Essential oil of Nepeta x faassenii Bergmans ex Stearn (N. mussinii Spreng. x N. nepetella L.): a comparison study

Analysis (GC and GC/MS) of an essential oil sample obtained from dry leaves of Nepeta x faassenii Bergmans ex Steam, a hybrid species produced by crossbreeding N. mussinii Spreng. with N. nepetella L., led to the identification of 109 constituents that represented 95.9% of the oil. The major constituents were 4aalpha,7alpha,7aalpha-nepetalactone (67.8%), 1,8-cineole (6.6%), germacrene D (4.8%), beta-pinene (2.7%), (E)-beta-ocimene (2.6%), 4aalpha,7beta,7aalpha-nepetalactone (2.3%) and (E)-beta-farnesene (1.0%). Chemical composition of the oil was compared, using multivariate statistical analyses (MVA) with those of the oils of other Nepeta taxa, in particular N. mussinii and N. nepetella. This was done in order to explore the mode of inheritance of the monoterpene biosynthetic apparatus of N. faassenii. Chemical composition of the volatiles of a Nepeta taxon (different populations) can be subject to variation due to environmental and geographical factors. To accommodate this fact in the MVAs, along side with N. faassenii essential oil, additional 6 oils (3 different populations of N. nuda L. and N. cataria L. from Serbia) were included in this study (isolated and analyzed (chemically and statistically)). The MVA analyses recognized N. faassenii as being closely related to both N. mussinii and N. nepetella. If the relative content of oil constituents per plant and not per chromatogram were used as variables in the MVA (this was done by simple multiplication of the yields and relative percentages of components) a higher degree of mutual similarity (in respect to the monoterpene biosynthesis) of N. faassenii to N. mussinii, than to the other parent species, was observed.     

Chemical composition and antibacterial activity of essential oil of Nepeta graciliflora Benth. (Lamiaceae)

The chemical composition of the essential oil obtained from aerial parts of Nepeta graciliflora was analysed, for the first time, by GC–FID and GC–MS. A total of 27 compounds were identified, constituting over 91.44% of oil composition. The oil was strongly characterised by sesquiterpenes (86.72%), with β-sesquiphellandrene (28.75%), caryophyllene oxide (12.15%), α-bisabolol (8.97%), α-bergamotene (8.51%), β-bisabolene (6.33%) and β-Caryophyllene (5.34%) as the main constituents. The in vitro activity of the essential oil was determined against four micro-organisms in comparison with chloramphenicol by the agar well diffusion and broth dilution method. The oil exhibited good activity against all tested organisms.     

Identification of essential oil components of Marrubium thessalum Boiss. & Heldr., growing wild in Greece

The essential oil of the Greek endemic species Marrubium thessalum Boiss. & Heldr. (Lamiaceae) was obtained by the hydrodistillation of its aerial parts during the flowering stage. The composition of the oil was analysed by GC and GC-MS. Thirty compounds were identified. The oil was devoid of monoterpenes, while sesquiterpenes constituted the major fraction. The main components of the oil were caryophyllene oxide (21.7%), β-caryophyllene (17.6%), germacrene D (15.3%), β-bisabolene (12.6%) and trans-β-farnesene (8.1%).     

Chemical constituents and antioxidant activity of essential oil and organic extract from the peel and kernel parts of Citrus japonica Thunb. (kumquat) from Iran

The constituents of essential oils and organic extracts from peel and kernels of Citrus japonica were analysed by GC and GC/MS. The content of essential oil in peel and kernel was 1.1 and 0.8% based on dry weight. The essential oil of C. japonica peel and kernel was characterised by a higher amount of limonene (51.0 and 47.1%) and germacrene D (12.1 and 6.3%), and the hexane extracts of its peel and kernel were characterised by a higher amount of dodecanol-1(12.9 and 20.8%) and linolenic acid (13.1 and 16.3%), respectively. The antioxidant activities of oils were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. The results indicate that both oils from different parts of C. japonica possess considerable antioxidant activity. The fruit peel and kernel essential oil could thus be useful in the industries, chiefly in the food and pharmaceutical industries.     

