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1.
Chem Biodivers ; 21(2): e202300913, 2024 Feb.
Article in English | MEDLINE | ID: mdl-38116908

ABSTRACT

Anthemis tricolor is an endemic species of Cyprus, and there is very limited information on its chemistry and pharmacological activities. The study aims to identify the in-vitro cytotoxic and acetylcholinesterase activities of Anthemis tricolor. The compounds responsible for the activities were also identified. Potent extracts of A. tricolor were subjected to preparative isolation and spectral structure determination studies. The chloroform extract contained many components, and due to the small quantity of extract available, enough pure compound(s) cannot be obtained for structure determination studies, though the n-hexane extract afforded two known compounds, totarol (1) and taraxasterol (2). The structures of the compounds (1 and 2) were determined by 1 H and 13 C NMR experiments. The pure compounds were also tested for their acetylcholinesterase inhibitory properties. For compound 1, the IC50 value was found to be 87.88 µg/mL. However, no inhibition was seen for 2. Anthemis tricolor was established to be a valuable source of pharmacologically active compounds and requires further studies.


Subject(s)
Abietanes , Anthemis , Antineoplastic Agents , Acetylcholinesterase , Anthemis/chemistry , Cholinesterase Inhibitors/pharmacology , Cholinesterase Inhibitors/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry
2.
Bol. latinoam. Caribe plantas med. aromát ; 21(1): 108-122, ene. 2022. ilus, tab
Article in English | LILACS | ID: biblio-1372494

ABSTRACT

Cota tinctoria is a medicinal plant which has been used for management of cancer in folk medicine of various regions. The aim of present study is to investigate cytotoxic activity of different concentrations of hydroalcoholic extract of C. tinctoria flowers on gastric (AGS) and liver (Hep-G2) cancer cell lines as well as Human Natural GUM fibroblast (HUGU) cells. Cell mortality rates were examined after 24, 48 and 72 h incubations using the MTT assay. IC50of extract on AGS cells after 24, 48 and 72h was 1.46, 1.29 and 1.14 µg/mL respectively. The extract demonstrated IC50 of 5.15, 3.92 and 2.89 µg/mL on Hep-G2 cells after 24, 48 and 72 h respectively. No cytotoxic effect was detected on HUGU (Human Natural GUM fibroblast) cells. C. tinctoria seems to have a promising potential to be considered as a source for anticancer drug discovery. However, more experimental and clinical studies are required.


Cota tinctoria es una planta medicinal que se ha utilizado para el tratamiento del cáncer en la medicina popular de varias regiones. El objetivo del presente estudio es investigar la actividad citotóxica de diferentes concentraciones de extracto hidroalcohólico de flores de C. tinctoria en líneas celulares de cáncer gástrico (AGS) e hígado (Hep-G2), así como en células de fibroblasto GUM humano natural (HUGU). Se examinaron las tasas de mortalidad celular después de incubaciones de 24, 48 y 72 h utilizando el ensayo MTT. La CI50 del extracto en células AGS después de 24, 48 y 72 h fue de 1,46; 1,29 y 1,14 µg respectivamente. El extracto demostró una CI50 de 5,15, 3,92 y 2,89 µg/mL en células Hep-G2 después de 24, 48 y 72 h, respectivamente. No se detectó ningún efecto citotóxico en las células HUGU (fibroblasto GUM humano natural). C. tinctoria parece tener un potencial prometedor para ser considerada como una fuente de descubrimiento de fármacos contra el cáncer. Sin embargo, se requieren más estudios experimentales y clínicos.


Subject(s)
Plant Extracts/administration & dosage , Asteraceae/chemistry , Cell Line, Tumor/drug effects , Liver Neoplasms/drug therapy , Antineoplastic Agents, Phytogenic/administration & dosage , Stomach Neoplasms/drug therapy , Flavonoids/analysis , Plant Extracts/pharmacology , Plant Extracts/chemistry , Cell Culture Techniques , Anthemis/chemistry , Phenolic Compounds/analysis , Hep G2 Cells/drug effects , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry
3.
Arch Microbiol ; 202(8): 2105-2115, 2020 Oct.
Article in English | MEDLINE | ID: mdl-32500253

ABSTRACT

In this study, the antibacterial, anti-efflux, anti-biofilm, anti-slime (exopolysaccharide) production and urease inhibitory efficacies of green synthesized gold nanoparticles (AuNPs) coated Anthemis atropatana extract against multidrug- resistant (MDR) Klebsiella pneumoniae strains were evaluated. The green synthesized AuNPs were characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDX), X-ray diffractometer (XRD), particle size distribution, zeta potential and Fourier-transform infrared spectroscopy (FTIR). Then, antibacterial, anti-slime (exopolysaccharide) production, anti-biofilm and anti-efflux activities of AuNPs were investigated using micro-dilation, Congored agar, microtiter plate and MIC of ethidium bromide methods, respectively. Subsequently, the expression of mrkA, wzm and acrB genes was evaluated using quantitative Real-Time PCR (qRT-PCR). The synthesized AuNPs exhibited antibacterial activity against MDR strains of K. pneumoniae (minimum inhibitory concentration (MIC) of 6.25-50 µg/ml), as well as showed significant anti-slime (exopolysaccharide) production, anti-biofilm and anti-efflux activities against MDR strains. AuNPs showed significant inhibition against jack-bean urease and down-regulated the expression of mrkA, wzm and acrB genes. Moreover, the in vitro cytotoxic activity confirmed by MTT assay on the HEK-293 normal cell line showed negligible cytotoxicity. Thus, the present study suggests the potential use of AuNPs in the development of novel therapeutics for the prevention of biofilm-associated K. pneumoniae infections.


