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Phytochemical investigation of the whole plant of Filago vulgaris Lam. (Asteraceae) resulted in the isolation and characterization of seven compounds, including a rare methoxylated flavonol (araneol), tetrahydrofurofuranolignans (pinoresinol and syringaresinol), p-hydroxybenzaldehyde, vanillin, vanillic acid and scopoletin. The structures of the co...
Persicaria maculosa (Polygonaceae) has been used as edible and as medicinal plant since ancient times. As a result of multistep chromatographic purifications, chalcones [2′-hydroxy-3′,4′,6′-trimethoxychalcone (1), pashanone (2), pinostrobin chalcone (3)], flavanones [6-hydroxy-5,7-dimethoxyflavanone (4), pinostrobin (5), onysilin (6), 5-hydroxy-7,8...
Projected regional climate change modifies the circulation and the radiation effects, which influence urban air pollution (UAP) and urban heat island (UHI) properties. Besides the primary effects of climate change on these urban stressors, the human health effects are also reviewed. The change is derived from the average 4.5 W m⁻² radiation increme...
Physalin D was isolated from the methanol extract of Physalis alkekengi L. fruits by combination of different chromatographic methods (CPC, TLC, HPLC). The structure was elucidated based on 1H and 13C NMR spectral analysis with the aid of 2D-correlation spectroscopy (1H, 1H-COSY, HSQC and HMBC) and comparison with literature data. The quantity of p...
The present study aimed at the phytochemical and pharmacological investigation of Sideritis montana L. (Lamiaceae). Two new abietane diterpenes [sideritins A (1) and B (2)] were isolated from the methanol extract of the plant. Six known compounds [pomiferin E (3), 9α,13α-epi-dioxyabiet-8(14)-en-18-ol (4), paulownin (5), 6-methoxysakuranetin (6), 3-...
Background:
Transient Receptor Potential Vanilloid 1 (TRPV1) confers noxious heat and inflammatory pain signals in the peripheral nervous system. Clinical trial of resiniferatoxin from Euphorbia species is successfully aimed at TRPV1 in cancer pain management and heading toward new selective painkiller status that further validates this target for...
In the course of our pharmacological screening of Polygonaceae species occurring in the Carpathian Basin the extracts prepared from the roots of Rumex thyrsiflorus showed promising antiproliferative, xanthine oxidase inhibitory and antibacterial activities. The present work deals with the isolation of compounds from the root of the plant. After mul...
Background:
Centaurea virgata Lam. is a species widely used in the traditional medicine in Turkey for the treatment of diabetes, allergy and gastric ulcers. The rationale of its use in the therapy has not been studied previously, therefore the present work aimed at the chemical-pharmacological evaluation of the plant.
Objective:
The xanthine oxi...
The Úrkút manganese deposit, one of the World's largest, is located in the central part of the Transdanubian Range, western Hungary. The deposit is interbedded with Mesozoic limemarlstone. The Fe-Mn-oxide indications of a feeder and mound zone embedded in limemarlstone at the footwall of the Mn-carbonate ore deposit were studied using 45 samples (Ú...
Human platelets contain conventional (α and β) and novel isoforms of PKC (δ and θ), and PKC activation can result in platelet aggregation and secretion reaction that are important for thrombus formation. Several tumor-promoting Euphorbiaceae diterpenes are known to act as direct activators of PKC, but many types of such diterpenes have not been stu...
GIRK channels are activated by a large number of G protein-coupled receptors and regulate the electrical activity of neurons, cardiac atrial myocytes, and β-pancreatic cells. Abnormalities in GIRK channel function have been implicated in the pathophysiology of neuropathic pain, drug addiction, and cardiac arrhythmias. In the heart, GIRK channels ar...
Two novel, (I) and (II), and one known jatrophane diterpene are isolated from the title species and evaluated for their multidrug resistance reversing activity.
