Reinvestigation of carvotanacetone after 100 years along with minor terpenoid constituents of Blumea malcolmii Hook. F. essential oil

Reinvestigation of essential oil constituents of Blumea malcolmii Hook. F. (Asteraceae) was carried out after 100 years using gas chromatography equipped with flame ionisation detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). Eighteen constituents, representing 99.2% of the total oil, were identified. The major compound was identified by GC/MS and NMR (¹H and ¹³C) as carvotanacetone (92.1%). The minor compounds of essential oil have also been identified for the first time in B. malcolmii. The oil was found to be rich in oxygenated monoterpene-type constituents (95.0%).     

A detailed study of the volatile components of Plectranthus asirensis of Saudi Arabian origin

Essential oil composition of Plectranthus asirensis grown in Saudi Arabia was chemically analysed for the first time by various gas chromatography techniques (GC–MS, GC–FID, Co–GC, LRI determination and database and literature searches) using two different stationary phase columns (polar and nonpolar). This analysis led to the characterisation of a total of 124 components representing 98.5% of the total oil composition. The results revealed that P. asirensis oil was mainly dominated by monoterpenoids (90.7%) in which most representative constituents were thymol (66.0 ± 0.36%), γ-terpinene (14.0 ± 0.18%), p-cymene (5.2 ± 0.06%) and β-caryophyllene (3.0 ± 0.03%). It is worth mentioning here that this is the first report on the phytochemical constituents of P. asirensis.     

Application of Comprehensive Two‐Dimensional Gas Chromatography (GC×GC) to the Qualitative Analysis of Essential Oils

This paper investigates the separation of moderately complex samples by comprehensive two‐dimensional gas chromatography (GC×GC). The analysis of peppermint (Mentha piperita) and spearmint (Mentha spicata) essential oil components, including acetates, alcohols, furans, ketones, sesquiterpenes, and terpenes, was achieved by one‐dimensional gas chromatography with quadrupole mass spectrometry detection (GC/MSD) and GC×GC with flame ionization detection. Peppermint essential oil was found to contain 89 identifiable peaks by GC×GC compared to 30 peaks in the GC/MSD chromatogram. Likewise, 68 peaks were found in the GC×GC chromatogram of spearmint (compared to 28 in GC/MSD). Plots of the first dimension versus second dimension retention times provided a fingerprint of the two essential oils, which revealed 52 similar compounds between the two essential oils as opposed to 18 matches by 1D GC.     

E,E-α-Farnesene rich essential oil of Saraca asoca (Roxb.) Wilde flower

Saraca asoca (Roxb.) Wilde (Fabaceae) commonly known as ‘Ashoka’ is a highly valued medicinal plant categorised ‘vulnerable’ by International Union for Conservation of Nature. The hydro-distilled essential oil from the flowers of S. asoca was investigated using gas chromatography equipped with a flame ionisation detector (GC-FID) and gas chromatography coupled with a mass spectrometry (GC/MS). Twenty-eight compounds representing 95.8% of the total oil were identified. The major constituents of the essential oil were E,E-α-farnesene (41.2%), hexadecanoic acid (15.3%), methyl salicylate (9.5%) and Z-lanceol (6.6%). The oil was found to be rich in sesquiterpene hydrocarbon-type constituents.     

Senna occidentalis (L.) Link and Senna hirsuta (L.) H. S. Irwin & Barneby: constituents of fruit essential oils and antimicrobial activity

Senna occidentalis and S. hirsuta are mostly gathered from the wild for medicinal use and have a disagreeable odour when crushed. The volatile oils isolated from fresh fruits of S. occidentalis and S. hirsuta were subjected to gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS) and antimicrobial assays. GC and GC-MS analyses permitted the identification of 58 constituents. S. occidentalis oil was dominated by cyperene (10.8%), β-caryophyllene (10.4%), limonene (8.0%) and caryophyllene oxide (6.8%). The main components of S. hirsuta fruit oil were benzyl benzoate (24.7%), τ-cadinol (18.9%), 2,5-dimethoxy-p-cymene (14.6%) and β-caryophyllene (5.1%). S. occidentalis fruit oil exhibited better antimicrobial activity (MIC 78–312 μg/mL) against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Aspergillus niger compared with S. hirsuta oil. The compositions and the activities of the fruit essential oils of S. occidentalis and S. hirsuta are reported for the first time.     