Subject(s)
Anthemis/chemistry , Drug Resistance, Multiple/drug effects , Gold/pharmacology , Klebsiella pneumoniae/drug effects , Metal Nanoparticles , Plant Extracts/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Biofilms/drug effects , Enzyme Activation/drug effects , Gene Expression Regulation/drug effects , Gold/chemistry , HEK293 Cells , Humans , Metal Nanoparticles/chemistry , Microbial Sensitivity Tests , Plant Extracts/chemistry , Urease/metabolism
4.
Molecules ; 24(14)2019 Jul 16.
Article in English | MEDLINE | ID: mdl-31315236

ABSTRACT

Ethyl acetate (EA), methanol (MeOH), and aqueous extracts of aerial parts of Anthemis tinctoria var. pallida (ATP) and A. cretica subsp. tenuiloba (ACT) were investigated for their phenol and flavonoid content, antioxidant, and key enzyme inhibitory potentials. All extracts displayed antiradical effects, with MeOH and aqueous extracts being a superior source of antioxidants. On the other hand, EA and MeOH extracts were potent against AChE and BChE. Enzyme inhibitory effects against tyrosinase and α-glucosidase were observed, as well. We also studied Anthemis extracts in an ex vivo experimental neurotoxicity paradigm. We assayed extract influence on oxidative stress and neurotransmission biomarkers, including lactate dehydrogenase (LDH) and serotonin (5-HT), in isolated rat cortex challenged with K+ 60 mM Krebs-Ringer buffer (excitotoxicity stimulus). An untargeted proteomic analysis was finally performed in order to explore the putative mechanism in the brain. The pharmacological study highlighted the capability of ACT water extract to blunt K+ 60 mM increase in LDH level and 5-HT turnover, and restore physiological activity of specific proteins involved in neuron morphology and neurotransmission, including NEFMs, VAMP-2, and PKCγ, thus further supporting the neuroprotective role of ACT water extract.


Subject(s)
Anthemis/chemistry , Flavonoids/chemistry , Neuroprotective Agents/chemistry , Phenols/chemistry , Acetylcholinesterase/metabolism , Antioxidants/chemistry , Antioxidants/pharmacology , Brain/drug effects , Brain/metabolism , Butyrylcholinesterase/metabolism , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/pharmacology , Flavonoids/pharmacology , GPI-Linked Proteins/metabolism , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Monophenol Monooxygenase/antagonists & inhibitors , Neuroprotective Agents/pharmacology , Phenols/pharmacology , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , alpha-Glucosidases/metabolism
5.
J Pharm Biomed Anal ; 173: 75-85, 2019 Sep 05.
Article in English | MEDLINE | ID: mdl-31121457

ABSTRACT

The phytochemical composition of different extracts obtained from stinking chamomile (Anthemis cotula L.) was investigated. Ethanol was used as solvent and accelerated solvent extraction (ASE), microwave assisted extraction (MAE), maceration, soxhlet extraction (SE), and ultrasound assisted extraction (UAE) were applied on plant material. Comparison of the phytochemical contents, antioxidant, and enzyme inhibitory properties were performed. The most abundant sesquiterpene in the extracts was anthecotuloide, while the most present phenolics were caffeoyl quinic acid, quercetin, and kaempferol derivatives. UAE extract was the most efficient in the extraction of sesquiterpenoids and polyphenols. Considering the assays on antioxidant activity and enzyme inhibition, ASE extract showed highest phenolic content (62.92 mg gallic acid equivalent/g extract). Likewise, this extract showed highest radical scavenging (103.44 mg trolox equivalent [TE]/g extract and 155.70 mg TE/g extract, for DPPH and ABTS assays respectively) and reducing power potential (435.32 and 317.89 mg TE/g extract, for CUPRAC and FRAP assays, respectively). The different extracts showed similar results in the enzyme inhibition assays suggesting that the extraction methods used have no effect on observed enzyme activities. Novelty of our findings are the inhibitory action of the ethanol extract of A. cotula aerial parts on key enzymes associated with Alzheimer's disease (acetyl cholinesterase, butyryl cholinesterase), type 2 diabetes (α-amylase, α-glucosidase), and skin hyperpigmentation disorders (tyrosinase). Data collected from the present work further appraises the multiple potential biological properties of stinking chamomile suggesting the need for further investigation on its constituents.


