Abstract—According to IR, 13 C and 1 H NMR, APT, 1D NOE, 2D heteronuclear 1 H/ 13 C HSQC and 2D DOSY experiments the main chemical constituent of high-molecular preparations from Symphytum asperum, S. caucasicum, S. officinale and Anchusa italica (Boraginaceae) was found to be caffeic acid-derived polyether, namely poly[3-(3,4-dihydroxyphenyl)glyceric acid] (PDPGA) or poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene]. Most carboxylic groups of this polymer of A. italica are methylated. Keywords—Anchusa, poly[3-(3,4-dihydroxyphenyl)glyceric acid], poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], Symphytum. I. INTRODUCTION ITHIN the field of pharmacologically active biopolymers the area of stable polyethers seems rather new and attractive. In the last decade water-soluble high- molecular fractions from several species of two genera (Symphytum and Anchusa) of Boraginaceae family Symphytum asperum (HM-SA), S. caucasicum (HM-SC), S. officinale (HM- SO) and A. italica (HM-AI) roots were isolated [1]-[3]. The presented special communication summarizes data concerning novel caffeic acid-derived polyether – the main constituent of above mentioned preparations. II. MATERIALS AND METHODS A. Materials Roots of S. asperum, S. caucasicum, S. officinale and A. italica were collected in Ajara region (S. asperum) and Tbilisi suburbs (S. caucasicum, S. officinale, and A. italica) in May- June. Voucher specimens are stored at the Tbilisi State Medical University Institute of Pharmacochemistry Herbarium. V. Barbakadze and K. Mulkijanyan are with the Tbilisi State Medical University Institute of Pharmacochemistry, Laboratory of Plant Biopolymers, Tbilisi, 0159, Georgia, (phone: 995595531509; fax: 995322520023; e-mail: v_barbakadze@ hotmail.com, karmulk@gmail.com). L. Gogilashvili is with the Tbilisi State Medical University Institute of Pharmacochemistry, Laboratory of Plant Biopolymers, Tbilisi, 0159, Georgia, (phone: 995599347042; fax: 995322520023; e-mail: lagogila@mail.ru). L. Amiranashvili is with the Tbilisi State Medical University Institute of Pharmacochemistry, Laboratory of Plant Biopolymers, Tbilisi, 0159, Georgia, (phone: 995577723144; fax: 995322520023; e-mail: amiranale@ mail.ru). M. Merlani is with the Tbilisi State Medical University Institute of Pharmacochemistry, Laboratory of Plant Biopolymers, Tbilisi, 0159, Georgia, (phone: 995599761117; fax: 995322520023; e-mail: maiamer@ hotmail.com). B. General Experimental Procedures Crude polysaccharides from the roots of S. asperum, S. caucasicum, S. officinale and A. italica were obtained as described in [1]. The high-molecular caffeic acid-derived preparations from crude polysaccharides were isolated by ultrafiltration on membrane filter with cut-off value of 1000 kDa. UV spectra were recorded on a Hitachi 150-20 spectrophotometer; IR spectra were registered on a Jasco FT/IR-410 spectrophotometer; NMR were taken on a Bruker DRX-500 spectrometer for 1% solutions of the polymers in D 2 O at 80ºC using acetone ( H 2.225 ppm,  C 31.45 ppm) as the internal standard. The 2D HSQC spectra were obtained using the Bruker standard software. Pre-irradiation time for the 1D NOE experiment was 1 s, the signal of pre-irradiated proton in the difference spectrum was taken as 100%. For the 2D DOSY experiments, a Bruker pulse sequence that incorporated stimulated echo and longitudinal eddy currents and bipolar gradients for diffusion was used for both optimization of diffusion time and gradient pulse duration (1D) and then diffusion measurement (2D). CD spectra were performed on a Jasco J-715 instrument (Jasco Co., Tokyo, Japan) equipped with peltier temperature control system. For all measurements, 1 mm path length quartz cells, 1 nm bandwidth, 0.2 nm resolution, 1 s response and a scan speed of 50 nm/min for each spectrum were used. III. RESULTS AND DISCUSSION The ultrafiltration of crude polysaccharides from S. asperum, S. caucasicum, S. officinale and A. italica allowed to remove most polysaccharides and to obtain biologically active water- soluble high-molecular preparations with molecular masses exceeding 1 MDa. The UV spectra of HM-SA, HM-SC, HM-SO and HM-AI were identical to each other. They exhibited the same absorption maxima indicative of the phenolic nature of the preparations. IR spectra of HM-SA, HM-SC, HM-SO, and HM- AI fractions were also identical and contained absorption bands typical of phenolcarboxylic acids [1]-[3]. The 13 C NMR spectra of HM-SA, HM-SC, and HM-SO were completely identical [1], [2]. Interestingly, the signals of the residual carbohydrate components are practically unobservable in the spectra of these preparations, probably due to their variegated monosaccharide composition; only nine distinct signals corresponding to the carbon atoms of the substituted phenylpropionic acid fragment were observed (Fig. 1). It follows from the spectra obtained using the APT technique [1] (Fig. 2) that five signals should be assigned to V. Barbakadze, L. Gogilashvili, L. Amiranashvili, M. Merlani, K .Mulkijanyan Poly[3-(3,4-dihydroxyphenyl)Glyceric Acid] with Potential Therapeutic Effect W World Academy of Science, Engineering and Technology International Journal of Chemical and Molecular Engineering Vol:8, No:11, 2014 1273 International Scholarly and Scientific Research & Innovation 8(11) 2014 ISNI:0000000091950263 Open Science Index, Chemical and Molecular Engineering Vol:8, No:11, 2014 publications.waset.org/10002956/pdf