- Chain conformations and steady-shear viscosity properties of pectic polysaccharides from apple and tomato
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In this study, apple pectin (AP) and tomato pectin (TP) were demonstrated to be a high-ester (74.8%) polysaccharide with the weight-average molecular weight (Mw) of ~ 243 kDa and a low-ester (45.9%) polysaccharide with the Mw of ~ 19 kDa, respectively. The semi-rigid chain conformations of pectic polysaccharides in NaNO3 aqueous solution were deduced according to the Smidsr?d “B values” of AP (0.025) and TP (0.029), while AP and TP exhibited higher stiffness in water due to the electric repulsion of carboxyl groups, which was visually observed by AFM images. Under steady shear, the shear-thickening behaviors of AP and TP in NaNO3 aqueous solutions were observed in the shear rate range of ?1, which were attributed to the disruption of the ordered arrangement induced by semi-rigid pectin chains into randomly entangled structure by weak shear force. AP exhibited stronger shear-thickening behavior due to the formation of more entanglements resulted from the higher Mw and longer side chains highly branched at rhamngalacturonan region. This study provides the scientific basis for the construction of the relationship of steady-shear property with chain conformation and molecular weight of pectin.
- Hu, Shihao,Nie, Shaoping,Wang, Junqiao,Wang, Qiang,Xu, Xiaojuan
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- A novel acid polysaccharide from Boletus edulis: extraction, characteristics and antitumor activities in vitro
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A novel cold-water-soluble polysaccharide (BEP), with a molecular weight of 6.0 × 106?Da, was isolated from Boletus edulis. BEP consists of galactose, glucose, xylose, mannose, glucuronic, and galacturonic acid in a ratio of 0.34:0.28:0.28:2.57:1.00:0.44. The IR results showed that BEP was an acid polysaccharide, containing α-type and β-type glucoside bonds. MTT assay showed BEP could inhibit cell proliferation significantly. Morphological observation demonstrated that BEP-treated MDA-MB-231 and Ca761 cells exhibited typical apoptotic morphological features. Flow cytometry analysis revealed that BEP caused mitochondrial membrane potential collapse. Annexin V-FITC/PI staining indicated that BEP induced apoptosis of MDA-MB-231 and Ca761 cells through cell block in S phase and G0/G1 phase, respectively. Western blot results showed that BEP could increase the Bax/Bcl-2 ratios, promote the release of cytochrome C, and activate the expression of caspase-3 and caspase-9 in MDA-MB-231 and Ca761 cells. In conclusion, our results demonstrated that BEP could inhibit the proliferation of breast cancer cells and induce apoptosis through mitochondrial pathways.
- Meng, Ting,Yu, Sha-sha,Ji, Hai-yu,Xu, Xiao-meng,Liu, An-jun
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- A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential
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The novel natural low-molecular-mass polysaccharide (SLWPP-3) from pumpkin (Cucurbia moschata) was separated from the waste supernatant after macromolecular polysaccharide production and purified using a DEAE cellulose-52 column and gel-filtration chromatography. Chemical and instrumental studies revealed that SLWPP-3 with a molecular mass of 3.5 kDa was composed of rhamnose, glucose, arabinose, galactose and uronic acid with a weight ratio of 1: 1: 4: 6: 15, and primarily contained →3,6)-β-D-Galp-(1→, →4)-α-GalpA-(1→(OMe), →4)-α-GalpA-(1→, →2,4)-α-D-Rhap-(1→, →3)-β-D-Galp-(1→, →4)-α-D-Glcp, and →4)-β-D-Galp residues in the backbone. The branch chain passes were connected to the main chain through the O-4 atom of glucose and O-3 atom of arabinose. Physiologically, the ability of SLWPP-3 to inhibit carbohydrate-digesting enzymes and DPPH and ABTS radicals, as well as protect pancreatic β cells from oxidative damage by decreasing MDA levels and increasing SOD activities, was confirmed. The findings elucidated the structural types of pumpkin polysaccharides and revealed a potential adjuvant natural product with hypoglycemic effects.