Characterization of a new epoxy-hydroxycarvotanacetone derivative from the leaf essential oil of Laggera pterodonta from Côte d’Ivoire

The leaf essential oil of Laggera pterodonta (DC.) Sch. Bip. ex Oliv. (Asteraceae) collected in the Eastern Côte d’Ivoire was investigated using a combination of chromatographic (GC-RI, CC, pc-GC) and spectroscopic (GC-MS, ¹³C NMR) techniques. Eighty-three components accounting for 98.0% of the whole composition were identified with 2,5-dimethoxy-p-cymene (43.3%), sabinene (14.1%), α-humulene (9.8%), (E)-β-caryophyllene (7.2%) and germacrene D (5.2%) as major compounds. This study led to the structural elucidation of a new natural compound, (3αH,4βH,6αH,1αMe)-1,6-epoxy-3-hydroxycarvotanacetone, angelic acid ester from the leaf oil by 1D and 2D NMR spectroscopy.     

Chemical investigation of the essential oil from berries and needles of common juniper (Juniperus communis L.) growing wild in Estonia

The essential oils obtained by simultaneous distillation and extraction (SDE) from the fresh and dried needles and dried berries of Juniperus communis L. of Estonian origin were subjected to GC-FID and GC-MS analyses. The yields of the oils ranged between 0.2% and 0.6% from juniper berries and between 0.5% and 1.0% from needles (dried weight). A total of 87 compounds were identified, representing over 95% of the oil. The major compounds in the needle oil were monoterpenes α-pinene (33.3-45.6%), sabinene (0.2-15.4%), limonene (2.8-4.6%) and sesquiterpenes (E)-β-caryophyllene (0.8-10.3%), α-humulene (0.8-6.2%) and germacrene D (3.0-7.8%). The juniper berry oil was rich in α-pinene (53.6-62.3%), β-myrcene (6.5-6.9%) and germacrene D (4.5-6.1%). The main oxygenated terpenoids found in the needle oil were germacrene D-4-ol (0.4-4.0%) and α-cadinol (to 2.7%). The oil from fresh needles contained high amounts of (E)-2-hexenal (3.7-11.7%).     

Essential oil composition of aerial parts from Algerian Anacyclus monanthos subsp. cyrtolepidioides (Pomel) Humphries

The chemical composition of the essential oil from the aerial parts of Anacyclus monanthos subsp. cyrtolepidioides (Pomel) Humphries (Asteraceae) growing in a semi-arid region of Algeria was investigated for the first time. The essential oil was obtained by hydrodistillation and fully characterized by gas chromatography-mass spectrometry (GC-MS). A total of 97 compounds were identified. The essential oil was found to be rich in trans-chrysanthenyl acetate (9.8 ± 2.0%), (E)-β-farnesene (7.4 ± 1.5%), germacrene D (6.9 ± 1.3%) and myristicin (4.8 ± 0.8%).     

Analysis of essential oils from Scutellaria orientalis ssp. alpina and S. utriculata by GC and GC-MS

The chemical composition of the essential oils obtained from aerial parts of Scutellaria orientalis L. ssp. alpina (Boiss.) O. Schwarz and S. utriculata Labill. growing wild in Lebanon, were analyzed by GC and GC-MS. In S. orientalis ssp. alpina, strongly characterized by sesquiterpenes (41.2%) and particularly sesquiterpene hydrocarbons (31.7%), hexahydrofarnesylacetone (11.7%) was recognized as the main constituent, together with hexadecanoic acid (7.6%), caryophyllene (7.4%), caryophyllene oxide (6.8%), 4-vinylguaiacol (5.4%) and germacrene D (5.4%). S. utriculata oil was instead constituted above all by monoterpenes (42.2%), particularly oxygen containing monoterpenes (39.9%), and in this oil the main compounds were linalool (20.1%), 4-vinyl guaiacol (15.5%), alpha-terpineol (8.9%), (E)-nerolidol (8.9%) and geraniol (8.2%).     

