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Special Issue "Polysaccharides: Organic Chemistry, Bioactivity and Analysis, including Those from Medicinal Plants and Fungi"

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products".

Deadline for manuscript submissions: closed (1 June 2008)

Special Issue Editor

Guest Editor
Dr. Shao-ping Li (Website)

State Key Laboratory for Quality Control in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao SAR, China
Interests: extraction, isolation and determination of active ingredients, especially polysaccharides and volatile compounds, in Chinese herbs; methods development for quality control of Chinese herbs; active ingredients and product development of Cordyceps

Special Issue Information

Important additional information, Open Access:

This special issue will be fully Open Access with publishing fees paid by authors (see http://www.mdpi.org/oaj-supports.htm). Open Access increases publicity and promotes more frequent citations as indicated by several studies. (Added on 9 November 2007)
Leading Papers (most of these are review papers):
  1. Mazumder, S.; Lerouge, P.; Loutelier-Bourhis, C.; Driouich, A.; Ray, B. Structural characterisation of hemicellulosic polysaccharides from Benincasa hispida using specific enzyme hydrolysis, ion exchange chromatography and MALDI-TOF mass spectroscopy. Carbohydr. Polym. 2005, 59, 231–238.
  2. Xu, H.; Zhang, Y.Y.; Zhang, J.W.; Chen, D.F.. Int. J. Immunopharmacol. 2007, 7, 175–182.
  3. Omarsdottir, S.; Petersen, B.O.; Paulsen, B.S.; Togola, A.; Duusb, J.; Olafsdottir, E.S. Carbohydr. Res. 2006, 341, 2449–2455.
  4. Jia, L.M.; Liu, L.; Dong, Q.; Fang, J.N.. Carbohydr. Res. 2004, 339, 2667-2671.
  5. Ga, O.G.de; Martıneza, M.; Sanabria, L.; Pinto, G.L.de; Igartuburu, J.M.. Food Hydrocol. 2005, 19, 37–43.
  6. Reis, R.A.; Tischer, C.A.; Gorin, P.A.J.; Iacomini, M.. FEMS Microbiol. Lett. 2002, 210, 1-5.
  7. Yang, J.H.; Du, Y.M.; Huang, R.H.; Wan, Y.Y.; Li, T.Y.. Int. J. Biol. Macromol. 2002, 31, 55-62.
  8. Barton, C.J.; Tailford, L.E.; Welchman, H.; Zhang, Z.; Gilbert, H.J.; Dupree, P.; Goubet, F.. Planta 2006, 224, 163–174.
  9. Wang, Q.J.; Fang, Y.Z.. J. Chromatogr. B 2004, 812, 309–324.
  10. Zhang, M.; Cui, S.W.; Cheung, P.C.K.; Wang, Q.. Trends Food Sci. Tech. 2007, 18, 4-19.
  11. Volpi, N.; Maccari, F.. J. Chromatogr. B 2006, 834, 1–13.
  12. Paulsen, B.S.; Olafsdottir, E.S.; Ingolfsdottir, K.. J. Chromatogr. A 2002, 967, 163–171.
  13. Lo, T.C.T.; Jiang, Y.H.; Chao, A.L.J.; Chang, C.A.. Anal. Chimica. Acta 2007, 584, 50–56.
  14. Ban, E.; Choi, O.; Ryu, J.; Yoo, Y.S.. Electrophoresis 2001, 22, 2217–2221.
  15. Hui,C.W.; Di, X.. J. Chromatogr. B 2004, 812, 241–257.
  16. Li, S.P.; Zhang, G.H.; Zeng, Q.; Huang, Z.G.; Wang, Y.T.; Dong, T.T.X.; Tsim, K.W.K.. Phytomedicine 2006, 13, 428-433.
  17. Lin, Z.B.; Zhang, H.N.. Acta. Pharmacol. Sin. 2004, 25, 1387-1395.
  18. Schepetkin, I.A.; Quinn, M.T.. Int. J. Immunopharmacol. 2006, 6, 317– 333.
  19. Chen, J.R.; Hu, T.J.; Zheng, R.L.. Int. J. Immunopharmacol. 2007, 7, 547–553.
  20. Lin, Y.L.; Zhang, L.N.; Chen, L.; Jin, Y.; Zeng, F.B.; Jin, J.; Wan, B.; Cheung, P.C.K.. Int. J. Biol. Macromol. 2004, 34, 231–236.

