scholarly journals Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils

Biomolecules ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 916 ◽  
Author(s):  
Igor Schepetkin ◽  
Gulmira Özek ◽  
Temel Özek ◽  
Liliya Kirpotina ◽  
Andrei Khlebnikov ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Protein Kinase ◽  
Essential Oils ◽  
Mitogen Activated Protein Kinase ◽  
Gas Chromatography Mass Spectrometry ◽  
Immunomodulatory Activity ◽  
Therapeutic Effects ◽  
Active Components ◽  
Oxygenated Monoterpenes ◽  
Germacrene D

Hypericum L. (Hypericaceae) extracts have been used for their therapeutic effects; however, not much is known about the immunomodulatory activity of essential oils extracted from this plant. We isolated essential oils from the flowers and leaves of H. perforatum and analyzed their chemical composition and innate immunomodulatory activity. Analysis of flower (HEOFl) versus leaf (HEOLv) essential oils using gas chromatography–mass spectrometry revealed that HEOFl was comprised mainly of monoterpenes (52.8%), with an abundance of oxygenated monoterpenes, including cis-p-menth-3-en-1,2-diol (9.1%), α-terpineol (6.1%), terpinen-4-ol (7.4%), and limonen-4-ol (3.2%), whereas the sesquiterpenes were found in trace amounts. In contrast, HEOLv was primarily composed of sesquiterpenes (63.2%), including germacrene D (25.7%) and β-caryophyllene (9.5%). HEOLv also contained oxygenated monoterpenes, including terpinen-4-ol (2.6%), while monoterpene hydrocarbons were found in trace amounts. Both HEOFl and HEOLv inhibited neutrophil Ca2+ mobilization, chemotaxis, and reactive oxygen species (ROS) production, with HEOLv being much more active than HEOFl. Furthermore, the pure sesquiterpenes germacrene D, β-caryophyllene, and α-humulene also inhibited these neutrophil responses, suggesting that these compounds represented the active components of HEOLv. Although reverse pharmacophore mapping suggested that potential protein targets of germacrene D, β-caryophyllene, bicyclogermacrene, and α-humulene could be PIM1 and mitogen-activated protein kinase (MAPK)-activated protein kinase 2 (MAPKAK2), a kinase binding affinity assay did not support this finding, implying that other biological targets are involved. Our results provide a cellular and molecular basis to explain at least part of the beneficial immunotherapeutic properties of the H. perforatum essential oils.

Aristolochia triangularis Cham. stems and leaves essential oils and their antimicrobial and antimycobacterial effects

2020 ◽  
Vol 10 ◽  
Author(s):  
Ionara I. Dalcol ◽  
Alessandra O. Pereira ◽  
Luisa H. Paz ◽  
Gabriela Benetti ◽  
Fallon S. Siqueira ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Essential Oils ◽  
Candida Glabrata ◽  
Skin Diseases ◽  
Enterobacter Aerogenes ◽  
Gas Chromatography Mass Spectrometry ◽  
Moderate Activity ◽  
Circulatory System Diseases ◽  
Germacrene D ◽  
Stems And Leaves