Essential oil composition of Cachrys cristata--a rare and endangered species in the flora of Serbia

Cachrys cristata DC. (Apiaceace) is a rare and critically endangered species in the flora of Serbia. Essential oil isolated by hydrodistillation from the aerial parts and fruits of this species was analyzed using combined GC and GC/MS. The oil from the aerial parts was rich in sesquiterpenes (45.7%) and oxygenated sesquiterpenes (32.9%), while the fruit oil consisted of a higher percentage of sesquiterpenes (48.3%) and oxygenated sesquiterpenes (36.7%). The dominant constituents in the oil from aerial parts were phytol (13.1%) and germacrene D (12.9%), while in the fruit oil suberosin (19.7%) and germacrene D (12.3%) were the most abundant.     

Essential oil composition and antibacterial activity of Monticalia greenmaniana (Asteraceae)

The essential oils from fresh aerial parts of Monticalia greenmaniana (Hieron) C. Jeffrey (Asteraceae) collected in March, were analyzed by GC/MS. Oil yields (w/v) of 0.1% (flowers), 0.07%, (stems) and 0.1% (leaves) were obtained by hydrodistillation. Thirteen, sixteen and eighteen components, respectively, were identified by comparison of their mass spectra with those in the Wiley GC-MS Library data base. The major components of the flower and stem oils were 1-nonane (38.8% flowers; 33.5% stems), alpha-pinene (29.0% flowers; 14.8% stems) and germacrene D (15.6% flowers; 18.6% stems). However, in the leaf oil, germacrene D was observed at 50.7%, followed by beta-cedrene at 8.4%. The leaf essential oil showed a broad spectrum of antibacterial activity against the important human pathogenic Gram-positive and Gram-negative bacteria Staphylococcus aureus (ATCC 25923), Enterococcus faecalis (ATCC 19433), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853) and Klebsiella pneumoniae (ATCC 25955) with MIC values ranging from 75 to 6000 ppm.     

Chemical composition and insecticidal activity against Sitophilus zeamais of the essential oils derived from Artemisia giraldii and Artemisia subdigitata

The aim of this research was to determine the chemical composition and insecticidal activity of the essential oils derived from flowering aerial parts of Artemisia giraldii Pamp. and A. subdigitata Mattf. (Family: Asteraceae) against the maize weevil (Sitophilus zeamais Motsch.). Essential oils of aerial parts of A. giraldii and A. subdigitata were obtained from hydrodistillation and investigated by GC and GC-MS. A total of 48 and 33 components of the essential oils of A. giraldii and A. subdigitata were identified, respectively. The principal compounds in A. giraldii essential oil were β-pinene (13.18%), iso-elemicin (10.08%), germacrene D (5.68%), 4-terpineol (5.43%) and (Z)-β-ocimene (5.06%). 1,8-Cineole (12.26%) and α-curcumene (10.77%) were the two main components of the essential oil of A. subdigitata, followed by β-pinene (7.38%), borneol (6.23%) and eugenol (5.87%). The essential oils of A. giraldii and A. subdigitata possessed fumigant toxicity against the maize weevils with LC50 values of 6.29 and 17.01 mg/L air, respectively. The two essential oils of A. giraldii and A. subdigitata also exhibited contact toxicity against S. zeamais adults with LD50 values of 40.51 and 76.34 μg/adult, respectively. The results indicated that the two essential oils show potential in terms of fumigant and contact toxicity against grain storage insects.     

Essential oil composition of three species of Scutellaria from Turkey

The chemical compositions of the essential oils obtained by hydrodistillation from the aerial parts of Scutellaria diffusa, Scutellaria heterophylla and Scutellaria salviifolia were separately identified simultaneously by gas chromatography and gas chromatography-mass spectrometry. The main components were determined as hexadecanoic acid (30%) and caryophyllene oxide (9%) in the oil of S. diffusa. Germacrene D (21%), hexadecanoic acid (16%) and β-caryophyllene (13%) were found as major components in the oil of S. heterophylla. The main components of the oil of S. salviifolia were germacrene D (40%), bicyclogermacrene (14%) and β-caryophyllene (11%). Overall, individually 63, 68 and 43 constituents were identified in the aerial parts of S. diffusa, S. heterophylla and S. salviifolia essential oils representing 92.1%, 89.9% and 90% of the total, respectively.     

