Essential oil from Artemisia herba-alba Asso grown wild in Algeria: Variability assessment and comparison with an updated literature survey

The chemical variability of the essential oils of Artemisia herba-alba Asso aerial parts, collected at Algeria was evaluated. A. herba-alba populations were collected in four regions, Benifouda; Bougaa; Boussaada and Boutaleb, at two different periods, July (flowering phase), and October and November (vegetative phase). The essential oils were isolated by hydrodistillation and analyzed by Gas Chromatography (GC) and Gas Chromatography-Mass Spectrometry (GC-MS). The essential oils yield ranged between 0.2% and 0.9% (v/d.w.). Fifty components were identified in A. herba-alba oils, oxygen-containing monoterpenes being dominant in all cases (72–80%). Camphor (17–33%), α-thujone (7–28%) and chrysanthenone (4–19%) were the major oil components. Despite the similarity in main components, three types of oils could be defined, (a) α-thujone : camphor (23–28:17–28%), (b) camphor : chrysanthenone (33:12%) and (c) α-thujone : camphor : chrysanthenone (24:19:19%). The comparison between the present data and an updated survey of the existing literature reinforces the major variability of A. herba-alba essential oils and stresses the importance of obtaining a defined chemical type crop production avoiding the wild harvest.     

The Chemical Profiling of Essential Oils from Different Tissues of Cinnamomum camphora L. and Their Antimicrobial Activities

Cinnamomum camphora L. is grown as an ornamental plant, used as raw material for furniture, as a source of camphor, and its essential oil can be used as an important source for perfume as well as alternative medicine. A comparative investigation of essential oil compositions and antimicrobial activities of different tissues of C. camphora was carried out. The essential oils were extracted by hydrodistillation with a Clevenger apparatus and their compositions were evaluated through gas chromatography-mass spectrometry (GC-MS), enantiomeric composition by chiral GC-MS, and antimicrobial properties were assayed by measuring minimum inhibitory concentrations (MICs). Different plant tissues had different extraction yields, with the leaf having the highest yield. GC-MS analysis revealed the presence of 18, 75, 87, 67, 67, and 74 compounds in leaf, branch, wood, root, leaf/branch, and leaf/branch/wood, respectively. The significance of combining tissues is to enable extraction of commercial quality essential oils without the need to separate them. The oxygenated monoterpene camphor was the major component in all tissues of C. camphora except for safrole in the root. With chiral GC-MS, the enantiomeric distributions of 12, 12, 13, 14, and 14 chiral compounds in branch, wood, root, leaf/branch, and leaf/branch/wood, respectively, were determined. The variation in composition and enantiomeric distribution in the different tissues of C. camphora may be attributed to the different defense requirements of these tissues. The wood essential oil showed effective antibacterial activity against Serratia marcescens with an MIC of 39.1 μg/mL. Similarly, the mixture of leaf/branch/wood essential oils displayed good antifungal activity against Aspergillus niger and Aspergillus fumigatus while the leaf essential oil was notably active against Trichophyton rubrum. C. camphora essential oils showed variable antimicrobial activities against dermal and pulmonary-borne microbes.     

Efficient separation of Cinnamomum camphora leaf essential oil and in vitro evaluation of its antifungal activity

Cinnamomum camphora leaf essential oil (CEO) was extracted using enzymatic-ultrasound pretreatment followed by microwave assisted extraction (EUP-MAE) method and simultaneously studied as a mycelial growth inhibitor against five important pathogens which cause potato dry rot. The optimum EUP-MAE conditions with a real CEO yield of 19.23 ± 0.12 mg/g were obtained through Plackett–Burman design and Box–Behnken design as follows: 3 % of enzyme dosage, 2 h of pretreatment time, 5 of pH, 210 W of ultrasound power, 50 °C pretreatment temperature, 16 mL/g of water to solid ratio, 30 min of microwave time and 500 W of microwave power. Compared to the reference methods, EUP-MAE possessed a highest CEO yield than these of ultrasound-microwave assisted extraction (U-MAE) and traditional hydrodistillation (HD). Gas chromatography-mass spectrometry (GC–MS) analysis demonstrated that eucalyptol, camphor, and α-terpineol were the three main constituents of CEO. Results from in vitro antifungal activity assay revealed that the mycelial growths of all the five tested Fusarium solani, Fusarium culmorum, Fusarium trichothecioides, Fusarium sporotrioides, and Fusarium avenaceum were apparently affected by CEO. These findings not only provide a potential paradigm for the separation of plant essential oil, but also guarantee a promising utilization of the CEO for potato protection to control the Fusarium spp.     