Essential oil composition and biological activity from Artemisia caerulescens subsp. densiflora (Viv.) Gamisans ex Kerguélen & Lambinon (Asteraceae), an endemic species in the habitat of La Maddalena Archipelago

The purpose of this study was to investigate the composition of the essential oil obtained from a population of Artemisia caerulescens subsp. densiflora growing in Razzoli, an island in the La Maddalena Archipelago (Sardinia, Italy). A. caerulescens sups. densiflora Viv. (Asteraceae), a wild herb, seldom studied in the Mediterranean, represents one of the many rare endemic species growing in North Sardinia. The essential oil composition was analysed by means of GC/MS analysis, which showed davana ethers as the major volatile components, accounting together for 17.5%, followed by (E)-nerolidol (4.5%), β-oplopenone (3.3%), cis-sabinene hydrate (5.2%) and terpinen-4-ol (4.7%). The oil was tested for antioxidant activity by means of DPPH test, inhibition of lipid oxidation test and hypochlorous acid test, which showed a quite interesting scavenger capacity. For the first time, we reported the cytotoxic activity of the essential oil of A. caerulescens subsp. densiflora, against three human tumour cell lines (A375, MDA-MB231 and HCT116), with IC₅₀ values in the range 5.20–7.61 μg/mL, which deserved further studies to support its use as chemopreventive agent. Finally, the antimicrobial activity of the essential oil, displayed on a panel of human pathogens, was very low.     

Essential oil composition of Rydingia michauxii (Briq.) Scheen & V.A. Albert endemic of Iran

The chemical composition of the essential oil (EO) obtained from the aerial parts of Rydingia michauxii (Briq.) Scheen & V.A. Albert was analysed by gas chromatography and gas chromatography/mass spectrometry (GC/MS). Eighty components were identified in the oil with caryophyllene oxide (20.1%), trans-verbenol (10.2%), linalool (5.3%) and humulene epoxide II (4.6%) as main constituents. We reported here the chemical compositions of R. michauxii EOs from southern Zagros of Iran with a distinct chemical profile for the first time.     

Study on essential oils from the leaves of two Vietnamese plants: Jasminum subtriplinerve C.L. Blume and Vitex quinata (Lour) F.N. Williams

The essential oil constituents of the leaves of Jasminum subtriplinerve (Oleaceae) and Vitex quinata (Verbanaceae) cultivated in Vietnam were analysed by gas chromatography – flame ionisation detector (GC–FID) and gas chromatography – mass spectrometry (GC–MS) techniques. The main constituents identified in J. subtriplinerve were mainly oxygenated monoterpenes represented by linalool (44.2%), α-terpineol (15.5%), geraniol (19.4%) and cis-linalool oxide (8.8%). The quantitative significant components of V. quinata were terpene hydrocarbons comprising of β-pinene (30.1%), β-caryophyllene (26.9%) and β-elemene (7.4%). The chemical compositions of the essential oils are being reported for the first time.     

Commercial Origanum compactum Benth. and Cinnamomum zeylanicum Blume essential oils against natural mycoflora in Valencia rice

Chemical composition of commercial Origanum compactum and Cinnamomum zeylanicum essential oils and the antifungal activity against pathogenic fungi isolated from Mediterranean rice grains have been investigated. Sixty-one compounds accounting for more than 99.5% of the total essential oil were identified by using gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). Carvacrol (43.26%), thymol (21.64%) and their biogenetic precursors p-cymene (13.95%) and γ-terpinene (11.28%) were the main compounds in oregano essential oil, while the phenylpropanoids, eugenol (62.75%), eugenol acetate (16.36%) and (E)-cinnamyl acetate (6.65%) were found in cinnamon essential oil. Both essential oils at 300 μg/mL showed antifungal activity against all tested strains. O. compactum essential oil showed the best antifungal activity towards Fusarium species and Bipolaris oryzae with a total inhibition of the mycelial growth. In inoculated rice grains at lower doses (100 and 200 μg/mL) significantly reduced the fungal infection, so O. compactum essential oil could be used as ecofriendly preservative for field and stored Valencia rice.     

Sesquiterpene-rich volatile constituents of Ipomoea obscura (L.) Ker-Gawl.

The hydro-distilled essential oil from flowering aerial parts of Ipomoea obscura (L.) Ker-Gawl. (Convolvulaceae) was investigated by using gas chromatography equipped with a flame ionisation detector GC-FID and gas chromatography coupled with a mass spectrometry (GC/MS). Forty-two components, representing 97.1% of the total oil, were identified. The major constituents of the essential oil were α-bulnesene (23.8%), α-humulene (13.7%) and seychellene (11.2%). The other minor constituents were α-guaiene (8.3%), β-caryophyllene (7.1%), γ-terpinene (4.2%), hexadecanoic acid (3.0%) and β-elemene (2.7%). The oil was found to be rich in sesquiterpene hydrocarbon type constituents (78.4%).     

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%.     

