhibition of nitric oxide production was assessed in lipopolysaccharide-activated RAW264.7 cells. Results: GC-MS analysis identified 71 compounds, constituting 99.3% of the essential oil. Key constituents included carvacrol (20.8%), caryophyllene oxide (11.0%), cis-β-guaiene (6.4%), khusimone (3.9%), bicycloelemene (3.7%), and spathulenol (3.7%). The essential oil exhibited a moderate antioxidant effect (half maximal inhibitory concentration [IC50] = 208.37 ± 10.67 µg/mL) and significant anti-inflammatory activity (IC50 = 28.09 ± 1.53 µg/mL). Conclusion: The essential oil derived from L balansae leaves showcases potential as an anti-inflammatory and antioxidant agent, as indicated by its chemical composition and biological activities. These findings suggest promising avenues for further research in the development of therapeutic agents from natural sources.

Chemical characterization, antioxidant, antimicrobial, enzyme inhibitory and cytotoxic activities of Illicium lanceolatum essential oils

Illicium lanceolatum is a medicinal and aromatic plant widely distributed in the south of China. The reports on chemical composition and biological activities of its essential oils (EOs) were very limited. In this study, Illicium lanceolatum EOs were extracted by hydro distillation, and analyzed by GC–MS and GC-FID. DPPH radical scavenging assay, ABTS cation radical scavenging assay and ferric reducing/antioxidant power (FRAP) assay were used for antioxidant activity evaluation. Minimum inhibitory concentrations (MICs) and minimum microbiocidal concentrations (MMCs) against 9 microorganisms were determined. The inhibitory effects on tyrosinase, α-glucosidase and cholinesterases were evaluated and cytotoxic activities were evaluated using MTT assay. The results revealed 110 identified compounds, with asaricin, eucalyptol, linalool and caryophyllene oxide as major compounds. Eucalyptol was the most abundant compound in the stem, leaf and fruit EOs while asaricin accounted for 50.52 ± 0.33 % in the root EO. Very weak radical scavenging capacities were noticed for all EOs, but the root EO showed moderate antioxidant activity (176.33 ± 4.52 mg TE/g of EO) in the FRAP assay, which could be attributed to asaricin. The root EO displayed better antimicrobial activities than other three EOs, with MIC values as 3.13 mg/mL against three bacteria including Staphylococcus aureus BNCC 186335, Bacillus cereus BNCC 103930 and Listeria monocytogenes BNCC 336877. Camphor and borneol were found to be important antimicrobial compounds. No inhibitory effect on α-glucosidase was found. The leaf EO displayed better acetylcholinesterase inhibitory activity (17.79 ± 0.32 mg GE/g of EO) while the root EO showed better tyrosinase (30.34 ± 0.40 mg KAE/g of EO) and butyrylcholinesterase (43.25 ± 1.50 mg GE/g of EO) inhibitory activities. Molecular docking between active compounds and enzymes revealed the main interactions as hydrophobic interaction, hydrogen bond and π-stacking. All EOs displayed weak cytotoxicity to HK-2 cells of normal kidney at six tested concentrations. The leaf EO showed strong anticancer activities to HepG2 cells at the concentration of 500 μg/mL. I. lanceolatum EOs showed promising prospects with possible applications in pharmaceutical and cosmetic industries.

Chemical components in the essential oils and ultrasonic extraction of amanus sage pholomis longifolia var. Longifolia boiss. &amp; bl

In the present study the essential oil components of the flowers and leaves of Amanus sage Pholomis longifolia var. longifolia boiss. &amp; Bl by ultrasonic extraction and steam distillation method were determined. According to the chemical composition analysis of Amanus Sage plant using ultrasonic extraction method, major components were methyl-7-octadecenoate (69.02%) and methyl elaidate (16.87%). The essential oil contents of flowers and leaves of the Amanus sage plant were also determined by steam distillation method. When the essential oil components of the flower were examined, the main components were found to be tricosane (22.39%), caryophyllene (22.17%), alpha-cubebene (14.4305), beta-farnesene (7.7%) and linalool (4.69%). On the other hand the main components in the the leaves were caryophyllene oxide (27.20%), fenchone (18.63%), 1,8-cineole (6.12%), camphor (4.82%), and alpha-cubebene (4.11%). Bioactive properties of the components of Amanus sage obtained from both the ultrasonic extraction and steam distillation methods showed that this plant has important medicinal and aromatic properties. Bangladesh J. Bot. 52(2): 799-803, 2023 (September)

Repellent efficacy of the nanogel containing Acroptilon repens essential oil in comparison with DEET against Anopheles stephensi

ObjectiveMalaria is a vector-borne disease that causes many deaths worldwide; repellents are a practical approach to malaria prevention, especially in endemic regions.ResultsGas chromatography-mass spectrometry analysis was used to identify compounds in Acroptilon repens essential oil (EO). Alpha-copaene (15.67%), α-cubenen (3.76%), caryophyllene oxide (14.00%), 1-heptadecane (5.61%), and δ-cadinene (2.84) were five major compounds. After that, the nanoemulsion containing the EO with a particle size of 46 ± 4 nm, SPAN 0.85, PDI 0.4, and zeta potential − 5.7 ± 0.4 mV was prepared. Then, it was gellified by adding CMC (carboxymethyl cellulose) to the nanoemulsion. Besides, ATR-FTIR analysis (Attenuated Total Reflection-Fourier Transform InfraRed) was used to confirm the EO’s successful loading in the nanogel. Finally, the protection time and repellent activity of nanogel compared to DEET (N, N-diethyl-meta-toluamide) were investigated against Anopheles stephensi. Interestingly, the nanogel with a protection time of 310 ± 45 min was significantly more potent than DEET (160 ± 17 min). It could thus be considered for future investigation against other mosquitoes.