Subject(s)
Anthemis/chemistry , Chemical Fractionation/methods , Plant Extracts/isolation & purification , Chromatography, High Pressure Liquid/methods , Enzyme Inhibitors/analysis , Enzyme Inhibitors/isolation & purification , Enzyme Inhibitors/pharmacology , Free Radical Scavengers/analysis , Free Radical Scavengers/isolation & purification , Free Radical Scavengers/pharmacology , Lactones/analysis , Lactones/isolation & purification , Microwaves , Plant Components, Aerial/chemistry , Plant Extracts/analysis , Plant Extracts/pharmacology , Polyphenols/analysis , Polyphenols/isolation & purification , Sesquiterpenes/analysis , Sesquiterpenes/isolation & purification , Solvents/chemistry , Ultrasonic Waves
6.
Food Res Int ; 116: 419-429, 2019 02.
Article in English | MEDLINE | ID: mdl-30716964

ABSTRACT

Amaranth, quinoa and chia are non-conventional sources of proteins whose interest has increased in recent years due to their excellent nutritional value. Vegetable proteins can be used as food ingredients to replace animal proteins in human diet. The present article provides a comprehensive analysis of amaranth, quinoa and chia proteins and focuses on their solubility, superficial, gelling and textural properties as well as on the biological activities of enzymatic hydrolyzates.


Subject(s)
Amaranthus/chemistry , Anthemis/chemistry , Chenopodium quinoa/chemistry , Functional Food , Nutritive Value , Chemical Phenomena , Color , Diet , Dietary Proteins , Emulsifying Agents , Humans , Plant Extracts/chemistry , Plant Proteins/chemistry , Solubility
7.
Nat Prod Res ; 33(7): 970-979, 2019 Apr.
Article in English | MEDLINE | ID: mdl-27046790

ABSTRACT

In the present study, the chemical composition of the essential oil from the aerial parts of Anthemis secundiramea Biv. subsp. secundiramea L. collected in Sicily was evaluated by GC and gas chromatography-mass spectrometry. The main components of A. secundiramea were (Z)-lyratyl acetate (14.6%), (Z)-chrysanthenyl acetate (9.9%), (Z)-chrysanthenol (8.7%) and (E)-chrysanthenyl acetate (7.7%). The comparing with other studied oils of genus Anthemis belonging to the same clade is discussed. Antibacterial and antifungal activities against some micro-organisms infesting historical art craft, were also determined.


Subject(s)
Anthemis/chemistry , Oils, Volatile/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Art , Asteraceae/chemistry , Bridged Bicyclo Compounds/analysis , Gas Chromatography-Mass Spectrometry , Monoterpenes/analysis , Plant Oils/chemistry , Sicily
8.
Microb Pathog ; 119: 233-240, 2018 Jun.
Article in English | MEDLINE | ID: mdl-29684540

ABSTRACT

Anthemis species are traditionally used to treat infectious and inflammatory processes, among others clinical disturbances. In the current study, the chemical composition, the total phenolic and flavonoid contents, the antioxidant, anticholinesterase, antimicrobial, and antibiofilm activities of Anthemis stiparum subsp. sabulicola aerial parts methanolic extract (As-ME) and essential oil (As-EO) were investigated. The chemical composition of As-EO was established by GC-MS and GC-FID. Total phenolic and flavonoid contents of As-ME were spectrophotometrically determined. Diphenyl-1-picrylhydrazyl (DPPH●) radical scavenging, cupric reducing antioxidant capacity (CUPRAC) and ß-carotene bleaching assays were applied to evaluate the antioxidant potential. The anticholinesterase activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes were carried out spectrophotometrically. The antimicrobial activity was assessed by Minimal Inhibitory Concentration (MIC) using broth microdilution method against 7 ATCC® bacterial and one ATCC® yeast reference strains. The antibiofilm effect was determined quantifying the percentage of adhesion inhibition. GC-MS and GC-FID identified 72 compounds (99.02%), being As-EO predominantly constituted by germacrene D (11.13%), t-cadinol (11.01%), camphor (6.73%), spathulenol (6.50%) and isoamyl salicylate (6.45%). The total phenolic and flavonoid contents of As-ME were 13.6 ±â€¯0.03 and 5.9 ±â€¯0.04 pyrocatechol equivalents and quercetin equivalents, respectively. In ß-carotene-linoleic acid assay, As-ME showed the best lipid peroxidation inhibition activity with an IC50 = 9.96 µg/mL followed by As-EO with an IC50 = 619.98 µg/mL. In contrast, in DPPH assay, As-ME and As-EO showed moderate to low activity with an IC50 = 92.69 µg/mL for As-ME and 917.69 µg/mL for As-EO. While in CUPRAC assay, As-EO and As-ME indicated a less to moderate reducing activity. As-ME inhibited AChE (IC50 = 490.46 µg/mL) and BChE (IC50 = 142.07 µg/mL), while As-EO was inactive against AChE and revealed a discreet inhibitory action against BChE (IC50 = 212.14 µg/mL). As-ME displayed better antimicrobial activity than As-EO, being active against Staphylococcus aureus (ATCC® 25923) and Bacillus subtilis (ATCC® 6633), with MIC of 1.56 mg/mL. An expressive fungal adhesion inhibition (80.02%) on Candida albicans (ATCC® 10239) was detected with As-ME at 6.25 mg/mL. These results showed that A. stiparum subsp. sabulicola is a natural source of active compounds with antibiotic and antibiofilm effects against S. aureus and B. subtilis, and C. albicans, respectively, and also presents antioxidant and anticholinesterase properties.


