Eryngial: An α,ß-Unsaturated Fatty Aldehyde as the Major Phytotoxin in Spiny Coriander (Eryngium foetidum L.) Essential Oil.

Weed species many times possess allelochemicals as a part of their survival strategy. These metabolites can be potential targets in search of natural phytotoxins. This study aims to evaluate the phytotoxic ability of fatty aldehyde-rich essential oil from spiny coriander (Eryngium foetidum) leaves, also known as fitweed or spiritweed and to further identify the active phytotoxins. This oil dose-dependently inhibited the wheatgrass coleoptile and radicle growth in multiple bioassays with half maximal inhibitory concentration (IC50) 30.6-56.7 µg/mL, while exhibiting a less pronounced effect on the germination (IC50 181.8 µg/mL). The phytotoxicity assessment of two oil constituents identified eryngial (trans-2-dodecenal), exclusively major fatty aldehydic constituent as the potent growth inhibitor with IC50 in the range 20.8-36.2 µg/mL during an early phase of wheatgrass emergence. Eryngial-inspired screening of eleven saturated fatty aldehydes and alcohols did not find a significantly higher phytotoxic potency. In an open vessel, eryngial as the supplementation in agar medium, dose-dependently inhibited the growth of pre-germinated seeds of one monocot (bermudagrass) and one dicot (green amaranth) weed species with IC50 in the range 23.8-65.4 µg/mL. The current study identified eryngial, an α,ß-unsaturated fatty aldehyde of coriander origin to be a promising phytotoxic candidate for weed control.

Chemical Composition of the Essential Oils of the Iberian Peninsula Endemic Species Eryngium dilatatum Lam.

Eryngium dilatatum Lam. is a thorny Iberian Peninsula endemic species belonging to the Apiaceae family that has not been previously analysed from a chemical point of view. Following our studies on this genus, we characterized the chemical composition of the essential oils from the different parts (inflorescences, stems + leaves, and roots) of this species; these parts were gathered in Cádiz (Spain). The specimens were collected in July during the flowering period and air-dried before the oil extraction by hydro-distillation. The essential oils were analysed by gas chromatography and gas chromatography coupled with mass spectrometry. The different parts of the plant yielded low amounts of pale yellow oil, with the roots being the fraction that provided the lowest amount of oil. The chemical characterization of the essential oils showed qualitative and quantitative differences between the fractions examined, but all of them showed the same principal compound, germacrene D (9.1-46.5%). Similarly, all the fractions shared most of their representative constituents, with their percentage compositions being different from one sample to the other: α-cadinol (3.8%), bicyclogermacrene (3.5%), octanal (3.1%), and spathulenol (2.5%) were found in the inflorescences; octanal (8.1%), α-cadinol (3.7%), δ-cadinene (3.6%), (E)-caryophyllene (2.6%), bicyclogermacrene (2.5%), and spathulenol (2.4%) were found in the stems and leaves; and spathulenol (4.6%), α-cadinol (4.4%), khusinol (3.2%), α-muurolol (3.1%), and δ-cadinene (2.6%) were found in the roots. As far as we know, this is the first report about the chemical composition of this endemic species of the Iberian Peninsula. It contributes to the knowledge of this species and to the genus to which it belongs. This species could be considered as a natural source of germacrene D, which is a sesquiterpene hydrocarbon with active properties.

Phytochemical Diversity Comparison in Leaves and Roots of Wild and Micropropagated Latvian Sea Holly (Eryngium maritimum L.).