The present study focused on the investigation of the inhibition of cyclooxygenase-2 and nuclear factor kappa B1 gene expression, nitric oxide production, leukotriene biosynthesis (5-lipoxygenase), and cyclooxygenase-1 and cyclooxygenase-2 enzymes of Onopordum acanthium, and the isolation and identification of its active compounds. From the chlorof...
Phytochemical investigation of the MeOH extract obtained from the aerial parts of the annual weed Euphorbia exigua L. resulted in the isolation of two novel (1, 2) and one known (3) jatrophane diterpenes. Their structures were established by extensive 1D- and 2D-NMR spectroscopy and HR-ESI-MS. The isolated compounds were evaluated for multidrug res...
Two new arylbenzofuran-type neolignans, 1″-dehydroegonol 3″-methyl ether (1) and egonol 3″-methyl ether (2), and four known lignan derivatives, namely, helioxanthin (3), (7E)-7,8-dehydroheliobuphthalmin (4), heliobuphthalmin (5), and 7-acetoxyhinokinin (6), were isolated from a chloroform-soluble partition of the methanol extract of the fresh roots...
There is heightened interest in the field of stroke recovery as there is need for agents that would prevent the debilitating effects of the disorder, thereby tremendously reducing the societal and economic costs associated with it. In this study, the isolation of two flavonoids - quercetin-3-O-galactoside (1) and quercetin-3-O-arabinoside (2) - fro...
The identity of the predominating tin(II)-hydroxide complex formed in hyper-alkaline aqueous solution (0.2 CNaOH 12 mol⋅dm-3) has been determined by potentiomet¬ric titrations, Raman, Mössbauer and XANES spectroscopy, supplemented by quantum chemical calculations. Thermodyna¬mic studies using a H2/Pt electrode up to free hydroxide concentration...
The extract of Artemisia asiatica herb with antiproliferative activity against four human tumor cell lines (A2780, A431, HeLa, and MCF7) was analyzed by the MTT assay, and bioassay-directed fractionation was carried out in order to identify the compounds responsible for the cytotoxic activity. Guaianolide (1-4), seco-guianolide (5), germacranolide...
Bipolaris oryzae is a phytopathogenic fungus causing a brown spot disease in rice, and produces substance that strongly perturbs motility and membrane integrities of boar spermatozoa. The substance was isolated from the liquid culture of the fungal strain using extraction and a multi-step semi-preparative HPLC procedures. Based on the results of ma...
The content of anthocyanin derivatives, antioxidant activity, and phenolic content were determined in black elderberry (Sambucus nigra L.), sweet cherry (Prunus avium L.), blackberry (Rubus fruticosus L.), black currant (Ribes nigrum L.), and blackthorn (Prunus Spinosa L.). The extraction efficiency was examined of several solvents including hot wa...
The discovery of the interaction of plant-derived N-alkylamides (NAAs) and the mammalian endocannabinoid system (ECS) and the existence of a plant endogenous Nacylethanolamine
signaling system have led to the re-evaluation of this group of compounds. Herein, the isolation of seven
NAAs and the assessment of their effects on major protein targets in...
The discovery of the interaction of plant-derived N-alkylamides (NAAs) and the mammalian endocannabinoid system (ECS) and the existence of a plant endogenous N-acylethanolamine signaling system have led to the re-evaluation of this group of compounds. Herein, the isolation of seven NAAs and the assessment of their effects on major protein targets i...
1
Bioassay-guided fractionation of a CHCl3 extract of the leaves of Xanthium italicum Moretti led to the isolation of four xanthanolides: xanthatin (), 4-epixanthanol ( 2 ), 4-epiisoxanthanol ( 3 ), and 2-hydroxyxanthinosin ( 4 ). Their structures were determined by means of 1D and 2D NMR spectroscopy, including ¹ H- ¹ H COSY, NOESY, HSQC and HMBC...