Chemical composition and antimicrobial activity of the essential oil from Ambrosia trifida L

The essential oil obtained by steam distillation of dried aerial parts of Ambrosia trifida L. from Northeast China was analyzed by GC and GC-MS. The essential oil yield based on dried plant material was 0.12% and thirty-five compounds (corresponding to 86.7% of the total weight) were identified. The main components were: bornyl acetate (15.5%), borneol (8.5%), caryophyllene oxide (8.3%), alpha-pinene (8.0%), germacrene D (6.3%), beta-caryophyllene (4.6%), trans-carveol (2.9%), beta-myrcene (2.6%), camphor (2.4%) and limonene (3.2%). A. trifida essential oil demonstrated bactericidal and fungicidal activity against six bacterial strains and two fungal strains, using the agar diffusion method.     

Two new eudesman-4α-ol epoxides from the stem essential oil of Laggera pterodonta from Côte d’Ivoire

Abstract

The investigation of the stem essential oil of Laggera pterodonta (DC.) Sch. Bip. ex Oliv. (Asteraceae) from Côte d’Ivoire was carried out, using a combination of chromatographic (GC-RI, CC, pc-GC) and spectroscopic (GC-MS, ¹³C NMR) techniques. This study led to the identification of fifty constituents of which two new natural compounds 7β,11β-epoxy-eudesman-4α-ol and 7α,11α-epoxy-eudesman-4α-ol. Their structures were elucidated by 1?D and 2?D NMR spectroscopy after pc-GC purifying. Finally, 98.9% of the whole composition of the oil was identified with a high amount of 2,5-dimethoxy-p-cymene (78.9%). The other significant components were α-humulene (6.2%), (E)-β-caryophyllene (1.7%), thymyl methyl oxide (1.7%), α-phellandrene (1.5%), p-cymene (1.2%), (3αH,4βH,6αH,1αMe)-1,6-epoxy-3-hydroxycarvotanacetone angelic acid ester (1.1%) and 10-epi-γ-eudesmol (1.0%).     

Bioactivity and chemical composition of the leaf essential oils of Zanthoxylum rhoifolium and Zanthoxylum setulosum from Monteverde, Costa Rica

The leaf essential oils of Zanthoxylum rhoifolium and Zanthoxylum setulosum (Rutaceae) from Monteverde, Costa Rica have been obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry. The principal constituents of Z. rhoifolium leaf oil were germacrene D (14.6%), limonene (12.5%), trans-2-hexenal (11.3%), beta-elemene (9.2%), 2-undecanone (9.2%), myrcene (7.9%), bicyclogermacrene (7.5%), and germacrene A (5.2%). The leaf oil of Z. setulosum was composed largely of beta-phellandrene (37.5%), beta-caryophyllene (13.7%), alpha-pinene (11.9%), germacrene D (10.9%), myrcene (5.9%), and nerolidol (5.4%). The essential oils were screened for in-vitro cytotoxic activity against Hep G2, MCF-7, and PC-3 human tumor cell lines; antibacterial activity against Bacillus cereus, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli; and for Artemia salina (brine shrimp) lethality. Neither Z. rhoifolium nor Z. setulosum leaf oils exhibited cytotoxicity or antibacterial activity. Both oils showed activity against A. salina.     

Essential oil composition of endemic Tanacetum zahlbruckneri (Nab.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey

In this study, water-distilled essential oils from the flowers of Tanacetum zahlbruckneri and flowers and stems of Tanacetum tabrisianum from Turkey were analysed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The flower oil of T. zahlbruckneri was characterised by the sesquiterpenes germacrene D (29.7%) and spathulenol (12%). Flower (A) and stem (B) oil of T. tabrisianum was characterised by 1,8-cineole: 17.6% (A), 22.5% (B), hexadecanoic acid: 10.3% (A), 8% (B), decanoic acid: 5.8% (A) and trans-linalooloxide acetate: 5.3% (A), 4% (B). Unlike a previous report on the essential oil composition of T. tabrisianum, in this study a 1,8-cineole and hexadecanoic acid-rich oil with a low percentage of caryophyllene oxide and spathulenol was obtained. The composition of the essential oil of endemic T. zahlbruckneri was investigated for the first time.     