The goal of the current study was to compare the chemical composition of the roots, shoots, and leaves of wild-growing Eryngium maritimum L., and of in vitro and in field-cultivated plants in Latvia. The essential oil yield obtained by hydrodistillation ranged from 0.14% to 0.54%, while analysis of the chemical composition using GC-MS revealed a total of 44 different volatiles, with differences in the types and amounts of volatiles between the leaves and roots. Using 96-well plate techniques, the concentration of total phenolic compounds, saponins, and sugars in the aqueous ethanolic extracts of E. maritimum were assessed, along with their capacity to scavenge stable DPPH radicals. Extracts from roots had a lower concentration of total phenolic compounds compared to those from the leaves of wild grown and cultivated plants but did not differ from in vitro shoots. Root, leaf, and shoot samples of the same genotype from different growth conditions had approximately the same concentration of total saponins, while total sugar concentrations were higher in the roots. The growth conditions had a significant effect on the concentration of total phenolic compounds and antiradical activity, with differences that were significant observed between plant aboveground and belowground parts. Analysis using UHPLC-ESI-q-TOF-MS revealed 63 compounds, with amino acids and hydroxycinnamic acid derivatives (such as chlorogenic and rosmarinic acid) being the major compound groups that significantly differed between plant growth conditions. We also demonstrated that rapid screening of volatile compounds in in vitro plants using headspace gas chromatography mass spectrometry analyses can predict the formation of marker compounds in the same mericlones grown in field conditions. These findings provide valuable insights into the chemical composition of E. maritimum and its potential for use in various applications.

Ethnobotany, Biological Activities and Phytochemical Compounds of Some Species of the Genus Eryngium (Apiaceae), from the Central-Western Region of Mexico.

There are approximately 250 species of Eryngium L. distributed throughout the world, with North America and South America being centers of diversity on this continent. In the central-western region of Mexico there may be around 28 species of this genus. Some Eryngium species are cultivated as leafy vegetables, ornamental, and medicinal plants. In traditional medicine they are used to treat respiratory and gastrointestinal conditions, diabetes, and dyslipidemia, among others. This review addresses the phytochemistry and biological activities, as well as traditional uses, distribution, and characteristics of the eight species of Eryngium reported as medicinal in the central-western region of Mexico: E. cymosum, E. longifolium, E. fluitans (or mexicanum), E. beecheyanum, E. carlinae, E. comosum, E. heterophyllum, and E. nasturtiifolium. The extracts of the different Eryngium spp. have shown biological activities such as hypoglycemic, hypocholesterolemic, renoprotective, anti-inflammatory, antibacterial, and antioxidant, among others. E. carlinae is the most studied species, and phytochemical analyses, performed mainly by high-performance liquid chromatography (HPLC) and gas chromatography coupled with mass spectrometry (GC-MS), have shown its content of terpenoids, fatty acids, organic acids, phenolic acids, flavonoids, sterols, saccharides, polyalcohols, and aromatic and aliphatic aldehydes. According to the results of this review on Eryngium spp., they constitute a relevant alternative as a source of bioactive compounds for pharmaceutical, food, and other industries. However, there is a lot of research to be conducted regarding phytochemistry, biological activities, cultivation, and propagation, in those species with few or no reports.

Effect of Elicitation with (+)-Usnic Acid on Accumulation of Phenolic Acids and Flavonoids in Agitated Microshoots of Eryngium alpinum L.

The present work was aimed at studying the potential of elicitation on the accumulation of phenolic compounds in in vitro shoot cultures of Eryngium alpinum L., a protected plant from the Apiaceae family. The study examined the influence of (+)-usnic acid on the biomass growth as well as on the biosynthesis of the desired flavonoids and phenolic acids in the cultured microshoots. The phenolic compound content was determined by HPLC-DAD. The flavonoid of the highest concentration was isoquercetin, and the phenolic acids of the highest amount were rosmarinic acid, caffeic acid and 3,4-dihydroxyphenylacetic acid, both in the non-elicited and elicited biomass. Isoquercetin accumulation was efficiently increased by a longer elicitation with a lower concentration of lichenic compound (107.17 ± 4.67 mg/100 g DW) or a shorter elicitation with a higher concentration of acid (127.54 ± 11.34 and 108.37 ± 12.1 mg/100 g DW). Rosmarinic acid production generally remained high in all elicited and non-elicited microshoots. The highest content of this acid was recorded at 24 h of elicitation with 3.125 µM usnic acid (512.69 ± 4.89 mg/100 g DW). The process of elicitation with (+)-usnic acid, a well-known lichenic compound with allelopathic nature, may therefore be an effective technique of enhancing phenolic compound accumulation in alpine eryngo microshoot biomass.

