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Composition of Tanacetum annuum L. Oil from Morocco
Abstract
Fresh aerial parts of Tanacetum annuum L. from Morocco were steam distilled to produce an oil in 0.5% yield. The oil was fractionated on the silica gel column and analyzed by GC and GC/MS using MS and retention index data and more than 130 constituents were identified. The major components of the oil were chamazulene (38–17%), myrcene (14–1%), sabinene (8.6–4%), β-eudesmol (7–3%) and camphor (18–4%). Seasonal variation of the oil composition suggested that the chamazulene content decreases and the myrcene content increases from June to October.
... Studies have reported that there is a significant amount of chamazulene in the blue tansy plant. Greche et al. (1999) determined the essential oil yield of the Tanacetum annuum plant grown in Morocco as 0.5% and found that the main components of the essential oil were chamazulene (38 17%), myrcene (14 1%), sabinene (8.6 -eudesmol. (7 3%) and camphor (18 4%). ...
... (7 3%) and camphor (18 4%). According to Greche et al. (1999), Seasonal variation of the oil composition suggested that the chamazulene content decreases and the myrcene content increases from June to October. ...
Chamazulene (C14H16) is a bicyclic sesquiterpenoid polyalkene and is an important compound used as an anti-inflammatory agent in herbal medicines and cosmetic products. Chamazulene is not a natural product, but is formed by the decomposition of its precursor, matricin, during steam distillation of plants. Chamazulene gives colour to the essential oil in blue tones depending on its concentration. In the essential oil, it creates a light blue colour at low concentration, and a dark blue colour at high concentration. The plants that supply chamazulene in the world are limited. The most produced plant as a source of chamazulene is German chamomile (Matricaria recutita). This species has 3.4% chamazulene in α-bisabolol oxide A/(E)-β-farnesene (Egypt) chemotype, 2.7-7.6% in α-bisabolol oxide A (Egypt, Germany, Netherlands) chemotype, α-bisabolol oxide A/α-bisabolol oxide 8.2% in B (Brazil) chemotype, 17.6% in Farnesene/chamazulene (Bulgaria), 10.8-21.8% in α-bisabolol/(E)-β-farnesene (Finland) and 23.4% in α-bisabolol oxide A/chamazulene (Germany) chemotype. Germany, Hungary, Slovakia, Argentina, Egypt, Chile, Russia, Poland, Czech Republic, Belgium, Brazil, France, Spain and Greece are among the countries with the highest production in the world. In chamomile, both agricultural production is made and it is collected from nature. As an agricultural product, it is cultivated in Egypt, Germany, Argentina, Poland and to a lesser extent in Chile, Czech Republic, Slovakia, Spain and a few Balkan countries (Bosnia and Herzegovina, Bulgaria, Croatia and Serbia), Hungary, Albania, Bulgaria, Croatia, Kosovo and it is also collected from nature in countries such as Macedonia. On the other hand, chamazulene contains 0-4.4% in Roman chamomile essential oil (Chamaemelum nobile L.), 19.7% in yarrow (Achillea millefolium L.), 7.0-38.3% in blue tansy (Tanacetum annuum L.), 0-1.7% in Scots pine (Pinus sylvestris L.), 22.4% in mugwood (Artemisia arborescens L.) and 5.6% in Northern Cyprus pine (Callitris intratropica L.).
... These findings provide valuable insights into the chemical composition of the oil and may have implications for its potential applications in various domains. Nonetheless, further investigations may be required to fully comprehend the implications of these chemical components and their interactions in the oil [34]. In a subsequent study conducted by the same author, it was observed that the chemical profile of T. annuum L. oil is marked by the prevalence of sabinene (22.3%), camphor (13.2%), β-pinene (10.1%), and P-cymene (8.9%) as the primary compounds [24]. ...
... Chemical Composition of the Essential Oil of Tanacetum annuum L. from the Tangier region (Essential oil studied: EO 1 , Essential oil studied by Ref.[34]: EO 2 , Essential oil studied by Ref.[25]: EO 3 . ...
