Chromato-Mass-Spectrometric Identification of Glycosides of Phenylethylamides of Hydroxycinnamic Acids in a Suspension Cell Culture of Mandragora turcomanica

Abstract

Abstract A detailed UPLC-ESI-MS study was performed on secondary metabolites in the biomass of a suspension plant cell culture of Turkmenian mandrake (Mandragora turcomanica Mizgir.), which has been maintained for over 30 years. Both compounds widespread in plants (amides of hydroxycinnamic acids with putrescine and feruloyltyramine) and very rare metabolites (glycosides of phenylethylamides of hydroxycinnamic acids) have been identified. The identification of compounds was carried out using ultra-performance liquid chromatography combined with high-resolution mass spectrometry with electrospray ionization (UPLC-ESI-MS) and detection of positive and negative ion modes. Structural analysis of glycosides of phenylethylamides of ferulic acid was carried out on the basis of interpreting MS spectra obtained by fragmentation of protonated molecular ions [M + H]+ of these compounds in the ionization source. Based on the obtained results, the presence of five hexosides of ferulic acid, three of which were with tyramine residues and one each with methoxytyramine and octopamine residues, respectively, in the M. turcomanica cells cultivated in vitro was revealed. One of the detected glycosides belongs to a very rare group of plant metabolites: feruloyltyramine dihexosides. The obtained results confirm the concept developed in the authors' works on the change in specialized metabolism of plant cells cultivated in vitro and indicate that dedifferentiated proliferating cells retain the ability to form a complex set of secondary metabolites, which contradicts the prevailing ideas about the loss or decrease in the intensity of specialized metabolism in plant cell cultures.