Antimicrobial and Light-Enhanced Antimicrobial Activities, Cytotoxicity and Chemical Variability of All Tunisian Eryngium Species.

This study was performed on all Eryngium species growing in Tunisia in order to evaluate their intra and interspecies variabilities and to investigate their biological activities. These species are used in traditional medicine, and literature about the phytochemical investigations of most of them is scarce. Antimicrobial and light-enhanced activities were tested against multiresistant microorganisms and extended spectrum beta-lactamase producing bacteria (ESBL). All studied species showed antimicrobial effect with several MIC values lower than 70 µg/ml. Tested Eryngium species have proven to be a promising source of photoactive compounds, while light-enhanced activity offers an alternative for the inactivation of pathogenic microorganisms which is currently subjected to a great interest. This is the first report of this activity in genus Eryngium. A significant improvement of antimicrobial activity with UV irradiation was observed, mainly for E. dichotomum, E. ilicifolium and E. triquetrum. Cytotoxicity, studied for the first time for the most species, was evaluated against cancer (J774) and non-cancer (WI38) human cell lines. Chemical composition of volatile compounds presented in the most active crude extracts (petroleum ether extracts) of the aerial parts was investigated using GC/MS analysis and was submitted to statistical analyses. It revealed their high content of bioactive phytochemicals, particularly oxygenated sesquiterpenes like spathulenol, ledol and α-bisabolol but also hydrocarbon sesquiterpenes such as ß-bisabolene and copaene, as well as polyacetylene derivatives such as falcarinol. Statistical analyses permitted to evaluate the interrelations between all Tunisian Eryngium species.

Phytochemical Screening and Acanthamoebic Activity of Shoots from in Vitro Cultures and in Vivo Plants of Eryngium alpinum L.-The Endangered and Protected Species.

Genetically uniform shoots of Eryngium alpinum L. cultured in vitro were subjected to the qualitative analysis applying the UPLC-HESI-HRMS technique. In vitro cultures give the opportunity to perform the phytochemical studies on the protected species without harvesting the plant material from the natural environment. The phytochemical screening of the crude methanolic extracts of shoots, both from in vitro cultures and in vivo plants, revealed the presence of phenolic acids, coumarins, flavonoids, triterpenoid saponins, amino acids, or dipeptides. Active compounds detected are known to have medicinal importance, and for this reason, the present study represents a preliminary investigation of the extracts against pathogenic and opportunistic amoeba. Among the extracts tested, the extract of shoots from in vitro cultures exhibited remarkable amoebicidal action against trophozoites. On the second day of treatment, the extract at the concentrations of 5 mg/mL, 2.5 mg/mL, and 0.5 mg/mL showed the highest antiamoebicidal effect: the inhibition of trophozoites reached 81.14%, 66.38%, and 54.99%, respectively. To our best knowledge, the present report is the first to show the phytochemical screening and to discuss the antiamoebic activity of Eryngium alpinum L. shoots, both from in vitro cultures and in vivo plants.

Comparison of extraction methods for chemical composition, antibacterial, depigmenting and antioxidant activities of Eryngium maritimum.

OBJECTIVE: The objective is to develop a natural cosmetic ingredient from Eryngium maritimum regarding the high interest of consumer in these ingredients for cosmetic use. METHODS: Five eco-friendly techniques of extraction were applied to Eryngium maritimum aerial parts among conventional reflux extraction (with green solvent) and alternative techniques (supercritical fluid extraction (SFE), microwave-assisted extraction (MAE), ultrasound-assisted extraction (UAE) and ultrasound combined with microwave extraction (UAE + MAE)). Several criteria were evaluated to allow the optimal choice for an industrialized ingredient: yield of extraction, chemical composition and biological activities such as antimicrobial, antioxidant, anti-collagenase and anti-tyrosinase activities. The extracts were analysed by liquid chromatography mass spectrometry (LC-HRMS), and the hierarchical Pearson classification (HCA) allowed to highlight the group of metabolites preferably extracted depending on the technique of extraction used. RESULTS: The biological results highlight that SFE and 80% ethanol reflux extracts have the best responses to biological activities such as antimicrobial, depigmenting and antioxidant activities, followed by water reflux extraction. Their activities might be due to the presence of different groups of metabolites favourably extracted by these techniques. CONCLUSION: Among these extractions, water reflux extraction provided the optimal results considering the compromise between extraction yield and biological activities for the development of a cosmetic ingredient.