Extensive chromatographic purification of the alkaloid fraction of Aconitum vulparia Rchb. led to the isolation of a new norditerpene alkaloid, vulparine (1), besides the known compounds septentriodine (2), finetiadine (3), anthranoyllycoctonine (4), N-methyl-N-deethyllycoctonine (5) and delectinine (6). The structure of the new compound was determ...
The MeOH extract of the aerial parts of Artemisia asiatica significantly inhibited the xanthine oxidase (XO) induced uric acid production. Flavonoids were isolated from the active extract and identified as eupatilin (1), hispidulin (2), jaceosidin (3), cirsilineol (4), 5,7,4',5'-tetrahydroxy-6,3'-dimethoxyflavone (5), 6- methoxytricin (6) and chrys...
Onopordum acanthium has been considered in traditional medicine to be effective against different cancers. The chloroform extracts of the root, which displayed antiproliferative effect against human tumor cell lines, was subjected to bioactivity-guided multistep chromatographic separation. This experiment resulted in the isolation of the sesquiterp...
Five new sesquiterpenes, neurolobatin A (1), neurolobatin B (2), 5β-hydroxy-8β-isovaleroyloxy-9α-hydroxycalyculatolide (3), 3-epi-desacetylisovaleroylheliangine (4), and 3β-acetoxy-8β-isovaleroyloxyreynosin (5), were isolated from the aerial parts of Neurolaena lobata . The structures were established by means of a combined spectroscopic data analy...
A new aconitane alkaloid, 1-O-demethylswatinine (1), was isolated from the root of Aconitum moldavicum together with the known compounds cammaconine (2), columbianine (3), swatinine (4), gigactonine (5), delcosine (6), lycoctonine (7), and ajacine (8). The structures were established by means of HRESIMS, 1D and 2D NMR spectroscopy, including 1H-1H...
The G protein-activated inwardly rectifying K+ channel-modulatory activities of Polygonum persicaria extracts were investigated by using an automated patch-clamp method, with the aim of identifying natural sources of promising ion channel-blocking compounds. The chloroform extract of the whole plant at 0.1 mg/mL exhibited high G protein-activated i...
Reliable and sensitive chromatographic methods have been developed and applied to determine derivatized di- and tripeptides: aspartame, carnosine, glutathione, alanyl-glutamine, and γ-glutamyl-cysteine. Photodiode-array detection was used for dansyl-chloride derivatives, while fluorescent detection was carried out for orthophthaldialdehyde derivati...
Polygonum persicaria L. is a morphologically extremely variable perennial plant, naturalized in various parts of the world. Previous phytochemical studies revealed the presence of stilbenes, flavonoids and phenolic acids in the plant. In vitro pharmacological studies demonstrated its antibacterial, antifungal, insecticidal and anti-inflammatory act...
A primary mechanism of resistance to multiple anticancer drugs is the overproduction of permeability glycoprotein (P gp) in plasma membranes of resistant cells. The P gp acts as an energy-dependent efflux pump, reducing the intracellular accumulation of drug molecules. In recent years, considerable attention has been devoted to the development of n...
Diterpenes occurring in plants of the Euphorbiaceae family are of considerable interest as concerns natural product drug discovery programs because of the wide range of potentially valuable biological activities and the broad structural diversity due to the different polycyclic and macrocyclic skeletons and various aliphatic and aromatic ester grou...
Contrary to suggestions in the literature, it has been proven that Al(iii) forms a 1 : 1 complex with gluconate (hereafter Gluc(-)) in strongly alkaline (pH > 12) aqueous solutions. The complex formation was proven via(27)Al and (1)H NMR, freezing-point depression, polarimetric measurements as well as potentiometric and conductometric titrations. T...
Diterpene alkaloids neoline (1), napelline (2), isotalatizidine (3), karakoline (4), senbusine A (5), senbusine C (6), aconitine (7) and taurenine (8) were identified from Aconitum napellus L. subsp. firmum, four (2-4, 6) of which are reported for the first time from this plant. The structures were determined by means of LC-MS, 1D and 2D NMR spectr...
