Poly[3-(3,4-dihydroxyphenyl)glyceric Acid], A New Biologically Active Polymer from Symphytum Asperum Lepech. and S.Caucasicum Bieb. (Boraginaceae)

Barbakadze, Vakhtang; Kemertelidze, E. P.; Targamadze, I. L.; Mulkijanyan, Karen; Shashkov, Alexander S.; Усов, А. И.

doi:10.3390/10091135

Cited by 16 publications

(28 citation statements)

References 18 publications

(22 reference statements)

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“…These were fractionated by ultrafiltration [1, 6] to afford watersoluble high-molecular-weight (>1000 kDa) preparations HP-et and HP-ac, respectively. UV and IR spectra of HP-et and HP-ac were very similar to those of previously isolated simple polyethers from S. asperum and S. caucasicum [2][3][4][5].…”

supporting

confidence: 52%

“…Thus, 13 C NMR, PMR, and 2D heteronuclear 1 H/ 13 C HSQC spectra of HP-et and HP-ac were identical to those of the high-molecular-weight fractions from S. asperum and S. caucasicum, which consisted mainly of poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene] [2][3][4][5]. Therefore, we concluded that the main component of HP-et and HP-ac was the same simple polyether with the repeating unit 3-(3,4-dihydroxyphenyl)glyceric acid, which contains two asymmetric C atoms.…”

mentioning

confidence: 74%

“…Its highmolecular-weight fraction (>1000 kDa) exhibits immuno-modulating (anticomplementary) activity [1]. It was shown previously that the main component of such high-molecular-weight (>1000 kDa) preparations from roots and stems of Caucasus comfrey species S. asperum and S. caucasicum is a regularly substituted poly(oxyethylene), namely poly [3-(3,4-dihydroxyphenyl)glyceric acid] or poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene] [2][3][4][5], which possesses antioxidant activity [6][7][8][9]. This previously unknown in nature phenolic biopolymer was isolated for the first time.…”

mentioning

confidence: 99%

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Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Symphytum officinale roots and its biological activity

et al. 2009

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IR and NMR spectroscopy, were isolated from roots of Symphytum officinale. They exhibit antioxidant activity as expressed in a decrease of active oxygen species (AOS) by interfering directly in their formation process by polymorphonuclear neutrophils (PMN) and binding directly AOS.Key words: Symphytum officinale, 3-(3,4-dihydroxyphenyl)glyceric acid, poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], antioxidant activity.Comfrey (Symphytum officinale, Boraginaceae) has been used since antiquity to treat wounds and fractures. Its highmolecular-weight fraction (>1000 kDa) exhibits immuno-modulating (anticomplementary) activity [1]. It was shown previously that the main component of such high-molecular-weight (>1000 kDa) preparations from roots and stems of Caucasus comfrey species S. asperum and S. caucasicum is a regularly substituted poly(oxyethylene), namely poly[3-(3,4-dihydroxyphenyl)glyceric acid] or poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene] [2-5], which possesses antioxidant activity [6][7][8][9]. This previously unknown in nature phenolic biopolymer was isolated for the first time. This polymer of a caffeic acid derivative is a representative of a new class of natural simple polyethers with 3-(3,4-dihydroxyphenyl)glyceric acid as the repeating unit.The goal of our research was to isolate water-soluble high-molecular-weight (>1000 kDa) preparations (HP) from total polysaccharides from roots of comfrey and to study the structure of their main component using IR and NMR spectroscopy. Furthermore, we studied their ability to block the formation of active oxygen species (AOS). It is known that AOS formed by activated polymorphonuclear neutrophils (PMN) play an important role in the protection of an organism from foreign microorganisms [9]. However, the surrounding tissue is threatened when PMN begin to produce an excess of AOS [10,11].An increase of AOS can also be observed during chronic damage when the enzyme xanthineoxidase (XO) catalyzes conversion of oxygen into superoxide anion, which damages tissue. During this process, XO converts hypoxanthine (HX) into xanthine and then uric acid.Consequently, binding of superoxide anion formed by activation of PMN and by XO is very important for treating wounds and inflammations [12].Natural compounds that influence the human complement system and/or the AOS formation process can be used to prevent tissue damage during various pathological conditions. Total polysaccharides from S. officinale roots were isolated by the literature method [13] and precipitated by ethanol to afford TP-et; by acetone from the mother liquor, TP-ac. These were fractionated by ultrafiltration [1, 6] to afford watersoluble high-molecular-weight (>1000 kDa) preparations HP-et and HP-ac, respectively. Table 1 lists the sugar content in these preparations.