Comparative Studies on Essential Oil and Phenolic Content with In Vitro Antioxidant,Anticholinesterase, Antimicrobial Activities of Achillea biebersteinii Afan. and A. millefolium subsp. millefolium Afan. L. Growing in Eastern Turkey

The potential applications of Achillea species in various industries have encouraged the examination of their phytochemical components along with their biological potential. In the present study, phenolic contents and essential oil compositions together with the in vitro biological activities of the aerial parts from Achillea biebersteinii Afan. and Achillea millefolium subsp. millefolium Afan. collected from Turkey were evaluated. Different solvent extracts (n-hexane, chloroform, methanol, water) were prepared and their antimicrobial, anticholinesterase, and antioxidant activities were studied. The LC-MS/MS results revealed the presence of 16 different phenolic compounds, including chlorogenic acid, rutin, quercetin, and luteolin glycosides, in methanolic extracts. According to GC-FID and GC/MS results, the primary components of the oils were identified as 1,8-cineole (32.5%), piperitone (14.4%), and camphor (13.7%) in A. biebersteinii and 1,8-cineole (12.3%) and β-eudesmol (8.9%) in A. millefolium subsp. millefolium. The infusion and methanolic extracts of both species were found to be rich in their total phenolic content as well as their antioxidant and anticholinesterase activity. In contrast, the n-hexane and chloroform extracts of both species showed strong antimicrobial activity with MIC values ranging from 15 to 2000 μg/mL. Our findings suggest that the investigated Achillea species could be evaluated as potent natural agents, and further studies into the promising extracts are needed.     

Essential Oils from Residual Foliage of Forest Tree and Shrub Species: Yield and Antioxidant Capacity

Increasing applications and markets for essential oils could bring new opportunities for cost-effective and sustainable management of unused forestry biomass; however, better knowledge of the production and application of such essential oils is necessary. The objective of this work is to contribute to greater knowledge of the essential oil production on a pilot scale from foliage biomass of wild shrubs and tree residues produced in some forestry enhancement operations and to study their antioxidant capacity (ORAC—oxygen radical absorbance capacity). Fresh biomass (twigs) of seven species (E. globulus, E. nitens, P. pinaster, P. sylvestris, R. officinalis, C. ladanifer, and J. communis) was manually collected in Spain in two different periods and was ground at 30 mm and distilled in a 30 L stainless steel still with saturated steam. The essential oil components were identified by GC–MS and quantified by GC–FID, and their antioxidant activity was determined with the ORAC method. Promising results on essential oil yield were obtained with E. globulus, E. nitens, R. officinalis, and J. communis. All essential oils studied exhibited antioxidant capacity by the ORAC assay, particularly that from C. ladanifer. Moreover, oxygenated sesquiterpenes contents, one of the minor components of oils, were significantly correlated with ORAC values.     