Subject(s)
Anthemis/chemistry , Anti-Infective Agents/pharmacology , Antioxidants/pharmacology , Cholinesterase Inhibitors/pharmacology , Oils, Volatile/pharmacology , Bacillus subtilis/drug effects , Biofilms , Candida albicans/drug effects , Flavonoids , Methanol , Microbial Sensitivity Tests , Oils, Volatile/chemistry , Oils, Volatile/metabolism , Phenols , Plant Extracts/pharmacology , Staphylococcus aureus/drug effects
9.
Parasit Vectors ; 11(1): 269, 2018 04 25.
Article in English | MEDLINE | ID: mdl-29695271

ABSTRACT

BACKGROUND: Infections of sheep with gastrointestinal parasites, especially Haemonchus contortus, have caused serious losses in livestock production, particularly after the emergence of resistance to conventional anthelmintics. The search for new anthelmintic agents, especially those of botanical origin, has grown substantially due to the perspective of less contamination of meat and milk, as well as other advantages related to their cost and accessibility in less developed countries. The aim of this study was to evaluate the in vitro anthelmintic activity of essential oils of the plant species Citrus aurantifolia, Anthemis nobile and Lavandula officinalis against the main developmental stages of the parasite H. contortus. RESULTS: Plant species were selected based on substantial ethnopharmacological information. Analysis of the composition of each oil by gas chromatography coupled to mass spectrometry (GC-MS) demonstrated the presence of limonene (56.37%), isobutyl angelate (29.26%) and linalool acetate (35.97%) as the major constituents in C. aurantifolia, A. nobile and L. officinalis, respectively. Different concentrations of each oil were tested in vitro for their capacity to inhibit egg hatching (EHT), larval development (LDT) and adult worm motility (AWMT) using a multidrug-resistant strain of H. contortus (Embrapa 2010). The IC50 values obtained for the oils of C. aurantifolia, A. nobile and L. officinalis were 0.694, 0.842 and 0.316 mg/ml in the EHT and 0.044, 0.117 and 0.280 mg/ml in the LDT, respectively. The three oils were able to inhibit adult worm motility completely within the first 8-12 h of observation in the AWMT. CONCLUSIONS: The present results demonstrate significant anthelmintic activity of the three oils against the different developmental stages of H. contortus. Furthermore, this study is of ethnopharmacological importance by validating the anthelmintic activity of the oils studied. Although new experiments are necessary, these data contribute to the development of pharmaceutical-veterinary products for sheep farming by opening up new therapeutic possibilities against gastrointestinal infections caused by H. contortus.


Subject(s)
Anthelmintics/pharmacology , Anthemis/chemistry , Citrus/chemistry , Haemonchus/drug effects , Lavandula/chemistry , Oils, Volatile/pharmacology , Animals , Anthelmintics/isolation & purification , Biological Assay , Gas Chromatography-Mass Spectrometry , Haemonchus/physiology , Inhibitory Concentration 50 , Larva/drug effects , Larva/physiology , Locomotion/drug effects , Oils, Volatile/chemistry , Oils, Volatile/isolation & purification , Sheep , Survival Analysis
10.
Artif Cells Nanomed Biotechnol ; 46(1): 160-168, 2018 Feb.
Article in English | MEDLINE | ID: mdl-28368661

ABSTRACT

This study aim to synthesize silver nanoparticles (AgNPs) using Anthemis atropatana extract and to evaluate their chemical characteristics and antimicrobial and cytotoxic effects. The biosynthesis of AgNPs is verified using UV-visible spectrum which showing maximum absorption in 430 nm wavelength. Transmission electron microscope (TEM) and scanning electron microscope (SEM) results revealed that AgNPs has a spherical shape with an average size of 38.89 nanometres. The crystalline structure of green synthesized AgNPs in optimal conditions was confirmed by XRD analysis. The pattern of XRD peaks related to face-centred cubic (fcc) (111), (200), (220), (311) and (222) observed. Also, FTIR results verified the AgNPs synthesis using plant extract. In biological tests, the MTT results indicate the dose dependence of cytotoxic effects of AgNPs on colon cancer cell lines (HT29). The AgNPs had maximum cytotoxicity on HT29 cancer cell line at 100 µg/ml concentration, which were statistically significant comparing control cells (p < .001). Moreover, real time PCR and flow cytometry results confirmed the apoptotic effects of AgNPs. According to the results, it seems that the green synthesis of AgNPs is an eco-friendly and cost effective approach. This research provides insight into the development of new anticancer and antibacterial agents.