OBJECTIF: L'objectif est d'évaluer différentes méthodes d'extraction permettant l'obtention d'un ingrédient cosmétique naturel, à partir d'Eryngium maritimum, efficace biologiquement, et respectant les principes du développement durable et de la beauté éthique et responsable. MÉTHODES: Cinq techniques d'extraction respectueuses de l'environnement ont été appliquées à des parties aériennes d'Eryngium maritimum tels que le reflux conventionnel (avec des solvants agrosourcés) et des techniques alternatives (extraction au fluide supercritique (SFE), extraction assistée par micro-ondes (MAE), extraction assistée par ultrasons (UAE) et ultrasons combinés aux micro-ondes (UAE + MAE)). Plusieurs critères ont été évalués pour permettre le choix optimal d'un ingrédient cosmétique efficace, naturel et industrialisable : rendement d'extraction, composition chimique (sureté) et efficacités biologiques (antibactérien, antioxydant, anti-âge et dépigmentant). Les extraits ont été analysés par chromatographie liquide spectrométrie de masse (LC-HRMS), et la classification par hiérarchie de Pearson (HCA) a permis de mettre relier les groupes de métabolites extraits de préférence par technique d'extraction testée. RÉSULTATS: Les résultats biologiques mettent en évidence que les extractions par SFE et à reflux par éthanol 80% permettaient les meilleures réponses (les plus importantes) pour des activités antimicrobiennes, éclaircissantes et antioxydantes, devant l'extraction à reflux par l'eau. Leurs activités pourraient être dues à la présence préférentielle de certains groupes de métabolites extraits plus favorablement par ces techniques. CONCLUSION: Parmi les extractions testées, l'extraction par reflux à l'eau (procédé respectueux de l'environnement) d'Eryngium maritimum, fournit le meilleur compromis en termes d'efficacités biologiques plurielles, de rendement d'extraction et de productivité/consommation énergétique, pour le développement d'un ingrédient cosmétique 'ecofriendly'.

Essential Oil of Algerian Eryngium campestre: Chemical Variability and Evaluation of Biological Activities.

The chemical composition of essential oils extracted from aerial parts of Eryngium campestre collected in 37 localities from Western Algeria was characterized using GC-FID and GC/MS analyses. Altogether, 52 components, which accounted for 70.1 to 86.8% of the total composition oils were identified. The main compounds were Germacrene D (0.4-53.4%), Campestrolide (1.6-35.3%), Germacrene B (0.2-21.5%), Myrcene (0.1-8.4%), α-Cadinol (0.2-7.6%), Spathulenol (0.1-7.6%), Eudesma-4(15)-7-dien-1-ß-ol (0.1-7.6%) and τ-Cadinol (0.3-5.5%). The chemical compositions of essential oils obtained from separate organs and during the complete vegetative cycle of the plant were also studied. With the uncommon 17-membered ring lactone named Campestrolide as the main component, Algerian E. campestre essential oils exhibited a remarkable chemical composition. A study of the chemical variability using statistical analysis allowed the discrimination of two main clusters according to the geographical position of samples. The study contributes to the better understanding of the relationship between the plant and its environment. Moreover, the antimicrobial activity of the essential oil was assessed against twelve strains bacteria and two yeasts involved in foodborne and nosocomial infections using paper disc diffusion and dilution agar assays. The in vitro study demonstrated a strong activity against Gram-positive strains such as S. aureus, B. cereus, and E. faecalis. The cytotoxicity and antiparasitic activities (on Lmm and Tbb) of the collective essential oil and one sample rich in campestrolide, as well as some enriched fractions or fractions containing other terpenic compounds, were also analyzed. Campestrolide seems to be one compound responsible for the cytotoxic and antileishmanial effect, while myrcene or/and trans-ß-farnesene have a more selective antitrypanosomal activity.

