The preparation and antioxidant activity of glucosamine sulfate

Glucosamine sulfate was prepared from glucosamine hydrochloride that was produced by acidic hydrolysis of chitin by ion-exchange method. Optical rotation and elemental analysis characterized the degree of its purity. In addition, the antioxidant potency of chitosan derivative-glucosamine sulfate was investigated in various established in vitro systems, such as superoxide (O (2) (-) )/hydroxyl (center dot OH) radicals scavenging, reducing power, iron ion chelating. The following results are obtained: first, glucosamine sulfate had pronounced scavenging effect on superoxide radical. For example the O (2) (-) scavenging activity of glucosamine sulfate was 92.11% at 0.8 mg/mL. Second, the center dot OH scavenging activity of glucosamine sulfate was also strong, and was about 50% at 3.2 mg/mL. Third, the reducing power of glucosamine sulfate was more pronounced. The reducing power of glucosamine sulfate was 0.643 at 0.75 mg/mL. However, its potency for ferrous ion chelating was weak. Furthermore, except for ferrous ion chelating potency, the scavenging rate of radical and reducing power of glucosamine sulfate were concentration-dependent and increased with their increasing concentrations, but its ferrous ion chelating potency decreased with the increasing concentration. The multiple antioxidant activities of glucosamine sulfate were evidents of reducing power and superoxide/hydroxyl radicals scavenging ability. These in vitro results suggest the possibility that glucosamine sulfate could be used effectively as an ingredient in health or functional food, to alleviate oxidative stress.

In vitro antioxidant activities of acetylated, phosphorylated and benzoylated derivatives of porphyran extracted from Porphyra haitanensis

Porphyran extracted from red algae Porphyra haitanensis is a sulfated polysaccharide, which possesses excellent antioxidant activities. In this study, we prepared the acetylated, phosphorylated and benzoylated derivatives of porphyran. And then the antioxidant activities of all the samples were investigated including scavenging effects of superoxide and hydroxyl radicals and reducing power. The results of chemical analysis and FT-IR spectrum showed the modifications of porphyran were successful. And in addition, we found that certain derivative exhibited stronger antioxidant activity than raw material. And the mechanism of the structure-function relationship of these derivatives needs to be attended to. (C) 2009 Elsevier Ltd. All rights reserved.

Preparation of the different derivatives of the low-molecular-weight porphyran from Porphyra haitanensis and their antioxidant activities in vitro

Porphyran extracted from Porphyra haitanensis is a sulfated polysaccharide, which possesses excellent antioxidant activities. In this study, we prepared one low-molecular-weight porphyran and its sulfated, acetylated, phosphorylated and benzoylated derivatives. Their antioxidant activities were investigated including scavenging effect of superoxide, hydroxyl and 1,1-diphenyl-2-picrylhydrazyl radicals. The results of chemical analysis and FT-IR spectrums showed the modification was successful. And in addition, we found that certain derivative exhibited stronger antioxidant activity than low-molecular-weight porphyran. The benzoylated derivative showed the most excellent antioxidant activity in three assays, so this derivative needs to be attended to. (C) 2009 Elsevier B.V. All rights reserved.

The synthesis and antioxidant activity of the Schiff bases of chitosan and carboxymethyl chitosan

Five kinds of Schiff bases of chitosan and carboxymethyl chitosan (CMCTS) have been prepared according to a previous method and the antioxidant activity was studied using an established system, such as superoxide and hydroxyl radical scavenging. Obvious differences between the Schiff bases of chitosan and CMCTS were observed, which might be related to contents of the active hydroxyl and amino groups in the molecular chains. (c) 2005 Elsevier Ltd. All rights reserved.

Antioxidant activity of different sulfate content derivatives of polysaccharide extracted from Ulva pertusa (Chlorophyta) in vitro

Polysaccharide extracted from Ulva pertusa (Chlorophyta) is a group of sulfated heteropolysaccharide; for simplicity, the sulfated polysaccharide is referred to as ulvan in this paper. In this study, different sulfate content ulvans were prepared with sulfur trioxide/N,N-diinethylformamide (SO3-DMF) in formamide, and their antioxidant activities were investigated including scavenging activity of superoxide and hydroxyl radicals, reducing Power and metal chelating ability. As expected, we obtained several satisfying results, as follows: firstly, high sulfate content ulvans had more effective scavenging activity on hydroxyl radical than natural ulvan. Secondly, comparing with natural ulvan, high sulfate content ulvans exhibited stronger reducing power. Thirdly, HU4 (sulfate content, 30.8%) and HU5 (sulfate content, 32.8%) showed more pronounce chelating ability on ferrous ion at high concentration than other samples. (c) 2005 Elsevier B.V. All rights reserved.