Subject(s)
Anthemis/chemistry , Metal Nanoparticles/chemistry , Plant Extracts/chemistry , Silver/chemistry , Silver/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Apoptosis/drug effects , Bacteria/drug effects , Chemistry Techniques, Synthetic , Green Chemistry Technology , HT29 Cells , Humans , Plant Leaves/chemistry
11.
IET Nanobiotechnol ; 11(5): 538-545, 2017 Aug.
Article in English | MEDLINE | ID: mdl-28745286

ABSTRACT

This study demonstrates a clean, non-toxic and environment friendly synthetic strategy for the preparation of the Natrolite zeolite/Cu nanoparticles (NPs) using Natrolite zeolite as a natural support and Anthemis xylopoda flowers aqueous extract as a reducing and stabilising agent for the synthesis of Cu NPs. Cu NPs with 20 nm diameter were immobilised homogeneously on the surface of Natrolite zeolite. The synthesised Natrolite zeolite/Cu NPs was used as an environmentally benign catalyst for the reduction of 4-nitrophenol, congo red and methylene blue in aqueous media at an ambient temperature. It has been found that the catalyst can be reused several times without any decrease in activity.


Subject(s)
Congo Red/chemistry , Copper/chemistry , Green Chemistry Technology , Metal Nanoparticles/chemistry , Methylene Blue/chemistry , Nitrophenols/chemistry , Silicates/chemistry , Zeolites/chemistry , Anthemis/chemistry , Catalysis , Flowers/chemistry , Microscopy, Electron, Scanning , Microscopy, Electron, Transmission , Oxidation-Reduction , Plant Extracts/chemistry , Spectrometry, X-Ray Emission , Thermogravimetry
12.
Nat Prod Res ; 31(23): 2759-2767, 2017 Dec.
Article in English | MEDLINE | ID: mdl-28278620

ABSTRACT

The chemical composition of the essential oils isolated from the aerial parts of Anthemis arvensis L. subsp. arvensis, Anthemis cretica subsp. messanensis (Brullo) Giardina & Raimondo and from flowers and leaves of Anthemis cretica subsp. columnae (Ten.) Frezén were determinated by GC-FID and GC-MS analyses. Torreyol (85.4%) was recognised as the main constituent of the Anthemis arvensis subsp. arvensis essential oil, while in the essential oils of Anthemis cretica subsp. messanensis, collected on the rock and cultivated in Hortus Botanicus Panormitanus, (E)-chrysanthenyl acetate (28.8 and 24.2% resp.), 14-hydroxy-α-humulene (8.1 and 5.3% resp.), santolina triene (8 and 5.8% resp.) and α-pinene (6.7 and 5.4% resp.) prevailed. 18-cineole (13.3 and 12.2% resp.), was the main component of both flower and leaf oils of Anthemis cretica subsp. columnae together with δ-cadinene (9.0 and 8.2% resp.) and (E)-caryophyllene (8.3 and 5.6% resp.).


Subject(s)
Anthemis/chemistry , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Oils, Volatile/chemistry , Bicyclic Monoterpenes , Bridged Bicyclo Compounds/analysis , Cyclohexanols/analysis , Drug Evaluation, Preclinical/methods , Eucalyptol , Flowers/chemistry , Gas Chromatography-Mass Spectrometry , Microbial Sensitivity Tests , Monoterpenes/analysis , Oils, Volatile/analysis , Plant Leaves/chemistry , Polycyclic Sesquiterpenes , Sesquiterpenes/analysis , Sicily
13.
Pharm Biol ; 54(10): 2044-9, 2016 Oct.
Article in English | MEDLINE | ID: mdl-26864903

ABSTRACT

Context The genus Anthemis L. (Asteraceae) comprises about 195 species which are widely used in the pharmaceutical, cosmetic and food industries. Objective Anthemis mirheydari Iranshar, an endemic plant from Iran, was investigated for its cytotoxic properties and chemical constituents. Materials and methods The whole parts of the plant (320 g) were extracted by dichloromethane and methanol for four days, successively. The cytotoxic activity of both dichloromethane and methanol extracts were assayed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric methods against three human cancer cell lines including LS180, MCF-7 and MOLT-4. Different concentrations (10-100 µg/mL) of the plant extracts were tested to obtain IC50 values. The dichloromethane extract of A. mirheydari was subjected to silica gel-column and thin layer chromatography for purification of its chemical constituents and the isolated compounds were further tested against MOLT-4 cells. The structures of the pure compounds were elucidated using different spectral data including nuclear magnetic resonance and electron impact mass spectra. Results The IC50 values of the dichloromethane extract were 30.8 ± 6.7, 25.2 ± 6.5 and 8.6 ± 1.1 µg/mL (means ± standard error) for the above-mentioned cell lines, respectively. Two triterpenoids, taraxasterol (1) and pseudotaraxasterol (2), one sterol, ß-sitosterol (3) and one coumarin, 7-methoxycoumarin (4) were isolated from the extract. The IC50 of the mixture of compounds 1 and 2 as well as compounds 3 and 4 were higher (>100 µM) than that reported for the dichloromethane extract against MOLT-4 cells. Conclusion The dichloromethane extract was the most active one among the tested material.


