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Synthesis and Antimicrobial Activity of N-(6-Carboxyl Cyclohex-3-ene Carbonyl) Chitosan with Different Degrees of Substitution 不同取代度N-(6-羧基环己基-3-烯羰基)壳聚糖的合成及抑菌活性研究
Pub Date : 2016-10-23 DOI: 10.1155/2016/6046232
M. Badawy, E. Rabea
Five products of -(6-carboxyl cyclohex-3-ene carbonyl) chitosan as antimicrobial agents were prepared by reaction of chitosan with tetrahydrophthalic anhydride (THPA) at different degrees of substitution (DS). The antimicrobial activity was evaluated against four plant bacteria and eight fungi. The results proved that the inhibitory property and water solubility of the synthesized chitosan derivatives, with increase of the DS, exhibited a remarkable improvement over chitosan. The product with a DS of 0.40 was the most active one with MIC of 510, 735, 240, and 385 mg/L against Erwinia carotovora, Ralstonia solanacearum, Rhodococcus fascians, and Rhizobium radiobacter, respectively, and also in mycelial growth inhibition against Alternaria alternata (EC50 = 683 mg/L), Botrytis cinerea (EC50 = 774 mg/L), Botryodiplodia theobromae (EC50 = 501 mg/L), Fusarium oxysporum (EC50 = 500 mg/L), F. solani (EC50 = 260 mg/L), Penicillium digitatum (EC50 = 417 mg/L), Phytophthora infestans (EC50 = 298 mg/L), and Sclerotinia sclerotiorum (EC50 = 763 mg/L). These compounds based on a biodegradable and biocompatible chitosan could be used as potentially antimicrobial agents in crop protection instead of hazardous synthetic pesticides.
以不同取代度的邻苯二甲酸四氢酐(THPA)为原料,制备了5种-(6-羧基环己基-3-烯羰基)壳聚糖抗菌剂。测定了其对4种植物细菌和8种真菌的抑菌活性。结果表明,随着DS的增加,合成的壳聚糖衍生物的抑制性能和水溶性比壳聚糖有显著提高。该产物的抑菌活性为0.40,抑菌MIC分别为510、735、240、385 mg/L,抑菌效果最佳,抑菌MIC分别为胡萝卜葡萄球菌、茄青霉、葡萄红球菌和放射线根瘤菌,抑菌效果也较好,抑菌效果分别为:交替孢霉(EC50 = 683 mg/L)、葡萄灰霉病菌(EC50 = 774 mg/L)、茶树芽孢杆菌(EC50 = 501 mg/L)、尖孢镰刀菌(EC50 = 500 mg/L)、茄青霉(EC50 = 260 mg/L)、指状青霉(EC50 = 417 mg/L)。疫霉(Phytophthora infestans, EC50 = 298 mg/L)和菌核菌(Sclerotinia sclerotiorum, EC50 = 763 mg/L)。这些化合物基于可生物降解和生物相容性的壳聚糖,可以作为潜在的抗菌剂来替代有害的合成农药。
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引用次数: 4
Biosynthesis and Biological Activity of Carbasugars 碳糖的生物合成及生物活性研究
Pub Date : 2016-07-31 DOI: 10.1155/2016/4760548
Silvia Roscales, J. Plumet
The first synthesis of carbasugars, compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene moiety, was described in 1966 by Professor G. E. McCasland’s group. Seven years later, the first true natural carbasugar (5a-carba-R-D-galactopyranose) was isolated from a fermentation broth of Streptomyces sp. MA-4145. In the following decades, the chemistry and biology of carbasugars have been extensively studied. Most of these compounds show interesting biological properties, especially enzymatic inhibitory activities, and, in consequence, an important number of analogues have also been prepared in the search for improved biological activities. The aim of this review is to give coverage on the progress made in two important aspects of these compounds: the elucidation of their biosynthesis and the consideration of their biological properties, including the extensively studied carbapyranoses as well as the much less studied carbafuranoses.