Background: Aristolochia triangularis Cham., popularly known as the "cipó-mil-homens", "angelicó" and "ypê-mi", is applied for the treatment of wounds, skin diseases (6,7), digestive and circulatory system diseases as an antipyretic and for malaria fever. Objective: In this work we investigated the chemical composition, the antimicrobial and antimycobacterial activities of the essential oils (EOs) extracted from A. triangularis fresh stems and leaves collected in Southern Brazil. Methods: Fresh stems and fresh leaves of Aristolochia triangularis Cham. were separately subjected to hydrodistillation using a Clevenger-type apparatus. The chemical composition of the essential oils (EOs) were analyzed by gas chromatography/mass spectrometry (GC/MS). The oil samples were evaluated for their antimycobacterial, antibacterial and antifungal activities against twenty-four microorganisms. Results: Hydrodistillation of fresh stems and leaves of A. triangularis resulted in 0.16% (w/w) and 0.37% (w/w) respectively of light-yellow oils. Germacrene D is found in 13.2 - 13.5% in both EOs. The constituent most abundant in the stems EO (19.18%) was the oxygenated diterpene ent-Kaur-16-en-19-al (10), along with E-nerolidol (17.89%). The main constituents of the leaves EO were bicyclogermacrene (24.79%), β-elemene (11.30%), E-caryophyllene (10.40%) and germacrene A (9.42%), in addition to the previously mentioned germacrene D. The stems and leaves EOs showed capacity to inhibit the Gram-negative Enterobacter aerogenes and the stems EO capacity to inhibit Staphylococcus aureus, with MIC values of 31.2 µg/mL. S. aureus was moderately sensitive to leaves EO, while stems EO displayed moderate activity against Enterococcus faecalis and Salmonella typhimurium (MIC values of 62.5 µg/mL). Candida glabrata was highly susceptible to both EOs (MIC values < 3.9 µg/mL). The EOs showed moderate potential to inhibit the growth of Cryptococcus gatti and Cryptococcus neoformans (MICs of 62.5 μg/mL). Conclusion: The A. triangularis essential oils from stems and leaves displayed capacity to inhibit Enterobacter aerogenes (MIC values of 31.2 µg/mL) and high antifungal effect against Candida glabrata (MIC values of <3.9 µg/mL). Mycobacterium massiliense and M. abscessus were susceptible to the leaves EO, with MICs of 39.06 μg/mL. These results showed the A. triangularis essential oils potential as antifungal and antimycobacterial to be used in the development of new antibiotic.

Chemical composition of the essential oils of four Polyalthia species from Malaysia

2020 ◽  
Vol 75 (11-12) ◽  
pp. 473-478
Author(s):  
Natasa Mohd Shakri ◽  
Wan Mohd Nuzul Hakimi Wan Salleh ◽  
Shamsul Khamis ◽  
Nor Azah Mohamad Ali ◽  
Shazlyn Milleana Shaharudin
Keyword(s):  
Gas Chromatography ◽  
Chemical Composition ◽  
Essential Oil ◽  
Essential Oils ◽  
Folk Medicine ◽  
Principal Component ◽  
Gas Chromatography Mass Spectrometry ◽  
Chemical Compositions ◽  
Gastrointestinal Ulcer ◽  
Germacrene D

AbstractPolyalthia is one of the largest genera in the Annonaceae family, and has been widely used in folk medicine for the treatment of rheumatic fever, gastrointestinal ulcer, and generalized body pain. The present investigation reports on the extraction by hydrodistillation and the composition of the essential oils of four Polyalthia species (P. sumatrana, P. stenopetalla, P. cauliflora, and P. rumphii) growing in Malaysia. The chemical composition of these essential oils was determined by gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). The multivariate analysis was determined using principal component analysis (PCA) and hierarchical clustering analysis (HCA) methods. The results revealed that the studied essential oils are made up principally of bicyclogermacrene (18.8%), cis-calamenene (14.6%) and β-elemene (11.9%) for P. sumatrana; α-cadinol (13.0%) and δ-cadinene (10.2%) for P. stenopetalla; δ-elemene (38.1%) and β-cubebene (33.1%) for P. cauliflora; and finally germacrene D (33.3%) and bicyclogermacrene for P. rumphii. PCA score and HCA plots revealed that the essential oils were classified into three separated clusters of P. cauliflora (Cluster I), P. sumatrana (Cluster II), and P. stenopetalla, and P. rumphii (Cluster III) based on their characteristic chemical compositions. Our findings demonstrate that the essential oil could be useful for the characterization, pharmaceutical, and therapeutic applications of Polyalthia essential oil.

scholarly journals ANALYSIS OF ESSENTIAL OIL CONSTITUENTS OF THREE ANNONA SPECIES GROWING IN KERALA, INDIA

2021 ◽  
Vol 12 (5) ◽  
pp. 45-48
Author(s):  
Sonia Mol Joseph ◽  
Amala Dev A R
Keyword(s):  
Chemical Composition ◽  
Essential Oil ◽  
Essential Oils ◽  
Mass Spectrometry Analysis ◽  
Gas Chromatography Mass Spectrometry ◽  
Spectrometry Analysis ◽  
South Indian ◽  
Germacrene D ◽  
Leaf Essential Oil ◽  
The Common