- Huang, Linlin,Li, Fei,Li, Quanhong,Liang, Li,Wei, Yunlu,Yu, Guoyong
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- Novel polysaccharide from Chaenomeles speciosa seeds: Structural characterization, α-amylase and α-glucosidase inhibitory activity evaluation
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Purification and structural characterization of a novel polysaccharide fraction from Chaenomeles speciosa seeds were investigated. After hot water extraction and ethanol precipitation, the crude polysaccharide was sequentially purified with Cellulose DEAE-52 and gel-filtration chromatography, and a highly purified polysaccharide fraction (F3) was obtained. The structure of F3 was characterized by high-performance gel permeation chromatography (HPGPC), high performance liquid chromatography (HPLC), ultraviolet-visible (UV), Fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR) spectrum, together with methylation, scanning electron microscopy (SEM), atomic force microscope (AFM), and Congo-red test analysis. The results indicated that F3 was a homogeneous polysaccharide fraction with a molecular weight of 8.65 × 106 Da, and it was composed of Rha, GlcA, Gal, and Ara in a molar ratio of 6.34:5.73:47.14:40.13. The backbone of F3 was consisted of →3,6)-Galp-(1→, and the side chains of F3 were composed of Araf-(1→, →4)-GlcpA-(1→, →4)-Galp-(1→ and →3)-Rhap-(1→. The hypoglycemic assays demonstrated F3 had good α-amylase and α-glucosidase inhibition activities, and their IC50 values were 6.24 mg/mL and 4.59 mg/mL respectively. Thus, the polysaccharide from Chaenomeles speciose could be applied as a potential natural source in retarding postprandial hyperglycemia effects.
- Cheng, Jiang,Deng, Yejun,Huang, Lixin,Liu, Lujie,Wang, Xiang,Xie, Pujun,Zhang, Caihong
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p. 755 - 766
(2020/03/18)
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- Chemical characterization and antioxidant activities of polysaccharides isolated from the stems of Parthenocissus tricuspidata
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Four polysaccharides, PTP–1, PTP–2, PTP–3 and PTP–4, were obtained from the water extraction of the stems of P. tricuspidata by anion exchange chromatography and gel filtration. The antioxidant activities of four PTPs were investigated, exhibiting different antioxidant activities, in which PTP?4 performed noticeable, with strong superoxide radical activity (comparable to BHT), high DPPH radical activity (78.53% at 1250 μg/mL), moderate hydroxyl radical scavenging activity and reducing power activity. Furthermore, the chemical structure of PTP?4 was measured by FT-IR, GC, 1H and 13C NMR spectra, indicating its mainly composition of the arabinose, xylose, galactose, glucuronic acid, and mannose. Thus, the stems of P. tricuspidata could be used as a potential source for natural antioxidant.
- Liang, Xiaoxia,Gao, Yingying,Fei, Wenbo,Zou, Yuanfeng,He, Min,Yin, Lizi,Yuan, Zhixiang,Yin, Zhongqiong,Zhang, Wei
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- Saponins from European Licorice Roots (Glycyrrhiza glabra)
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European licorice roots (Glycyrrhiza glabra), used in the food and beverage industry due to their distinctive sweet and typical licorice flavor, were fractionated, with the triterpenoid saponins isolated and their chemical structures determined by means o
- Schmid, Christian,Dawid, Corinna,Peters, Verena,Hofmann, Thomas
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p. 1734 - 1744
(2018/09/10)
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- A cytotoxic flavonol glycoside from Melaleuca leucadendra leaves extract with immunostimulant activity
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Leaves of Melaleuca leucadendra contain the novel flavonol glycoside, myricetin 3-O-β-4C1-galactopyranuronoid. In addition, known fifteen phenolics were identified. All isolates are characterized for the first time from this plant. Structures were established by conventional methods and confirmed by spectral methods of analysis, including one and two-dimensional nuclear magnetic resonance spectroscopy (1D and 2D-NMR) and high resolution electro-spray ionization mass spectrometry (HRESIMS), as well. Assessment of some immunological and biological efficacy, of the extract in combination with a parallel cytotoxicity evaluation, using the method of cellular reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) technique was carried out. Besides, evaluation of the antioxidant effectiveness, using the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the oxygen radical absorption capacity (ORAC) methods was performed. In addition, the cytotoxicity against liver (Huh-7), breast (MCF-7) and prostate (PC-3) cancers using the neutral red assay (NRU) technique for the extract and the new flavonol glycoside also, was assessed.
- Hashim,Swilam,Moustafa,Bakry,Labib,Barakat,Singab,Linscheid,Nawwar
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- Dhasingreoside: New flavonoid from the stems and leaves of Gaultheria fragrantissima
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A new flavonoid, dhasingreoside (1) and seven known compounds, quercetin 3-O-β-d-galacturonopyranoside (2), quercetin 3-O-β-d-galactopyranoside (3), quercetin 3-O-β-d-glucuronopyranoside (4), quercetin 3-O-α-l-rhamnopyranoside (5), (-)-epicatechin (6), salicylic acid (7) and gaultherin (8), have been isolated from the shade-dried stems and leaves of Gaultheria fragrantissima, commonly known as Dhasingre in Nepal. The structures were elucidated on the basis of physical, chemical and spectroscopic methods. Among known compounds, five compounds (3-6 and 8) were isolated for the first time from G. fragrantissima. In vitro antioxidant activity of all the isolated compounds was evaluated by 1,1-diphenyl-2-picrylhydrazyl free radical-scavenging assay. Dhasingreoside (1) and other compounds (2-6) showed significant free radical-scavenging activity.