Identification of Chlorinated Phenyl and Phenoxy Substituted Dibenzodioxin,Dibenzofuran, and Diphenyl Ether Homologs in Commercial Grade Pentachlorophenol

Abstract

As part of a bioassay study by the National Toxicology Program, technical grade pentachlorophenol (PCP) was analyzed for chlorinated impurities using capillary gas chromatography/mass spectrometry (GC/MS). Several high molecular weight impurities eluting after octachlorodibenzodioxin were detected during the analysis of this material. These impurities were tentatively identified according to structural classes as chlorinated triphenyl ethers, dibenzodioxin phenyl ethers, phenyldibenzodioxins, and dibenzofuran phenyl ethers.     

Composition and antioxidant activity of Senecio nudicaulis Wall. ex DC. (Asteraceae): a medicinal plant growing wild in Himachal Pradesh,India

The composition of essential oil isolated from Senecio nudicaulis Wall. ex DC. growing wild in Himachal Pradesh, India, was analysed, for the first time, by capillary gas chromatography (GC) and GC–mass spectrometry. A total of 30 components representing 95.3% of the total oil were identified. The essential oil was characterised by a high content of oxygenated sesquiterpenes (54.97%) with caryophyllene oxide (24.99%) as the major component. Other significant constituents were humulene epoxide-II (21.25%), α-humulene (18.75%), β-caryophyllene (9.67%), epi-α-cadinol (2.90%), epi-α-muurolol (2.03%), β-cedrene (1.76%), longiborneol (1.76%), 1-tridecene (1.16%) and citronellol (1.13%). The oil was screened for antioxidant activity using DPPH, ABTS and nitric oxide-scavenging assay. The oil was found to exhibit significant antioxidant activity by scavenging DPPH, ABTS and nitric oxide radicals with IC₅₀ values of 10.61 ± 0.14 μg mL^? 1, 11.85 ± 0.28 μg mL^? 1 and 11.29 ± 0.42 μg mL^? 1, respectively.     

Thermal analysis and gas chromatography coupled mass spectrometry analyses of hydroxypropyl-β-cyclodextrin inclusion complex containing Lippia gracilis essential oil

Inclusion complexation with cyclodextrins is an effective way to improve stability and turn liquid materials into re-dispersible and easy-to-handle powders. In the present work, the complexation of L. gracilis essential oil, already recognized as a potent larvicide material, with hydroxylpropyl-β-cyclodextrin was performed using slurry and paste procedures and the complexes obtained were evaluated. The gas chromatography coupled to mass spectrometry (GC/MS) analysis showed a total volatile content of 99.24% in the L. gracilis oil. The characterization of the complex involved the analysis of the original essential oil, the surface, and the total extracted oils. The major components in L. gracilis essential oil were identified as carvacrol (23.52%), p-cymene (15.82%), γ-terpinene (14.17%), and thymol (7.27%). GC/MS results showed significant differences between the original oil, the slurry, and paste complexation. Thermal characterization indicates the occurrence of complexation, mainly in paste complexes, which presents a TG–DTA peak at 230–275 °C, probably related to oil loss.     

Chemical composition of the essential oil from the leaves of Anaxagorea brevipes (Annonaceae) and evaluation of its bioactivity

The essential oil obtained by hydrodistillation from leaves of Anaxagorea brevipes was analysed by gas chromatography fitted with a flame ionisation detector (GC–FID) and coupled to mass spectrometry (GC–MS). Thirty one components were identified, representing around 75.7% of total oil. The major components were β-eudesmol (13.16%), α-eudesmol (13.05%), γ-eudesmol (7.54%), guaiol (5.12%), caryophyllene oxide (4.18%) and β-bisabolene (4.10%). The essential oil showed antimicrobial activity against Gram-positive bacteria and yeast with the MIC values between 25.0 and 100 μg/mL. The highest antiproliferative activity was observed for the oil against MCF-7 (breast, TGI = 12.8 μg/mL), NCI-H460 (lung, TGI = 13.0 μg/mL) and PC-3 (prostate, TGI = 9.6 μg/mL) cell lines, while against no cancer cell line HaCat (keratinocyte) the TGI was 38.8 μg/mL. The oil exhibited a small antioxidant activity assessed through ORAC-FL assay (517 μmol TE/g). This is the first report regarding the chemical composition and bioactivity of A. brevipes essential oil.     