Nutritional Evaluation of Non-Conventional Vegetables in Brazil.

The objective of this study was to characterize the nutritional compounds of interest present in vegetables known as non-conventional, in Brazil. The following evaluations were carried out: antioxidant activity, phenolic compounds, vitamin C, calories, carbohydrates, humidity, lipids, proteins, fiber, acidity and quantification of minerals (P, K, Ca, Mg, S, Cu, Fe, Mn, Zn and B). The species studied were Amaranthus hybridus L., Amaranthus viridis L., Basella alba L., Eryngium campestre L., Hibiscus sabdariffa L., Lactuca canadensis L., Rumex acetosa L., Stachys byzantina K. Koch, Tropaeolum majus L. and Xanthosoma sagittifolium L. Representative samples of plant structures of interest were harvested from each species suitable for human consumption such as leaves, flowers and flower buds. The results were submitted to multivariate analysis - principal components analysis (PCA). All the species present nutritional compounds of interest in different levels among the evaluated structures.

Chemical Composition and Biological Investigations of Eryngium triquetrum Essential Oil from Algeria.

The chemical composition, antibacterial and antioxidant activities of the essential oil obtained from Eryngium triquetrum from Algeria were studied. The chemical composition of sample oils from 25 locations was investigated using GC-FID and GC/MS. Twenty-four components representing always more than 87% were identified in essential oils from total aerial parts of plants, stems, flowers and roots. Falcarinol is highly dominant in the essential oil from the roots (95.5%). The relative abundance of falcarinol in the aerial parts correlates with the phenological stages of the plant. Aerial parts of E. triquetrum produce an essential oil dominated by falcarinol during the early flowering stage, and then there is a decrease in falcarinol and rebalancing of octanal during the flowering stage. To our knowledge, the present study is the first report of the chemical composition of E. triquetrum essential oil. Evaluation of the antibacterial activity by means of the paper disc diffusion method and minimum inhibitory concentration assays, showed a moderate efficiency of E. triquetrum essential oil. Using the DPPH method, the interesting antioxidant activity of E. triquetrum essential oil was established. These activities could be attributed to the dominance of falcarinol. The outcome of our literature search on the occurrence of falcarinol in essential oils suggests that E. triquetrum from Algeria could be considered as a possible source of natural falcarinol.

Structural Elucidation and Cytotoxicity of a New 17-Membered Ring Lactone from Algerian Eryngium campestre.

The chemical composition of a hexanic extract of Eryngium campestre, obtained from its aerial parts, was investigated by GC-FID, GC/MS, HRMS, NMR and VCD analyses. The main compounds were germacrene D (23.6%), eudesma-4(15)-7-dien-1-ß-ol (8.2%) and falcarindiol (9.4%), which are associated with a new uncommon and naturally found 17-membered ring lactone. This 17-membered ring features conjugated acetylenic bonds, named campestrolide (23.0%). The crude extract showed moderate antitrypanosomal (Trypanosoma brucei brucei), antileishmanial (Leishmania mexicana mexicana) and anticancer (cancerous macrophage-like murine cells) activities, and also displayed cytotoxicity, (human normal fibroblasts) in similar concentration ranges (IC50 = 3.0, 3.9, 4.0 and 4.4 µg/mL respectively). Likewise, campestrolide displayed low activity on all tested cells (IC50: 12.5⁻19.5 µM) except on Trypanosoma, on which it was very active and moderately selective (IC50 = 2.2 µM. SI= 8.9). In conclusion, the new compound that has been described, displaying a singular structure, possesses interesting antitrypanosomal activity that should be further investigated and improved.

Chemical composition and antioxidant activity of the volatile fraction extracted from air-dried fruits of Tunisian Eryngium maritimum L. ecotypes.