Following a preliminary exploration of the conformational space by the PM3 and HF/6-31 G*ab initio methods the conformational characteristics of the scarcely available Z isomer of an α-pyridyl-substituted cinnamic acid dimer [Z-2(3′-pyridyl)-3-phenylpropanoic acid] was studied by NMR spectroscopy (NOESY measurements) in DMSO(d6), methanol(d4) and c...
Rectal drug delivery is currently at the focus of attention. Surfactants promote drug release from the suppository bases and enhance the formulation properties. The aim of our work was to develop a sample preparation method for HPLC analysis for a suppository base containing 95% hard fat, 2.5% Tween 20 and 2.5% Tween 60. A conventional sample prepa...
The equilibria and structure of complexes formed between the Ca(2+) ion and the heptagluconate (Hglu(-)) ion in both neutral and alkaline solutions have been studied. In alkaline solutions an uncharged, multinuclear complex is formed with the composition of Ca3Hglu2(OH)4 (or [Ca3Hglu2H-4](0)) with an unexpectedly high stability constant (lg β32-4 =...
The change of ochratoxin A (OTA) content during must fermentation processes in different white, rose and red must samples was investigated by the use of selected yeast strains of Saccharomyces cerevisiae as starter cultures. Levels of OTA in wine must and lees were determined by high-performance liquid chromatography (HPLC) combined with diode arra...
Different types of oligosaccharides have been investigated in order to reveal their thermal degradation characteristics. Relevance of this work is confirmed by the wide-spread use of these carbohydrates (fructo-oligosaccharides, cyclodextrins, raffinose and resistant starch) in the food industry, especially in the bakery industry, which implies hig...
Interaction of amino acids and carbohydrates at elevated temperatures leads to the formation of versatile compounds whose chemical feature has just been partly revealed so far.Major objective of this study was to characterise the composition of reaction mixtures forming as a result of various types of Maillard-reaction. Transformation products were...
Four novel (1–4) and one known (5) diterpene polyesters with the jatrophane skeleton were isolated from a methanol extract of the aerial parts of the East Asian weed Euphorbia mongolica Prokh. The isolated compounds were characterized structurally and evaluated for multidrug resistance (MDR) reversing activity on human MDR gene-transfected L5178 mo...
Bioassay-guided fractionation of the chloroform extract of Centaurea jacea L. afforded the isolation of cirsiliol, apigenin, hispidulin, eupatorin, isokaempferide, axillarin, centaureidin, 6-methoxykaempferol 3-methyl ether, trachelogenin, cnicin, 4'-acetylcnicin and three aliphatic glucose diesters, including the new natural product 1β-isobutanoyl...
Bryophyllum pinnatum (Lank.) Oken (Crassulaceae) is a perennial succulent herb widely used in traditional medicine to treat many ailments. Its wide range of uses in folk medicine justifies its being called "life plant" or "resurrection plant", prompting researchers' interest. We describe here the isolation and structure elucidation of antimicrobial...
Two new and one known cyclomyrsinane-type diterpenes (1–3) were isolated from the methanol extract of the whole, undried plant of Euphorbia falcata, native to Hungary. The structures and relative configuration of the compounds were established on the basis of extensive spectroscopic analysis, including HRESIMS and one- and two-dimensional NMR techn...
Two new alkylbenzoquinone derivatives, named as ardisiaquinone J (1) and K (2) were isolated from the MeOH extract of the stem of Ardisia kivuensis Taton (Myrsinaceae), together with the known lupeol and β-sitosterol. Their structures were elucidated on the basis of spectroscopic analysis and comparison with authentic samples. The new compounds exh...
Four new premyrsinane-type diterpenes (1–4) were isolated from the methanol extract of the whole, undried plant of Euphorbia falcata. Their structures were determined by a combination of 1D and 2D NMR (COSY, HMBC, HSQC and NOESY) techniques and mass spectral data as di-, tetra-, penta- and hexaesters of diterpene polyols, esterified with acetic, be...