Keywords

  • organic chemistry
  • chemical characteristic
  • analysis
  • medicinal chemistry
  • material science
  • biomaterials
  • bioassay
  • pharmacological activity
  • medicinal plant
  • herb
  • herbal medicine
  • chinese medicine
  • fungus
  • mushroom

Published Papers (12 papers)

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Research

Jump to: Review

Open AccessArticle Molecular Weight and Monosaccharide Composition of Astragalus Polysaccharides
Molecules 2008, 13(10), 2408-2415; doi:10.3390/molecules13102408
Received: 22 August 2008 / Revised: 24 September 2008 / Accepted: 26 September 2008 / Published: 1 October 2008
Cited by 17 | PDF Full-text (298 KB) | HTML Full-text | XML Full-text
Abstract
Two polysaccharides (APS-I and APS-II) were isolated from the water extract of Radix Astragali and purified through ethanol precipitation, deproteination and by ion-exchange and gel-filtration chromatography. Their molecular weight was determined using high performance liquid chromatography and gel permeation chromatography (HPLC-GPC) and [...] Read more.
Two polysaccharides (APS-I and APS-II) were isolated from the water extract of Radix Astragali and purified through ethanol precipitation, deproteination and by ion-exchange and gel-filtration chromatography. Their molecular weight was determined using high performance liquid chromatography and gel permeation chromatography (HPLC-GPC) and their monosaccharide composition was analyzed by TLC and HPLC methods, using a refractive index detector (RID) and an NH2 column. It was shown that APS-I consisted of arabinose and glucose and APS-II consisted of rhamnose, arabinose and glucose, in a molar ratio of 1:3.45 and 1:6.25:17.86, respectively. The molecular weights (Mw) of APS-I and APS-II were 1,699,100 Da and 1,197,600 Da, respectively. Full article
Figures

