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Abstract

As part of our ongoing study on the valorization of aromatic plants, the present study was designed to elucidate the composition, scavenging potential, anti-inflammatory activity and cytotoxicity of Margotia gummifera essential oils.Umbels were submitted to hydrodistillation in a Clevenger-type apparatus and the oils were analyzed by GC and GC–MS. For the anti-inflammatory activity, an in vitro model of lipopolysaccharide-stimulated macrophages was used and the inhibition of nitric oxide (NO) production was quantified through the Griess reagent, in the presence of the essential oil or its main compounds. NO scavenging potential was assessed using an NO donor and the cytotoxicity was evaluated on macrophages, keratinocytes and alveolar epithelial cells.The oils were characterized by high contents of monoterpene hydrocarbons, being the major compounds myrcene (20.4–23.0%) and sabinene (21.0–23.5%). The oil, myrcene and sabinene significantly inhibited NO production without affecting cell viability and showed a very effective NO scavenging potential, sabinene being the most active compound.These results suggest that M. gummifera essential oil, sabinene and myrcene should be explored as a natural source of new antioxidant and anti-inflammatory drugs for the development of food supplements, nutraceuticals or plant-based medicines.

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... Although this is the first report on the anti-inflammatory potential of C. maritimum essential oil, other studies demonstrated the anti-inflammatory potential of other essential oils rich in sabinene. Indeed, albeit the essential oils from Oenanthe crocata (sabinene 29 %) (Valente et al., 2013a) and Margotia gummifera (sabinene 21.0-23.5 %) (Valente et al., 2013b) have been reported as anti-inflammatory, their activity is weaker than the one reported herein. ...
... Other studies showed the anti-inflammatory potential of two major compounds, γ-terpinene and sabinene. Valente (Valente et al., 2013a(Valente et al., , 2013b showed that the anti-inflammatory effect of sabinene is only significant on high doses (1.05 mg/mL). In turn, γ-terpinene was shown to inhibit the inflammatory response in an animal model of inflammation (Ramalho et al., 2015). ...
... Interestingly, sabinene demonstrated NO scavenging ability (Valente et al., 2013b) although in much higher doses than the ones tested here. ...
Article
Aromatic and medicinal plants, such as those from the Apiaceae family, and their metabolites, namely essential oils are of great industrial interest and a source of biologically relevant compounds. Essential oils are the major resource obtained during the hydrodistillation of aromatic plants, however, this process also originates high amounts of residual water. Although this by-product is discarded, it is conceivable that this water may be rich in non-volatile compounds which possess interesting biological properties. Therefore, the aim of this work is to analyze the oil and the hydrodistillation residual water of Crithmum maritimum L. (sea fennel), a highly aromatic plant widely used in many European countries and highlight the bioactive potential of both products. High performance liquid chromatography-photodiode array detector-mass spectrometry (HPLC-DAD-MS/MS) analysis of the hydrodistillation residual water showed a profile rich in hydroxycinnamic acids and small amounts of flavone and flavonol glycosides. Chemical analysis of the essential oil by gas chromatography coupled with mass spectrometry (GC-–MS) has revealed that γ-terpinene (33.6 %), sabinene (32.0 %) and thymol methyl ether (15.7 %) are the major compounds. The antioxidant potential of the residual water was disclosed by the 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and a composition-activity relationship was unveiled by thin layer chromatography (TLC). The anti-inflammatory potential was demonstrated by using an in vitro model of inflammation (lipopolysaccharide (LPS)-stimulated macrophages). Furthermore, the antifungal potential was evaluated by the capacity to inhibit two important virulence factors in Candida albicans. Our results show that the residual water have a promising antioxidant potential as measured by DPPH scavenging assay (IC50 of 650 ± 160 μg/mL). Chlorogenic acid and quercetin derivatives found in the hydrodistillation residual water are the mainly contributors for this activity. The essential oil of C. maritimum (3.125 μg/mL) decreases the production of nitric oxide in LPS-stimulated macrophages by 37 % without affecting cell viability. In addition, the essential oil has a strong effect on virulence factors of C. albicans through inhibiting the formation of the germ tube by more than 50 % at 30 μg/mL besides, it is able to inhibit biofilm formation by decreasing both the biomass and the cell viability. Summing up, the present work highlights that the essential oil of Crithmum maritimum and the non-volatile extract rich in hydroxycinnamic acids and flavonoid glycosides, obtained after the hydrodistillation process have important biological activities, thus endorsing the industrial exploitation of this plant.