The volatile chemical composition of leaf essential oils of three Annona species (Annona cherimola, Annona muricata and Annona squamosa) from the different regions of Kerala, South Indian was determined using gas chromatography-mass spectrometry analysis. A total of 41 constituents belonging to monoterpenoids, sesquiterpenoids and diterpenoids were identified. Monoterpenes and sesquiterpenoids were the major class of volatile compounds in most of the Annona species examined. The study led to the identification of major compounds as germacrene D (23.5%), bicyclogermacrene (14.6%) and β-caryophyllene (11.7%) in A. cherimola, α-pinene (13.3%), β-caryophyllene (11.2%) and β-pinene (10.1%) in A. muricata, and β-caryophyllene (11.9%) and α-pinene (8.2%) in A. squamosa respectively. The examined essential oils showed that β-caryophyllene is the common constituent identified in all the three species and other constituents are more specific for each species under study. Present investigation reports, a comparison of essential oil compositions of three Annona species from Kerala. Results of this study prove that essential oils examined have considerable dissimilarity in chemical composition with previously reported leaf essential oil compositions from other regions. A chemotaxonomic analysis of these essential oils based on the distribution of compounds has revealed an efficient method to differentiate Annona species unambiguously.

scholarly journals The influence of the chemical composition of essential oils of Clausena lansium seeds on the growth of Candida strains

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Yinzheng Ma ◽  
Yuanxiao Wang ◽  
Xia Zhou ◽  
Heng Yang ◽  
Huixin Zhang ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Antifungal Activity ◽  
Essential Oils ◽  
Synergistic Effects ◽  
Scientific Evidence ◽  
Inhibition Zone ◽  
Gas Chromatography Mass Spectrometry ◽  
Active Components ◽  
Traditional Use ◽  
The Difference

AbstractClausena lansium (Lour.) Skeels seeds have been shown to have diverse beneficial medical value due to their unique active components. This study analysed the composition of essential oils (EOs) of C. lansium seeds and investigated their potential antifungal effects against Candida strains. A total of forty-six components were identified in all samples by gas chromatography-mass spectrometry (GC–MS). The main components were sabinene, β-phellandrene and 4-terpineol. Thirteen EOs of C. lansium seeds were classified into three clusters based on their components. Cluster analysis showed that the difference between the tropics and subtropics was the greatest. These EOs and the three main chemicals showed different antifungal activities against five Candida species (C. albicans, C. tropicalis, C. glabrata, C. krusei and C. parapsilosis). The antifungal activity against C. glabrata and C. krusei was higher than that against other Candida strains. EOs of C. lansium seeds displayed noteworthy antifungal activity against both sensitive and fluconazole-resistant strains, with inhibition zone diameters in the range of 9.4–23.4 mm. Comprehensive analysis illustrated the importance of sabinene, β-phellandrene and 4-terpineol to antifungal activity, and there may be some synergistic effects with other components. These results represent the first report about the correlation between the chemical composition of EOs of C. lansium seeds and antifungal activity. Taken together, the results obtained provide scientific evidence for the traditional use of C. lansium seeds waste.

Chemical Composition and Antibacterial Activity of Essential Oils from the Leaves, Fruits and Stems of Lantana camara L. from the South China

2013 ◽  
Vol 781-784 ◽  
pp. 1060-1063 ◽  
Author(s):  
Feng Zhu ◽  
Wei Hong Lu ◽  
Jia Hui Pan ◽  
Mei Zhen Huang ◽  
Jing Shu Wu
Keyword(s):  
Antibacterial Activity ◽  
Chemical Composition ◽  
Essential Oils ◽  
South China ◽  
Antibacterial Activities ◽  
Lantana Camara ◽  
Gas Chromatography Mass Spectrometry ◽  
Dilution Method ◽  
The South ◽  
Germacrene D