The primary objective of the present inquiry was to assess the impact of gamma irradiation on the chemical composition and antibacterial potential of the essential oil extracted from the aerial parts of Moroccan Tanacetum annuum L. to this end, two distinct irradiation doses of 5 kGy and 10 kGy were administered to the essential oil, and the resultant effects were evaluated via analysis of the oil's chemical composition and antibacterial activity. The study findings have revealed that irradiation technology possesses the remarkable ability to modulate the concentrations of specific chemical constituents in a manner that effectively amplifies the antibacterial activity of the essential oil. Moreover, the technology has evinced the generation of novel compounds while also demonstrating the eradication of certain pre-existing ones upon the oil's exposure to irradiation. These discoveries have emphasized the potential of irradiation technology for augmenting the chemical profile of essential oils, thereby mitigating the risk of contamination via microbiological, physical, or chemical means, ultimately enhancing the therapeutic efficacy of the plant and its essential oil. Furthermore, the results of this study signify the possibility of harnessing irradiation technology in the production of various natural products and essential oils. The present research has thus broadened the horizons for the application of irradiation technology in advancing the potency and safety of essential oils, paving the way for a diverse range of applications in different fields, such as medicine.
... Referring to the studies carried out on this oil and taking into account the change which characterizes the chemical pro le of the EO of this genus in general and in particular of the species Tanacetum annuum L., we can say that our oil is characterized by a high percentage of the chemical compounds it contains as shown in Fig. 3, also as we see, for example, for H. Greche et al, found that more than 130 compounds, representing about 90% of the oil, have been identi ed. Chamazulene was the major component of the oil (28%), while of the 16 monoterpene hydrocarbons identi ed (23.1%) the most important were sabinene (6.4%), β-pinene (3.1%) and myrcene (4.4%), and 3,6-dihydrochamazulene (3.7%) (Greche et al., 1999). ...
The study aims to evaluate the Moroccan Tanacetum annuum L. essential oil by studying the effect of gamma irradiation on both the chemical composition and antibacterial activity, this is done by exposing the oil extracted from the dry aerial parts of the plant by hydrodistillation to irradiation dose of 5kGy and 10kGy.
The obtained results proved that irradiation technology can actually raise the percentage of chemical compounds that would increase the biological activity of the essential oil. This allows to increase the potential of the plant studied and its biological effectiveness, also the irradiation process has proven the ability to raise the quality of the chemical composition both in terms to reduce the risk of contamination it can be microbiological, physical, and chemical of one of the most abundant medicinal plants in northern Morocco.
... Usually essential oils of Tanacetum species are rich in αthujone, camphor, 1,8-cineole and borneol. However in some cases carvone, α-pinene, sesquiterpene type and other type of compounds were also encountered as main components in Tanacetum oils 6,7,15,[17][18][19][20][21][22][23][24][25] . ...
Water-distilled essential oil from flowers of Tanacetum mucroniferum from Turkey were analyzed by GC and GC-MS. The flower oil of T. mucroniferum was characterized with oxygenated monoterpenes and oxygenated sesquiterpenes. Main components of the oil were 1,8-cineole 21.9 % and camphor 6.4 %. Antioxidant activity of the oil was determined at various concentrations and incubation time by DPPH radical protocol. Highest activity was observed at 20 mg/mL concentration (22.31 %) with 60 minutes incubation time. When compared with positive control α-tocopherol (96.59 %) at same conditions oil showed low DPPH scavenging activity. T. mucroniferum was reported to be an intermediate species between T. sipikorense and T. aucheranum. Essential oil composition of T. mucroniferum was investigated for the first time and similarities with previously reported T. aucheranum essential oil was compared.
... Usually essential oils of Tanacetum species are rich in αthujone, camphor, 1,8-cineole and borneol. However in some cases carvone, α-pinene, sesquiterpene type and other type of compounds were also encountered as main components in Tanacetum oils 6,7,15,[17][18][19][20][21][22][23][24][25] . ...
Water-distilled essential oil from flowers of Tanacetum mucroniferum from Turkey were
analyzed by GC and GC-MS. The flower oil of T. mucroniferum was characterized with oxygenated monoterpenes
and oxygenated sesquiterpenes. Main components of the oil were 1,8-cineole 21.9 % and camphor 6.4 %.
Antioxidant activity of the oil was determined at various concentrations and incubation time by DPPH radical
protocol. Highest activity was observed at 20 mg/mL concentration (22.31 %) with 60 minutes incubation
time. When compared with positive control α-tocopherol (96.59 %) at same conditions oil showed low DPPH
scavenging activity. T. mucroniferum was reported to be an intermediate species between T. sipikorense and T.
aucheranum. Essential oil composition of T. mucroniferum was investigated for the first time and similarities
with previously reported T. aucheranum essential oil was compared.