Chemical Composition and Biological Activities of Essential Oils from the Leaves,Stems, and Roots of Kadsura coccinea

The chemical composition and biological activities of the essential oils from the leaves, stems, and roots of Kadsura coccinea (K. coccinea) were investigated. The essential oils were extracted by hydro distillation and analyzed by gas chromatography mass spectrometry (GC-MS) and gas chromatography with flame ionization detector (GC-FID). Antioxidant activities of the essential oils were examined with DPPH radical scavenging assay, ABTS cation radical scavenging assay, and ferric reducing antioxidant power assay. Antimicrobial activities were evaluated by determining minimum inhibitory concentrations (MIC) and minimum microbiocidal concentrations (MMC). Acetylcholinesterase and butyrylcholinesterase inhibitory activity of the essential oils were also tested. A total of 46, 44, and 47 components were identified in the leaf, stem, and root oils, representing 95.66%, 97.35%, and 92.72% of total composition, respectively. The major compounds of three essential oils were α-pinene (16.60–42.02%), β-pinene (10.03–18.82%), camphene (1.56–10.95%), borneol (0.50–7.71%), δ-cadinene (1.52–7.06%), and β-elemene (1.86–4.45%). The essential oils were found to have weak antioxidant activities and cholinesterase inhibition activities. The essential oils showed more inhibitory effects against Staphylococcus aureus (S. aureus) than those of other strains. The highest antimicrobial activity was observed in the root oil against S. aureus, with MIC of 0.78 mg/mL. Therefore, K. coccinea essential oils might be considered as a natural antibacterial agent against S. aureus with potential application in food and pharmaceutical industries.     

Enrichment of the thymoquinone content in volatile oil from Satureja montana using supercritical fluid extraction

Supercritical fluid extraction (SFE) of the volatile oil from Satureja montana L. was performed under different conditions of pressure (90 and 100 bar), temperature (40 and 50°C), mean particle sizes (0.4, 0.6 and 0.8 mm) and CO₂ flow rate (0.8, 1.1 and 1.3 kg/h) to understand the influence of these parameters on the composition and yield of this oil. The results were compared with those obtained for the essential oil isolated by hydrodistillation (HD). The volatile and the essential oil were analysed by GC and GC‐MS. The main compounds are carvacrol (52.2–62.0% for HD vs. 41.7–64.5% for SFE), thymol (8.6–11.0% for HD vs. 6.0–11.3% for SFE), p‐cymene (6.9–12.8% for HD vs. 6.0–17.8% for SFE), γ‐terpinene (6.4–9.4% for HD vs. 2.3–6.0% for SFE) and β‐bisabolene (2.0–2.7% for HD vs. 2.2–3.5% for SFE). The major difference between SFE and HD was the relative amount of thymoquinone, an oxygenated monoterpene with important biological activities, which can be ten‐fold higher in volatile oil (1.6–3.0 for SFE vs. 0.2% for HD). The morphology of the glandular trichomes of S. montana and the effect of the grinding process on them was also evaluated by SEM.     

酸枣果肉中挥发性化学成分分析

报道了用蒸馏-萃取法提取酸枣果肉中挥发性物质,测得酸枣果肉挥发油的含量为1．80％,用GC／MS法从酸枣果肉挥发油中分离并确定出43种化学成分。用峰面积归一化法通过化学工作站数据处理系统,得出各化学成分在挥发油中的相对百分含量。其中主要成分为酸类化合物占挥发油总量的52．26％,酚类化合物为9．34％,酯类化合物为23．05％,醛类化合物为2．77％,醚类化合物为2．66％,烷烃化合物为1．89％,其它类化合物仅占3．77％。共占酸枣果肉中挥发油总量的95．62％。     

Essential oil composition of <Emphasis Type="Italic">Santolina etrusca</Emphasis> from Italy

The essential oil composition of aerial parts of Santolina etrusca Marchi & D’Amato from Italy was analyzed by GC and GC/MS. Twenty-nine compounds of oil were identified representing 97.1% of the oil. The most abundant compounds were viridiflorol (17.9%), terpinen-4-ol (14.4%), myrcene (11.8%), β-pinene (9.9%), and cis-muurola-4(14),5-diene (9.9%). To the best of our knowledge, this is the first report on the GC/MS determination of the essential oil composition of S. etrusca. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 38–39, January–February, 2007.     

Chemical composition of the essential oil from Thapsia garganica L. (Apiaceae) grown wild in Sicily and its antimicrobial activity

In this study, the chemical composition of the essential oil from flowers and leaves of Thapsia garganica L. collected in Sicily was evaluated by GC and GC–MS. The main components of T. garganica flower oil (T.f.) were chamazulene (58.3%), humulene oxide II (9.0%), tricosane (8.2%) and pentacosane (8.2%). Also the oil from leaves (T.l.) was characterised by high content of chamazulene (49.2%). Other abundant metabolites were 1,4-dimethylazulene (18.5%), (E)-phytol (6.3%) and neophytadiene (5.1%). The comparison with other studied oils of genus Thapsia is discussed. Antimicrobial activity against several micro-organisms, including some ones infesting historical art craft, was also determined.