Antioxidant activity of different molecular weight sulfated polysaccharides from Ulva pertusa Kjellm (Chlorophyta)

Polysaccharides extracted from Ulva pertusa Kjellm ( Chlorophyta) are a group of sulfated heteropolysaccharides, the ulvans. In this study, different molecular weight ulvans were prepared by H2O2 degradation and their antioxidant activities investigated including superoxide and hydroxyl radical scavenging activity, reducing power and metal chelating ability. The molecular weights of natural and degraded ulvans were 151.7, 64.5, 58.0, and 28.2 kDa, respectively, as determined by high performance gel permeation chromatography. Among the four samples, U-3 ( the lowest molecular weight sample) showed significant inhibitory effects on superoxide and hydroxyl radicals with IC50 values of 22.1 mu g mL(-1) and 2.8 mg mL(-1); its reducing power and metal chelating ability were also the strongest among the four samples. All the other samples also demonstrated strong activity against superoxide radicals. The results indicated that molecular weight had a significant effect on the antioxidant activity of ulvan with low molecular weight ulvan having stronger antioxidant activity.

Antioxidant activity of differently regioselective chitosan sulfates in vitro

Differently regioselective chitosan sulfates were prepared according to Hanno Baumann's methods. Their antioxidant potencies were investigated employing various established in vitro systems, such as 1,1-diphenyl-2-picrylhydrazyl (DPPH)/superoxide/hydroxyl radicals scavenging, reducing power, iron ion chelating and total antioxidant activity. All kinds of sulfated chitosans (HCTS, TSCTS, SCTS, TCTS) showed strong inhibitory activity toward superoxide radical by the PMS-NADH system compared to Vc. According to the above-mentioned order their IC50 were 0.012, 0.040, 0.015, 0.022mg/mL, respectively, however, scavenging activity of Vc on superoxide radical was 68.19% at 2.0mg/mL. Scavenging activity of superoxide radical was found to be in the order of HCTS > SCTS > TCTS > TSCTS > Vc. Furthermore, all kinds of sulfated chitosans exhibited strong concentration-dependent inhibition of deoxyribose oxidation. Except for HCTS, others had stronger scavenging activity on hydroxyl radical than Vc. Scavenging effect of TSCTS on 1, 1 -diphenyl-2-picrylhydrazy] radical was little lower than that of BHA, but better than that of others. All kinds of sulfated chitosans were efficient in the reducing power, especially TSCTS. TSCTS and TCTS showed considerable ferrous ion chelating potency. The data obtained in vitro models clearly establish the antioxidant potency of all kinds of sulfated chitosans. These in vitro results suggested the possibility that sulfated chitosans could be effectively employed as ingredient in health or functional food, to alleviate oxidative stress. However, comprehensive studies need to be conducted to ascertain the in vivo safety of sulfated chitosans in experimental animal models. (C) 2004 Elsevier Ltd. All rights reserved.

Preparation of high-molecular weight and high-sulfate content chitosans and their potential antioxidant activity in vitro

The influence of molecular weight and substitution degree of sulfated polysaccharides on their biological activity is considered in majority of works involving the anticoagulant or antiviral properties of these substances. Therefore, the present paper describes the effect of preparation conditions of sulfated chitosans on their molecular weight and sulfur content, such as different reaction time, acid solvent and temperature. Foregoing literature expounded the action of dichloroacetic acid (DCAA) as acid solvent in homogeneous reaction. However, DCAA is expensive and noxious, therefore, in the present paper cheap and non-noxious formic acid (88%) was in place of DCAA. Furthermore, during reaction formic acid was not dehydrated. Under formic acid we obtained the satisfying results that was higher yield and equivalent sulfur contents compared to DCAA. IR and C-13 NMR spectrums proved the structure of the resultant obtained under formic acid or DCAA to be same. Now, it has not been reported for formic acid as acid solvent in homogeneous reaction of chitosan sulfatation. In this present paper, we also determined antioxidant activity of high-molecular weight and high-sulfate-content chitosans (HCTS). The results showed that HCTS could scavenge superoxide and hydroxyl radical. Its IC50 is 0.012 and 3.269 mg/mL, respectively. It had obviously reducing power and slight chelating activity. The data obtained in in vitro models clearly establish the antioxidant potency of HCTS. It is a potential antioxidant in vitro. (C) 2005 Elsevier Ltd. All rights reserved.