Open AccessArticle Structure Determination of β-Glucans from Ganoderma lucidum with Matrix-assisted Laser Desorption/ionization (MALDI) Mass Spectrometry
Molecules 2008, 13(8), 1538-1550; doi:10.3390/molecules13081538
Received: 26 May 2008 / Revised: 21 June 2008 / Accepted: 25 July 2008 / Published: 3 August 2008
Cited by 20 | PDF Full-text (481 KB) | HTML Full-text | XML Full-text
Abstract
A novel method that uses matrix-assisted laser desorption/ionization (MALDI) mass spectrometry to analyze molecular weight and sequencing of glucan in Ganoderma lucidum is presented. Thus, β-glucan, which was isolated from fruiting bodies of G. lucidum, was measured in a direct and [...] Read more.
A novel method that uses matrix-assisted laser desorption/ionization (MALDI) mass spectrometry to analyze molecular weight and sequencing of glucan in Ganoderma lucidum is presented. Thus, β-glucan, which was isolated from fruiting bodies of G. lucidum, was measured in a direct and fast way using MALDI mass spectrometry. In addition, tandem mass spectrometry of permethylated glucans of G. lucidum, dextran, curdlan and maltohexaose were also pursued and different fragment patterns were obtained. The G. lucidum glucan structure was determined and this method for linkage analysis of permethylated glucan has been proven feasible. Full article
Open AccessArticle Preparation of Chitosan from Brine Shrimp (Artemia urmiana) Cyst Shells and Effects of Different Chemical Processing Sequences on the Physicochemical and Functional Properties of the Product
Molecules 2008, 13(6), 1263-1274; doi:10.3390/molecules13061263
Received: 24 April 2008 / Revised: 8 May 2008 / Accepted: 9 May 2008 / Published: 6 June 2008
Cited by 36 | PDF Full-text (147 KB) | HTML Full-text | XML Full-text
Abstract
Chitosan (CS) was prepared from Artemia urmiana cyst shells using the same chemical process as described for the other crustacean species, with minor adjustments in the treatment conditions. The influence of modifications of the CS production process on the physiochemical and functional [...] Read more.
Chitosan (CS) was prepared from Artemia urmiana cyst shells using the same chemical process as described for the other crustacean species, with minor adjustments in the treatment conditions. The influence of modifications of the CS production process on the physiochemical and functional properties of the CS obtained was examined. The study results indicate that Artemia urmiana cyst shells are a rich source of chitin as 29.3-34.5% of the shell’s dry weight consisted of this material. Compared to crab CS (selected as an example of CS from a different crustacean source) Artemia CS exhibited a medium molecular weight (4.5-5.7 ×105 Da), lower degree of deacetylation (67-74%) and lower viscosity (29-91 centiposes). The physicochemical characteristics (e.g., ash, nitrogen and molecular weight) and functional properties (e.g., water binding capacity and antibacterial activity) of the prepared Artemia CSs were enhanced, compared to control and commercial samples, by varying the processing step sequence. Full article
Open AccessArticle Structural Patterns of Rhamnogalacturonans Modulating Hsp-27 Expression in Cultured Human Keratinocytes
Molecules 2008, 13(5), 1207-1218; doi:10.3390/molecules13051207
Received: 13 March 2008 / Revised: 19 May 1995 / Accepted: 19 May 2008 / Published: 27 May 2008
Cited by 5 | PDF Full-text (97 KB) | HTML Full-text | XML Full-text
Abstract
Polysaccharide extracts were obtained from chestnut bran (Castanea sativa), grape marc (Vitis vinifera) and apple marc (Malus spp.) and fractionated by size exclusion chromatography after endopolygalacturonase degradation. Compositional and linkage analyses by GC and GC-MS showed the characteristic rhamnogalacturonan structure with [...] Read more.
