Salinity-induced osmotic, ionic and oxidative stress responses were investigated on Asakaze/Manas wheat/barley addition lines 7H, 7HL and 7HS, together with their barley (salt-tolerant) and wheat ...(relatively salt-sensitive) parents. Growth, photosynthetic activity, chlorophyll degradation, proline, glycine betaine accumulation, sugar metabolism, Na+ and K+ uptake and transport processes and the role of polyamines and antioxidants were studied in young plants grown in hydroponic culture with or without salt treatment. Changes in plant growth and photosynthetic activity of plants demonstrated that the salt tolerance of the addition lines 7H and 7HL was similar to that of barley parent cv. Manas, while the sensitivity of the addition line 7HS was similar to that of the wheat parent cv. Asakaze. The Na accumulation in the roots and shoots did not differ between the addition lines and wheat parent. The activation of various genes related to Na uptake and transport was not correlated with the salt tolerance of the genotypes. These results indicated that the direct regulation of Na transport processes is not the main reason for the salt tolerance of these genotypes. Salt treatment induced a complex metabolic rearrangement in both the roots and shoots of all the genotypes. Elevated proline accumulation in the roots and enhanced sugar metabolism in the shoots were found to be important for salt tolerance in the 7H and 7HL addition lines and in barley cv. Manas. In wheat cv. Asakaze and the 7HS addition line the polyamine metabolism was activated. It seems that osmotic adjustment is a more important process in the improvement of salt tolerance in 7H addition lines than the direct regulation of Na transport processes or antioxidant defence.
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 drug discovery efforts. Evodia species, used in traditional medicine for hundreds of years, are a recognised source of different TRPV1 agonists, but no antagonist has yet been reported.
In a search for painkiller leads, we noted for the first time a TRPV1 antagonist activity in the fresh fruits of Tetradium daniellii (Benn.) T.G. Hartley (syn. Evodia hupehensis Dode).
Through a combination of extraction and purification methods with functional TRPV1-specific Ca2+ uptake assays (bioactivity-guided fractionation/isolation/purification); we isolated a new painkiller candidate that is a distant structural homologue of capsiate exovanilloids and endovanilloids such as anandamide, but a putative competitive inhibitor of the TRPV1. Four additional inactive compounds (N-isobutyl-4,5-epoxy-2E-decadienamide, geranylpsoralen, 8-(7′,8′-epoxygeranyloxy)psoralen, and xanthotoxol) were also co-purified with pellitorine. Their structures were established by extensive 1D- and 2D-NMR spectroscopic analysis.
1H- and 13C NMR determination of the chemical structure revealed it to be pellitorine, (2E,4E)-N-(2-methylpropyl)deca-2,4-dienamide, which can compete structurally with algesics released in inflammation. In contrast to previous isolates from Evodia species, pellitorine blocked capsaicin-evoked Ca2+ uptake with an IC50 of 154 µg/ml (0.69 mM/l). N-Isobutyl-4,5-epoxy-2E-decadienamide and geranylpsoralen, 8-(7′,8′-epoxygeranyloxy)psoralen, and xanthotoxol did not affect the TRPV1.
This is the first evidence that pellitorine, an aliphatic alkylamide analogue of capsaicin, can serve as an antagonist of the TRPV1 and may inhibit exovanilloid-induced pain.
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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 mass spectrometric and 2D NMR techniques, the bioactive molecule was identified as ophiobolin A, a previously described sesterterpene-type compound. The purified ophiobolin A exhibited strong motility inhibition and viability reduction on boar spermatozoa. Furthermore, it damaged the sperm mitochondria significantly at sublethal concentration by the dissipation of transmembrane potential in the mitochondrial inner membrane, while the plasma membrane permeability barrier remained intact. The study demonstrated that the cytotoxicity of ophiobolin A toward somatic cell lines is higher by 1-2 orders of magnitude compared to other mitochondriotoxic mycotoxins, and towards sperm cells unique by replacing the progressive motility by shivering tail beating at low exposure concentration.