Tanacetum annuum L. is a Mediterranean plant, commonly known as Blue Tansy due to its blue colour as an essential oil, which is widely used for medicinal purposes. However, there are no studies on the bioactive compounds (especially, phenolic compounds) and the biological properties of their organic extracts. Herein, the purpose of the present work was to investigate the chemical composition of the essential oil and crude extracts of the T. annuum aerial parts collected from northern Morocco and to evaluate their antioxidant and antifungal activity against Fusarium oxysporum f. sp. albedinis, an agent causing Bayoud disease of the date palm, an important food source and commercial perennial crop in the Sahara and North Africa. Chemically, Folin–Ciocalteu and aluminium chloride colourimetric methods were used to determine the total phenolic (TPC) and total flavonoid (TFC) contents, respectively; polyphenols were characterized using HPLC-MS, while GC-MS was used to analyse the essential oil composition. Moreover, the evaluation of antioxidant and antifungal activities was carried out using the DPPH test and microdilution method, respectively. The results showed that the three T. annuum parts (stems, leaves and flowers) extracts contained important TPC and TFC with values varied between 51.32 and 116.32 mg/g of dry crude extract (DCE). HPLC-MS analysis revealed the identification and quantification of 19 phenolic acids and flavonoids with an emphasis on apigenin 7-glucoside (4540 µg/g of dry weight (DW)), luteolin 7-glucoside (2804 µg/g DW) and salicylic acid (1878 µg/g DW). Additionally, 39 biomolecules were identified in the essential oil using GC-MS, which were predominated by camphor (16.69%), α-pinene (12.37%), bornyl acetate (11.97%) and limonene (11.10%). The methanolic and hydro-methanolic extracts of T. annuum parts demonstrated a strong antioxidant property with IC50 values ranging between 0.22 and 0.65 mg/mL. Concerning antifungal activity, the essential oil and crude extracts of the Moroccan Blue Tansy exhibited a potent capacity against F. oxysporum f. sp. albedinis at low concentrations, with MIC and MFC values of 3.33 and 4.58 µL/mL for the essential oil and values of 3.33 and 9.17 mg/mL for crude extracts, respectively. Overall, these results demonstrated T. annuum as an important source of bioactive compounds and contribute significantly to the potential of using essential oils and extracts for controlling the Bayoud disease of date palms. Moreover, the finding suggests that T. annuum can be highly useful for phytosanitary and pharmaceutical industries.
The development of effective control strategies targeting non-native ambrosia beetles (Coleoptera: Curculioni-dae: Scolytinae and Platypodinae) represents an emerging challenge. This is due both to their rapid spread into climatically suitable newly invaded regions rich in susceptible host plants and to the limited knowledge concerning sustainable management tools. In this context, the use of botanical insecticides, such as plant essential oils (EOs), is considered a promising option in Integrated Pest Management (IPM) strategies as an alternative to conventional insecticides for sustainable crop protection. Here, the impact of five EO nanoemulsions (Rosmarinus officinalis L. cultivar verbenone, Carlina acaulis L., Laurus nobilis L., Cupressus sempervirens L., and Betula alba L.) on the choice behavior, host colonization and progeny production by the invasive ambrosia beetle Xylosandrus compactus (Eichhoff) was evaluated under laboratory and semi-field conditions. The chemical composition of tested EOs was firstly evaluated by means of gas chromatography-mass spectrometry (GC-MS) analyses. Then, EO nanoemulsions were prepared and characterized through dynamic light scattering (DLS). Tested EO nano-emulsions showed single or bimodal droplet size distributions in the nanometric range. Results highlighted a significant repellent activity of R. officinalis cv. verbenone and C. acaulis EO nanoemulsions (at 3% EO concentration). However, the trend for repellence of the R. officinalis EO against the beetle was not confirmed at decreasing EO concentrations (i.e., 1% and 0.5%). Nanoemulsions based on C. acaulis EO significantly affected the beetle choices regardless of the tested EO concentration. Indeed, in no choice bioassays, a significantly lower number of individuals started infesting stems treated with these nanoemulsions. On the other hand, no effect of the EO treatment was found on the number of offspring produced by survived beetle females. The repellence by R. officinalis and C. acaulis EOs was confirmed in semi-field conditions. Overall, our findings provide new insights toward the use of R. officinalis and C. acaulis EOs as repellents of X. compactus, suggesting their future incorporation in non-chemical strategies, such as 'push-pull', as part of sustainable IPM packages targeting this invasive pest.
