Phylogenetic relationships of the genus Chamaecyparis inferred from leaf essential oil

The species differentiation between Chamaecyparis formosensis, C. obtusa var. formosana, and C. obtusa, based on the composition of the leaf essential oils, was studied. The characterization of the oils by GC-FID and GC/MS analyses showed remarkable differences between these three essential oils. Cluster analysis (CA) and principal-component analysis (PCA) distinguished three groups of essential oils. The C. formosensis oil was dominated by α-pinene while those isolated from C. obtusa var. formosana and C. obtusa were characterized by high levels of (-)-thujopsene and α-terpinyl acetate, respectively. Moreover, the phylogenetic relationships of the genus Chamaecyparis were in agreement with previous findings based on morphological and molecular evidence. In addition, the essential oils from C. obtusa var. formosana could be classified into three chemical types, according to their different characteristic main compounds (β-elemol, (-)-thujopsene, and cis-thujopsenal). The biochemical correlations between the major constituents of the Chamaecyparis species were examined and their relationship is discussed.     

The Comparison of the Chemical Composition from Natural Atractylodes macrocephala Koidz and Its Tissue Culture

The essential oils of the rhizomes from natural A. macrocephala and its tissus culture have been extracted. The chemical components of these essential oils have been determined and compared by TLC and GC-MSD. Their chemical components are identical and thirteen components have been identified as β-humulene, ρ-elemol, α-humulene, α-curcumene, 3β-ace-toxyatractylon and isobutenolide, A, selina-4(14)-7(ll) diene-8-one, atractylon, anhydrobutenolide, palmitic acid, butenolid A, eudesmol and hydroxybutenolide. Six compounds are first reported containing in A. macrocephala.     

Variations in insecticidal activity and chemical compositions of leaf essential oils from Cryptomeria japonica at different ages

The larvicidal effects of the essential oils extracted from the leaves of Cryptomeria japonica at different ages (58, 42, and 26 years old) against 2 mosquito species, Aedes aegypti and Aedes albopictus, were studied. The analysis of major constituents of these essential oils was also investigated. Results obtained from the larvicidal tests, using essential oil from the leaves of 58-year-old C. japonica was found to be most effective against both A. aegypti and A. albopictus larvae, indicating tree age has significant influence on mosquito larvicidal activity. In addition, the eleven pure constituents from C. japonica leaf essential oil were also tested individually against the two mosquito larvae. Among them, alpha-terpinene, gamma-terpinene, p-cymene, 3-carene, terpinolene, and beta-myrcene shows strong larvicidal effect against the two mosquito larvae. Among these pure constituents, 3-carene exhibits the best larvicidal effect against A. aegypti and terpinolene shows an excellent inhibitory action against A. albopictus larvae. The results of this study show that the leaf essential oil and its effective constituents might be considered as a potent source for the production of fine natural larvicides.     

The Chemical Constituents of the Essential Oil from the Flowers,Leaves and Peels of Citrus aurantium

Citrus aurantium L. var. amara Engl., is a better species of sour oranges. There are essential oils in the flowers, the peels, the leaves and the branches of C. aurantium. The flower oil can be used in the preparation of perfumes of high quality. The peel oil is used mainly for the flavor-endowing of soft drinks, alcoholic drinks, bread, confectionaries and cakes. In order to control the quality of the essential oils and to improve them, we have systema- tically studied the chemical constituents of the flowers, the leaves and the peals of C. aurantium with our preparation. 12 main components were separated by silica gel column chromatography. The following 33 chemical components were identified by IR, GC-MS and GC retention index: α-thujene, α-pinene, camphene, β-pinene, myrcene, limonene, β-ocimene, trans-linalooloxide (furanoid), cis-linalooloxide (furanoid), linalool, 1,4-p-methadien-7-ol, trans-pinocarveol, camphor, terpinen-4-ol α-terpineol, nerol, citral-b, geraniol, linalylacetate, citrala, trans-linalooloxide (pyranoid), methyl anthranilate, terpinyl acetate, cis-linalooloxide (pyranoid), neryl acetate. geranyl acetate, nonanal, β-caryophyllene, α-humulene, γ-muurolene, β-nerolidol, farnesol, α- nerolidol. GC retention index of 33 compounds were measured. A fast method for routine determination is presented.     