Subject(s)
Anthemis/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Neoplasms/drug therapy , Plant Extracts/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Survival/drug effects , Chromatography, Thin Layer , Cisplatin/pharmacology , Dose-Response Relationship, Drug , Humans , Inhibitory Concentration 50 , MCF-7 Cells , Magnetic Resonance Spectroscopy , Mass Spectrometry , Methanol/chemistry , Methylene Chloride/chemistry , Neoplasms/pathology , Phytotherapy , Plant Extracts/isolation & purification , Plants, Medicinal , Solvents/chemistry
14.
BMC Complement Altern Med ; 14: 297, 2014 Aug 12.
Article in English | MEDLINE | ID: mdl-25112895

ABSTRACT

BACKGROUND: Anthemis palestina (Asteraceae) extends across the Mediterranean region, southwest Asia and eastern Africa. Although traditionally used for several applications, in vitro investigation of biological functions associated with Anthemis palestina essential oil had never been reported. METHODS: The air-dried flowers of Anthemis palestina were subjected to hydrodistillation to yield the oil. The antioxidant activity of the hydrodistilled oil was characterized using various in vitro model systems such as DPPH, ferric-reducing antioxidant power and hydroxyl radical scavenging activity. Antibacterial activity was tested against six bacterial species, representing both Gram positive and Gram negative bacteria. Antifungal activity was evaluated using three Candida species. The minimum inhibitory concentration (MIC) for each examined microorganism was determined using the microdilution method. The oil's antiproliferative effects against eight human cancer cell lines were also studied and the lethal doses that resulted in 50% reduction of cell viability (LD50) were determined. RESULTS: The results indicate that the essential oil of Anthemis palestina exhibited substantial antioxidant activities as demonstrated with DPPH, ferric reducing antioxidant power, and hydroxyl radical scavenging activity. In addition, a broad-spectrum antibacterial activity of the oil was revealed with better susceptibility of Gram positive bacteria towards the oil. The MIC values ranged between 6-75 µg/ml. Besides, the oil demonstrated a moderate inhibitory effect on the three Candida species examined; with MIC values ranging between 48-95 µg/ml. Potent cytotoxic activities, especially against HeLa cell line; with LD50 of 32 µg/ml, BJAB cell line; with LD50 of 57 µg/ml, and Caco-2 cell line; with LD50 of 61 µg/ml, were observed. CONCLUSION: The results obtained indicate high potential of Anthemis palestina essential oil as bioactive oil, for nutraceutical and medical applications, possessing antioxidant, antimicrobial and antiproliferative activities.


Subject(s)
Anthemis/chemistry , Anti-Infective Agents/pharmacology , Antineoplastic Agents/pharmacology , Antioxidants/pharmacology , Oils, Volatile/pharmacology , Plant Extracts/pharmacology , Anti-Infective Agents/chemistry , Antineoplastic Agents/chemistry , Antioxidants/chemistry , Bacteria/drug effects , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Microbial Sensitivity Tests , Oils, Volatile/chemistry , Plant Extracts/chemistry
15.
Mol Biol Rep ; 41(3): 1703-11, 2014 Mar.
Article in English | MEDLINE | ID: mdl-24413991

ABSTRACT

Extracts of Anthemis hyalina (Ah), Nigella sativa (Ns) and peels of Citrus sinensis (Cs) have been used as folk medicine to fight antimicrobial diseases. To evaluate the effect of extracts of Ah, Ns and Cs on the replication of coronavirus (CoV) and on the expression of TRP genes during coronavirus infection, HeLa-CEACAM1a (HeLa-epithelial carcinoembryonic antigen-related cell adhesion molecule 1a) cells were inoculated with MHV-A59 (mouse hepatitis virus-A59) at moi of 30. 1/50 dilution of the extracts was found to be the safe active dose. ELISA kits were used to detect the human IL-8 levels. Total RNA was isolated from the infected cells and cDNA was synthesized. Fluidigm Dynamic Array nanofluidic chip 96.96 was used to analyze the mRNA expression of 21 TRP genes and two control genes. Data was analyzed using the BioMark digital array software. Determinations of relative gene expression values were carried out by using the 2(-∆∆Ct) method (normalized threshold cycle (Ct) value of sample minus normalized Ct value of control). TCID50/ml (tissue culture infectious dose that will produce cytopathic effect in 50% of the inoculated tissue culture cells) was found for treatments to determine the viral loads. The inflammatory cytokine IL-8 level was found to increase for both 24 and 48 h time points following Ns extract treatment. TRPA1, TRPC4, TRPM6, TRPM7, TRPM8 and TRPV4 were the genes which expression levels changed significantly after Ah, Ns or Cs extract treatments. The virus load decreased when any of the Ah, Ns or Cs extracts was added to the CoV infected cells with Ah extract treatment leading to undetectable virus load for both 6 and 8 hpi. Although all the extract treatments had an effect on IL-8 secretion, TRP gene expression and virus load after CoV infection, it was the Ah extract treatment that showed the biggest difference in virus load. Therefore Ah extract is the best candidate in our hands that contains potential treatment molecule(s).