Polysaccharide extracts were obtained from chestnut bran (Castanea sativa), grape marc (Vitis vinifera) and apple marc (Malus spp.) and fractionated by size exclusion chromatography after endopolygalacturonase degradation. Compositional and linkage analyses by GC and GC-MS showed the characteristic rhamnogalacturonan structure with specific arabinan (apple marc) and type II arabinogalactan (chestnut bran, grape marc) side chains. Type II arabinogalactan rhamnogalacturonan from chestnut bran significantly stimulated the in vitro differentiation of human keratinocytes, giving evidence of a tight structure-function relationship. This molecule comprises short and ramified 3- and 3,6-β- D-galactan and 5- and 3,5-α-L-arabinan side chains, but also contains significant amounts of t-Xyl and 4-Xyl with a characteristic 2:1 ratio. Enzymatic hydrolysis of this polysaccharide produced fragments of lower molecular weight with unchanged xylose content which conserved the same ability to stimulate human keratinocyte differentiation. It could be then speculated that dimeric xylosyl-xylose and/or longer oligomeric xylose side chains attached to a galacturonan and closely associated to hairy rhamno-galacturonan domains are essential patterns that could determine the biological activity of pectins. Full article
Open AccessArticle The Influence of Hofmeister Series Ions on Hyaluronan Swelling and Viscosity
Molecules 2008, 13(5), 1025-1034; doi:10.3390/molecules13051025
Received: 28 February 2008 / Revised: 17 April 2008 / Accepted: 30 April 2008 / Published: 1 May 2008
Cited by 16 | PDF Full-text (488 KB) | HTML Full-text | XML Full-text
Abstract
The dissolution of hyaluronan in water leads to its degradation, and as a resultits molecular weight decreases. The degradation of hyaluronan is mainly influenced bytemperature, solution composition, and also its pH. This study describes the influence ofHofmeister series ions on hyaluronan behaviour [...] Read more.
The dissolution of hyaluronan in water leads to its degradation, and as a resultits molecular weight decreases. The degradation of hyaluronan is mainly influenced bytemperature, solution composition, and also its pH. This study describes the influence ofHofmeister series ions on hyaluronan behaviour and hyaluronan film swelling bysolutions of these ions. It was found that Hofmeister ions show lyotropic effectsinfluencing the entanglement of hyaluronan coils and their expansion from solid polymerfilms into swollen gel state. The hydrophobic and hydrophilic interactions in the structureof hyaluronan macromolecules are represented by the mutual diffusion coefficient D(c),the mean mutual diffusion coefficient Ds , the expansion work of coil swelling RAδ,s, theactivation enthalpy of diffusion connected with swelling HD,s and kinematic viscosity ofhyaluronan-ions solutions ν. Full article
Open AccessArticle Synthesis and Characterization of Konjac Glucomannan-Graft-Polyacrylamide via γ-Irradiation
Molecules 2008, 13(3), 490-500; doi:10.3390/molecules13030490
Received: 16 January 2008 / Revised: 20 February 2008 / Accepted: 20 February 2008 / Published: 1 March 2008
Cited by 20 | PDF Full-text (301 KB) | HTML Full-text | XML Full-text
Abstract
The synthesis of konjac glucomannan-graft-polyacrylamide (KGM-g-PAM) wascarried out at 25°C by γ-irradiation under a N2 atmosphere. The effects of absorbedradiation dosage and monomer concentration on grafting yield and water absorbency werestudied. The grafted copolymers were characterized using Fourier Transform Infrared(FTIR) spectroscopy, [...] Read more.
The synthesis of konjac glucomannan-graft-polyacrylamide (KGM-g-PAM) wascarried out at 25°C by γ-irradiation under a N2 atmosphere. The effects of absorbedradiation dosage and monomer concentration on grafting yield and water absorbency werestudied. The grafted copolymers were characterized using Fourier Transform Infrared(FTIR) spectroscopy, nuclear magnetic resonance (NMR), x-ray diffraction (XRD),thermogravimetric analysis (TGA) and gel permeation chromatography (GPC). Thegrafting yield was observed to increase with increasing absorbed dosage and monomerconcentration. Compared with the original KGM, the grafted copolymers exhibited betterthermal stability and water absorbency. The results suggest that γ-irradiation is convenientand efficient for inducing graft copolymerization of KGM and acrylamide (AM). Full article