Studies on the Essential Oils in the Leaves of Cinnamomum paucifiorum Nees

This paper shows the chemical constituents of the essential oils from the leaves of Cinnamoum pauciflorum Nees. By applying the techniques of fractional distillation, column chromatography, TlC, GC and IR, the following 13 components have been separated and identified: three monoterpenes–α–pinene (1.28%), camphene (0.17%), and p-cymenc (0.14%); five oxygenated monoterpenes–1,8-cineole (0.85%), lina-lool (14.35%), α-terpineol (0.22%), safrole (69.70%) and eugenol (4.20%), two aldehyde compoundes–nonyladehyde (0.16%) and decytadehyde (0.40%); two sesquiter–pene–β–caryophyllene (0.11%) and β–bisabolene (0.05%); one oxygenated sesquiter–pene-nerolidol (0.75%). In addition, the variations of the content of the major components of tile oils in various months have been determined.     

Chemical Studies on the Essential Oils of Foeniculum vulgare

Twenty seven chemical constituents of oils from sweet leaves, flowers and fruits of Foeniculum vulgare Mill. are examined by GC and GC-MS with both different chromatographic columns. They are 1,1-diethoxyethane, α-thujene, α-pinene, camphene, sabinene, β-pinene, myrcene, α- phellandrene, p-cymene, limonene, cineole, γ-terpinene, fenchone, camphor, terpinen-4-ol, α-terpineol, estragole, verbenone, fenchol acetate, carveol, trans-fenchol acetate, carvone, anethole, anisaldehyde, trans-anethole, methoxyphenyl acetone and benzoic acid, 4-methoxy-, othylester. The limonene is 57.8% in the essential oil from leaves, 34.2% from flowers, 13.1% from fruits, The trans-anethole is 21.8% in the essential oil from leaves, 41.2% from flowers, 63.4% from fruits.     

Variability in essential oil composition of Piper dilatatum L.C. Rich

Twelve samples of air-dried aerial parts of Piper dilatatum L. C. Rich yielded essential oils and their volatile constituents were analyzed by GC and GC–MS. Sesquiterpenes, both hydrocarbons and oxygenated, were the most highly represented classes, the former ranging from 31.5% to 87.7% and the latter varying from 1.8% to 49.4%. Using hierarchical cluster analysis, the oils were divided into seven groups, whose main constituents were: (E)-caryophyllene, α-cadinol and germacrene D (group A); spathulenol, bicyclogermacrene and (Z)-β-ocimene, (group B); spathulenol, germacrene D and (E)-nerolidol, (group C); germacrene D, limonene, α-phellandrene and bicyclogermacrene (group D); β-elemene, germacrene D and β-pinene (group E); curzerene, p-cymene and α-eudesmol (group F); and (Z)-α-bisabolene, curzerene and germacrene D (group G). We have seen that Piper oils from the Amazon present as major constituents terpenoids and phenylpropanoids, always with the predominance of one over another. The essential oils of P. dilatatum presented in this paper, containing only mono- and sesquiterpenes as its major components, is further chemotaxonomic evidence of this dichotomy in the Piper genus.     

Antifungal Activity of the Essential Oils of Callitris neocaledonica and C. sulcata Heartwood (Cupressaceae)