Phytochemical study of whole, undried plants of Euphorbia esula led to the isolation of six new (1-6) jatrophane diterpene polyesters, named esulatins H-M, together with the known compounds 2α,3β,5α,7β,15β-pentaacetoxy-9α-nicotinoyloxyjatropha-6(17),11-dien-14-one (7), salicinolide (8), and euphosalicin (9). The structures and relative configuratio...
Abstract Relevance of research on prebiotic food components is recently largely enhanced as consumption of health-promoting functional
foodstuffs displays a definite increase. Since there is a direct correlation between oligomer distribution of inulin and its
prebiotic effect, it is of crucial importance to be capable to characterize its actual com...
Ca2+-complexation of d-glucose and d-sorbitol have been investigated with the aid of multinuclear (1H, 13C and 43Ca) NMR spectroscopy and ab initio quantum chemical calculations. Formation constants of the forming 1:1 complexes have been estimated from one-dimensional 13C NMR spectra obtained at constant ionic strength (1M NaCl). Binding sites were...
The cytotoxic activities of the n-hexane, chloroform and aqueous methanolic fractions prepared from the methanolic extract of the leaves of 23 Salvia taxa were studied for their cell growth-inhibitory activity against human cervix adenocarcinoma (HeLa), skin carcinoma (A431) and breast adenocarcinoma (MCF7) cells using the MTT assay. The n-hexane f...
The term lipo-alkaloid is used for C 19 aconitane alkaloids containing one or two long-chain fatty acid residues. Lipo-alkaloids are transesterified derivatives of the most toxic and highly effective diester-type diterpene alkaloids, such as aconitine, hypaconitine, mesaconitine. Lipo-alkaloids are native minor compounds of aconite drugs, but their...
A new norditerpene alkaloid, 10-hydroxy-8- O-methyltalatizamine (1), was isolated from the whole plant of ACONITUM ANTHORA L. besides the known isotalatizidine (2) and hetisinone (3). The structures were determined by means of HR-ESI-MS, 1D and 2D NMR spectroscopy, including ¹H-¹H COSY, NOESY, HSQC and HMBC experiments, resulting in complete ¹H and...
Bioassay-guided fractionation of the N-hexane and CHCl₃ phases of the methanol extract of the roots of Conyza canadensis (L.) Cronquist led to the isolation of two new dihydropyranones named conyzapyranone A (1) and B (2), and the known 4 Z,8 Z-matricaria- γ-lactone (3), 4 E,8 Z-matricaria- γ-lactone (4), 9,12,13-trihydroxy-10(E)-octadecenoic acid...
Phytochemical study of the aerial parts of Euphorbia grandicornis led to the isolation of two new tigliane diterpenes, 16-angeloyloxy-13α-isobutanoyloxy-4β,9α,20-trihydroxytiglia-1,5-diene-3,7-dione (1) and 16-angeloyloxy-13α-isobutanoyloxy-4β,9α,7β-trihydroxytiglia-1,5-dien-3-one (2). The structures and relative configuration of the new compounds...
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
The antiproliferative effects of n-hexane, chloroform and aqueous methanol extracts prepared from the whole plant of Centaurea arenaria M.B. ex Willd. were investigated against cervix adenocarcinoma (HeLa), breast adenocarcinoma (MCF7) and skin epidermoid carcinoma (A431) cells, using the MTT assay. The chloroform extract displayed high tumour cell...
Processed aconite drugs are widely used in Eastern medicine as painkillers and antirheumatic agents. It is known that the traditional processing of aconite drugs increases the amount of lipo-alkaloids. In order to obtain information about the pharmacological potential of these compounds, semisynthesis of 9 aconitine-derived lipo-alkaloids was carri...
Complexation of d-gluconate (Gluc(-)) with Ca(2+) has been investigated via (1)H, (13)C and (43)Ca NMR spectroscopy in aqueous solutions in the presence of high concentration background electrolytes (1MI4M (NaCl) ionic strength). From the ionic strength dependence of its formation constant, the stability constant at 6pH11 and at I-->0M has been der...