碳糖的第一次合成是在1966年由G. E. McCasland教授的小组描述的,碳糖是一种单糖环上的氧被亚甲基取代的化合物。七年后,第一个真正的天然碳糖(5a-碳- r - d -半乳糖糖)从链霉菌sp. MA-4145的发酵液中分离出来。在接下来的几十年里,碳糖的化学和生物学得到了广泛的研究。这些化合物中的大多数显示出有趣的生物学特性,特别是酶抑制活性,因此,在寻找改进的生物活性方面也制备了大量类似物。本文综述了这类化合物的两个重要方面的研究进展:对其生物合成的阐述和对其生物学特性的考虑,包括研究广泛的碳吡喃糖和研究较少的碳吡喃糖。
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引用次数: 22
Dissolution of (1-3),(1-4)-β-Glucans in Pressurized Hot Water: Quantitative Assessment of the Degradation and the Effective Extraction (1-3),(1-4)-β-葡聚糖在加压热水中的溶解:降解和有效提取的定量评价
Pub Date : 2016-05-17 DOI: 10.1155/2016/2189837
Ó. Benito-Román, A. Martín-Cortés, M. J. Cocero, E. Alonso
The purpose of this work was to study the behavior of (1-3)(1-4)-β-D-glucan in pressurized hot water. For this purpose, solid β-glucan (450 kDa) was put in water and heated at different temperatures (120, 150, and 170°C) for different times (5 to 360 minutes). At 120°C it was found that the highest soluble β-glucan concentration was measured after 60 minutes; at 150 and 170°C optimal times were 45 and 20 minutes, respectively. The maximum amount of β-glucan dissolved in each of the optimal conditions was 1.5, 2.2, and 2.0 g/L, respectively. Under those conditions an important reduction was observed in the molecular weight: at 120°C and 60 min it was 63 kDa; at 150°C and 45 min it was reduced down to 8 kDa; and at 170°C and 20 min it was only 7 kDa. Besides this reduction in the MW some hydrolysis products, such as glucose and HMF, were observed. These results revealed the convenience of using PHW to dissolve β-glucans since the operation times, compared to the conventional process (55°C, 3 h), were reduced despite the fact that the MW was significantly reduced once the β-glucan was dissolved; therefore, PHW can be used to extract β-glucans from barley under controlled conditions in order to prevent severe degradation.
研究了(1-3)(1-4)-β- d -葡聚糖在高压热水中的行为。为此,将固体β-葡聚糖(450 kDa)放入水中,在不同温度(120、150、170℃)下加热不同时间(5 ~ 360分钟)。在120℃下,60分钟后β-葡聚糖的可溶性浓度最高;在150°C和170°C时,最佳时间分别为45分钟和20分钟。各优化条件下β-葡聚糖的最大溶出量分别为1.5、2.2和2.0 g/L。在这些条件下,观察到分子量的显著降低:在120°C和60 min时,分子量为63 kDa;在150℃、45 min时降至8 kDa;在170°C和20 min时仅为7 kDa。除了分子量的降低外,还观察到一些水解产物,如葡萄糖和HMF。这些结果表明,使用PHW溶解β-葡聚糖的便利性,因为与常规工艺(55℃,3 h)相比,操作时间减少了,尽管一旦β-葡聚糖溶解,MW显著降低;因此,PHW可以在控制条件下从大麦中提取β-葡聚糖,以防止严重降解。
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引用次数: 9
Total Chlorine-Free Bleaching of Populus deltoides Kraft Pulp by Oxone Oxone对杨木硫酸盐浆的全无氯漂白研究
Pub Date : 2015-08-12 DOI: 10.1155/2015/381242
Mohsen Miri, A. Ghasemian, H. Resalati, F. Zeinaly
Since the bleaching process is one of the most important environmental pollutant stages in the pulp and paper industry, here, the total chlorine-free (TCF) bleaching of poplar kraft pulp by applying Oxone and peroxide under alkaline conditions has been investigated. The pulp samples were bleached in two stages of Oxone () treatment using an A sequence (A: acid pretreatment), and then the treated pulps were bleached by peroxide (P) to achieve target brightness (about 80%). The influence of various reaction parameters such as alkali charge, temperature, reaction time, and bleaching agent dosage was optimized. The final achieved brightness was more than 78%. Accelerated aging experiments showed more stability in brightness for the Oxone treated pulp, because alkali Oxone bleaching stops thermal degradation. Similarly, the AP bleaching sequence was found to be effective in regaining some strength that had been lost during acidification of the pulp. Improvement in pulp strength made with acid treatment was achieved along with significant amount of lignin removal and it demonstrates the feasibility of Oxone in TCF bleaching. Furthermore, other results indicated the feasibility of Oxone bleaching as an environmentally favorable alternative TCF bleaching sequence, compared with elemental chlorine-free bleaching approaches and also other TCF bleaching sequences.