Mortality due to fungal infections has increased substantially, becoming a worldwide problem in public health. As a contribution to the discovery of new antifungal agents, the properties of the heartwood essential oils of two trees growing in New Caledonia, Callitris neocaledonica and C. sulcata (Cupressaceae) were investigated. The essential oils extracted by hydrodistillation were characterized by GC-FID and GC/MS analyses. From C. neocaledonica oil, 31 constituents were identified, representing 97.0% of the total oil composition, which was mainly constituted by oxygenated sesquiterpenes (88%). Among them, guaiol (1; 30.2%), bulnesol (2; 12.5%), α-eudesmol (3; 10.5%), β-eudesmol (4; 10.5%), γ-eudesmol (10.2%), and elemol (4.9%) predominated. The chemical composition of C. sulcata oil, from which 39 constituents were identified (96.8% of the total oil composition), showed some similarities with that of C. neocaledonica oil. The major constituents were also oxygenated sesquiterpenes, accounting for 78.5% of the oil, amongst them, mainly compounds 1 (16.1%), 3 and 4 (9.7% each), as well as 2 (7.4%). The antifungal activity of the oils against clinical isolates of four dermatophytic fungi (Trichophyton mentagrophytes, T. rubrum, Microsporum canis, and M. gypseum) and six yeasts (Candida albicans, C. parapsilosis, C. glabrata, C. krusei, Cryptococcus neoformans, and Cryptococcus gattii) was tested by determining minimum inhibitory concentrations (MICs) using the microdilution method. The best antifungal activities of the C. neocaledonica and C. sulcata oils were obtained against C. krusei (MICs of 3.9 and 0.975?μg/ml, resp.). These MIC values were similar to those of the reference drugs itraconazole and fluconazole (1.0 and 0.5?mg/ml, resp.). The oils were also subjected to a screening for their possible DPPH(.) (2,2-diphenyl-1-picrylhydrazyl) radical-scavenging activity. C. neocaledonica essential oil was more active than C. sulcata oil (93.3 vs. 32.2% DPPH(.) scavenged at 250?μg/ml).     

Chemical compositions of Casuarina equisetifolia L., Eucalyptus toreliana L. and Ficus elastica Roxb. ex Hornem cultivated in Nigeria

Essential oils were obtained by separate hydrodistillation of three different plants cultivated in Nigeria and analysed comprehensively for their constituents by means of gas chromatography (GC) and gas chromatography-mass spectrometry (GC–MS). The leaf essential oil of Casuarina equisetifolia L. (Casuarinaceae) comprised mainly of pentadecanal (32.0%) and 1,8-cineole (13.1%), with significant amounts of apiole (7.2%), α-phellandrene (7.0%) and α-terpinene (6.9%), while the fruit oil was dominated by caryophyllene-oxide (11.7%), trans-linalool oxide (11.5%), 1,8-cineole (9.7%), α-terpineol (8.8%) and α-pinene (8.5%). On the other hand, 1,8-cineole (39.4%) and α-terpinyl acetate (10.7%) occurred in large quantities in the essential oils of the leaf of Eucalyptus toreliana L. (Myrtaceae). The oil also features high levels of sabinene (5.9%), caryophyllene-oxide (4.7%) and α-pinene (4.2%). The main compounds identified in the leaf oil of Ficus elastica Roxb. ex Hornem. (Moraceae) were 6,10,14-trimethyl-2-pentadecanone (25.9%), geranyl acetone (9.9%), heneicosene (8.4%) and 1,8-cineole (8.2%).     

Essential Oil of Lepidium virginicum: Protective Activity on Anthracnose Disease and Preservation Effect on the Nutraceutical Content of Tamarillo Fruit (Solanum betaceum)

The essential oil from the annual plant Lepidium virginicum L. was chemically characterized in three consecutive years (2018–2020). The essential oils were evaluated in vitro and in situ on the causal agent of anthracnose in tamarillo fruits (Solanum betaceum). The main volatile constituents were phenylacetonitrile (>60 %), linalool (>10 %), limonene (>7 %) and α-terpineol (>5 %). The essential oil (MIC, 19–30 μg mL⁻¹), phenylacetonitrile (MIC, 45 μg mL⁻¹) and α-terpineol (MIC, 73 μg mL⁻¹) caused a significant inhibition in the conidial viability from a wild strain of Colletotrichum acutatum, which was isolated and identified as a causal agent of anthracnose. The inoculation of conidia from C. acutatum in non-symptomatic tamarillo fruits, followed by the in situ treatment with different concentrations of the essential oil (>30 μg mL⁻¹), phenylacetonitrile and α-terpineol, significantly (p<0.01) avoided the degradation of anthocyanins (delphinidin 3-O-rutinoside, cyanidin 3-O-rutinoside and pelargonidin 3-O-rutinoside) and carotenoids (β-cryptoxanthin and β-carotene) as well as retarded yellowing and necrosis triggered by anthracnose at least for 10 days. Our results suggest the potential use of the essential oil from L. virginicum as a natural component to preserve the nutraceutical content of tamarillo fruits against C. acutatum infection.     