The chemical composition of the hydrodistilled essential oils from the leaves, fruits and stems ofLantana camaraL. from the South China were analyzed by gas chromatography/mass spectrometry. The GC/MS analysis revealed the sesquiterpenoids germacrene D (20.0%),trans-caryophyllene (14.8%) andα-humulene (5.8%) as major constituents in the leaf oil, and palmitic acid (22.5%), stearic acid (12.6%) and germacrene D (7.0%) as major constituents in the fruit oil, while the major constituents in the stem oil were germacrene D (31.0%),β-elemene (17.6%) andα-phellendrene (6.7%). The essential oils were tested for antibacterial activity against 6 strains, using broth dilution method. Both the leaf and stem oils showed moderate inhibitory activity againstStaphylococcus aureus,S. epidermidis,Bacillus subtilis,Bacillus dysenteriae,B. proteus, andEscherichia coli. High percentage of sesquiterpenes in the oils were primary responsible for the antibacterial activities.

scholarly journals Chemical composition of the volatile oil of Cardiopetalum calophyllum collected in the Cerrado area

2016 ◽  
Vol 46 (5) ◽  
pp. 937-942 ◽  
Author(s):  
Marcelo Nogueira Xavier ◽  
Cássia Cristina Fernandes Alves ◽  
Cristiane de Melo Cazal ◽  
Nathalia Horrana Santos
Keyword(s):  
Chemical Composition ◽  
Essential Oil ◽  
Essential Oils ◽  
Chemical Compounds ◽  
Volatile Oil ◽  
Gas Chromatography Mass Spectrometry ◽  
Diverse Species ◽  
The Family ◽  
Sesquiterpene Hydrocarbons ◽  
Germacrene D

ABSTRACT: The Annonaceae family consists of ~135 genera with diverse species and a large number of chemical compounds arising from the secondary metabolism. However, the chemical composition of the essential oil of several species of the family such as Cardiopetalum calophyllum has not been completely determined. In this study, the essential oils extracted from the leaves, flowers, and fruits of C. calophyllum , collected in typical areas of the Cerrado of Goiás, were characterized. The essential oil was extracted by hydrodistillation for 4h using a Clevenger apparatus. The chemical analysis was carried out by gas chromatography-mass spectrometry (GC-MS), and the constituents were identified by comparing the spectra and retention index obtained with those available in the literature. Twenty three compounds were identified in the essential oil of leaves; the oxygenated sesquiterpene, spathulenol (28.78%), was the major compound. Twenty five compounds were identified in the flowers, mainly comprising sesquiterpene hydrocarbons, germacrene-D (37.03%) and germacrene-B (13.72%). Seventeen compounds were reported in fruits, mainly comprising sesquiterpene hydrocarbons, germacrene-D (28.19%) and germacrene-B (20.90%), and an oxygenated sesquiterpene, spathulenol (11.53%). This is the first report on the chemical composition of the essential oils from leaves, flowers, and fruits of C. calophyllum.

scholarly journals Essential oils of Baccharis trinervis (Asteraceae) from Costa Rica

2017 ◽  
Vol 65 (4) ◽  
pp. 1307 ◽  
Author(s):  
Carlos Chaverri ◽  
José F. Cicció
Keyword(s):  
Gas Chromatography ◽  
Costa Rica ◽  
Chemical Composition ◽  
Essential Oils ◽  
Central America ◽  
Fused Silica ◽  
Gas Chromatography Mass Spectrometry ◽  
Caryophyllene Oxide ◽  
Mass Spectral Fragmentation ◽  
Germacrene D

