Synthesized phosphorylated and aminated derivatives of fucoidan and their potential antioxidant activity in vitro

Three sulfated polysaccharide derivatives (phosphorylated and aminated fucoidan) were synthesized, and their potential antioxidant activities were investigated employing various established in vitro systems. Two methods were used in phosphorylation fucoidan: polyphosphoric acid and POCl3 method. Aminated fucoidan was prepared using the epichlorohydrin and ammonia water. All fucoidan derivatives possessed considerable antioxidant activity, and exhibited stronger antioxidant ability than fucoidan in certain tests. The phosphorylated fucoidan showed stronger hydroxyl radical and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and reducing power. The mechanism on influence the antioxidant activity of samples of phosphate and amino group was indicated. (C) 2008 Elsevier B.V. All rights reserved.

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.

Antimicrobial activity of hydroxylbenzenesulfonailides derivatives of chitosan, chitosan sulfates and carboxymethyl chitosan

Chitosan, carboxymethyl chitosan (CIVICS) and chitosan sulfates (CSS) with different molecular weight were modified by reacting with 4-hydroxyl-5-chloride-1,3-benzene-disulfo-chloride or 2-hydroxyl-5-chloride-1,3 -benzene-disulfo-chloride to give 12 kinds of new hydroxylbenzenesulfonailides derivatives of them. The preparation conditions of the derivatives were discussed in this paper, and their structures were characterized by FT-IR and C-13 NMR spectroscopy. The solubility of the derivatives was measured in the experiment. In addition, their antimicrobial activities against four bacteria and five crop-threatening pathogenic fungi were tested in the experiment. Besides, the rule and mechanism of their antibacterial activities were discussed in this paper. (C) 2009 Published by Elsevier B.V.

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.

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 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.

Synthesis and antifungal properties of sulfanilamide derivatives of chitosan

Sulfanilamide derivatives of chitosan (2-(4-acetamido-2-sulfanimide)-chitosan (HSACS, LSACS), 2-(4-acetamido-2-sulfanimide)-6-sulfo-chitosan (HSACSS, LSACSS) and 2-(4-acetamido-2-sulfanimide)-6-carboxymethyl-chitosan (HSACMCS, LSACMCS)) were prepared using different molecular weights of chitosan (CS), carboxymethyl chitosan (CMCS) and chitosan sulfates (CSS) reacted with 4-acetamidobenzene sulfonyl chloride in dimethylsulfoxide solution. The structures of the derivatives were characterized by FT-IR spectroscopy and elemental analysis, which showed that the substitution degree of sulfanilamide group of HSACS, HSACSS, HSACMCS, LSACS, LSACSS and LSACMCS were 0.623, 0.492, 0.515, 0.576, 0.463 and 0.477, respectively. The solubility of the derivatives (pH < 7.5) was higher than that of chitosan (pH < 6.5). The antifungal activities of the derivatives against Aiternaria solani and Phomopsis asparagi were evaluated based on the method of Jasso et al. in the experiment. The results indicated that all the prepared sulfanilamide derivatives had a significant inhibiting effect on the investigated fungi in the polymer concentration range from 50 to 500 mu g mL(-1). The antifungal activities of the derivatives increased with increasing the molecular weight, concentration or the substitution degree. The sulfanilamide derivatives of CS, CMCS and CSS show stronger antifungal activities than CS, CMCS and CSS. (C) 2007 Elsevier Ltd. All rights reserved.

Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro

Three different acyl thiourea derivatives of chitosan (CS) were synthesized and their structures were characterized by FT-IR spectroscopy and elemental analysis. The antimicrobial behaviors of CS and its derivatives against four species of bacteria (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Sarcina) and four crop-threatening pathogenic fungi (Alternaria solani, Fusarium oxysporum f. sp. vasinfectum, Colletotrichum gloeosporioides (Penz.) Saec, and Phyllisticta zingiberi) were investigated. The results indicated that the antimicrobial activities of the acyl thiourea derivatives are much better than that of the parent CS. The minimum value of MIC and MBC of the derivatives against E coli was 15.62 and 62.49 mu g/mL, respectively. All of the acyl thiourea derivatives had a significant inhibitory effect on the fungi in concentrations of 50 - 500 mu g/mL; the maximum inhibitory index was 66.67%. The antifungal activities of the chloracetyl thiourea derivatives of CS are noticeably higher than the acetyl and benzoyl thiourea derivatives. The degree of grafting of the acyl thiourea group in the derivatives was related to antifungal activity; higher substitution resulted in stronger antifungal activity. (c) 2007 Elsevier Ltd. All rights reserved.