Review

Jump to: Research

Open AccessReview Marine Derived Polysaccharides for Biomedical Applications: Chemical Modification Approaches
Molecules 2008, 13(9), 2069-2106; doi:10.3390/molecules13092069
Received: 26 May 2008 / Revised: 2 July 2008 / Accepted: 25 July 2008 / Published: 3 September 2008
Cited by 130 | PDF Full-text (1479 KB) | HTML Full-text | XML Full-text
Abstract
Polysaccharide-based biomaterials are an emerging class in several biomedical fields such as tissue regeneration, particularly for cartilage, drug delivery devices and gelentrapment systems for the immobilization of cells. Important properties of the polysaccharides include controllable biological activity, biodegradability, and their ability to [...] Read more.
Polysaccharide-based biomaterials are an emerging class in several biomedical fields such as tissue regeneration, particularly for cartilage, drug delivery devices and gelentrapment systems for the immobilization of cells. Important properties of the polysaccharides include controllable biological activity, biodegradability, and their ability to form hydrogels. Most of the polysaccharides used derive from natural sources; particularly, alginate and chitin, two polysaccharides which have an extensive history of use in medicine, pharmacy and basic sciences, and can be easily extracted from marine plants (algae kelp) and crab shells, respectively. The recent rediscovery of poly-saccharidebased materials is also attributable to new synthetic routes for their chemical modification, with the aim of promoting new biological activities and/or to modify the final properties of the biomaterials for specific purposes. These synthetic strategies also involve the combination of polysaccharides with other polymers. A review of the more recent research in the field of chemical modification of alginate, chitin and its derivative chitosan is presented. Moreover, we report as case studies the results of our recent work concerning various different approaches and applications of polysaccharide-based biomaterials, such as the realization of novel composites based on calcium sulphate blended with alginate and with a chemically modified chitosan, the synthesis of novel alginate-poly(ethylene glycol) copolymers and the development of a family of materials based on alginate and acrylic polymers of potential interest as drug delivery systems. Full article
Open AccessReview Trehalose and Trehalose-based Polymers for Environmentally Benign, Biocompatible and Bioactive Materials
Molecules 2008, 13(8), 1773-1816; doi:10.3390/molecules13081773
Received: 13 July 2008 / Accepted: 11 August 2008 / Published: 21 August 2008
Cited by 39 | PDF Full-text (1744 KB) | HTML Full-text | XML Full-text
Abstract
Trehalose is a non-reducing disaccharide that is found in many organisms but not in mammals. This sugar plays important roles in cryptobiosis of selaginella mosses, tardigrades (water bears), and other animals which revive with water from a state of suspended animation induced [...] Read more.
Trehalose is a non-reducing disaccharide that is found in many organisms but not in mammals. This sugar plays important roles in cryptobiosis of selaginella mosses, tardigrades (water bears), and other animals which revive with water from a state of suspended animation induced by desiccation. The interesting properties of trehalose are due to its unique symmetrical low-energy structure, wherein two glucose units are bonded face-to-face by 1→1-glucoside links. The Hayashibara Co. Ltd., is credited for developing an inexpensive, environmentally benign and industrial-scale process for the enzymatic conversion of α-1,4-linked polyhexoses to α,α-D-trehalose, which made it easy to explore novel food, industrial, and medicinal uses for trehalose and its derivatives. Trehalosechemistry is a relatively new and emerging field, and polymers of trehalose derivatives appear environmentally benign, biocompatible, and biodegradable. The discriminating properties of trehalose are attributed to its structure, symmetry, solubility, kinetic and thermodynamic stability and versatility. While syntheses of trehalose-based polymer networks can be straightforward, syntheses and characterization of well defined linear polymers with tailored properties using trehalose-based monomers is challenging, and typically involves protection and deprotection of hydroxyl groups to attain desired structural, morphological, biological, and physical and chemical properties in the resulting products. In this review, we will overview known literature on trehalose’s fascinating involvement in cryptobiology; highlight its applications in many fields; and then discuss methods we used to prepare new trehalose-based monomers and polymers and explain their properties. Full article
Open AccessReview Fucoidan: Structure and Bioactivity
Molecules 2008, 13(8), 1671-1695; doi:10.3390/molecules13081671
Received: 20 June 2008 / Revised: 22 July 2008 / Accepted: 28 July 2008 / Published: 12 August 2008
Cited by 298 | PDF Full-text (301 KB) | HTML Full-text | XML Full-text
Abstract
Fucoidan refers to a type of polysaccharide which contains substantial percentages of L-fucose and sulfate ester groups, mainly derived from brown seaweed. For the past decade fucoidan has been extensively studied due to its numerous interesting biological activities. Recently the search for [...] Read more.
