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Polycratic reversed-phase high-performance liquid chromatography (RPHPLC) was used for estimation of the octanol/water partition coefficient for three highly hydrophobic long chain orcinol homologs. The homologs studied (C 15:0, C 17:0 and C 19:0) showed high preference for hydrophobic phase as evidenced by their high octanol/water partition coefficient (log P o/w ) values of 7.02-7.74; 8.71-9.47 and 10.49-11.32 for the 95% prediction interval, respectively. Experimentally estimated values were compared with log P values calculated with the use of several fragmental systems. The experimental values of log P o/w are in best agreement to those calculated with the use of the Klopman system (Klopman, Gv Namboodiri, K. & Schochet, M., 1985, /. Comput. Chem. 6,28-38). The lack of appropriate standard compounds with known log P 0/w in the range over 6 markedly affected the accuracy of experimental determinations.
The study analysed the effect of modification of phenolic resin with alkylresorcinols and H2O2 on properties of softwood and hardwood plywood resinated with such modified PF resins. Conducted tests showed that the application of PF resin modified with alkylresorcinols makes it possible to manufacture plywood with improved properties, especially bond quality, than those of the control plywood pressed under identical conditions. In turn, the introduction of H2O2 both to pure PF resin and resin modified with alkylresorcinols improves properties of plywood as a result of enhanced reactivity and increased chemical adhesion of resin to wood. Moreover, applied PF resin modification methods make it possible to manufacture plywood with very good properties at pressing time reduced by 25%.
Incubation of soybean lipoxygenase isoenzymes (L-1, L-2, and L-3) with total resorcinolic lipids isolated from wheat bran or their purified homologs (5-n-pentadecylresorcinol and 5-n-tricosylresorcinol) led to apparent inhibition of all three isoenzyme activities. The IC50 values determined for studied compounds showed that the inhibitory activity was related to the length of the resorcinolic lipid aliphatic chain and was more effective for homolog with longer chain attached to 1,3-dihydroxybenzene ring in metha position. Similar dependence on the length of the alkylresorcinol side chain was observed also for Ki values. The 5-n-tricosylresorcinol (23:0 AR) was found to be the most efficient inhibitor of soybean lipoxygenases with IC50 values in the range of several µM regardless of the substrate used (linoleic acid or arachidonic acid). All alkylresorcinols studied caused increase of apparent KM values and decrease of VMAX values of the enzymes thus suggested the mixed type of lipoxygenase inhibition.
Alkylresorcinol homologs form stable monomolecular layers at air-water interface. Their interaction with proteins present in the subphase results in an increase of alkylresorcinol molecular packing in the extent dependent upon the protein studied. Strongest effects were observed for proteins with large hydrophobic regions, e.g. glycophorin or serum albumin. Interaction of proteins with alkylresorcinol monolayers is stronger than with phospholipids. A decrease and a shift of intrinsic protein fluorescence upon interaction with the compounds studied support their involvement in alteration of hydrophobic regions. For trypsin, 50% quenching was observed at the alkylresorcinol/trypsin ratio of 0.75. Concomitantly, an apparent inhibition of the enzymatic activity was noted. These results indicate that direct interaction of alkylresorcinols and modulation of enzymatic activities should be recognised as a significant part of the biological effect of these cereal bran components.
The antimutagenic activity of alkylresorcinols from cereal grains and anthocyanins from Aronia melanocarpa fruit were compared in three short-term mphocyte tests: a sister chromatid exchange test, a cytokinesis-blocked micronucleus assay and a thioguanine-resistance test. It was noticed that both tested compounds significantly decreased the rate and frequency of mutations induced in cultured lymphocytes with two standard mtagens: benzo[a]pyrene and mitomycin C. Alkylresorcinols appeared to be acre potent antimutagenic compounds than anthocyanins. Anthocyanins exhibited a stronger inhibitory effect on the generation and release of free radicals by human granulocytes in vitro, as measured with the NBT-reduction test. The results suggest that alkylresorcinols and anthocyanins exerted an antimutagenic influence through multifarious mechanisms, one of which could be a limitation of free radical involvement in mutagenesis.
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