由于漂白过程是制浆造纸工业中最重要的环境污染阶段之一,本文研究了在碱性条件下使用氧酮和过氧化物对杨木硫酸盐纸浆进行全无氯(TCF)漂白。纸浆样品采用A顺序(A:酸预处理)在Oxone()处理的两个阶段进行漂白,然后经过过氧化氢(P)漂白,达到目标亮度(约80%)。优化了碱量、温度、反应时间、漂白剂用量等参数对反应效果的影响。最终实现的亮度达到78%以上。加速老化实验表明,碱氧化纸浆的亮度更稳定,因为碱氧化纸浆的热降解停止。同样,发现AP漂白序列对恢复在纸浆酸化过程中失去的一些强度是有效的。酸处理提高了纸浆的强度,同时去除了大量的木质素,证明了Oxone在TCF漂白中的可行性。此外,其他结果表明,与单质无氯漂白方法和其他TCF漂白序列相比,Oxone漂白作为一种环境友好的TCF漂白序列的可行性。
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引用次数: 9
A New Generation of Glycoconjugated Azo Dyes Based on Aminosugars 基于氨基糖的新一代糖缀合偶氮染料
Pub Date : 2015-07-29 DOI: 10.1155/2015/235763
L. Guazzelli, G. Catelani, F. D’Andrea
The third generation of glycoconjugated azo dyes (GADs) was prepared linking monoazo dyes to 6-amino-6-deoxy-d-galactose or 6′amino-6′-deoxylactose through mixed amido-ester connections. The complementary conjugation reactions were studied using the succinyl derivative of either the acetal protected aminosugar or the azo dye. Target “naturalized” GADs were obtained after acid hydrolysis of the acetal protecting groups present on the sugar moiety.
通过混合酰胺-酯连接,制备了第三代糖偶氮染料(GADs)。用缩醛保护的氨基糖或偶氮染料的琥珀酰衍生物研究了互补偶联反应。目标“自然化”GADs是通过酸水解糖部分上的缩醛保护基团得到的。
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引用次数: 0
Physicochemical Properties and Antioxidant Activity of Chitin and Chitosan Prepared from Pacific White Shrimp Waste 太平洋白对虾废制备甲壳素和壳聚糖的理化性质及抗氧化活性研究
Pub Date : 2015-02-16 DOI: 10.1155/2015/706259
Trang Si Trung, H. N. D. Bao
Chitin and chitosan, valuable marine biopolymers, recovered from shrimp waste, are an abundant by-product of the shrimp processing industry in Vietnam, at an estimated 200000 metric tons per year. The obtained chitin and chitosan are characterized by their purity and functional properties. The polymers show good quality with low residual ash and protein content (<1%). The antioxidant potency of chitosan is evaluated by several different in vitro systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging, total reducing power, and inhibition of lipid peroxidation. The DPPH free radical scavenging, total reducing power, and lipid peroxidation inhibition activities of chitosan at varying concentration (0.125 to 1.0 mg/mL) range from 3.7 to 16.8%, 0.05 to 0.15, and 1.7 to 15.1%, respectively. This study demonstrates that chitin and chitosan, of good quality and having characteristics compatible with a broad range of applications, can be prepared from white shrimp waste.
