Stimulatory effect of N-(1-deoxy-beta-d-fructopyranos-1-yl)-l-proline on antibody production in mice.

Synthesized N-(1-deoxy-beta-d-fructopyranos-1-yl)-l-proline (Fru-Pro), an Amadori rearrangement product, has been investigated for its immunomodulatory effects. We evaluated the effects of Fru-Pro on the in vivo and in vitro activity in the regulation of the mice immune response. Haemagglutination antibody titre, plaque forming cell assay, E-rosette forming assay and cytotoxic test were studied. It has been demonstrated that the compound shows immunostimulating properties. In conclusion, present investigation suggests that the Fru-Pro is biologically functional, improves the immune system and might be regarded as an immune response modulator.

Crystal structure of N-(1-deoxy-beta-D-fructopyranos-1-yl)-L-proline-an Amadori compound.

Here we report the crystal structure data on N-(1-deoxy-beta-D-fructopyranos-1-yl)-L-proline (Fru-Pro)-an Amadori compound. X-ray crystal and molecular structures of its two isomorphous crystalline forms, (Fru-Pro)xMeOH, C(11)H(19)NO(7)xCH(4)O (1a) and (Fru-Pro)x2H(2)O, C(11)H(19)NO(7)x2H(2)O (1b) were determined. In 1a and 1b the compound crystallizes as the beta-anomer with the overall geometry of Fru-Pro zwitterions being very similar. Fructose ring adopts the chair (2)C(5) conformation with the proline moiety bonded to equatorial C-1 atom and remaining in a trans-gauche (tg) orientation with respect to the sugar ring. The five-membered pyrrolidine ring adopts an envelope conformation, with the Cbeta atom puckered. Fructosyl and carboxylate groups are in bisectional and axial positions of pyrrolidine ring, respectively. The overall molecular geometry of Fru-Pro zwitterions, especially the relative orientation of sugar and amino acid moieties, is stabilized by intramolecular, three-centred N-H...O(Fru)/O(Pro) hydrogen bonds (with bifurcated acceptor) formed between aminium and hydroxyl/carboxylate groups. The packing diagrams are very similar in both 1a and 1b with the adjacent zwitterions linked to each other by the extensive network of O-H...O and C-H...O hydrogen bonds to form channels along the a-axis, filled up with solvent molecules.

HPLC determination of phenolic acids and antioxidant activity in concentrated peat extract--a natural immunomodulator.

The aim of this study was to devise a method for identification and quantification of phenolic acids in concentrated peat extract samples. The simple reversed-phase HPLC method for simultaneous determination of several phenolic acids was developed. The method was validated and it was suitable for the analysis of phenolic acids in peat extracts. This method allowed identifying eight phenolic acids in peat extracts. Phenolic profiles of two samples of peat extract obtained from different medicinal peats were similar, although variations in amounts of individual phenolic acids were observed. Also, slight variations in total phenolic content were detected. The antioxidant activity of peat extracts was evaluated with spectrophotometric ABTS assay. Differences in antioxidant activity were observed for two samples of peat extract produced from different peat varieties. This differences probably reflected phenolic composition of peat extracts.