... Importantly, (+)-limonene has shown antinociceptive activity [25] and anti-inflammatory activity [26,27]. Sabinene has shown antiinflammatory effects [28,29]. Myrcene demonstrated antinociceptive activity [30,31] as well as antiinflammatory activity [28]. ...
... Sabinene has shown antiinflammatory effects [28,29]. Myrcene demonstrated antinociceptive activity [30,31] as well as antiinflammatory activity [28]. ...
Article
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ellow rabbitbrush (Chrysothamnus viscidiflorus) is native to the Great Basin of NorthAmerica and the plant was part of the traditional medicine of Native Americans in theregion. There has been very little previous work on essential oils of Chrysothamnus, andno reports on C. viscidiflorus essential oil. Therefore, the purpose of this work was toevaluate the chemical composition of C. viscidiflorus essential oil. The aerial parts of C.viscidiflorus were collected from southwestern Idaho, the essential oil obtained byhydrodistillation and analyzed by gas chromatographic methods. The essential oil wasobtained in 1.121% yield and was dominated by monoterpene hydrocarbons (82.6%),including (–)-β-pinene (41.3%), (+)-limonene (17.4%), (+)-sabinene (9.1%), myrcene (4.2%),and (E)-β-ocimene (4.2%). This is the first report on the essential oil characterization of C.viscidiflorus, and adds to our understanding of the volatile phytochemistry ofChrysothamnus. Biological activities of the major components in the essential oil areconsistent with the traditional Native American use of the plant.
... Many essential oils from aromatic plants such as Margotia gummifera (Desf.) Lange [9], Schinus areira L. [10], Lavandula angustifolia Mill. [11], Matricaria chamomilla L. [12], and Cordia verbenacea D.C. [13] have been proven to have lung-related anti-inflammatory effects. ...
Article
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Alveolar macrophage is the predominant cell type in the lung and is thought to be the major target for anti-inflammatory therapy in chronic obstructive pulmonary disease (COPD). Aromatherapy using natural essential oils with anti-inflammatory effects for inhalable administration is a potential complementary and alternative therapy for COPD treatment. The Gardenia jasminoides flower is famous for its fragrance in East Asia and is used for treating colds and lung problems in folk medicine. Therefore, in the present study, flower essential oils from two main medicinal gardenia varieties (G. jasminoides J. Ellis and G. jasminoides f. longicarpa Z.W. Xie & M. Okada) were extracted by hydro-distillation, and their chemical components were analyzed by GC-MS. The anti-inflammatory effects of the two essential oils and their main ingredients were further studied on lipopolysaccharide (LPS)-induced models in murine alveolar macrophages (MH-S). The results indicated that the chemical constituents of the two gardenia varieties were quite different. Alcohol accounted for 53.8% of the G. jasminoides essential oil, followed by terpenes (16.01%). Terpenes accounted for 34.32% of the G. jasminoides f. longicarpa essential oil, followed by alcohols (19.6%) and esters (13.85%). Both the two gardenia essential oils inhibited the LPS-induced nitric oxide (NO) release and reduced the production of tumor necrosis factor-α (TNF-α) and prostaglandin E2 (PGE2) in the MH-S cells. Linalool and α-farnesene dose-dependently reduced the NO release in the MH-S cells. Linalool and α-farnesene did not affect the PGE2 production but regulated the expression of TNF- α. In addition to linalool and α-farnesene, other components in the gardenia flower essential oils appeared to be able to act as anti-inflammatory agents and influence the PGE2 pathway.
... In the previous study, linalool, as the most predominant component of H. puerense EO, suppressed the secretion of LPS-induced IL-6 and TNF-α both in vitro and in vivo and could be a potential candidate to treat inflammation-related diseases [60]. Furthermore, other main components of EO, including β-pinene, γ-terpinene, terpinen-4-ol, α-pinene, sabinene, E-nerolidol, and p-cymene possess anti-inflammatory properties, as shown in previous studies [36,[61][62][63][64][65]. Therefore, the anti-inflammatory effect of the EO may be attributed to these main ingredients. ...