Subject(s)
Coronavirus Infections/drug therapy , Coronavirus/drug effects , Plant Extracts/administration & dosage , Transient Receptor Potential Channels/biosynthesis , Animals , Anthemis/chemistry , Citrus sinensis/chemistry , Coronavirus/growth & development , Coronavirus Infections/pathology , Coronavirus Infections/virology , Gene Expression Regulation, Viral/drug effects , HeLa Cells , Humans , Interleukin-8/genetics , Medicine, Traditional , Mice , Nigella sativa/chemistry , Plant Extracts/chemistry , Virus Replication/drug effects
16.
Food Chem Toxicol ; 62: 554-65, 2013 Dec.
Article in English | MEDLINE | ID: mdl-24055768

ABSTRACT

To determine the exact structure of previously tentatively identified minor essential-oil constituents of a Chamomile species (Antemis segetalis Ten. (Asteraceae)), we have synthesized a small combinatorial library of 54 regioisomeric allylmethoxyphenyl pentanoates and 2-pentenoates (49 completely new compounds). GC-MS in combination with 1D- and 2D-NMR analyses of the library compounds provided unambiguous data that led to a straightforward identification of the mentioned A. segetalis constituents as eugenyl angelate, 2-methylbutanoate and 3-methylbutanoate (0.21, 0.22, and 0.13 mg/100 g of fresh plant material, respectively). To assess the safety and potential beneficial pharmacological uses of these naturally occurring esters and several other library compounds (these were tested to provide relevant data for a SAR (structure-activity relationship) analysis), we have studied the effect of these compounds in several models of toxicity (acute toxicity against Artemia salina, cytotoxicity against two cell lines (fibroblast and melanoma)), as well as their acetylcholinesterase inhibitory and antibacterial activities. Anthemis segetalis constituents showed low to moderate activity in all tests. The obtained results suggest that the intake of these compounds in naturally available amounts, on their own, would probably not represent a risk to human health but the possible adverse interactions with the plant matrix should not be neglected.


Subject(s)
Anthemis/chemistry , Drug Evaluation, Preclinical/methods , Esters/toxicity , Oils, Volatile/chemistry , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Artemia/drug effects , Cell Line, Tumor/drug effects , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/pharmacology , Combinatorial Chemistry Techniques/methods , Esters/chemistry , Esters/pharmacokinetics , Eugenol/analogs & derivatives , Eugenol/chemistry , Eugenol/toxicity , Gas Chromatography-Mass Spectrometry , Humans , Magnetic Resonance Spectroscopy , Melanoma/drug therapy , Oils, Volatile/analysis , Oils, Volatile/toxicity , Structure-Activity Relationship , Toxicity Tests, Acute
17.
Nat Prod Commun ; 7(10): 1379-82, 2012 Oct.
Article in English | MEDLINE | ID: mdl-23157016

ABSTRACT

In the present study the chemical composition of the essential oils from aerial parts and roots of Anthemis mixta L. and A. tomentosa L. was evaluated by GC and GC-MS, and their antibacterial activity tested against ten bacterial species. Hexadecanoic acid (15.2%) was recognized as the main constituent ofA. mixta, together with tau-cadinol (6.7%), while in both aerial parts and roots of A. tomentosa nonacosane (21.9% and 20.7%), heptacosane (8.1% and 6.0%), hexadecanoic acid (8.1% and 27.1%) and hexahydrofarnesylacetone (6.8% and 5.5%) prevailed. The oils from aerial parts of both species showed a good activity against Gram-positive bacteria. These results suggest that the plants could be potentially used in food manufacture and cosmetology as preservative agents or in medicine as new antibiotics.


Subject(s)
Anthemis/chemistry , Anti-Bacterial Agents/pharmacology , Oils, Volatile/analysis , Oils, Volatile/pharmacology , Bacteria/drug effects , Food Preservatives , Gas Chromatography-Mass Spectrometry , Gram-Positive Bacteria/drug effects , Microbial Sensitivity Tests , Oils, Volatile/isolation & purification , Palmitic Acid/chemistry , Palmitic Acid/pharmacology , Plant Leaves/chemistry
18.
Nat Prod Res ; 26(17): 1594-601, 2012.
Article in English | MEDLINE | ID: mdl-22124231

ABSTRACT

Anthemis wiedemanniana is known in folk medicine for the treatment of microbial infections, cancer and also urinary and pulmonary problems. In this study, the chemical composition of the essential oil from A. wiedemanniana was evaluated and its antibacterial activity was tested against 10 bacterial strains. The oil was also tested for its potentiality to inhibit nitric oxide production in RAW 264.7 macrophages and for its cytotoxicity against four human cancer cell lines. A. wiedemanniana oil, rich of oxygenated monoterpenes (25.4%), showed a good antibacterial activity against Gram-positive bacteria and a good activity against the two Gram-negative bacteria, Escherichia coli and Proteus vulgaris. Besides that, it exhibited a high inhibitory effect on the LPS-induced nitrite production and a strong cytotoxic activity, especially against amelanotic melanoma (C32) and large lung cell carcinoma (COR-L23) cell lines.