Epilobium angustifolium L. Essential Oil—Biological Activity and Enhancement of the Skin Penetration of Drugs—In Vitro Study

Epilobium angustifolium L. is a popular medicinal plant found in many regions of the world. This plant contains small amounts of essential oil whose composition and properties have not been extensively investigated. There are few reports in the literature on the antioxidant and antifungal properties of this essential oil and the possibility of applying it as a potential promoter of the skin penetration of drugs. The essential oil was obtained by distillation using a Clavenger type apparatus. The chemical composition was analyzed by the GC-MS method. The major active compounds of E. angustifolium L. essential oil (EOEa) were terpenes, including α-caryophyllene oxide, eucalyptol, β-linalool, camphor, (S)-carvone, and β-caryophyllene. The analyzed essential oil was also characterized by antioxidant activity amounting to 78% RSA (Radical Scavenging Activity). Antifungal activity against the strains Aspergillus niger, A. ochraceus, A. parasiticum, and Penicillium cyclopium was also determined. The largest inhibition zone was observed for strains from the Aspergillus group. The EOEa enhanced the percutaneous penetration of ibuprofen and lidocaine. After a 24 h test, the content of terpene in the skin and the acceptor fluid was examined. It has been shown that the main compounds contained in the essential oil do not penetrate through the skin, but accumulate in it. Additionally, FTIR-ATR analysis showed a disturbance of the stratum corneum (SC) lipids caused by the essential oil application. Due to its rich composition and high biological activity, EOEa may be a potential candidate to be applied, for example, in the pharmaceutical or cosmetic industries. Moreover, due to the reaction of the essential oil components with SC lipids, the EOEa could be an effective permeation enhancer of topically applied hydrophilic and lipophilic drugs.     

Phytochemistry,Bioactivities and Traditional Uses of Michelia × alba

Michelia × alba (M. alba) is a flowering tree best known for its essential oil, which has long been used as a fragrance ingredient for perfume and cosmetics. In addition, the plant has been used in traditional medicine in Asia and dates back hundreds of years. To date, there is a limited number of publications on the bioactivities of M. alba, which focused on its tyrosinase inhibition, antimicrobial, antidiabetic, anti-inflammatory, and antioxidant activities. Nevertheless, M. alba may have additional unexplored bioactivities associated with its bioactive compounds such as linalool (72.8% in flower oil and 80.1% in leaf oil), α-terpineol (6.04% flower oil), phenylethyl alcohol (2.58% flower oil), β-pinene (2.39% flower oil), and geraniol (1.23% flower oil). Notably, these compounds have previously been reported to exhibit therapeutic activities such as anti-cancer, anti-inflammation, anti-depression, anti-ulcer, anti-hypertriglyceridemia, and anti-hypertensive activities. In this review paper, we examine and discuss the scientific evidence on the phytochemistry, bioactivities, and traditional uses of M. alba. Here, we report a total of 168 M. alba biological compounds and highlight the therapeutic potential of its key bioactive compounds. This review may provide insights into the therapeutic potential of M. alba and its biologically active components for the prevention and treatment of diseases and management of human health and wellness.     

In Vitro Anti-Inflammatory Activity of Cotula anthemoides Essential Oil and In Silico Molecular Docking of Its Bioactives

The genus Cotula (Asteraceae) comprises about 80 species, amongst them Cotula anthemoides L. It is a wild plant growing in Egypt that possesses many traditional uses as a headache, colic, and chest cold remedy. In our study, the chemical composition of C. anthemoides essential oils was analyzed using GC-MS spectroscopy. Sixteen components of leave and stem oils and thirteen components of flower oils were characterized. The main components in both essential oil parts were camphor (88.79% and 86.45%) and trans-thujone (5.14% and 10.40%) in the leaves and stems and the flowers, respectively. The anti-inflammatory activity of the oils in lipopolysaccharide-stimulated RAW 264.7 macrophage cells was evaluated. The flower oil showed its predominant effect in the amelioration of proinflammatory cytokines and tumor necrosis factor-α, as well as cyclooxygenase-2. The bornyl acetate showed the highest affinity for the cyclooxygenase-2 receptor, while compound cis-p-menth-2-ene-1-ol had the best affinity for the tumor necrosis factor receptor, according to the results of molecular docking. In addition, the molecule cis-β-farnesene showed promising dual affinity for both studied receptors. Our findings show that essential oils from C. anthemoides have anti-inflammatory properties through their control over the generation of inflammatory mediators. These findings suggest that C. anthemoides essential oils could lead to the discovery of novel sources of anti-inflammatory treatments.     

