Molecular complexes of triterpene glycosides with L-histidine and their biological activity

Abstract

Aim. To investigate the complexation of L-histidine (His) with hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabino pyranoside (α-hederin) and its 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester (hederasaponin C); to study the effect of glycosides, His, and their mixtures at Avena sativa L. seed germination. Methods. Electrospray ionization mass spectrometry. Results. The mass spectra of glycosides mixed with His are received and interpreted. The comparative analysis of biological activity of individual substances and their complexes is performed. Conclusions. For the first time, the composition of aforesaid complexes is established by mass spectrometry. Complexes have appeared less toxic, than individual glycosides

Molecular complexes of the triterpene glycosides with L-tyrosine and their biological activity

“…The electrospray ionization mass spectrometry was used to study the complexation of glycosides 1 and 2 with L-phenylalanine (Phe) [23], L-tryptophan (Trp) [15] and L-histidine (His) [24]. Besides, we have established the effect of these complexes on the germinating ability of seeds and further development of Avena sativa L. sprouts [24][25][26]. However, Tyr complexes were previously analyzed only by UV-spectrometry [27].…”

“…The germinating ability of A. sativa L. seeds (Poaceae (Gramineae) family) was checked in the laboratory conditions at room temperature (23-25°C) as described in [24]. The results are presented in Table 2.…”

“…The peak intensities of these ions are in the ratio of 24:1 which indicated the prevalence of the complex of equimolar composition. Previously, using the electrospray ionization mass-spectrometry we showed that for the glycosides 1 and 2 and amino acids (Trp, Phe and His) the complexes of 1:1 composition are the most typical [15,23,24]. The amino acid Tyr differs from Phe structurally only by the presence of a hydroxyl group.…”

“…Previously we established that the complexes of glycosides 1 and 2 with Phe [25] and His [24] are less toxic than individual glycosides. Vice versa, the complexes with Trp proved to be more toxic [26].…”