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Biologically Active Sugar-Based Biopolyether Poly[3-(3,4-Dihydroxyphenyl)Glyceric Acid] from the Stems and Roots of Paracynoglossum imeretinum (Kusn.) M.Pop

Abstract:

The high-molecular water-soluble mucilage fractions from stems and roots of Paracynoglossum imeretinum (Boraginaceae family) were isolated. According to data of UV, IR, liquid-state 1H, 13C NMR, gCOSY and 2D heteronuclear1H/13C gHSQCED experiments, the main chemical constituent of these water-soluble high-molecular fractions from Paracynoglossum imeretinum stems (HMF-PS) and roots (HMF-PR), respectively, was found to be biologically active caffeic acid-derived polymer poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], which is also referred to as poly[3-(3,4-dihyd-roxyphenyl)glyceric acid] (PDPGA). PDPGA was previously detected in high-molecular mucilage fractions of Symphytum asperum, S. caucasicum, S. grandiflorum, S. officinale, Anchusa italica, Cynoglossum officinale and Borago officinalis. The detection of this compound in different genera of the Boraginaceae family is interesting, as this unusual caffeic acid-derived polymer could be considered as a chemotaxonomic marker among Boraginaceae plants. Thus, PDPGA is interesting due to the importance of its chemotaxonomic significance, the potential biomedical applications of the Boraginaceae plants and the chemical importance of PDPGA. The presence of poly[3-(3,4-dihydroxyphenyl)glyceric acid] in multiple Boraginaceae species expands the resources of raw materials for this biologically active polymer.