BACKGROUND: Eryngium maritimum L., also known as 'sea holly', is a typical dune plant species belonging to the Apiaceae family and commonly used in Tunisia for therapeutic purposes in folk medicine. In the present study, the chemical composition and antioxidant activity of the volatile fraction extracted from air-dried fruits of five Tunisian E. maritimum ecotypes were determined. RESULTS: The total volatile amount ranged from 0.31% to 0.93% (w d.w.-1 ). Sixty-six volatile components were identified by means of GC-MS and accounted for 77.05-86.65% of the total extracted volatile oil. The majority of the identified metabolites were hydrocarbon sesquiterpenes and oxygenated sesquiterpenes, amounting on average to 46.69% and 30.01% of total volatiles, respectively. The principal individual components were germacrene D (13.62-31.71%), 15-hydroxy-α-muurolene (12.04-18.58%), and germacrene B (6.77-15.04%). Significant differences were noticed among E. maritimum populations. The volatile profile of E. maritimum fruits was consistently different from those of the aerial parts and roots of plants of the same species reported in previous investigations. Average radical scavenging capacity of the volatile fraction, as determined by DPPH and ABTS tests, was twice higher than that of the Trolox control. CONCLUSION: This study characterised for the first time the fruits of E. maritimum for the composition and radical-scavenging capacity of their volatile fraction. The growth location confirmed as a pivotal factor in influencing the volatile profile of the fruits. © 2017 Society of Chemical Industry.

Cytotoxic Essential Oils from Eryngium campestre and Eryngium amethystinum (Apiaceae) Growing in Central Italy.

Eryngium campestre and E. amethystinum are thorny herbs belonging to the Apiaceae family and spontaneously growing in stony pastures and dry meadows, preferentially on calcareous substrates. In the Mediterranean countries, these plants have been used as a food or traditional remedies to treat various ailments. In the present work, we have analyzed the chemical composition of the essential oils distilled from the aerial parts by GC-FID and GC/MS, and evaluated their cytotoxic effects on a panel of human cancer cells, namely A375 (human malignant melanoma), MDA-MB 231 cells (human breast adenocarcinoma), and HCT116 cells (human colon carcinoma), by the MTT assay. Furthermore, the Eryngium essential oils were evaluated for antioxidant and acetylcholinesterase (AChE) activities. The two essential oils were rich in sesquiterpene hydrocarbons, with germacrene D as the major compound, accompanied by allo-aromadendrene, ß-elemene, spathulenol, and ledol. They turned out to be highly cytotoxic on the tumor cells, with IC50 values (1.65 - 5.32 and 1.57 - 2.99 µg/ml for E. amethystinum and E. campestre, respectively) comparable or close to those of the anticancer drug cisplatin. The E. amethystinum essential oil exhibited a moderate antioxidant activity, whereas that of E. campestre a weak AChE inhibition.

Phytochemical Study of Eryngium triquetrum: Isolation of Polyacetylenes and Lignans.

Phytochemical investigation of the ethyl acetate extract from the aerial parts of Eryngium triquetrum Vahl resulted in the isolation of new polyacetylenes, triquetridiol (6) and trans-epoxy-triquetrol (7a/7b, diastereomeric mixture), and the lignan demethoxy carolignan Z (8a/8b, erythro/threo pair), together with a series of related known metabolites. Additionally, some already reported phenolic and flavonoid compounds were also identified in the extract. Structural elucidation of the new compounds was made by spectroscopic analysis, mainly NMR and mass spectrometry. To the best of our knowledge, this is the first report of polyacetylenes and lignans from E. triquetrum.

Antibacterial and antifungal potentials of the solvents extracts from Eryngium caeruleum, Notholirion thomsonianum and Allium consanguineum.