几丁质和壳聚糖是宝贵的海洋生物聚合物,从虾的废料中回收,是越南虾加工工业的丰富副产品,估计每年有20万吨。所制得的几丁质和壳聚糖纯度高,功能性能好。聚合物质量好,残灰分低,蛋白质含量<1%。壳聚糖的抗氧化能力是通过几种不同的体外系统来评估的,包括1,1-二苯基-2-picrylhydrazyl (DPPH)自由基清除能力、总还原能力和脂质过氧化抑制能力。不同浓度(0.125 ~ 1.0 mg/mL)的壳聚糖对DPPH自由基的清除率、总还原力和脂质过氧化抑制活性分别为3.7 ~ 16.8%、0.05 ~ 0.15和1.7 ~ 15.1%。本研究表明,利用白对虾废料制备甲壳素和壳聚糖具有良好的品质和广泛的应用特性。
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引用次数: 73
Structure of a Rhamnogalacturonan Fragment from Apple Pectin: Implications for Pectin Architecture 苹果果胶中鼠李糖半乳乳酸片段的结构及其对果胶结构的意义
Pub Date : 2014-12-14 DOI: 10.1155/2014/347381
Xiangmei Wu, A. Mort
A commercial apple pectin was sequentially digested with the cloned enzymes endopolygalacturonase, galactanase, arabinofuranosidase, xylogalacturonase, and rhamnogalacturonan hydrolase. The rhamnogalacturonan hydrolase-generated oligosaccharides were separated by ultrafiltration, anion exchange, and size-exclusion chromatography. Fractions from the ion exchange chromatography were pooled, lyophilized, and screened by MALDI-TOF MS. An oligosaccharide (RGP14P3) was identified and its structure, α-D-GalpA--α-L-Rhap--α-D-GalpA--α-L-Rhap--α-D-GalpA, determined by 1D and 2D NMR spectrometry. This oligosaccharide probably represents a direct connection between homogalacturonan and rhamnogalacturonan in pectin. Alternatively, it could indicate that the nonreducing end of rhamnogalacturonan starts with a galacturonic acid residue.
用克隆的酶内聚半乳糖醛酸酶、半乳糖醛酸酶、阿拉伯糖葡核苷酶、木糖半乳糖醛酸酶和鼠李糖半乳糖醛酸水解酶依次对商品苹果果胶进行酶解。采用超滤法、阴离子交换法和排阻色谱法分离鼠李糖半乳糖酸水解酶生成的低聚糖。用MALDI-TOF ms对离子交换色谱所得的组分进行池化、冻干和筛选,鉴定出低聚糖(RGP14P3),并通过1D和2D核磁共振谱测定其结构为α-D-GalpA—α-L-Rhap—α-D-GalpA—α-L-Rhap—α-D-GalpA。这种低聚糖可能代表了果胶中的半乳果糖酸和鼠李糖半乳果糖酸之间的直接联系。或者,它可能表明鼠李糖半乳糖醛酸的非还原端开始于半乳糖醛酸残基。
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引用次数: 15
Kinetics and Mechanism of Micellar Catalyzed Oxidation of Dextrose by N-Bromosuccinimide in H2SO4 Medium n -溴代琥珀酰亚胺在H2SO4介质中胶束催化氧化葡萄糖的动力学及机理
Pub Date : 2014-12-01 DOI: 10.1155/2014/783521
Minu Singh
Kinetics and mechanism of micellar catalyzed N-bromosuccinimide oxidation of dextrose in H2SO4 medium was investigated under pseudo-first-order condition temperature of 40°C. The results of the reactions studied over a wide range of experimental conditions show that NBS shows a first order dependence, fractional order, on dextrose and negative fractional order dependence on sulfuric acid. The determined stoichiometric ratio was 1 : 1 (dextrose : N-bromosuccinimide). The variation of Hg(OAC)2 and succinimide (reaction product) has insignificant effect on reaction rate. Effects of surfactants, added acrylonitrile, added salts, and solvent composition variation have been studied. The Arrhenius activation energy and other thermodynamic activation parameters are evaluated. The rate law has been derived on the basis of obtained data. A plausible mechanism has been proposed from the results of kinetic studies, reaction stoichiometry, and product analysis. The role of anionic and nonionic micelle was best explained by the Berezin’s model.
