Preliminary investigation of water-soluble polysaccharides from Georgian plants

Barbakadze, V. V.; Gakhokidze, R. A.; Shengeliya, Z. S.; Усов, А. И.

doi:10.1007/bf00597702

Cited by 10 publications

(15 citation statements)

References 10 publications

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“…Sugars were converted to acetates and determined by GC using myo-inosite as an internal standard [7,8]. GC was performed in a gas chromatograph (Hewlett-Packard 5890) with a flame-ionization detector, capillary column (Ultra-1), and integrator (HP 3393A).…”

Section: Methodsmentioning

confidence: 99%

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Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Stems of Symphytum asperum and S. caucasicum

et al. 2005

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Two high-molecular-weight (>1000 kDa) water-soluble preparations were isolated from stems of Symphytum asperum and S. caucasicum. Their basic component was established as poly [oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], analogous to that of high-molecular-weight (>1000 kDa) preparations from roots of these same plants, using IR and NMR spectral data.Keywords: caffeic acid, 3-(3,4-dihydroxyphenyl)glyceric acid, Symphytum asperum, Symphytum caucasicum, poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene] Caucasian species of comfrey from the genus Symphytum L. have been used since antiquity to treat wounds and fractures. It was found that they possess analgesic, antimicrobial, and anti-inflammatory activities. They are also used for contusions, hematomas, ulcers, gastrointestinal infections, neuralgia, parodontosis, arthritis, and rheumatism [1].Despite the popularity of these plants in folk medicine, literature data on their chemical composition and biological activity are rather scant.Total polysaccharide preparations from roots of rough comfrey (S. asperum Lepech.) and Caucasian comfrey (S. caucasicum Bieb.) (Boraginaceae) exhibited anticomplementary activity [2,3]. Both preparations were fractionated and monitored for activity in order to establish the active principle. Ultrafiltration on membrane filters (1000 kDa pores) followed by dissolution of high-molecular-weight components in veronal-salt buffer (pH 7.35) and gel-permeation chromatography removed most ballast polysaccharides and afforded water-soluble high-molecular-weight (>1000 kDa) fractions. Both fractions contained some residual carbohydrates (25.7 and 26.9%, respectively) and possessed high anticomplementary activities [2, 3]. One fraction from roots of S. asperum also exhibited antioxidant, antilipoperoxidant, and anti-inflammatory activities [4]. The UV spectra of both preparations contained absorption maxima at 252, 282 (sh), and 286 nm in veronal-salt buffer (pH 7.35) and at 213, 237, 282 (sh), and 286 nm in water. We demonstrated previously on the basis of IR and NMR spectral data that the principal component of both high-molecular-weight water-soluble preparations from roots of S. asperum and S. caucasicum was a regularly substituted polyoxyethylene, namely poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene] [5,6]. This previously unknown natural phenolic biopolymer was isolated for the first time, is a polymer derived from caffeic acid, and represents a new class of natural esters with 3-(3,4-dihydroxyphenyl)glyceric acid as the repeating unit.The goal of the present investigation was to isolate water-soluble high-molecular-weight (>1000 kDa) preparations from the total polysaccharides from stems of rough comfrey (TRC) and Caucasian comfrey (TCC) and to compare the structures of the principal structural units using IR and NMR spectroscopies.TRC and TCC were isolated from total polysaccharides of S. asperum and S. caucasicum stems using the previously reported method [2,3]. Table 1 gives the amount of residual total sugars, fructose, ur...

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Section: Methodsmentioning

confidence: 99%

“…Total polysaccharide preparations of S. asperum and S. caucasicum stems were obtained (6.5 and 6.8%, respectively, of the air-dried stem mass) as described previously [7,8].…”

Section: Methodsmentioning

confidence: 99%

Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Stems of Symphytum asperum and S. caucasicum

et al. 2005

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“…13 C NMR spectra showed only nine distinct resonances for C atoms substituted by phenylpropionic acid, namely 3-(3,4-dihydroxyphenyl)glyceric acid (1). Two resonances belonged to protonated aliphatic C atoms bound to oxygen; six, to three protonated and three unprotonated C atoms of an aromatic ring.…”

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“…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.…”

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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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“…album'un yaprak ve ince dallarında yapılan çalışmalar sonucu glukoz, galaktoz, arabinoz, ramnoz, ksiloz, fruktoz, sakkaroz, rafinoz, stakioz, galakturonik asit, glukozamin, mannitol, sorbitol, hemiselüloz ve pektinin varlığı ortaya konmuştur. Ayrıca, yaprak ve meyvada inozitol saptanmıştır (1, 8,21,22,[24][25][26].…”

Section: Oz Ve Türevleriunclassified

Viscum album L. (Ökse Otu) Bitkisinin Kimyasal Bileşimi : Chemical Constituents of Viscum album L.

Ergün¹,

Deliorman²

1995

Ankara Universitesi Eczacilik Fakultesi Dergisi

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Preliminary investigation of water-soluble polysaccharides from Georgian plants

Cited by 10 publications

References 10 publications

Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Stems of Symphytum asperum and S. caucasicum

Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Stems of Symphytum asperum and S. caucasicum

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

Viscum album L. (Ökse Otu) Bitkisinin Kimyasal Bileşimi : Chemical Constituents of Viscum album L.

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