Baccharis is an Asteraceae genus of flowering plants, which has about 340 to 400 species, ranging from the Southern United States to the Southern extreme of Argentina and Chile through Central America and the Caribbean regions. The species Baccharis trinervis is a native shrub from Mexico, Central America and throughout South America. In Costa Rica, this species is commonly known as alcotán and the fresh leaves are used as a poultice on wounds and ulcers. The objective of the present research was to characterize the chemical composition of seven hydrodistilled essential oils of diverse morphological parts of B. trinervis. For this, samples were obtained from three locations in Costa Rica and standard laboratory analyses were followed. The essential oils were analyzed by capillary gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS) using the retention indices on a 5 % phenyl/dimethylpolysiloxane fused silica column in addition to mass spectral fragmentation patterns, which allowed the identification of 268 compounds. The essential oils consisted mainly of terpenoids (92.3 to 97.8 %). The major constituents from the leaf oils were caryophyllene oxide (0.1-22.5 %), viridiflorol (8.8-21.0 %), germacrene D (0.5-19.1 %), germacrene B (0.2-16.0 %), β-caryophyllene (3.5-9.1 %), spathulenol (0.1-8.3 %), δ-3-carene (2.0-6.8 %), and α-pinene (2.5-5.9 %). The flower oil consisted mainly of globulol (0-24 %), β-caryophyllene (9.5-17.1 %), cis-muurola-4(14), 5-diene (traces-13.7 %), germacrene D (4.3-9.9 %), bicyclogermacrene (5.9-8.3 %), ar-curcumene (0-8.0 %), spathulenol (4.3-4.8 %), caryophyllene oxide (3.1-4.7 %), and viridiflorol (0.3-4.7 %). The major components of the branch oil were germacrene B (1.4-18.7 %), germacrene D (14.7-15.6 %), β-caryophyllene (10.1-12.4 %), viridiflorol (0-11.5 %), globulol (0.6-11.3 %), δ-3-carene (4.1-8.1 %), β-phellandrene (1.5-6.5 %), and bicyclogermacrene (3.6-4.9 %). The essential oil composition differed markedly from that of previously studied oils of plants growing in Brazil, which contain two characteristic stereoisomeric methyl dec-2-en-4,6-diynoate compounds not detected in this study. This is the first report about the chemical composition of the essential oils obtained from this species growing wild in Costa Rica.

scholarly journals Chemical Composition and Immunomodulatory Activity of Essential Oils from Rhododendron albiflorum

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3652
Author(s):  
Igor A. Schepetkin ◽  
Gulmira Özek ◽  
Temel Özek ◽  
Liliya N. Kirpotina ◽  
Andrei I. Khlebnikov ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Essential Oils ◽  
Neutrophil Migration ◽  
Compositional Analysis ◽  
Microglial Cells ◽  
Formyl Peptide Receptor ◽  
Human Neutrophils ◽  
Immunomodulatory Activity ◽  
Hl60 Cells ◽  
Formyl Peptide

Rhododendron (Ericaceae) extracts contain flavonoids, chromones, terpenoids, steroids, and essential oils and are used in traditional ethnobotanical medicine. However, little is known about the immunomodulatory activity of essential oils isolated from these plants. Thus, we isolated essential oils from the flowers and leaves of R. albiflorum (cascade azalea) and analyzed their chemical composition and innate immunomodulatory activity. Compositional analysis of flower (REOFl) versus leaf (REOLv) essential oils revealed significant differences. REOFl was comprised mainly of monoterpenes (92%), whereas sesquiterpenes were found in relatively low amounts. In contrast, REOLv was primarily composed of sesquiterpenes (90.9%), with a small number of monoterpenes. REOLv and its primary sesquiterpenes (viridiflorol, spathulenol, curzerene, and germacrone) induced intracellular Ca2+ mobilization in human neutrophils, C20 microglial cells, and HL60 cells transfected with N-formyl peptide receptor 1 (FPR1) or FPR2. On the other hand, pretreatment with these essential oils or component compounds inhibited agonist-induced Ca2+ mobilization and chemotaxis in human neutrophils and agonist-induced Ca2+ mobilization in microglial cells and FPR-transfected HL60 cells, indicating that the direct effect of these compounds on [Ca2+]i desensitized the cells to subsequent agonist activation. Reverse pharmacophore mapping suggested several potential kinase targets for these compounds; however, these targets were not supported by kinase binding assays. Our results provide a cellular and molecular basis to explain at least part of the beneficial immunotherapeutic properties of the R. albiflorum essential oils and suggest that essential oils from leaves of this plant may be effective in modulating some innate immune responses, possibly by inhibition of neutrophil migration.