- Cong, Fei,Joshi, Khem Raj,Devkota, Hari Prasad,Watanabe, Takashi,Yahara, Shoji
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p. 1442 - 1448
(2015/03/05)
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- Effects of polysaccharide on chicks co-infected with Bordetella avium and Avian leukosis virus
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Chicks' co-infection with immunosuppressive virus and bacteria seriously threaten the development of the poultry industry. In this study, a model was established in which chicks were injected with either subgroup B ALV (ALV-B) + Bordetella avium (B. avium), or ALV-B + B. avium + Taishan Pinus massoniana pollen polysaccharide (TPPPS), or B. avium only, or B. avium + TPPPS. The data showed that the group injected with ALV-B and B. avium exhibited significant inhibition of the immune function and therefore increased pathogenicity compared with the group injected with B. avium-only. Application of TPPPS effectively alleviated immunosuppression, and body weights increased sharply in the TPPPS groups compared with non-TPPPS groups. To some extent, TPPPS may reduce the proliferation of ALV-B. These results suggest that Pinus pollen polysaccharides are beneficial treating co-infections with immunosuppressive virus and bacteria and therefore have potential for development into safe and effective immunoregulator.
- Guo, Fanxia,Xue, Cong,Wu, Cun,Zhao, Xue,Qu, Tinghe,He, Xiaohua,Guo, Zhongkun,Zhu, Ruiliang
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- Analysis of compositional carbohydrates in polysaccharides and foods by capillary zone electrophoresis
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A simple, sensitive and specific analytical method has been established for high efficient separation and simultaneously high sensitive determination of thirteen reducing carbohydrates, including aldohexose and aldopentoses as well as maltose and lactose. Reducing carbohydrates were derivatized with 1-phenyl-3-methyl-5-pyrazolone (PMP), separated by capillary zone electrophoresis (CZE) with use of methanol modifier in 175 mM borate buffer (pH 11.0), and detected by UV at 245 nm. The optimized CZE method was found to be well suited to examine the compositional reducing monosaccharides of the isolated polysaccharides from Lycopus lucidus and Jujube, and free mono- and disaccharides in beer and milk. Quantitative recoveries of the compositional carbohydrates in the samples were in the range of 93.2-104.0%, and RSD values ranged from 2.9% to 4.9%. The developed CZE method proves to be precise and practical for quality control of reducing carbohydrates, and will provide more highly efficient separation in food analysis in the future.
- Wang, Tong,Yang, Xingbin,Wang, Dongying,Jiao, Yadong,Wang, Yu,Zhao, Yan
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experimental part
p. 754 - 762
(2012/06/16)
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- Characterization of ulvan extracts to assess the effect of different steps in the extraction procedure
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An effective application development of the polysaccharide ulvan requires a comprehensive knowledge about the influence of the extraction process on composition of the extracts and in ulvan itself. In this context, the two main objectives of the present work are (1) the establishment of an efficient extraction process for ulvan and (2) development of an accurate characterization methodology to evaluate the extract composition and ulvan content. Three ulvan-rich extracts obtained by different schemes of extraction were studied. The methodology for the analysis was improved and a detailed analysis of extracted ulvan was provided. The polysaccharide is rich in ulvanobiuronic acid 3-sulfate type A [→4)-β-d-GlcAp-(1 → 4)-α-l-Rhap 3S-(1→], with minor amounts of ulvanobiuronic acid 3-sulfate type B [→4)-α-l-IdoAp-(1 → 4)-α-l-Rhap 3S-(1→]. The extract with the higher degree of purification is a high molecular weight polysaccharide (790 kDa) composed of rhamnose (22.4%), glucuronic acid (22.5%), xylose (3.7%), iduronic acid (3.1%) and glucose (1.0%). It is highly sulfated (32.2%) and contains 1.3% of proteins and 10.3% of inorganic material. Applying simple extraction scheme it was possible to obtain an extract from green algae with high content of ulvan without affecting the overall chemical structure of the polysaccharide.
- Costa, Carina,Alves, Anabela,Pinto, Paula R.,Sousa, Rui A.,Borges Da Silva, Eduardo A.,Reis, Rui L.,Rodrigues, Alírio E.