Extracts of Echinacea purpurea are extensively used in the therapy of common cold and upper respiratory tract infections as immunomodulators and anti-inflammatory agents. The extracts of the root and herb of E. purpurea have a complex chemical composition, including alkamides, caffeic acid conjugates, and polysaccharides. Alkamides, the main lipoph...
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
A high performance liquid chromatographic (HPLC) method for the simultaneous determination of seven biogenic amines (BAs) [histamine (HIS), tryptamine (TR), tyramine (TY), putrescine (PUT), cadaverine (CAD), spermidine (SPD), and spermine (SPM)] in food products has been developed. The technique was applied to determine the BA content of wine and b...
A new eudesmanolide sesquiterpene, sivasinolide 6-O-angelate (1), was isolated from the aerial parts of Anthemis ruthenica together with the known compounds chrysanin (2), tanacin (3), 3 beta-hydroxycostunolide (4), centauridin (5), and centaureidin (6). The compounds were obtained by means of bioactivity-guided fractionation from the CHCl (3) extr...
Euphorbia is the largest genus in the family Euphorbiaceae, comprising about 2000 species. Hitherto many secondary metabolites with specific types of diterpene skeletons were isolated from these plants. Euphorbia diterpenes possess a number of interesting biological activities, such as antiproliferative, antiviral, multidrug resistance (MDR) revers...
Processed aconite drugs are widely used in Eastern medicine, principally as painkillers and antirheumatic agents. Active constituents of these drugs are aconitine-type diterpene alkaloids, which exhibit a broad spectrum of pharmacological activities, including antinociceptive and anti-inflammatory effects [1,2]. Unfortunately, most of the aconitine...
The antiproliferative activities of n-hexane, chloroform, aqueous-methanol and aqueous extracts of the aerial parts of the Achillea millefolium aggregate on three human tumour cell lines were investigated by means of MTT assays. The chloroform-soluble extract exerted high tumour cell proliferation inhibitory activities on HeLa and MCF-7 cells, and...
From the roots of Aconitum toxicum, acotoxicine (1), a new bisnorditerpene alkaloid, was isolated together with the structurally related delavaconitine, delavaconine, dolaconine, aconosine, and the norditerpene alkaloid neolinine. The structure of compound 1 was elucidated by spectroscopic data interpretation. Further, eight lipo-alkaloids (2-9) we...
Benzene and substituted derivatives (toluene, ortho-xylene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, anisole), when applied in large excess, react with 1,4 diols (pentan-1,4-diol,
hexan-2,5-diol, and 2,5-dimethylhexan-2,5-diol) or an oxolane (2,2,5,5-tetramethyltetrahydrofuran) in the presence of the
Br�nsted superacid trifluoromethanesulfon...
Extensive chromatographic purification of the alkaloid fraction of Aconitum vulparia Rchb. led to the isolation of a new norditerpene alkaloid, vulparine (1), besides the known compounds septentriodine (2), finetiadine (3), anthranoyllycoctonine (4), Af-methyl-N-deethyllycoctonine (5) and delectinine (6). The structure of the new compound was deter...
Acotoxinine (1), a new norditerpene alkaloid, was isolated from the roots of Aconitum toxicumRchb., together with the structurally related C19 diterpene alkaloids neoline (2) and aconitine (3) and C20 diterpene alkaloids songorine (4) and songoramine (5). The structures were elucidated by HR-MS and advanced NMR methods, including 1H-NMR, JMOD, 1H,1...
Four N-substituted and two N,N-disubstituted acetamides of related structures were studied with NMR spectroscopic and/or computational methods (force field, semiempirical and Hartree-Fock ab initio codes). The rotamers and the conformers were mapped. A possible extension of the amide conjugation and the existance/non-existance of the rotamers were...