Studies on the Chemical Constituents of the Hydrocarbon Fraction of the Essential Oils from Caryopteris tangutica and C. Glutinosa

The chemical constituents of the hydrocarbon fraction of essential oils of Caryopteris tangutica Maxim. and C. glutinosa Rehd were examined by means of GC-MS-COM and GC retention time data on a 45 m capillary column coated with OV- 101. 21 components have been saparated and identified, i.e. α-thujene, α-pinene, cam- phene, sabinene, β-pinene, β-myrcene, α-terpinene, p-cymene, limonene, β-ocimene-y, β- phellandrene, α-terpinolene, α-cubebene, α-copaene, α-cedrene, β-caryophyllene, γ-cadinene, 1-aromadendrene, α-humulene, β-bisabolene and δ-cadinene. The quantitative determination of these components was carried out by GLC also.     

Bioactivity of selected plant essential oils against the yellow fever mosquito Aedes aegypti larvae

The bioactivity of 14 essential oils from five plants has been studied using the brine shrimp lethality test and the Aedes aegypti larvicidal assay. All essential oils screened had LC50 values smaller than 200 microg/ml, showing significant lethality against brine shrimp. In addition, nine of the 14 essential oils tested showed toxicity against the fourth-instar A. aegypti larvae in 24 h (LC50<100 microg/ml). Of these, the leaf and bark essential oils of Cryptomeria japonica demonstrated high larvicidal activity, the most active being the leaf essential oil of C. japonica, with a LC50=37.6 microg/ml (LC90=71.9 microg/ml), followed by the bark essential oil of C. japonica also showing high activity against A. aegypti larvae, with a LC50=48.1 microg/ml (LC90=130.3 microg/ml). The results obtained from this study suggest that the leaf and bark essential oils of C. japonica are promising as larvicides against A. aegypti larvae and could be useful in the search for new natural larvicidal compounds.     

Salvia verbenaca L. essential oil: Variation of yield and composition according to collection site and phenophase

The effect of the collection sites and phenophase on yield and chemical composition of Salvia verbenaca essential oils was evaluated. The essential oil constituents were assessed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). The highest essential oil yields were observed for samples of the higher semi-arid bioclimate and at the flowering period. Eighty-five volatile constituents were identified and their percentages varied significantly (p < 0.05) depending on the collection site and the phenological stage. According to the plants origin, essential oils were dominated by monoterpene hydrocarbons, oxygenated monoterpenes and sesquiterpene hydrocarbons. The monoterpene hydrocarbons (31.9%) predominate at the flowering stage whereas oxygenated sesquiterpenes (27.5%) at the early fruiting stage. The sesquiterpene hydrocarbons (28.2%) was the most represented chemical class at late fruiting. On the basis of GC-MS data, the major identified volatile constituents were viridiflorol (3.4–17.7%), α-pinene (0.7–15.9%), β-caryophyllene (1.0–15.3%) and p-cymene (1.3–14.2%). S. verbenaca contains a diversity of bioactive constituents which shows large variations as affected by the collection sites and phenophase.     

箭叶橐吾挥发油化学成分的研究

运用气相色谱-质谱-计算机联用技术,结合标准谱库,对青海产箭叶橐吾的挥发油成分进行了研究,分离鉴定了39个化合物,主要成分为2-甲基丁烯酸(5．001％)、顺-β松油醇(2．082％)、反-β-松油醇(4．069％)、4-甲基-1-异丙基-R-3-环己烯-1-醇(15．467％)、十二烷(2．181％)、十四烷(2．276％)、Tau．-Muurolol(3．108％)、α-杜松醇(5．682％)、十六醛(2．266％)、6,10,14-三甲基-2-十五烷酮(3．421％)、三十烷(2．370％)、二十五烷(3．766％)等。     