Relevance of molecular weight of chitosan and its derivatives and their antioxidant activities in vitro

The antioxidant potency of different molecular weight (DMW) chitosan and sulfated chitosan derivatives was investigated employing various established in vitro systems, such as superoxide (O-2(.-))/hydroxyl ((OH)-O-.) radicals scavenging, reducing power, iron ion chelating. As expected, we obtained several satisfying results, as follows: Firstly, low molecular weight chitosan had stronger scavenging effect on O-2(.-) and (OH)-O-. than high molecular weight chitosan. For example the O-2(.-) scavenging activity of low molecular weight chitosan (9 kDa) and high molecular weight chitosan (760 kDa) were 85.86 % and 35.50 % at 1.6 mg/mL, respectively. Secondly, comparing with DMW chitosan, DMW sulfated chitosans had the stronger inhibition effect on 0(2)(.-). At 0.05 mg/mL, the scavenging activity on O-2(.-) reached 86.26 %, for low molecular weight chitosan sulfate (9 kDa), but that of low molecular weight chitosan (9 kDa) was 85.86 % at 1.6 mg/mL. As concerning chitosan and sulfated chitosan of the same molecular weight, scavenging activities of sulfated chitosan on superoxide and hydroxyl radicals were more pronounced than that of chitosan. Thirdly, low molecular weight chitosan sulfate had more effective scavenging activity on 02 and (OH)-O-. than that of high molecular weight chitosan sulfate. Fourthly, DMW chitosans and sulfated chitosans were efficient in the reducing power, especially LCTS. Their orders were found to be LCTS > CTS4 > HCTS > CTS3 > CTS2 > CTS1 > CTS. Fifthly, CTS4 showed more considerable ferrous ion-chelating potency than others. Finally, the scavenging rate and reducing power of DMW chitosan and sulfated derivatives increased with their increasing concentration. Moreover, change of DMW sulfated chitosans was the most pronounced within the experimental concentration. However, chelating effect of DMW chitosans were not concentration dependent except for CTS4 and CTS1. (C) 2004 Elsevier Ltd. All rights reserved.

Preparation of low-molecular-weight and high-sulfate-content chitosans under microwave radiation and their potential antioxidant activity in vitro

In the present paper microwave radiation has been used to introduce N-sulfo and O-sulfo groups into chitosan with a thigh degree of substitution and low-molecular weight. The sulfation of chitosan was performed in microwave ovens. It was found that microwave heating is a convenient way to obtain a wide range of products of different degrees of substitution and molecular weight only by changing reaction time or/and radiation power. Moreover, microwave radiation accelerated the degradation of sulfated chitosan, and the molecular weight of sulfated chitosan was considerably lower than that obtained by traditional heating. There are no differences in the chemical structure of sulfated chitosan obtained by microwave and by conventional technology. FTIR and C-13 NMR spectral analyses demonstrated that a significantly shorter time is required to obtain a satisfactory degree of substitution and molecular weight by microwave radiation than by conventional technology. In this present paper, we also determined antioxidant activity of low-molecular-weight and high-sulfate-content chitosans (LCTS). The results showed LCTS could scavenge superoxide and hydroxyl radical. Its IC50 is 0.025 and 1.32mg/mL, respectively. It is a potential antioxidant in vitro. (C) 2004 Published by Elsevier Ltd.

The structure of a sulfated galactan from Porphyra haitanensis and its in vivo antioxidant activity

The sulfated galactan fraction F1 isolated from the red seaweed, Porphyra haitanensis, showed typical porphyran structure. It has a linear backbone of alternating 3-linked beta-D-galactosyl units and 4-linked alpha-L-galactosyl 6-sulfate and 3,6-anhydro-alpha-L-galactosyl units. The L-residues are mainly composed of alpha-L-galactosyl 6-sulfate units, and the 3,6-anhydrogalactosyl units are minor. Partial methylation occurred at the C-6 position of the D-galactosyl units and at the C-2 position of the 3,6-anhydro-alpha-L-galactosyl units. Intraperitoneal administration of F1 significantly decreased the lipid peroxidation in aging mice. F1 treatment increased the total antioxidant capacity and the activity of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) in aging mice. The results indicated that F1 had significant in vivo antioxidant activity. (C) 2003 Elsevier Ltd. All rights reserved.