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experimental part
p. 537 - 546
(2012/06/15)
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- HYBRID COMPOUNDS BASED ON POLYOL(S) AND AT LEAST ONE OTHER MOLECULAR ENTITY, POLYMERIC OR NON-POLYMERIC, IN PARTICULAR OF THE POLYORGANOSILOXANE TYPE, PROCESS FOR THE PREPARATION THEREOF, AND APPLICATIONS THEREOF
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The invention relates to novel hybrid compounds comprising at least one polyon entity (Po)—for example oligomer or polymer—in which at least one of the hydroxyl functions of Po is substituted by at least one entity A that can be of a variable nature, for example polymer (e.g. polyorganosiloxane-POS), hydrocarbonated or mineral. The bond Ro between the entity Po and the entity A is obtained by means of “click chemistry” and corresponds to formula (II.1) or (II.2), Z representing —CH— or —N—. A is an entity selected from the group comprising the various polyols of Po, polyorganosiloxanes (POS), polyalkylene glycols, polyamides, polyesters, polystyrenes, alkyls, alkenyls, alkynyls, aryls, and combinations thereof, in addition to mineral materials such as silica and the combinations thereof. Said hybrid components can be used as emulsifiers, especially for cosmetics.
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- Process for the extraction of an active principle from tournesol, active principle obtained, and composition active against aging of the skin
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The object of the invention covers an extraction process for an active principle having anti-radical and anti-glycolation action to counter cutaneous aging. The invention also covers the obtained active principle, the cosmetic compositions using this active principle, and a process for countering aging.
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- The preparation and susceptibility to hydrolysis of novel O-galacturonoyl derivatives of carbohydrates
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D-Galacturonic acid or (1->4)-α-D-galacturonan reacted in aqueous pyridine in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide with alcohols to yield esters.The alcohols that gave high yields of D-galacturonoyl derivatives were primary and included methanol, ethanol, 1-propanol, D-glucose, D-galactose, methyl β-D-glucopyranoside, methyl β-D-galactopyranoside, and cellulose.D-Galacturonic acid itself readily gave an O-D-galacturonoyl-D-galacturonic acid.The proposed structure of one compound, methyl 6-O-D-galacturonoyl-β-D-glucopyranoside, was supported by 1H and 13C NMR data and the FAB mass-spectral data.Each ester was hydrolysed at pH 11 and 25 deg C within 1 h.O-D-Galacturonoyl-D-glucose was considerably more alkali labile than O-polygalacturonoyl-D-glucose, and O-D-galacturonoylcellulose had an intermediate stability.The esters were relatively stable to cold acid, but could be hydrolysed by M trifluoroacetic acid at 100 deg C for 1 h.The esters tested were resistant to digestion by "Driselase", although the glycosidic bonds of O-polygalacturonoyl D-glucose were hydrolysed to yield O-oligogalacturonoyl-D-glucoses of low molecular weight.The possible application of these analytical methods to the detection of O-uronoyl-type cross-links in cell-wall polysaccharides is discussed.
- Brown, John A.,Fry, Stephen C.
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- Preparation having excellent absorption property
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A preparation containing an absorption promoter selected from specific classes of water-soluble macromolecular compounds having chelating activity, preferably in the presence of a salt at a concentration such that the composition exhibits higher osmotic pressure than isotonic sodium chloride solution, and a medicine is found to promote absorption of the medicine through a gastrointestinal organ such as the colon, rectum, or vagina.
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- Acylated oligosaccharides from Klebsiella K63 capsular polysaccharide: depolymerization by partial hydrolysis and by bacteriophage-borne enzymes.
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The extracellular polysaccharide from Klebsiella K63 is unique in having acetic and formic ester groups attached to the D-galactopyranosyluronic residues in the trisaccharide repeating-sequence. These O-acyl substituents are shown to be somewhat resistant to mild hydrolysis by both acid and alkali. Bacteriophage-induced depolymerization of the polysaccharide generated a series of acylated oligosaccharides comprising one, or more, repeating unit(s). By mild hydrolysis with acid, the same series of oligomers was released from the polysaccharide, together with the corresponding non-acylated compounds and the expected acylated and non-acylated aldobiouronic acids. A study of these oligosaccharides, as well as of a number of their related compounds, is described, with particular emphasis on the methods used to locate the formic and acetic ester groups. The location of the O-acyl substituents on the galactosyluronic residues was further supported by the results obtained from the high-resolution, 400-MHz, p.m.r. spectra and 13C-n.m.r. spectra of a number of the oligosaccharides.
- Dutton,Merrifield
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p. 107 - 128
(2007/10/02)
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