The preparation and antioxidant activity of the sulfanilamide derivatives of chitosan and chitosan sulfates

Chitosan (CS) and chitosan sulfates (CSS) with different molecular weight (Mw) were reacted with 4-acetamidobenzene sulfonyl chloride to obtain sulfanilamide derivatives of chitosan and chitosan sulfates (LSACS, HSACS, LSACSS, HSACSS). The preparation conditions such as different reaction time, temperature, solvent, and the molar ratio of reaction materials are discussed in this paper. Their structures were characterized by FTIR spectroscopy and elemental analyses. The antioxidant activities of the derivatives were investigated employing various established in vitro systems, such as hydroxyl-radical (OH) superoxide anion (O-2(center dot-)) scavenging and reducing power. All kinds of the compounds (HCS, LCS, HCSS, LCSS, HSACS, LSACS, HSACSS, LSACSS) showed stronger scavenging activity on hydroxyl radical than ascorbic acid (Vc). The inhibitory activities of the derivatives toward superoxide radical by the PMS-NADH system were obvious. The experiment showed that the superoxide radical scavenging effect of sulfanilamide derivatives of chitosan and chitosan sulfates was stronger than that of original CS and CSS. All of the derivatives were efficient in the reducing power. The results indicated that the sulfanilamide group were grafted on CS and CSS increased the reducing power of them obviously. (c) 2007 Elsevier Ltd. All rights reserved.

Novel derivatives of chitosan and their antifungal activities in vitro

Three kinds of Schiff bases of carboxymethyl chitosan (CMCTS) were prepared, and their antifungal activities were assessed according to Jasso de Rodriguez's method. The results indicated that 2-(2-hydroxybenzylideneamino)-6-carboxymethylchitosan (HNCMCTS) and 2-(5-chloro-2-hydroxybenzylideneamino)-6-carboxymethylchitosan (HCCMCTS) had better inhibitory effects than those of chitosan or CMCTS against Fusarium oxysporium f. sp. vasinfectum, Alternaria solani, and Valsa mali. (c) 2005 Elsevier Ltd. All rights reserved.

In vitro antioxidant activity of acetylated and benzoylated derivatives of polysaccharide extracted from Ulva pertusa (Chlorophyta)

The antioxidant activity of natural ulvan and its derivatives (acetylated and benzoylated ulvans) in vitro was determined, including scavenging activity against superoxide and hydroxyl radicals, reducing power, and chelating ability. Obvious differences in antioxidant activity between natural ulvan and its derivatives were observed, moreover, the antioxidant activity of acetylated and benzoylated ulvans was stronger than that of natural ulvan. (C) 2006 Elsevier Ltd. All rights reserved.

Two new norisoprenoid derivatives from the red alga Gymnogongrus flabelliformis

Two new norisoprenoid derivatives have been isolated from the red alga Gymnogongrus flabelliformis. Their structures were elucidated as (3R, 6R, 7E)-(+)-3-O-phenylacetyl-4,7-megastigmadiene-9-one and (3R,7E)-(-)-3-O-phenylacetyl-5,7-megastigmadiene-9-one, respectively, by spectroscopic methods including HRMS, 1D and 2D NMR techniques.

Investigation on the corrosion inhibitive effect of 2H-pyrazole-triazole derivatives in acidic solution

Four research methods, such as weight loss test, electrochemical techniques, adsorption isotherm, and quantum chemical calculation, were employed in this paper to study the inhibition efficiency (IE) and inhibition mechanism of three 2H-pyrazole-triazole derivatives, BHOT, FHOT, and CHOT in 1 M HCl solution for mild steel. Using the electrochemical technique, three inhibitors were proved to show a mixed-type character for mild steel by suppressing both anodic and cathodic reactions on the steel surface. The adsorption models of three compounds were established at different temperatures according to their adsorption isotherms. The results of the quantum chemical calculation method indicated that the adsorption sites of 2H-pyrazole-triazole derivatives were strongly centralized on benzene ring, triazole ring, or other substituents. All the results showed that the three derivatives were excellent inhibitors in I M HCl solution for mild steel.

Corrosion inhibition of mild steel in acidic solution by some oxo-triazole derivatives

The oxo-triazole derivative (DTP) was synthesized and its inhibiting action on the corrosion of mild steel in sulphuric acid was investigated by means of weight loss, potentiodynamic polarization, EIS and SEM. The results revealed that DTP was an excellent inhibitor and the inhibition efficiencies obtained from weight loss experiment and electrochemical experiment were in good agreement. Potentiodynamic polarization studies clearly revealed that DTP acted essentially as the mixed-type inhibitor. Thermodynamic and kinetic parameters were obtained from weight loss of the different experimental temperatures, which suggested that at different temperatures (298-333 K) the adsorption of DTP on metal surface obeyed Langmuir adsorption isotherm model. (C) 2009 Elsevier Ltd. All rights reserved.