scholarly journals Molecular insights into cancer therapeutic effects of the dietary medicinal phytochemical withaferin A

2017 ◽  
Vol 76 (2) ◽  
pp. 96-105 ◽  
Author(s):  
Chandra Sekhar Chirumamilla ◽  
Claudina Pérez-Novo ◽  
Xaveer Van Ostade ◽  
Wim Vanden Berghe
Keyword(s):  
Protein Kinase ◽  
Cell Survival ◽  
Kinase Inhibitors ◽  
Acquired Resistance ◽  
Mammalian Target Of Rapamycin ◽  
Mitogen Activated Protein Kinase ◽  
Withaferin A ◽  
Therapeutic Effects ◽  
Iκb Kinase ◽  
Cancer Agent

Despite the worldwide research efforts to combat cancer, it remains a leading cause of death. Although various specific kinase inhibitors already have been approved for clinical cancer treatment, occurrence of intrinsic or acquired resistance and intermittent response over longer periods limits long-term success of single kinase-targeted therapies. In this respect, there is a renewed interest in polypharmaceutical natural compounds, which simultaneously target various hyperactivated kinases involved in tumour-inflammation, angiogenesis, cell survival, proliferation, metastasis and angiogenesis. The dietary medicinal phytochemical withaferin A (WA), isolated fromWithaferin somnifera(popular Indian name Ashwagandha), holds promise as a novel anti-cancer agent, which targets multiple cell survival kinase pathways, including IκB kinase/NF-κB, PI3 kinase/protein kinase B/mammalian target of rapamycin and mitogen-activated protein kinase/extracellular signal-regulated kinase amongst others. In this review, we propose a novel mechanism of WA-dependent kinase inhibition via electrophilic covalent targeting of cysteine residues in conserved kinase activation domains (kinase cysteinome), which could underlie its pleiotropic therapeutic effects in cancer signalling.

scholarly journals Essential Oil Composition ofPinus peuceGriseb. Needles and Twigs from Two National Parks of Kosovo

2016 ◽  
Vol 2016 ◽  
pp. 1-9 ◽  
Author(s):  
Avni Hajdari ◽  
Behxhet Mustafa ◽  
Dashnor Nebija ◽  
Hyrmete Selimi ◽  
Zeqir Veselaj ◽  
...  
Keyword(s):  
Gas Chromatography ◽  
Chemical Composition ◽  
Essential Oil ◽  
Essential Oils ◽  
National Park ◽  
Essential Oil Composition ◽  
Gas Chromatography Mass Spectrometry ◽  
Oil Composition ◽  
Plant Materials ◽  
Geographical Variations

The principal aim of this study was to analyze the chemical composition and qualitative and quantitative variability of essential oils obtained from seven naturally grown populations of thePinus peuceGrisebach, Pinaceae in Kosovo. Plant materials were collected from three populations in the Sharri National Park and from four other populations in the Bjeshkët e Nemuna National Park, in Kosovo. Essential oils were obtained by steam distillation and analyzed by GC-FID (Gas Chromatography-Flame Ionization Detection) and GC-MS (Gas Chromatography-Mass Spectrometry). The results showed that the yield of essential oils (v/wdry weight) varied depending on the origin of population and the plant organs and ranged from 0.7 to 3.3%. In total, 51 compounds were identified. The main compounds wereα-pinene (needles: 21.6–34.9%; twigs: 11.0–24%),β-phellandrene (needles: 4.1–27.7; twigs: 29.0–49.8%), andβ-pinene (needles: 10.0–16.1; twigs: 6.9–20.7%). HCA (Hierarchical Cluster Analysis) and PCA (Principal Component Analyses) were used to assess geographical variations in essential oil composition. Statistical analysis showed that the analyzed populations are grouped in three main clusters which seem to reflect microclimatic conditions on the chemical composition of the essential oils.

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