BACKGROUND: Herbal medicines have long been used for various ailments in various societies and natural bioactive compounds are gaining more and more importance due to various factors. In this context, three plant species i.e., Eryngium caeruleum, Notholirion thomsonianum and Allium consanguineum have been aimed for the scientific verification of their purported traditional uses against various infectious diseases. METHODS: In this study, three plants were assayed for antibacterial and antifungal potentials. The antibacterial investigations were performed via well diffusion method and nutrient broth dilution method. The bacterial strains used in the study were Enterococcus faecalis, Proteus mirabilis, Escherichia coli, Salmonella typhi, Klebsiella pneumonia and Pseudomonas aeruginosa. The antifungal potential was investigated by dilution method of Muller-Hinton agar media of the plants' samples. The fungal strains used were Aspergillis fumigatus, Aspergillis flavus and Aspergillis niger. Ceftriaxone and nystatin were used as standard drugs in antibacterial and antifungal assays respectively. RESULTS: Different fractions from N. thomsonianum were tested against five bacterial strains while the samples from A. consanguineum and E. caeruleum were tested against six bacterial strains. All the samples exhibited prominent antibacterial activity against the tested strains. Overall, chloroform and ethyl acetate fractions were found most potent among the three plants' samples. N. thomsonianum excelled among the three plants in antibacterial activity. Similarly, in antifungal assay, N. thomsonianum exhibited strong antifungal activity against the fungal strains. The chloroform fraction displayed MFCs of 175.67 ± 5.20***, 29.33 ± 5.48*** and 63.00 ± 4.93*** µg/ml against Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger respectively. The whole study demonstrates that all the three plant species were active against tested bacterial and fungal strains. CONCLUSION: It can be concluded from our findings that N. thomsonianum, A. consanguineum and E. caeruleum have broad antibacterial and antifungal potentials. In all of the plants' samples, chloroform and ethyl acetate fractions were more active. Furthermore, being the potent samples, the chloroform and ethyl acetate fractions of these plants can be subjected to column chromatography for the isolation of more effective antimicrobial drugs.

Chemical Composition and Antimicrobial Activity of the Essential Oil from Aerial Parts and Roots of Eryngium barrelieri Boiss. and Eryngium glomeratum Lam. from Tunisia.

The study of chemical composition and biological activity of unexplored essential oils may open new perspectives on their potential use in facing major health concerns such as drug-resistant infections. The present study investigates the chemical composition and antimicrobial effects of previously unstudied essential oils obtained from genus Eryngium: Eryngium glomeratum Lam. and Eryngium barrelieri Boiss. The chemical compositions of the essential oils from aerial parts and roots of both species were studied using GC and GC/MS analytical technics. The analysis led to the identification of 102 compounds totalizing 85 - 94% of all detected compounds. Essential oils were characterized by the predominance of oxygenated sesquiterpenes. The oils obtained from aerial parts were tested against 36 microbial strains by agar dilution method and showed minimum inhibitory concentrations (MIC) in the range of 2 - 625 µg/ml. A strong antibacterial activity against multiresistant Pseudomonas aeruginosa was observed especially from E. glomeratum essential oil with MIC value up to 2 µg/ml. These findings give significant information about the pharmacological activity of these essential oils, which suggest their potential use to develop new remedies, or as sources of active compounds.

The monoamine oxidase inhibitory activity of essential oils obtained from Eryngium species and their chemical composition.

CONTEXT: Monoamine oxidase (MAO) inhibitors are used in the treatment of depression, anxiety disorders, and the symptomatic treatment of Parkinson's disease. Eryngium, the most representative of the Apiaceae family, is well known for the presence of essential oils (EOs), which have already demonstrated MAO inhibitory potential. OBJECTIVE: The objective of this study is to evaluate the MAO inhibitory capacity of the EOs obtained from Eryngium floribundum Cham. & Schlecht. (EF), E. eriophorum Cham. & Schlecht. (EE), E. nudicaule Lam. (EN), E. horridum Malme (EH), and E. pandanifolium Cham. & Schlecht. (EP). MATERIALS AND METHODS: EOs were obtained from fresh whole plants by hydrodistillation (3 h). Chemical analyses were performed by GC/MS using apolar and polar columns, with oven temperature from 60 to 300 °C at 3 °C/min. The MAO-A and -B activities were evaluated in vitro by an end-point method using kynuramine as the substrate and mitochondrial suspension or human recombinant enzymes as the enzymatic source. DMSO 2%, clorgyline 10(-7) M, and pargyline 10(-6) M were used as controls. RESULTS AND DISCUSSION: EFEO, EEEO, ENEO, EHEO, and EPEO GC/MS analysis showed (E)-caryophyllene (4.9-10.8%), germacrene D (0.6-35.1%), bicyclogermacrene (10.4-17.2), spathulenol (0.4-36.0%), and globulol (1.4-18.6%) as main constituents. None of the EOs inhibited MAO-A activity (4 and 40 µg/mL). However, EHEO inhibited MAO-B activity with an IC50 value of 5.65 µg/mL (1-200 µg/mL). Pentadecane (10 µM), its major constituent (53.5%), did not display significant MAO-B inhibition. CONCLUSION: The study demonstrates the promising application of Eryngium species as a source of potential central nervous system bioactive secondary metabolites, specially related to neurodegenerative disorders.