Chromatographic analysis,antimicrobial and insecticidal activities of the essential oil of Phlomis floccosa D. Don.

The present study was conducted to investigate for the first time the chemical composition and insecticidal and antimicrobial properties of Phlomis floccosa D. Don. essential oil isolated by hydro‐distillation of its aerial parts. Qualitative and quantitative analyses of the essential oil on the basis of gas chromatography and mass spectrometry (GC/FID and GC/MS) revealed the presence of 59 organic volatiles representing 86.9% of the total constituents. The major compounds were germacrene‐D (19.7%) followed by β‐caryophyllene (15.5%), caryophyllene oxide (8.3%), hexadecenoic acid (7.9%) and carvacrol (6.1%). The broth microdilution method was conducted to test the antimicrobial activity of the essential oil against five pathogens: Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica, Staphylococcus aureus, Bacillus subtilis and the yeast Candida albicans. The oil of P. floccosa D. Don. shows promising activity against the Gram‐positive bacteria S. aureus and B. subtilis and the yeast C. albicans (minimum inhibitory concentration = 625 μg.mL^?1). The effectiveness of the essential oil was assessed on both Tribolium confusum and Sitophilus zeamais pest insects and it was more pronounced against T. confusum, showing a moderate mortality of 47.5%.     

The essential oils of the aerial parts of two Hypericum taxa (Hypericum triquetrifolium and Hypericum aviculariifolium subsp. depilatum var. depilatum (Clusiaceae)) from Turkey

In this study, essential oil compositions of two Hypericum L. taxa (Hypericum triquetrifolium Turra. and Hypericum aviculariifolium Jaub. et Spach subsp. depilatum var. depilatum (Freyn et Bornm.) Robson) naturally grown in Turkey were determined using gas chromatography and gas chromatography-mass spectrometry systems. The essential oils were obtained by hydrodistillation from the aerial parts of plants. A total of 45 compounds were identified in the essential oils of H. triquetrifolium; 1-hexanal (18.8%), 3-methylnonane (12.5%) and α-pinene (12.3%). In this study, 41 components were identified in H. aviculariifolium subsp. depilatum var. depilatum oil; α-pinene (52.1%), germacrene D (8.5%) and β-pinene (3.6%) were the predominant constituents. The essential oil analysis showed that monoterpene concentrations were higher than that of the sesquiterpenes in both oils. The results were discussed in the meaning of the usefulness of these plants and their chemicals as natural products and potential usage in chemotaxonomy.     

Constituents of the essential oil from aerial parts of Chromolaena odorata from Thailand

The chemical composition of the essential oil from the aerial parts of Chromolaena odorata, collected from Phitsanulok, Thailand was analyzed by means of GC-(FID) and GC-MS. Twenty-two constituents were identified. The major components were pregeijerene (17.6%), germacrene D (11.1%), alpha-pinene (8.4%), beta-caryophyllene (7.3%), vestitenone (6.5%), beta-pinene (5.6%), delta-cadinene (4.9%), geijerene (3.1%), bulnesol (2.9%), and trans-ocimene (2.2%).     

Composition and antimicrobial activity of Seseli montanum subsp. tommasinii essential oil

The essential oil isolated from Seseli montanum L. subsp. tommasinii Reich. f. was analyzed by GC/MS and the most abundant components were beta-pinene (30.2%), germacrene D (10.1%), sabinene (8.0%), alpha-pinene (7.2%) and limonene (6.6%). The antimicrobial effect of the essential oil was evaluated against four bacterial and four fungal species among which were food contaminants, spoilage fungi, and plant, fungal and animal pathogens. The oil possessed moderate to strong antimicrobial activity.