Subject(s)
Anthemis/chemistry , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Nitrites/metabolism , Oils, Volatile/chemistry , Oils, Volatile/pharmacology , Animals , Anti-Bacterial Agents/adverse effects , Anti-Bacterial Agents/chemistry , Antineoplastic Agents, Phytogenic/adverse effects , Antineoplastic Agents, Phytogenic/chemistry , Cell Line , Cell Line, Tumor , Cell Proliferation/drug effects , Escherichia coli/drug effects , Gram-Positive Bacteria/drug effects , Humans , Lipopolysaccharides/pharmacology , Mice , Microbial Sensitivity Tests , Monoterpenes/chemistry , Oils, Volatile/adverse effects , Proteus/drug effects
19.
Chem Biodivers ; 7(5): 1231-44, 2010 May.
Article in English | MEDLINE | ID: mdl-20491079

ABSTRACT

The essential-oil composition of six Anthemis taxa from several populations in Serbia and Montenegro, Anthemis triumfetti (L.) DC., A. tinctoria L., A. austriaca Jacq., A. ruthenica Bieb., A. cotula L., and A. cretica ssp. carpatica (Willd.) Grierson were analyzed by GC and GC/MS. The main constituents have been identified as follows: camphor (13.8-15.4%), alpha-pinene (5.2-9.3%), beta-pinene (4.9-7.8%), and (E)-caryophyllene (7.3-9.8%) in three populations, and cis-chrysanthenol (27.0%) and 1,8-cineole (8.4%) in one population of A. triumfetti; 1,8-cineole (9.0-25.8%) in the oils of five populations, and borneol (16.0%) and spatulenol (16.0%) in the oil of one population of A. tinctoria; cis-chrysanthenyl acetate (17.5-22.0%), beta-pinene (8.6-13.2%), and 1,8-cineole (7.2-10.4%) in the oils of A. austriaca; germacrene D (8.3-11.3%) and terpinen-4-ol (6.3-7.3%) in A. ruthenica oils; beta-cedrene (10.3-19.0%), (E)-beta-farnesene (7.8-13.5%), and germacrene D (5.2-9.1%) in the oils of A. cotula; cis-thujone (39.0%), trans-thujone (13.5%), and yomogi alcohol (7.1%) in the oil of A. cretica ssp. carpatica. The essential oil of A. austriaca was studied for the first time. A cluster analysis based on the relative percentages of all components of the essential oils was used to determine the distances between taxa and populations.


Subject(s)
Anthemis/chemistry , Oils, Volatile/chemistry , Plant Oils/chemistry , Anthemis/classification , Cluster Analysis , Gas Chromatography-Mass Spectrometry , Montenegro , Serbia
20.
J Smooth Muscle Res ; 46(1): 65-75, 2010.
Article in English | MEDLINE | ID: mdl-20383035

ABSTRACT

The aim of the present study is to determine the chemical composition of the essential oil extracted from the flowers of Anthemis mauritiana Maire & Sennen (EOAM) and to investigate its antispasmodic effects on intestinal smooth muscle. The phytochemical composition was revealed by gas chromatography-mass spectrometer. Eighteen compounds were identified representing 90.56% of the oil. The major constituents were described as alpha-pinene (27.02%), sabinene (15.25%), cedrenol (14.53%) germacrene (9.61%) geraniol formate (6.82%), and caryophylene (5.38%). EOAM (10-100 microg/ml) elicited reversible relaxation of spontaneous contractions of isolated rabbit jejunal smooth muscle preparations, and similarly inhibited contractions induced by high-potassium solution ([K(+)](o) = 76 mM) and carbachol (10(-6) M) with IC(50) values of 14.98 and 27.29 microg/ml, respectively. Furthermore, EOAM exhibited an inhibitory effect on the dose-response curves induced by carbachol and CaCl(2) on rat jejunum preparations. These results clearly demonstrated the antispasmodic effect of EOAM which was strongly suggested to be mainly due to an inhibitory effect on Ca(2+) influx through the membrane of jejunal smooth muscle cells.


Subject(s)
Anthemis/chemistry , Jejunum/drug effects , Muscle Contraction/drug effects , Muscle, Smooth/drug effects , Oils, Volatile/pharmacology , Parasympatholytics/pharmacology , Animals , Flowers/chemistry , In Vitro Techniques , Oils, Volatile/chemistry , Parasympatholytics/analysis , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Oils/chemistry , Plant Oils/pharmacology , Rabbits , Rats , Rats, Wistar
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