The identity of the predominating tin(ii)-hydroxide complex formed in hyper-alkaline aqueous solutions (0.2 ≤CNaOH≤ 12 mol dm(-3)) is determined by potentiometric titrations, Raman, Mössbauer and ...XANES spectroscopy, supplemented by quantum chemical calculations. Thermodynamic studies using a H2/Pt electrode up to free hydroxide concentrations of 1 mol dm(-3) showed the presence of a single monomeric complex with a tin(II) : hydroxide ratio of 1 : 3. This observation together with Raman and Mössbauer spectroscopic measurements supplemented by quantum mechanical calculations proved that the predominating complex is Sn(OH)3(-), and that the presence of the other possible complex, SnO(OH)(-), could not be proven with either experiments or simulations. The structure of the trihydroxidostannate(II) complex, Sn(OH)3(-), was determined by EXAFS and was found to be independent of the applied hydroxide and tin(II) concentrations. The mean Sn-O bond distance is short, 2.078 Å, and in very good agreement with the only structure reported in the solid state. It is also shown that at pH values above 13 the speciation of the predominant trihydroxidostannate(II) complex is not affected by the presence of high concentrations of chloride ions.
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 derived (logK(1,1)(0)=1.8+/-0.1). The protonation constant of Gluc(-) at I=1M (NaCl) ionic strength was also determined and was found to be logK(a)=3.24+/-0.01 ((13)C NMR) and logK(a)=3.23+/-0.01 ((1)H NMR). It was found that (1)H and (13)C NMR chemical shifts upon complexation (both with H(+) and with Ca(2+)) do not vary in an unchanging way with the distance from the Ca(2+)/H(+) binding site. From 2D (1)H-(43)Ca NMR spectra, simultaneous binding of Ca(2+) to the alcoholic OH on C2 and C3 was deduced. Molecular modelling results modulated this picture by revealing structures in which the Gluc(-) behaves as a multidentate ligand. The five-membered chelated initial structure was found to be thermodynamically more stable than that derived from a six-membered chelated initial structure.
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 and/or antioxidant components from the EtOAc extract of B. pinnatum.
The methanol extract displayed both antimicrobial activities with minimum inhibitory concentration (MIC) values ranging from 32 to 512 μg/ml and antioxidant property with an IC50 value of 52.48 μg/ml. Its partition enhanced the antimicrobial activity in EtOAc extract (MIC = 16-128 μg/ml) and reduced it in hexane extract (MIC = 256-1024 μg/ml). In addition, this process reduced the antioxidant activity in EtOAc and hexane extracts with IC50 values of 78.11 and 90.04 μg/ml respectively. Fractionation of EtOAc extract gave seven kaempferol rhamnosides, including; kaempferitrin (1), kaempferol 3-O-α-L-(2-acetyl)rhamnopyranoside-7-O-α-L-rhamnopyranoside (2), kaempferol 3-O-α-L-(3-acetyl)rhamnopyranoside-7-O-α-L-rhamnopyranoside (3), kaempferol 3-O-α-L-(4-acetyl)rhamnopyranoside-7-O-α-L-rhamnopyranoside (4), kaempferol 3-O-α-D- glucopyranoside-7-O-α-L-rhamnopyranoside (5), afzelin (6) and α-rhamnoisorobin (7). All these compounds, except 6 were isolated from this plant for the first time. Compound 7 was the most active, with MIC values ranging from 1 to 2 μg/ml and its antioxidant activity (IC50 = 0.71 μg/ml) was higher than that of the reference drug (IC50 = 0.96 μg/ml).
These findings demonstrate that Bryophyllum pinnatum and some of its isolated compounds have interesting antimicrobial and antioxidant properties, and therefore confirming the traditional use of B. pinnatum in the treatment of infectious and free radical damages.
We investigated the enantioselective heterogeneous hydrogenation of some fluoroketones, e.g. 4-(trifluoroacetyl)biphenyl (max. 67% ee), on modified Pt–alumina catalyst. The structure of the ...intermediate complex depends on whether hydrogenation is performed with or without trifluoroacetic acid.
The enantioselective heterogeneous hydrogenation of 2,2,2-trifluoroacetophenone (
1), 4-(trifluoroacetyl)biphenyl (
5) and other fluoroketones (
2–
4,
6–
8) on modified (by cinchonidine) Pt–alumina (E4759) in toluene solution with and without trifluoroacetic acid (TFA) has been investigated. The effects of the modifier concentration (0–10
mmol/l), hydrogen pressure (1–50
bar), temperature (263–301
K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 85% in case of
1, however 67% ee was achieved in case of
5.