Eryngial (trans-2-dodecenal), a bioactive compound from Eryngium foetidum: its identification, chemical isolation, characterization and comparison with ivermectin in vitro.

Methanol-water (4:1, v/v) crude extracts (50 mg mL(-1)) of 25 Jamaican medicinal plants were screened in vitro for anthelmintic activity using infective third-stage larvae of Strongyloides stercoralis. The most effective extract was further chemically scrutinized to isolate and identify the source of the bioactivity, and the efficacy of this compound was compared with ivermectin. Eosin exclusion (0.1 mg mL(-1)) served as the indicator of mortality in all bioassays. A crude extract of Eryngium foetidum (Apiaceae) was significantly (Probit Analysis, P<0.05) more potent than the other plant extracts, taking 18.9 h to kill 50% (LT50) of the larvae. Further, the petrol extract of E. foetidum was significantly more effective (Probit Analysis, P<0.05) at killing the larvae (LT50, 4.7 h) than either its methanol-water or dichloromethane extract. The latter two effected less than 1% larval mortality after 120 h. With bioassay-driven column chromatography of the petrol extract, trans-2-dodecenal (eryngial) was identified and chemically isolated as the main anthelmintic compound in E. foetidum. There was a significant difference between the 24 h LD50 values (mm) of trans-2-dodecenal (0.461) and ivermectin (2.251) but there was none between the 48 h LD50 values (mm): trans-2-dodecenal (0.411) and ivermectin (0.499) in vitro.

Leishmanicidal activity of a daucane sesquiterpene isolated from Eryngium foetidum.

CONTEXT: Eryngium foetidum L. (Apiaceae) is a traditional herb that has been used for numerous medicinal applications, including as a treatment for parasitic infections, especially in the Neotropics from where it originates. OBJECTIVE: This study evaluates the in vitro leishmanicidal and cytotoxicity activities of isolated compounds based on a bioassay-guided fractionation approach. MATERIALS AND METHODS: Defatted aerial parts of E. foetidum were subjected to extraction with methanol followed by partitioning with n-hexane, ethyl acetate and 50% methanol. Then, the first two fractions were subsequently fractionated by column chromatography and HPLC. Compound identity was confirmed by mass spectrometry and NMR spectroscopy. Leishmania tarentolae (promastigotes) and L. donovani (amastigotes) were used as testing parasites. L6 rat myoblasts were used for cytotoxicity. All extracts and fractions were tested at 20 µg/mL. RESULTS: The initial methanol extract showed 20% growth inhibition of L. tarentolae. Then, the n-hexane and ethyl acetate fractions were also active showing approximately 40% growth inhibition. From these two fractions, the following compounds were isolated: lasidiol p-methoxybenzoate (1), a daucane sesquiterpene; and 4-hydroxy-1,1,5-trimethyl-2-formyl-cyclohexadien-(2,5)-[α-acetoxymethyl-cis-crotonate] (2), a terpene aldehyde ester derivative. Compound 1 inhibited the growth of both L. tarentolae and L. donovani with IC50 values of 14.33 and 7.84 µM, respectively; and showed no cytotoxicity (IC50 > 50 µM). Compound 2 was inactive in the L. tarentolae assay (IC50 > 50 µM). DISCUSSION AND CONCLUSION: This study presented the bioassay-guided fractionation with the leishmanicidal and cytotoxicity activities of two compounds isolated for the first time from an Eryngium species.