研究了胶束催化n -溴代琥珀酰亚胺在40℃准一级条件下在H2SO4介质中氧化葡萄糖的动力学和机理。在广泛的实验条件下研究的反应结果表明,NBS对葡萄糖呈一阶、分数阶依赖性,对硫酸呈负分数阶依赖性。测定的化学计量比为1:1(葡萄糖:n -溴琥珀酰亚胺)。Hg(OAC)2和琥珀酰亚胺(反应产物)的变化对反应速率的影响不显著。研究了表面活性剂、添加的丙烯腈、添加的盐类以及溶剂组成的变化对反应的影响。计算了Arrhenius活化能和其他热力学活化参数。根据所获得的数据推导出了速率定律。从动力学研究、反应化学计量学和产物分析的结果,提出了一个合理的机理。阴离子胶束和非离子胶束的作用用Berezin的模型最好地解释了。
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引用次数: 1
Thio-β-D-glucosides: Synthesis and Evaluation as Glycosidase Inhibitors and Activators 硫代β- d -糖苷:作为糖苷酶抑制剂和活化剂的合成和评价
Pub Date : 2014-08-21 DOI: 10.1155/2014/941059
Andrey V. Samoshin, I. Dotsenko, Nataliya M. Samoshina, A. Franz, V. Samoshin
Structurally simple 1-thio-β-D-glucopyranosides were synthesized and tested as potential inhibitors toward several fungal glycosidases from Aspergillus oryzae and Penicillium canescens. Significant selective inhibition was observed for α- and β-glucosidases, while a weak to moderate activation for α- and β-galactosidases.
合成了结构简单的1-硫代-β- d -葡萄糖吡喃苷,并对米曲霉和癌变青霉的几种真菌糖苷酶进行了潜在的抑制剂测试。对α-和β-葡萄糖苷酶有明显的选择性抑制,而对α-和β-半乳糖糖苷酶有弱至中度的激活。
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引用次数: 6
Twenty Traditional Algerian Plants Used in Diabetes Therapy as Strong Inhibitors of α-Amylase Activity 20种阿尔及利亚传统植物作为α-淀粉酶活性强抑制剂用于糖尿病治疗
Pub Date : 2014-08-05 DOI: 10.1155/2014/287281
Ihcen Khacheba, A. Djeridane, M. Yousfi
In the present work, we have studied the inhibitory effects of aqueous and alcoholic extracts of six Algerian medicinal plants known by their therapeutic virtues against diabetes. The total phenolic compounds content, assayed using Folin-Ciocalteu’s reagent, of the samples ranged from 0.183 mg/g to 43.088 mg/g and from 1.197 mg/g to 7.445 mg/g, expressed as gallic acid equivalent (GAE), for the, respectively, whereas the total flavonoids concentrations, detected using 2% of the aluminium chloride, ranged from 0.41 mg/g to 11.613 mg/g and from 0.0097 mg/g to 1.591 mg/g, expressed as rutin equivalents (RE), for the aqueous and methanolic extracts, respectively. The major plants were found to inhibit enzymatic activities of Aspergillus oryzae-amylase in a concentration dependent manner. The values of the inhibition constants () have been determined according to the Dixon and Lineweaver-Burk methods. The results showed that the values were less than 55 ppm for the all extracts. A strong inhibition was found in the phenolic extract of Salvia officinalis with a of 8 ppm.
在目前的工作中,我们研究了六种阿尔及利亚药用植物的水提取物和酒精提取物的抑制作用,这些植物因其治疗糖尿病的优点而闻名。用Folin-Ciocalteu试剂测定样品中总酚类化合物含量为0.183 mg/g ~ 43.088 mg/g, 1.197 mg/g ~ 7.445 mg/g,分别以没食子酸当量(GAE)表示;用2%氯化铝测定样品中总黄酮浓度为0.41 mg/g ~ 11.613 mg/g, 0.0097 mg/g ~ 1.591 mg/g,分别以芦丁当量(RE)表示。主要植物对米曲霉淀粉酶活性的抑制呈浓度依赖性。根据Dixon和Lineweaver-Burk方法确定了抑制常数()的值。结果表明,各提取液的含量均小于55 ppm。结果表明,丹参酚类提取物在浓度为8 ppm时具有较强的抑制作用。
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引用次数: 19
期刊
International Journal of Carbohydrate Chemistry
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