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confidence: 74%

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Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Symphytum officinale roots and its biological activity

et al. 2009

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“…The UV spectra of high molecular weight (1000 kDal) fractions from the leaves of S asperum and S. caucasicum contained absorption peaks at 213, 237,282 (shoulder), and 286 nm in water [3,6]. The UV spectra of HMW-LSA and HMW-LSC lacked absorption peaks at 282 and 286 nm.…”

Section: Resultsmentioning

confidence: 97%

Extraction, composition and the antioxidant and anticomplement activities of high molecular weight fractions from the leaves of Symphytum asperum and S. caucasicum

et al. 2011

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High molecular weight fractions (> 1000 kDal) from the leaves of Symphytum asperum and S. caucasicum had anticomplement activity, were able to inhibit luminol-and lucigenin-dependent chemiluminescence (CL lum and CL luc respectively) induced by human polymorphonuclear neutrophils (PMN) after stimulation with opsonized zymosan, and could decrease the CL luc signal induced by superoxide anion formation in a cell-free hypoxanthine/xanthine oxidase system. The anticomplement and antioxidant activities of the high molecular weight fractions (> 1000 kDal) from the leaves of Symphytum asperum and S. caucasicum indicate that they might be used as anti-inflammatory and wound-healing agents.

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“…The responsible structural feature of caffeic acid derivatives for such activity is the existence of two adjacent hydroxyl functional groups in their aromatic ring. [16][17][18] This polymer is a representative of a new class of natural polyethers with a residue of 3-(3,4-dihydroxyphenyl)glyceric acid as the repeating unit. 14,15 According to NMR and IR spectral data, the main constituent of these preparations was found to be a regular caffeic acid-derived polyether, namely, poly-[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)-ethylene] (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antioxidant activity of 3-(3,4-dihydroxyphenyl)glyceric acid. Monomer of a biologically active polyether isolated from Symphytum asperum and S. caucasicum

Merlani¹,

Barbakadze²,

Gogilashvili³

et al. 2008

Planta Med

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The racemic and enantioselective synthesis of a novel glyceric acid derivative, namely, 2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid as well as the antioxidant activities is described. The virtually pure enantiomers, (1)-(2R,3S)-2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid and (2)-(2S,3R)-2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid were synthesized for the first time via Sharpless asymmetric dihydroxylation of trans-caffeic acid derivatives using the enantiocomplementary catalysts, (DHQD) 2 -PHAL and (DHQ) 2 -PHAL. The determination of enantiomeric purity of the novel chiral glyceric acid derivatives was performed by high-performance liquid chromatographic techniques on the stage of their alkylated precursors. The novel glyceric acid derivatives show strong antioxidant activity against hypochlorite and N,N-diphenyl-N-picryl-hydrazyl free radical. Their antioxidant activity is about 40-fold higher than that of the corresponding natural polyether and three-fold higher of trans-caffeic acid itself.

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Poly[3-(3,4-dihydroxyphenyl)glyceric Acid], A New Biologically Active Polymer from Symphytum Asperum Lepech. and S.Caucasicum Bieb. (Boraginaceae)

Cited by 16 publications

References 18 publications

Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Symphytum officinale roots and its biological activity

Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Symphytum officinale roots and its biological activity

Extraction, composition and the antioxidant and anticomplement activities of high molecular weight fractions from the leaves of Symphytum asperum and S. caucasicum

Synthesis and antioxidant activity of 3-(3,4-dihydroxyphenyl)glyceric acid. Monomer of a biologically active polyether isolated from Symphytum asperum and S. caucasicum

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