Article
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Hedychium puerense, a perennial rhizomatous herb, is used as an ornamental, medicinal, and edible plant in Yunnan Province, China. Essential oils from Hedychium plants are widely used in perfumes and traditional medicine, but there are no studies on the constituents and bioactivities of H. puerense essential oil (EO). Therefore, this study was designed to explore the chemical composition, antibacterial, enzyme-inhibitory, and anti-inflammatory activities of H. puerense rhizome EO. The gas chromatography with flame ionization or mass selective detection (GC-FID/MS) results indicated that H. puerense EO was mainly composed of linalool (26.5%), β-pinene (18.6%), γ-terpinene (12.1%), terpinen-4-ol (7.7%), α-pinene (5.8%), sabinene (4.9%), E-nerolidol (4.1%), and p-cymene (3.6%). For biological activities, H. puerense EO displayed broad-spectrum antibacterial properties against Enterococcus faecalis, Bacillus subtilis, Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, and Escherichia coli with diameter of inhibition zone (DIZ) values ranging from 7.44 to 10.30 mm, a minimal inhibitory concentration (MIC) of 3.13–6.25 mg/m), and a minimal bactericidal concentration (MBC) of 3.13–12.50 mg/mL. Moreover, the EO significantly inhibited acetylcholinesterase (AChE) (IC50 = 0.94 ± 0.02 mg/mL) and butyrylcholinesterase (BChE) (IC50 = 1.32 ± 0.06 mg/mL) activities, and exhibited a moderate inhibitory effect on α-glucosidase (IC50 = 5.42 ± 0.32 mg/mL) and tyrosinase (IC50 = 3.23 ± 0.21 mg/mL). Furthermore, the EO significantly suppressed the secretion of the pro-inflammatory mediator, nitric oxide (NO) (99.23 ± 0.26%), cytokines tumor necrosis factor-α (TNF-α) (97.14 ± 0.11%), and interleukin-6 (IL-6) (82.42 ± 0.16%) in lipopolysaccharide (LPS)-stimulated RAW264.7 cells at 250 μg/mL without cytotoxicity. Hence, H. puerense EO can be considered a bioactive, natural product that has great potential for utilization in the fields of food, cosmetics, and pharmaceutics.
... The laying stage was expectantly the stage where less nests had aromatic plants and less aromatic plant species were used, since in this period females only enter the nest to lay eggs and do not stay for long periods of time. MG was used in more nests than any other aromatic plant species in this stage; the main compounds of this species' essential oils (myrcene and sabinene), have a high anti-inflammatory effect [2], suggesting that some females may start nest sanitation early in the season. During incubation stage, females stay in nests for longer periods of time, hence number of nests that used each aromatic species increased, as well as number of aromatic species used. ...
Article
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Southwest Algeria has a significant but little studied biodiversity, closely associated with a diverse cultural heritage. Medicinal plants are commonly used by the local population as traditional therapeutic treatments. This study was carried out with the aim of inventorying the spontaneous species used by the populations of the Ain Sefra region (south-western Algeria) and to gather information on the ancestral know-how of the local populations in terms of therapeutic use. The ethno-botanical survey was carried out using a semi-structured questionnaire among local herbalists practising in the study area. The data collected was analysed using quantitative indices such as species use value (UV), informant consensus factor (FIC) and fidelity level (FL). The results showed that 48 spontaneous medicinal plants were recognised and identified as medicinal species. These plants belonged to 28 families, of which the families Asteraceae and Lamiaceae are the most represented with 18% and 12% respectively. The leaves are the most used parts for medicinal purposes with decoction being the most used mode. Thus according to the (UV) Juniperus thurifera L. and Cotula cinerea Delile are the most used. Thus Artemisia herb alba Asso had the highest level of fidelity (100%) for the treatment of gastrointestinal diseases. In conclusion, this study revealed that the local population of the Ain Sefra region has a strong ethnobotanical knowledge and still uses local spontaneous medicinal species to treat several diseases.
Article
Essential oils still remain as a source for the identification of promising biologically active molecules. The aim of this study was to determinate the chemical composition of essential oils from Eugenia cuspidifolia (EO1) and Eugenia tapacumensis (EO2), and their antiproliferative effects in human cancer cell lines. The essential oils were analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC–MS). Evaluation of cytotoxic effect was performed against different tumor line cells was performed through alamar blue assay, using different human cell line: malignant melanoma (SK-MEL-19), colorectal carcinoma (HCT116), breast adenocarcinoma (MCF7), gastric adenocarcinoma (ACP02). Subsequently, clonogenic survival, wound-healing assay, activity of metalloproteinases (MMPs), and comet assays were executed using only the more sensibility cell line to oils. A total of 24 different compounds were identified in the essential oils; the major components were caryophyllene oxide (57.46%, 55.95%) and α-copaene (3.75%, 13.67%) were the majority of detected compounds in both oils from EO1 and EO2, respectively. Essential oils reduce viability of tumor cells (MCF-7, HCT116, SK-Mel 19), according with values of IC50 between 12.37–26.17 μg mL−1. Essential oils showed high cytotoxic potential against HCT116 cell line, therefore this cell strain was selected for evaluation of anticancer potential. The EO1 and EO2 showed a reduction in cell colony formation, cell migration, and MMPs (MMP-2 and MMP-9) activities. In the comet assay, a high damage index was identified for EO2. In conclusion, the essential oils from these two Eugenia species analyzed have shown promising antitumoral results, with potential effect in HCT116 cell line.
