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

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.

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

Zeitschrift für Naturforschung C ◽

10.1515/znc-2020-0097 ◽

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.

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

International Journal of Research in Ayurveda and Pharmacy ◽

10.7897/2277-4343.1205141 ◽

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.

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

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.781-784.1060 ◽

2013 ◽

Vol 781-784 ◽

pp. 1060-1063 ◽

Cited By ~ 1

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.

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Essential Oil Chemical Composition and Headspace Volatiles Profile of Achillea coarctata from Serbia

Natural Product Communications ◽

10.1177/1934578x1601100431 ◽

2016 ◽

Vol 11 (4) ◽

pp. 1934578X1601100 ◽

Cited By ~ 1

Author(s):

Ivana R. Kostevski ◽

Goran M. Petrović ◽

Gordana S. Stojanović ◽

Jelena G. Stamenković ◽

Bojan K Zlatković

Keyword(s):

Chemical Composition ◽

Essential Oil ◽

Essential Oils ◽

Essential Oil Composition ◽

Oil Composition ◽

Headspace Volatiles ◽

Aerial Parts ◽

Germacrene D ◽

Leaf Oil ◽

Stems And Leaves

This study reports the essential oil composition and headspace volatiles profile of Achillea coarctata Poir. from Serbia. The inflorescences, stems and leaves, and the aerial parts of A. coarctata were analyzed separately. Germacrene D, α-terpineol and 1,8-cineole were the main constituents of the aerial parts essential oil; 1,8-cineole, cis-cadin-4-en-7-ol and α-terpineol were the most dominant compounds in the inflorescence essential oil, while the most abundant components in the stem and leaf oil were germacrene D, cis-cadin-4-en-7-ol and ledol. The percentages of monoterpenoids and sesquiterpenoids in the aerial parts were the same, while there were differences in distribution of these compound classes in inflorescence and stem and leaf essential oils. The major components of the headspace volatiles were the same for aerial parts, inflorescence and stem and leaves: 1,8-cineole, β-pinene and α-pinene.

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Chemical Composition and Immunomodulatory Activity of Hypericum perforatum Essential Oils

Biomolecules ◽

10.3390/biom10060916 ◽

2020 ◽

Vol 10 (6) ◽

pp. 916 ◽

Cited By ~ 1

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.

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

Ciência Rural ◽

10.1590/0103-8478cr20150371 ◽

2016 ◽

Vol 46 (5) ◽

pp. 937-942 ◽

Cited By ~ 3

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.

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Essential oils of Baccharis trinervis (Asteraceae) from Costa Rica

Revista de Biología Tropical ◽

10.15517/rbt.v65i4.27845 ◽

2017 ◽

Vol 65 (4) ◽

pp. 1307 ◽

Cited By ~ 1

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.

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

The Scientific World JOURNAL ◽

10.1155/2016/5393079 ◽

2016 ◽

Vol 2016 ◽

pp. 1-9 ◽

Cited By ~ 4

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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Comparison of the Chemical Composition and Antimicrobial Activity of Thymus serpyllum Essential Oils

Notulae Botanicae Horti Agrobotanici Cluj-Napoca ◽

10.15835/nbha4329899 ◽

2015 ◽

Vol 43 (2) ◽

pp. 432-438 ◽

Cited By ~ 5

Author(s):

Aneta WESOŁOWSKA ◽

Monika GRZESZCZUK ◽

Dorota JADCZAK ◽

Paweł NAWROTEK ◽

Magdalena STRUK

Keyword(s):

Antimicrobial Activity ◽

Chemical Composition ◽

Essential Oil ◽

Essential Oils ◽

Micrococcus Luteus ◽

Gas Chromatography Mass Spectrometry ◽

E Coli ◽

Thymus Serpyllum ◽

Main Components ◽

Total Oil

The chemical composition of the essential oils obtained by hydrodistillation from the aerial parts of Thymus serpyllum and Thymus serpyllum‘Aureus’ has been investigated by gas chromatography-mass spectrometry (GC-MS). Forty-seven compounds (99.67% of the total oil) wereidentified in the essential oil of T. serpyllum. The main components found in the oil were carvacrol (37.49%), -terpinene (10.79%), -caryophyllene (6.51%), p-cymene (6.06%), (E)--ocimene (4.63%) and -bisabolene (4.51%). Similarly, carvacrol (44.93%), -terpinene(10.08%), p-cymene (7.39%) and -caryophyllene (6.77%) dominated in the oil of T. serpyllum ‘Aureus’. A total of forty three compounds wereidentified in this oil, representing 99.49% of the total oil content. On the basis of the obtained data it was proved that the content of 1-octen-3-ol,eucalyptol, (Z)--ocimene, (E)--ocimene, -terpinene, carvacrol methyl ether, germacrene D and -bisabolene was significantly higher for T.serpyllum while T. serpyllum ‘Aureus’ was characterized by a significantly higher content of 3-octanone, 3-octanol, p-cymene, borneol andcarvacrol. The isolated essential oils were evaluated for their antimicrobial activity against nine reference strains (Escherichia coli, Staphylococcusaureus, Staphylococcus epidermidis, Streptococcus agalactiae, Enterococcus faecalis, Bacillus cereus, Micrococcus luteus, Proteus vulgaris and Candidaalbicans) by the microdilution technique. Based on this test, the minimum inhibitory concentrations (MIC) of essential oil were calculated. Thevolatile oil obtained from T. serpyllum showed the highest antimicrobial activity relative to the strain of E. coli (MIC=0.025 μL/mL) and to theyeast C. albicans (MIC=0.05 μL/mL). Similarly, a significant antimicrobial activity exhibited T. serpyllum ‘Aureus’ essential oil, although the MICvalues obtained in that case for E. coli and C. albicans strains were twice as high and were respectively 0.05 μL/mL and 0.1 μL/mL.

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Chemical Composition of the Essential Oil of Croton bonplandianus from India

Natural Product Communications ◽

10.1177/1934578x1400900234 ◽

2014 ◽

Vol 9 (2) ◽

pp. 1934578X1400900

Author(s):

Rajesh K. Joshi

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography ◽

Chemical Composition ◽

Essential Oil ◽

Gas Chromatography Mass Spectrometry ◽

Caryophyllene Oxide ◽

Aerial Parts ◽

Sesquiterpene Hydrocarbons ◽

Germacrene D ◽

Total Oil

The essential oil obtained from the aerial parts of Croton bonplandianus Baill. was analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). A total of 37 compounds have been identified, representing 96.2% of the total oil. The main constituents were identified as β-caryophyllene (16.7%), germacrene D (14.7%), borneol (8.3%), Z-β-damascenone (6.(%), isobornyl acetate (6.2%), α-humulene (6.1%), germacrene A (5.2%) and caryophyllene oxide (4.5%). The oil was rich in sesquiterpene hydrocarbons (60.1%).

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