It has been proposed that the compounds responsible for chiral induction are the intermediate complexes, the structure of which depends on whether hydrogenation is performed with or without TFA.
The enantioselective heterogeneous catalytic hydrogenation of trifluoromethylcyclohexyl ketone (2), on Pt-alumina (E4759) modified by different chiral compounds in toluene and ethanol solution with ...and without trifluoroacetic (TFA) has been investigated. The effects of the type of modifiers and their concentration (0–10 mmol/l), hydrogen pressure (1–100 bar), temperature (273–301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 48% in the case of CD. Depending on solvents the inversion of enantioselectivity was observed. The available information suggests that the compounds responsible for chiral induction are different intermediates, the structure of which depends mostly on the acidic or non-acidic nature of the hydrogenation medium.
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 chloroform soluble part of the MeOH extract prepared from aerial parts, lignans pinoresinol (1), syringaresinol (2), and medioresinol (3) and flavonoids hispidulin (4), nepetin (5), apigenin (6), and luteolin (7) were isolated by a combination of different chromatographic methods. The structures of the compounds were determined by means of mass spectrometry and 1D- and 2D-nuclear magnetic resonance spectroscopy, and by comparison of the spectral data with literature values. Extracts of different polarity and the isolated compounds obtained from the aerial parts, together with those previously isolated from the roots of the plant 4β,15-dihydro-3-dehydrozaluzanin C (8), zaluzanin C (9), 4β,15,11β,13-tetrahydrozaluzanin C (10), nitidanin diisovalerianate (11), 24-methylenecholesterol (12), and 13-oxo-9Z,11E-octadecadienoic acid (13), were evaluated for their inhibitory effects on cyclooxygenase-2 and nuclear factor kappa B1 gene expression, inducible nitric oxide synthase, 5-lipoxygenase, and cyclooxygenase-1 and cyclooxygenase-2 enzymes in in vitro assays. It was found that O. acanthium extracts exert strong inhibitory activities in vitro and some lignans, flavonoids, and sesquiterpenes may play a role in these activities. 4β,15-Dihydro-3-dehydrozaluzanin C and zaluzanin C at 20 µM were the most active constituents tested against lipopolysaccharide/interferon-γ-induced nitric oxide production (100.4 ± 0.5 % and 99.4 ± 0.8 %) in the inhibition of cyclooxygenase-2 (98.6 ± 0.2 % and 97.0 ± 1.1 %) and nuclear factor kappa B1 gene expression (76.7 ± 7.3 % and 69.9 ± 3.4 %). Furthermore, it was shown that these inhibitory effects are not due to cytotoxicity of the compounds.
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 analysed by GC-MS and HPLC-MS techniques. By regarding both the identified specific compounds, and the results of previous studies on Maillard-reaction routes and products, improved, specific, plausible transformation pathways were suggested. Predominant Maillard-reaction products in our analysis were found to be as follows: Schiff-base type compound, Amadori product, pentane-1,5-diamine, propa-dienilimino-etanal, 2-amino-6-{(1-Z)-2,3,4,5,6-pentahidroxo-hexylydeneamino-hexanoic-acid, 3-hydroxibut-3-en-2-one, 1-(5-aminopentil)aminohexane-1,2,3,4,5,6-hexol, 2,6-diaminohex-4-enoic acid. Progress of the Maillard-reaction as well as the increase in antioxidant activity was monitored under versatile conditions. Distinctive types of carbohydrates were involved in the experiments in order to point out the most appropriate one in respect of antioxidant activity and potential health benefits. These results made it possible to develop a new, lysine-fortified, health-beneficial, functional biscuit utilising the generation of antioxidants by Maillard-reaction, whose composition was also examined.
► A novel, lysine-fortified functional foodstuff was developed. ► Most health beneficial composition was elaborated in terms of antioxidant capacity. ► Residual lysine-content was established after thermal treatment. ► Maillard-reaction-driven products were analysed by GC-MS and HPLC-MS. ► Transformation pathway of Maillard-reaction of lysine-sugar model systems was suggested.
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