Identification des constituants de l'essence des aiguilles de Pinus pinaster

The chromatographic analysis of the volatile leaf oil of Pinus pinaster Ait. showed 42% of monoterpene hydrocarbons (α-pinene, camphene, β-pinene, myrcene, 3-carene, limonene, cis-ocimene, terpinolene, para-cymene, 35% of sesquiterpene hydrocarbons (cubebene, copaene, caryophyllene, humulene, germacrene D, α- and γ-muurolenes, δ- and γ-cadinenes) and 23% of oxygenated compounds including esters (linalyl, bornyl, geranyl, neryl and farnesyl acetates), alcohols (cis-hexenol, linalool, α-fenchol, trans-pinocarveol, terpinen-4-ol, α-terpineol, dihydrocarveol, guaiol, junenol and α-cadinol), one aldehyde (hexenal) and one ketone (piperitone). Three non terpenoid phenylethyl esters were also identified: phenylethyl isovalerate, methyl-2 burtyate and 3-3 dimethylacrylate. Some alcohols and mainly α-terpineol and linalool seemed to be formed during the steam distillation process, they were absent when the leaf oil was obtained by maceration of small portions of leaves in the usual solvents of terpenes.     

Chemical composition and bioactivity of Boswellia serrata Roxb. essential oil in relation to geographical variation

Oleo–gum–resin of Boswellia serrata Roxb. (Burseraceae) was collected from Shivpuri forest situated in northwestern district of Madhya Pradesh, India. The commercial samples were purchased from Mandsaur and Neemuch districts (the major herbal markets of Madhya Pradesh) for comparative study of their essential oils. The average essential oil contents in the commercial Neemuch samples (11.1%) were much better as compared to the wild collection from Shivpuri (6.1%) as well as commercial collection from Mandsaur (6.9%). The commercial samples contained higher percentage of monoterpene hydrocarbons (81.9–88.1%) including α-thujene (61.4–69.8%) as the major compound. The wild habitat contained higher percentage of oxygenated monoterpenoids/benzenoids (15.7%) and sesquiterpenes (19.2%) including α-terpineol (7.8%), terpinyl isobutyrate (5.1%), and eudesmol (11.5%). Further, the antimicrobial activities of these collections showed remarkable variation among the essential oils. On the other hand, wild habitat contained improved percentage of semi-polar compounds (34.9%) which might be responsible for enhanced antibacterial activity. Similarly, the winter collection from Neemuch (BS-N2) showed significant antioxidant activity, whereas the wild habitat did not show any antioxidant activity. The higher percentage of monoterpene hydrocarbons in commercial samples, especially δ-3-carene, α-pinene, and α-thujene, might be responsible for enhanced antifungal and antioxidant activities. The Pearson correlation values justify the bioactivity relationship of the major compounds with different microbial strains. It also justified the interaction among the major individual compounds.     

Comparative Chemical Composition and Acetylcholinesterase (AChE) Inhibitory Potential of Cinnamomum camphora and Cinnamomum tamala

Cinnamomum species have applications in the pharmaceutical and fragrance industry for wide biological and pharmaceutical activities. The present study investigates the chemical composition of the essential oils extracted from two species of Cinnamomum namely C. tamala and C. camphora. Chemical analysis showed E-cinnamyl acetate (56.14 %), E-cinnamaldehyde (20.15 %), and linalool (11.77 %) contributed as the major compounds of the 95.22 % of C. tamala leaves essential oil found rich in phenylpropanoids (76.96 %). C. camphora essential oil accounting for 93.57 % of the total oil composition was rich in 1,8-cineole (55.84 %), sabinene (14.37 %), and α-terpineol (10.49 %) making the oil abundant in oxygenated monoterpenes (70.63 %). Furthermore, the acetylcholinesterase inhibitory activity for both the essential oils was carried out using Ellman's colorimetric method. The acetylcholinesterase inhibitory potential at highest studied concentration of 1 mg/mL was observed to be 46.12±1.52 % for C. tamala and 53.61±2.66 % for C. camphora compared to the standard drug physostigmine (97.53±0.63 %) at 100 ng/ml. These multiple natural aromatic and fragrant characteristics with distinct chemical compositions offered by Cinnamon species provide varied benefits in the development of formulations that could be advantageous for the flavor and fragrance industry.     