Chapter
Essential oils are complex mixtures of volatile compounds produced by aromatic plants and extracted by distillation or expression. More than 3000 essential oils are known with about 300 being commercially relevant as perfume, cosmetic, cleaning, food, and pharmaceutical products. The main trade oils (over 1000 t/year) are those extracted from Citrus aurantifolia, Citrus limon, Citrus sinensis, Cymbopogon nardus, Cymbopogon winterianus, Eucalyptus citriodora, Eucalyptus globulus, Lavandula × intermedia, Mentha canadensis, Mentha × gracilis, Mentha × piperita, Ocotea odorifera, Pogostemon cablin, Sassafras albidum and Syzygium aromaticum. A remarkable progress in the development of analytical methods has contributed to a precise and more reliable characterization of essential oils. Volatile compounds of terpenoid origin, primarily monoterpenes and sesquiterpenes, have been identified as hydrocarbons and their oxygenated derivatives in the form of alcohols, aldehydes, ketones, esters, ethers, peroxydes, and phenols. Also, non-terpenoid compounds namely phenylpropanoids, fatty acids and their esters and, more rarely, nitrogen- and sulfur-containing compounds are also present. Numerous parameters (physiological, environmental, and genetic factors) influence essential oil composition and in order to ensure the best quality of commercialized oils, specific guidelines have been developed and should be considered. This chapter attempts to shed light on essential oils chemistry by pointing out biosynthetic aspects, relevant compounds in essential oil composition, and the major global trade oils.
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Adams, R. P. 2007. Identification of essential oil components by gas chromatography/ mass spectrometry, 4th Edition. Allured Publ., Carol Stream, IL Is out of print, but you can obtain a free pdf of it at www.juniperus.org
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The synthesis of (±)-11α-hydroxy-3-oxo-6αH,7αH,10βMe-eudesman-1,2-4,5-dien-6,12-olide (1), previously isolated from Melanoselinum decipiens, is described, and its structure has been corrected.
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Thymbra capitata and Thymus species are commonly known in Portugal as thyme and they are currently used as culinary herbs, as well as for ornamental, aromatizing and traditional medicinal purposes. The present work reports on the state of the art on the information available on the taxonomy, ethnobotany, cell and molecular biology of the Portuguese representatives of these genera and on the chemotaxonomy and antibacterial, antifungal and antioxidant activities of their essential oils and other volatile-containing extracts.
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A tetrazolium salt has been used to develop a quantitative colorimetric assay for mammalian cell survival and proliferation. The assay detects living, but not dead cells and the signal generated is dependent on the degree of activation of the cells. This method can therefore be used to measure cytotoxicity, proliferation or activation. The results can be read on a multiwell scanning spectrophotometer (ELISA reader) and show a high degree of precision. No washing steps are used in the assay. The main advantages of the colorimetric assay are its rapidity and precision, and the lack of any radioisotope. We have used the assay to measure proliferative lymphokines, mitogen stimulations and complement-mediated lysis.
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The synthesis of (+/-)-11alpha-hydroxy-3-oxo-6alphaH,7alphaH, 10betaMe-eudesman-1,2-4,5-dien-6,12-olide (1), previously isolated from Melanoselinum decipiens, is described, and its structure has been corrected.
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Organic compounds from terrestrial and marine organisms have extensive past and present use in the treatment of many diseases and serve as compounds of interest both in their natural form and as templates for synthetic modification. Over 20 new drugs launched on the market between 2000 and 2005, originating from terrestrial plants, terrestrial microorganisms, marine organisms, and terrestrial vertebrates and invertebrates, are described. These approved substances, representative of very wide chemical diversity, together with several other natural products or their analogs undergoing clinical trials, continue to demonstrate the importance of compounds from natural sources in modern drug discovery efforts.
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European Pharmacopoeia
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Inflammation, Chronic Diseases and Cancer -Cell and Molecular Biology, Immunology and Clinical Bases
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The Atlas of Spectral Data of Sesquiterpene Hydrocarbon
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Synthesis of (±)-11-hydroxy-3-oxo-6H
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