Rapid determination of essential oil compounds in Artemisia Selengensis Turcz by gas chromatography-mass spectrometry with microwave distillation and simultaneous solid-phase microextraction

In the work, for the first time, two solvent-free sample preparation techniques of microwave distillation (MD) and solid-phase microextraction (SPME) were combined, and developed for determination of essential oil compounds in traditional Chinese medicine (TCM). Using the proposed method, isolation, extraction and concentration of TCM essential oil compounds can be carried out in a single step. To demonstrate its feasibility, MD-SPME was compared with a conventional technique, steam distillation (SD), for gas chromatography-mass spectrometry (GC-MS) analysis of essential oil compounds in a TCM, Artemisia Selengensis Turcz. Forty-nine compounds in the TCM were separated and identified by the present method, while only 26 compounds were detected by SD method. Relative standard deviation (R.S.D.) values less than 9% show that the present method has good precision. The SD method required long time (6 h) to isolate of the essential oil, and large amount of organic solvent for further extraction, while MD-SPME needed little time (only 3 min) to prepare sample, and no organic solvent. These results show that MD-SPME-GC-MS is a simple, rapid and solvent-free method for determination of TCM essential oil.     

Behavioral and Antennal Responses of Tribolium confusum to Varronia globosa Essential Oil and Its Main Constituents: Perspective for Their Use as Repellent

Essential oils of aromatic plants represent an alternative to classical pest control with synthetic chemicals. They are especially promising for the alternative control of stored product pest insects. Here, we tested behavioral and electrophysiological responses of the stored product pest Tribolium confusum, to the essential oil of a Brazilian indigenous plant, Varronia globosa, collected in the Caatinga ecosystem. We analyzed the essential oil by GC-MS, tested the effects of the entire oil and its major components on the behavior of individual beetles in a four-way olfactometer, and investigated responses to these stimuli in electroantennogram recordings (EAG). We could identify 25 constituents in the essential oil of V. globosa, with anethole, caryophyllene and spathulenole as main components. The oil and its main component anethole had repellent effects already at low doses, whereas caryophyllene had only a repellent effect at a high dose. In addition, the essential oil abolished the attractive effect of the T. confusum aggregation pheromone. EAG recordings revealed dose-dependent responses to the individual components and increasing responses to the blend and even more to the entire oil. Our study reveals the potential of anethole and the essential oil of V. globosa in the management of stored product pests.     

Illicium verum (Star Anise) and Trans-Anethole as Valuable Raw Materials for Medicinal and Cosmetic Applications

Illicium verum Hook f. (star anise) is considered an important species in Traditional Chinese Medicine and is also used in contemporary medicine in East Asian countries. It occurs in natural habitats in southeastern parts of China and Vietnam, and is cultivated in various regions in China. The raw materials—Anisi stellati fructus and Anisi stellati aetheroleum obtained from this species exhibit expectorant and spasmolytic activities. The European Pharmacopoeia (4th edition) indicates that these raw materials have been used in allopathy since 2002. The biological activities of the above-mentioned raw materials are determined by the presence of valuable secondary metabolites such as monoterpenoids, sesquiterpenoids, phenylpropanoids, and flavonoids. Recent pharmacological studies on fruit extracts and the essential oil of this species have confirmed their antibacterial, antifungal, anti-inflammatory, and antioxidant activities and thus their medicinal and cosmetic value. The aim of this review was to examine the progress of phytochemical and pharmacological studies that focused on possible cosmetic applications. In addition to fruit extracts and essential oil, the current consensus on the safety of trans-anethole, which is the main compound of essential oil used in cosmetology, is underlined here.     

Chemical Composition of the Essential Oil of Rosmarinus officinalis Cultivated in the Algerian Sahara

The volatile compounds obtained by hydrodistillation of the aerial parts of Rosmarinus officinalis cultivated at the Algerian Sahara were analyzed by GC/MS. Thirty compounds were characterized representing 98.2% of the essential oil with 1,8-cineole (29.5%), 2-ethyl-4,5-dimethylphenol (12.0%) and camphor (11.5%) as the major components.     