不同生长年限巨尾桉叶挥发性成分GC-MS分析

为了分析不同年限巨尾桉叶挥发油的化学成分及生长年限对化学成分组成的影响,采用水蒸气蒸馏法,分别提取2006～2010年种植的巨尾桉叶片中的挥发性成分,并用气相色谱质谱联用技术分析鉴定其化学成分。结果表明:不同生长年限的巨尾桉叶片挥发油产量在0.55%～1.35%之间,随生长年限的增加而升高。利用GC-MS共鉴定出63个化合物,占总挥发油的93.00%～97.07%。其中相对含量较高的物质为:1,8-桉叶油素(55.72%～63.47%)、α-松油醇(9.78%～14.15%)、乙酸松油酯(4.96%～7.06%)、α-蒎烯(0.99%～4.31%)、龙脑(2.40%～4.89%)。由于生长年限的不同,挥发油中物质的组成及相对含量均存在差异。     

Chemical compositions,antimicrobial and herbicidal effects of essential oils isolated from Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum

The chemical composition of essential oils isolated from the aerial parts by hydrodistillation of Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum were analyzed by GC–MS. The oils contain similar major components. The major components of T. aucheranum oil were 1,8-cineole (23.8%), camphor (11.6%), terpinen-4-ol (7.2%), α-terpineol (6.5%), borneol (3.8%), (E)-thujone (3.2%), epi-α-cadinol (3.1%), and artemisia ketone (3.0%). Camphor (17.9%), 1,8-cineole (16.6%) and borneol (15.4%) were found to be predominant constituents in the oil of T. chiliophyllum. It is interesting to find that ester derivatives of dihydro-α-cyclogeranic acid (2,2,6-trimethylcyclohexylcarboxylate), dihydro-α-cyclogeranyl hexanoate (10.1%), dihydro-α-cyclogeranyl pentanoate (3.0%), dihydro-α-cyclogeranyl butanoate (2.1%) and dihydro-α-cyclogeranyl propionate (1.2%) are firstly found as chemotaxonomically important components in T. chiliophyllum oil. From these, dihydro-α-cyclogeranyl hexanoate was isolated on silica gel column chromatography and its structure was confirmed by spectroscopic methods. This is the first report on the occurrence of ester derivatives of dihydro-α-cyclogeranic acid in essential oils of Tanacetum species. The oils were also characterized to have relatively high amounts of oxygenated monoterpenes. Results of the antifungal testing by microbial growth inhibition assays showed that the oils completely inhibit the growth of 30 phytopathogenic fungi. However, their growth inhibition effects were lower than commercial benomyl. The oils tested for antibacterial activity against 33 bacterial strains showed a considerable antibacterial activity over a wide spectrum. Herbicidal effects of the oils on seed germination of Amaranthus retroflexus, Chenopodium album and Rumex crispus were also determined and the oils completely inhibited the seed germination and seedling growth of the plants.     

Chemical composition and antimicrobial activity of essential oils from Scabiosa arenaria Forssk: growing wild in Tunisia

The essential oils isolated from three organs, i.e., fruits, stems and leaves, and flowers, of the endemic North African plant Scabiosa arenaria Forssk. were screened for their chemical composition, as well as their possible antibacterial, anticandidal, and antifungal properties. According to the GC-FID and GC/MS analyses, 61 (99.26% of the total oil composition), 79 (98.43%), and 51 compounds (99.9%) were identified in the three oils, respectively. While α-thujone (34.39%), camphor (17.48%), and β-thujone (15.29%) constituted the major compounds of the fruit oil, chrysanthenone (23.43%), together with camphor (12.98%) and α-thujone (10.7%), were the main constituents of the stem and leaf oil. In the case of the flower oil, also chrysanthenone (38.52%), camphor (11.75%), and α-thujone (9.5%) were identified as the major compounds. Furthermore, the isolated oils were tested against 16 Gram-positive and Gram-negative bacteria, four Candida species, and nine phytopathogenic fungal strains. It was found that the oils exhibited interesting antibacterial and anticandidal activities, comparable to those of thymol, which was used as positive control, but no activity against the phytopathogenic fungal strains was observed.