The essential oils from aromatic plants are extracted from the plant world and used for thousands of years for their therapeutic properties, particularly anti infectious, often in the form of non-medicinal products. They play a significant role in plant defense and forest against natural aggression, including the fight against drought.
Their compounds, due to their physico-chemical characteristics are called volatile organic compounds (VOCs). This term is sometimes also used to describe other compounds, volatile at room temperature and carbon-based, but due to human activity and considered as pollutants, such as petrochemical derivatives in particular.
Terpenes, active substances found in essential oils and used for their therapeutic properties are issued at rates that can influence the chemical composition of the atmosphere. It is therefore necessary, as with any treatment, to take into account the tolerance of these natural substances, well studied in more than 1800 items. More than 2000 publications since 1995 have been devoted to pharmacology terpenes: it is mentioned in this study, these anti-inflammatory, decongestant, antiseptic, antiviral, antifungal, anti-parasitic, mucolytics, bile ducts, healing. Biological effects of essential oils are validated by many reliable and serious studies, as also are well documented data of toxicity and tolerance.
Their use in confined spaces and domestic, particularly in low doses, would be of great interest especially for their antimicrobial effects, namely virucidal, bactericidal and fungicidal.
In the current state of scientific knowledge, the benefit/risk ratio would be more in favor of their use with a good command of the recommendations of doses emitted into the environment.
The chemical composition of the essential oil obtained from Artemisia copa growing in the high valley region of Bolivia, Province of Cochabamba, was determined by a combination of GC and GC/MS measurements. The main constituents were β-thujone (42%), chamazulene (6.5%) and a homoterpene (6.0%) as well as limonene (5%) and α-pinene (4.8%).
Shoot oil of Tanacetum annuum was examined by GC and GC/MS and found to contain sabinene (22.3%) and camphor (13.2%) as major constituents. This oil was screened for its antifungal activity against Botrytis cinerea, Helminthosporium oryzae, Alternaria solani, Piricularia oryzae and Verticillium dahliae. T. annuum oil exhibited the strongest fungitoxicity by completely inhibiting the mycelial growth of each of the fungi at 5000 ppm.
The essential oil of Tanacetum macrophyllum growing wild in Turkey was obtained by hydrodistillation, and antimicrobial activity of the essential oil was tested against six bacteria and two yeasts including Candida albicans and Aspergillus niger by disc diffusion method. Further the oil of this plant was analyzed by GC and GC/MS technique. Best effect of the oil was against pseudomonas earuginosa. Twenty-eight components, representing 95.6% of the total oil, were identified. The main component of the oil was β-eudesmol (89.5%). The antioxidant activity of the essential oil was measured by the ferric reducing antioxidant power (FRAP) assay.
An investigation of the essential oil from the flowers of Tanacetum annuum led to the identification of 43 components, two of them having a homoditerpene skeleton. Five of these substances are new natural products.
During LSC of naturally occurring monoterpene hydrocarbon mixtures from essential oils using silica gel as adsorbent alterations in the composition of the mixtures were observed by means of gas chromatography. Impurities (metals) and active sites on dried silica gels were found to be responsible for a series of isomerizations of a number of the constituents. After purification by washing the silica gel with acid and base and after deactivation of the dried silica gel by adding water (5%) the isomerization processes could be avoided. This was tested by means of the monoterpene hydrocarbon mixtures of three essential oils and a number of pure monoterpene hydrocarbons.
A liquid-solid column chromatographic method for separation of mixtures of naturally occurring oxygen-containing monoterpenes has been developed. The LSC was carried out on a column of silica gel applying a 2.5%–50% gradient elution of ethyl ether in pentane and collecting a number of fractions. The enrichment of the various components in the fractions led to a better gas chromatographic separation and identification. The elution sequence during LSC gave extra information about the functional group of the compounds. Isomerization processes could be avoided by using purified and deactivated silica gel.
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