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.
Highlights
Plants are among the most chemically complex organisms
The amides of hydroxycinnamic acids with putrescine identified in the biomass of the cell suspension culture M. turcomanica are quite widespread in plants and are currently considered as storage forms involved in the regulation of homeostasis of this diamine in plant cells [26, 27]
Feruloyltyramine belongs to a small group of phenylethylamides of hydroxycinnamic acids widespread in plants: inducible metabolites involved in the biochemical reactions of plants to the effect of stress factors of various nature as well as precursors of a wide class of lignanamides [26]
Summary
Plants are among the most chemically complex organisms. The variable part of their composition is determined, first of all, by the formation and accumulation of substances of “specialized” metabolism (secondary metabolites), the role of which in the life of a plant is the subject of numerous discussions. Phytochemical study of plant cells in vitro is carried out in most cases by comparing the chromatographic profiles of extracts from the biomass of plant cell cultures with the chromatograms of standard samples of secondary metabolites characteristic of a particular plant (this strategy of phytochemical study of plant cell cultures can be conventionally designated as “classical”) [2]. This approach does not allow detecting the entire spectrum of compounds formed in cell cultures, which, apparently, underlies the widespread opinion about the limitedness of specialized metabolism in plant cells in vitro [13]. The “classical” strategy of phytochemical analysis does not always provide correct information on the diversity of secondary metabolites in plant cells in vitro
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