Campher

Camphor was isolated from camphor tree oil by by fractional destillation and recrystallized from ethanol. The UV‐, CD‐, IR‐ NMR‐ und MS‐spectra were recorded and are reproduced in the supplementary material. The NMR‐ and mass‐spectra have been interpreted and compared with theoretical calculations of the 13C chemical shifts. The project is a follow up of the recent book “Classics in Spectroscopy” by S. Berger und D. Sicker (Wiley‐VCH 2009).     

Identification of metabolomic markers of lavender and lavandin essential oils using mid-infrared spectroscopy

Lavender (Lavandula angustifolia) and lavandin (sterile hybrid of L. angustifolia P. Mill. × Lavandula latifolia (L.f.) Medikus) are widely cultivated in the Mediterranean area for produce essential oils. In this study, 80 lavandin and 55 lavender essential oil samples from various varieties were analyzed. Firstly, a chemometric treatment of mid-infrared spectra was used to evaluate the capacity of Partial Least Squares Discriminant Analysis (PLS-DA) regression to discriminate French lavandin and lavender essential oil (EO) samples and their varieties (Abrial, Fine, Grosso, Maillette, Matherone, Sumian and Super), and secondly, to quantify the main compounds such as linalyl acetate, linalool, eucalyptol and camphor by PLS regression using reference data from gas chromatography. The examination of PLS and PLS-DA regression coefficients allowed the identification of metabolomic markers. The lavender/lavandin EOs and their varieties were very well classified (100% for lavender/lavandin EOs and between 98 and 100% for varieties). The calibration models obtained by PLS regression for the determination of the main compound contents revealed good correlation (≥0.86) between the predicted and reference values. This method can be used to control the authenticity and traceability of lavender/lavandin and their varieties. Finally, mid-infrared and Raman spectroscopy results were compared.     

Antimicrobial and antioxidant activities of Artemisia herba-alba essential oil cultivated in Tunisian arid zone

This study was conceived to examine the antimicrobial and antioxidant activities of four essential oil types extracted by hydrodistillation from the aerial parts of Artemisia herba-alba cultivated in southern Tunisia. The chemical composition was investigated using both capillary GC and GC/MS techniques. β-thujone, α-thujone, α-thujone/β-thujone and 1,8-cineole/camphor/α-thujone/β-thujone were respectively, the major components of these oil types. The antimicrobial activity of different oils was tested using the diffusion method and by determining the inhibition zone. The results showed that all examined oil types had great potential of antimicrobial activity against strains. In addition, antioxidant capacity was assessed by different in vitro tests and weak activity was found for these A. herba-alba oils.     

Biodiversity and application prospects of fungal endophytes in the agarwood-producing genera,Aquilaria and Gyrinops (Thymelaeaceae): A review

Agarwood is originated from the resinous part of Aquilaria and Gyrinops plants and has been a precious biomaterial for applications in traditional medicine, perfumery, cosmetics, and religious purposes all over the world. In the wild, the formation of agarwood is related to the defense mechanism of the tree in response to physical damage that allows further microbial infestation into its wood, while having the whole tree covered with agarwood would take up a long time, and it rarely happens. For Aquilaria and Gyrinops, the presence of endophytes is mainly found derived from the tree. The isolated endophytes could be important sources of natural products, while some could contribute to the formation of agarwood in the tree, which is safe for the environment and human health. This review summarized the biodiversity of fungal endophytes recorded in Aquilaria and Gyrinops and their potential effects on host trees. Till now, 67 endophytic genera have been isolated from Aquilaria and Gyrinops, and 18 ones were found responsible for the promotion of agarwood formation. Additionally, 92 compounds have been reported to be produced by the agarwood endophytes, and 52 ones displayed biological activities, most of which have anti-inflammatory, anti-bacterial, and anti-cancer activities. Nevertheless, fungal endophytes are promising agents that deserved to be further studied and scaled up to a commercial level for the production of agarwood oil, but the role of endophytes in the agarwood host trees needs to be furtherly investigated in future studies.     