Antioxidant activities of sulfated polysaccharide fractions from Porphyra haitanesis

Three sulfated polysaccharide fractions (F1, F2, and F3) were isolated from Porphyra haitanesis, an important economic alga in China, through anion-exchange column chromatography and their in vitro antioxidant activities were investigated in this study. Galactose was the main sugar unit of the three fractions. The analytical results indicated that polysaccharide fractions from P. haitanesis had similar chemical components to porphyran from other species, but differed in their high sulfate content. The sulfate content of F1, F2 and F3 was 17.4%, 20.5% and 33.5% respectively. All three polysaccharide fractions showed antioxidant activities. They had strong scavenging effect on superoxide radical, and much weaker effect on hydroxyl free radical. Lipid peroxide in rat liver microsome was significantly inhibited, and H2O2 induced hemolysis of rat erythrocyte was partly inhibited by F1, F2 and F3. Among them, F3 showed strongest scavenging effect on superoxide radical; F2 had strongest effect on hydroxyl radical and lipid peroxide.

Preparation of 1,3,5-thiadiazine-2-thione derivatives of chitosan and their potential antioxidant activity in vitro

Three new kinds of 1,3,5-thiadiazine-2-thi one derivatives of chitosan with two different molecular weight (SATTCS1, SATTCS2, TITTCS1, TITTCS2, CITTCS1 and CITTCS2) have been prepared. Their structures were characterized by IR spectroscopy. The substitution degree of derivatives calculated by elemental analyses was 0.47, 0.42, 0.41, 0.38, 0.41 and 0.36, respectively. The result shows that substitution degree of derivatives was higher with lower molecular weight. The antioxidant activity was studied using an established system, such as bydroxyl radical scavenging, superoxide radical scavenging and reducing power. Antioxidant activity of the 1,3,5-thiadiazine-2-thione derivatives of chitosan were stronger than that of chitosans and antioxiclant activity of low molecular weight derivatives were stronger than that of high molecular weight derivatives. It is a potential antioxidant in vitro. (c) 2007 Elsevier Ltd. All rights reserved.

Antioxidant activity of sulfated polysaccharide fractions extracted from Laminaria japonica

Fucoidan, a group of sulfated heteropolysaccharide, was extracted from Laminaria japonica, an important economic alga species in China. Three sulfated polysaccharide fractions (F1, F2, and F3) were successfully isolated through anion-exchange column chromatography and had their antioxidant activities investigated employing various established in vitro systems, including superoxide and hydroxyl radical scavenging activity, chelating ability, and reducing power. Chemical analysis suggested that F1 and F3 were heteropolysaccharide in which galactose was the major component, while F2 was a typical fucoidan. All fractions possessed considerable antioxidant activity, and F1, F2 and F3 had stronger antioxidant ability than fucoidan in certain tests. The correlation between the sulfate content and scavenging superoxide radical ability was positive. Available data obtained with in vitro models suggested that the ratio of sulfate content/fucose was an effective indicator to antioxidant activity of the samples. (C) 2007 Elsevier B.V. All rights reserved.

Relevance of molecular weight of chitosan-N-2-hydroxypropyl trimethyl ammonium chloride and their antioxidant activities

The antioxidant potency of high/low molecular weight quatemary chitosan derivatives was investigated employing various established systems in vitro, such as superoxide (O-2(center dot-)) and hydroxyl (center dot OH) radicals scavenging, reducing power and iron ion chelating. As expected, we obtained several satisfying results, as follow: firstly, low molecular weight quaternary chitosan had stronger scavenging effect on O-2(center dot-) and center dot OH than high molecular weight quaternary chitosan. Secondly, the reducing power of low molecular weight quaternary chitosan was more pronounced than that of high molecular weight quaternary chitosan. Thirdly, ferrous ion chelating potency were showed to increase first and decrease afterwards with increasing concentration for two kinds of quaternary chitosans, namely, they have not concentration-dependence. However, the scavenging rate and reducing power of high and low molecular weight quaternary chitosans increased with their increasing conc centrations, and hence were concentration-dependent. (c) 2007 Elsevier Masson SAS. All rights reserved.