Fucoidan refers to a type of polysaccharide which contains substantial percentages of L-fucose and sulfate ester groups, mainly derived from brown seaweed. For the past decade fucoidan has been extensively studied due to its numerous interesting biological activities. Recently the search for new drugs has raised interest in fucoidans. In the past few years, several fucoidans’ structures have been solved, and many aspects of their biological activity have been elucidated. This review summarizes the research progress on the structure and bioactivity of fucoidan and the relationships between structure and bioactivity. Full article
Open AccessReview Composition and Applications of Aloe vera Leaf Gel
Molecules 2008, 13(8), 1599-1616; doi:10.3390/molecules13081599
Received: 28 May 2008 / Accepted: 25 July 2008 / Published: 8 August 2008
Cited by 194 | PDF Full-text (230 KB) | HTML Full-text | XML Full-text
Abstract
Many of the health benefits associated with Aloe vera have been attributed to the polysaccharides contained in the gel of the leaves. These biological activities include promotion of wound healing, antifungal activity, hypoglycemic or antidiabetic effects antiinflammatory, anticancer, immunomodulatory and gastroprotective properties. [...] Read more.
Many of the health benefits associated with Aloe vera have been attributed to the polysaccharides contained in the gel of the leaves. These biological activities include promotion of wound healing, antifungal activity, hypoglycemic or antidiabetic effects antiinflammatory, anticancer, immunomodulatory and gastroprotective properties. While the known biological activities of A. vera will be briefly discussed, it is the aim of this review to further highlight recently discovered effects and applications of the leaf gel. These effects include the potential of whole leaf or inner fillet gel liquid preparations of A. vera to enhance the intestinal absorption and bioavailability of co-administered compounds as well as enhancement of skin permeation. In addition, important pharmaceutical applications such as the use of the dried A. vera gel powder as an excipient in sustained release pharmaceutical dosage forms will be outlined. Full article
Open AccessReview Tomato Derived Polysaccharides for Biotechnological Applications: Chemical and Biological Approaches
Molecules 2008, 13(6), 1384-1398; doi:10.3390/molecules13061384
Received: 30 May 2008 / Revised: 17 June 2008 / Accepted: 17 June 2008 / Published: 19 June 2008
Cited by 8 | PDF Full-text (412 KB) | HTML Full-text | XML Full-text
Abstract
Recent studies concerning the isolation and purification of exopolysaccharides from suspension-cultured tomato (Lycopersicon esculentum L. var. San Marzano) cells and the description of a simple, rapid and low environmental impact method with for obtaining polysaccharides from solid tomato-processing industry wastes are [...] Read more.
Recent studies concerning the isolation and purification of exopolysaccharides from suspension-cultured tomato (Lycopersicon esculentum L. var. San Marzano) cells and the description of a simple, rapid and low environmental impact method with for obtaining polysaccharides from solid tomato-processing industry wastes are reported. Their chemical composition, rheological properties and partial primary structure were determined on the basis of spectroscopic analyses (UV, IR, GC-MS, 1H-, 13C-NMR). Moreover, the anticytotoxic activities of exopolysaccharides obtained from cultured tomato cells were tested in a brine shrimp bioassay and the preparation of biodegradable film by chemical processing of polysaccharides from solid tomato industry waste was also reported. Full article
Open AccessReview Application of Prodrugs to Inflammatory Diseases of the Gut
Molecules 2008, 13(2), 452-474; doi:10.3390/molecules13020452
Received: 26 January 2008 / Revised: 20 February 2008 / Accepted: 21 February 2008 / Published: 27 February 2008
Cited by 18 | PDF Full-text (152 KB) | HTML Full-text | XML Full-text | Correction | Supplementary Files
Abstract
Oral delivery is the most common and preferred route of drug administrationalthough the digestive tract exhibits several obstacles to drug delivery including motilityand intraluminal pH profiles. The gut milieu represents the largest mucosal surfaceexposed to microorganisms with 1010-12 colony forming bacteria/g [...] Read more.
Oral delivery is the most common and preferred route of drug administrationalthough the digestive tract exhibits several obstacles to drug delivery including motilityand intraluminal pH profiles. The gut milieu represents the largest mucosal surfaceexposed to microorganisms with 1010-12 colony forming bacteria/g of colonic content.Approximately, one third of fecal dry matter is made of bacteria/ bacterial components.Indeed, the normal gut microbiota is responsible for healthy digestion of dietary fibers(polysaccharides) and fermentation of short chain fatty acids such as acetate and butyratethat provide carbon sources (fuel) for these bacteria. Inflammatory bowel disease (IBD)results in breakage of the mucosal barrier, an altered microbiota and dysregulated gutimmunity. Prodrugs that are chemically constructed to target colonic release or aredegraded specifically by colonic bacteria, can be useful in the treatment of IBD. Thisreview describes the progress in digestive tract prodrug design and delivery in light of gutmetabolic activities. Full article

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