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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.
... Macrophages play a key role in chronic inflammation by producing various inflammatory mediators. Among these, nitric oxide (NO) is produced in excessive amount by one of the inflammatory enzymes, inducible nitric oxide synthase (iNOS), contributing to tissue damage and leading to various serious diseases such as rheumatoid arthritis, cancer, and neurodegenerative diseases [19][20][21]. Thus, discovering novel inhibitors of NO production is of significant interest. ...
... 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. ...
Chapter
Essential oils are the mixture of volatile ingredients and have been utilized extensively since antiquity. Regarding its bioactivity as an antibacterial, antiviral, antioxidant, and antidiabetic, the major significance and mode of action of these naturally occurring compounds are reviewed. Further, its crucial role in the suppression of cancer and chemoprevention is also emphasized. The traditional extraction methods such as steam distillation, hydrodistillation, hydro diffusion, and solvent extraction, and advanced (non-conventional) extraction methods such as solvent-free microwave extraction, subcritical extraction liquid, and supercritical fluid extraction have been discussed. Modern extraction techniques are thought to have the most potential because they require less time to extract, use less energy and less solvent, and emit less carbon dioxide. The chemical profile of essential oils has been explored in relation to several modern characterization approaches.
Chapter
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Chapter
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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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Since the middle ages, essential oils have been widely used for bactericidal, virucidal, fungicidal, antiparasitical, insecticidal, medicinal and cosmetic applications, especially nowadays in pharmaceutical, sanitary, cosmetic, agricultural and food industries. Because of the mode of extraction, mostly by distillation from aromatic plants, they contain a variety of volatile molecules such as terpenes and terpenoids, phenol-derived aromatic components and aliphatic components. In vitro physicochemical assays characterise most of them as antioxidants. However, recent work shows that in eukaryotic cells, essential oils can act as prooxidants affecting inner cell membranes and organelles such as mitochondria. Depending on type and concentration, they exhibit cytotoxic effects on living cells but are usually non-genotoxic. In some cases, changes in intracellular redox potential and mitochondrial dysfunction induced by essential oils can be associated with their capacity to exert antigenotoxic effects. These findings suggest that, at least in part, the encountered beneficial effects of essential oils are due to prooxidant effects on the cellular level.
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Inflammation, Chronic Diseases and Cancer -Cell and Molecular Biology, Immunology and Clinical Bases
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Synthesis of (±)-11-hydroxy-3-oxo-6H
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  • F M Guerra
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  • G M Massanet
Moreno-Dourado, F.J., Guerra, F.M., Aladro, F.J., Bustamante, J.M., Jorge, Z.D., Massanet, G.M., 2000. Synthesis of (±)-11-hydroxy-3-oxo-6H,7H,10Me- endesman-1,2-4,5-dien-6,12-olide. J. Nat. Prod. 63, 934–938.