Chemical Composition and Synergistic Potential of Mentha pulegium L. and Artemisia herba alba Asso. Essential Oils and Antibiotic against Multi-Drug Resistant Bacteria

The essential oils were obtained by hydrodistillation from aerial parts of Mentha pulegium L. (M. pulegium L.) and Artemisia herba alba (A. herba alba) Asso. and analyzed by gas chromatography–flame ionization detector chromatograpy (GC–FID) and gaz chromatography–mass spectrometry (GC–MS). The antibacterial activities of the oils were determined by the disk diffusion method and a microdilution broth assay against six bacteria stains. The combinations of these essential oils with antibiotics were evaluated against two multi-drug-resistant bacteria strains: imipenem-resistant Acinetobacter baumannii (IRAB S3310) and methicillin-resistant Staphylococcus aureus (MRSA S19). The chemical analysis of M. pulegium essential oil revealed the presence of pulegone (74.8%) and neoisomenthol (10.0%). A. herba alba essential oil was characterized by camphor (32.0%), α-thujone (13.7%), 1,8-cineole (9.8%), β-thujone (5.0%), bornéol (3.8%), camphene (3.6%), and p-cymene (2.1%). All strains tested except Pseudomonas aeruginosa were susceptible to these oils. The combinations of essential oils with antibiotics exerted synergism, antagonism, or indifferent effects. The best effect was observed with A. herba alba essential oil in association with cefoxitin (CX) against MRSA S19. However, for IRAB S3310, the strongest synergistic effect was observed with M. pulegium in association with amikacin (AK). This study demonstrated that M. pulegium and A. herba alba essential oils have antibacterial activities which could be potentiated by antibiotics especially in the case of IRAB S3310.     

Enantioselectivity in camphor pinacolisation

Total enantioselectivity has been observed in pinacol formation using Li/THF. (+) Camphor and (±) Camphor give the optically active and racemic form of a single pinacol whose stereochemistry has been established as endo:endo by X-ray analysis. An exo:endo pinacol is formed as the sole product if camphor is added to Li/NH₃. Tentative mechanism is proposed.     

Chemical composition and antimicrobial activity of the essential oil of Tanacetum walteri (Anthemideae-Asteraceae) from Iran

The composition and antimicrobial activity of the essential oil of Tanacetum walteri were studied. Aerial flowering parts of plant were collected from North Khorasan Province of Iran and the essential oil was isolated by hydrodistillation and analysed by GC-FID and GC-MS. Antimicrobial activity of the essential oil was determined by disc diffusion and MIC and MBC determination. Thirty-five compounds were identified in the oil of T. walteri accounting for 94.4% of the total oil. Thymol (22.5%), 1,8-cineole (8.2%), umbellulone (6.9%), α-bisabolol (6.3%) and camphor (5.3%) were as the principal constituents. The highest antimicrobial activity of the essential oil was observed against Staphylococcus aureus, Enterococcus faecalis and Klebsiella pneumoniae with MIC value of 0.63 mg/mL. The inhibitory effect of the essential oil of T. walteri could be attributed mainly to the high levels of phenolic compound thymol and oxygenated terpenes in essential oil.     

The effect of camphor and borneol on rat thymocyte viability and oxidative stress

Camphor and borneol are wildly distributed in the essential oils of medicinal plants from various parts of the World. Our study has been carried out to evaluate the effect of these two bicyclic monoterpenes on rat thymocytes. Camphor and borneol at concentrations of 0.5 and 5 μg/mL did not induce significant toxicity on the immune system cells, while a significant increase of thymocyte viability was detected when cells were incubated with 50 μg/mL of camphor. A significant increase of cell viability was similarly detected when thymocytes were cultivated with borneol at concentrations of 0.5 and 5 μg/mL. The role of camphor and borneol in reactive oxygen species (ROS) production and mitochondrial membrane potential (MMP) disturbances in rat thymocytes as well as their potential mechanism(s) of action were also discussed.