THE COMPLEX WORLD OF POLYSACCHARIDES Edited by Desiree Nedra Karunaratne The Complex World of Polysaccharides http://dx.doi.org/10.5772/2947 Edited by Desiree Nedra Karunaratne Contributors Susana P. Miranda Castro, Eva G. Lizárraga Paulín, Stefan Kwiatkowski, Stefan Edgar Kwiatkowski, Rosa Eugenia Reyes, Carolina Romo González, Rafael Coria Jiménez, Maribel Ortiz Herrera, Alejandra Aquino Andrade, Tanya V. Ivashina, Vladimir N. Ksenzenko, Shauna L. Reckseidler-Zenteno, Natalya Nikolaevna Trofimova, Elena Nikolaevna Medvedeva, Nadezhda Viktorovna Ivanova, Yuriy Alekseevich Malkov, Vasiliy Anatolievich Babkin, Mona A. Esawy, Eman F. Ahmed, Wafaa A. Helmy, Nahla M. Mansour, Waled M. El-Senousy, Mounir M. El- Safty, Desiree Nedra Karunaratne, R.G.U. Jayalal, V. Karunaratne, Richard A. Cunha, Thereza A. Soares, Victor H. Rusu, Frederico J.S. Pontes, Eduardo F. Franca, Roberto D. Lins, Aleksandr N. Zimnitskii, V. Poinsot, M.A. Carpéné, F. Couderc, Ranieri Urbani, Paola Sist, Galja Pletikapić, Tea Mišić Radić, Vesna Svetličić, Vera Žutić, Pierre Lembre, Cécile Lorentz, Patrick Di Martino, Amit K. Ghosh, Prasun Bandyopadhyay, Alireza Alishahi, Rosa M. Raybaudi-Massilia, Jonathan Mosqueda-Melgar, Marina Dello Staffolo, Alicia E. Bevilacqua, María Susana Rodríguez, Liliana Albertengo, María Victoria Busi, Mariana Martín, Diego F. Gomez-Casati, Edmund M. K. Lui, Chike G. Azike, José A. Guerrero-Analco, Ahmad A. Romeh, Hua Pei, Sherif J. Kaldas, John T. Arnason, Paul A. Charpentier, María Josefina Carlucci, Cecilia Gabriela Mateu, María Carolina Artuso, Luis Alberto Scolaro, Mohit S. Verma, Frank X. Gu, A. V. Dushkin, T. G. Tolstikova, M. V. Khvostov, G. A. Tolstikov, Máira Regina Rodrigues, Alexandre de Souza e Silva, Fábio Vieira Lacerda, Dodi Safari, Ger Rijkers, Harm Snippe Published by InTech Janeza Trdine 9, 51000 Rijeka, Croatia Copyright © 2012 InTech All chapters are Open Access distributed under the Creative Commons Attribution 3.0 license, which allows users to download, copy and build upon published articles even for commercial purposes, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. After this work has been published by InTech, authors have the right to republish it, in whole or part, in any publication of which they are the author, and to make other personal use of the work. Any republication, referencing or personal use of the work must explicitly identify the original source. Notice Statements and opinions expressed in the chapters are these of the individual contributors and not necessarily those of the editors or publisher. No responsibility is accepted for the accuracy of information contained in the published chapters. The publisher assumes no responsibility for any damage or injury to persons or property arising out of the use of any materials, instructions, methods or ideas contained in the book. Publishing Process Manager Marina Jozipovic Typesetting InTech Prepress, Novi Sad Cover InTech Design Team First published October, 2012 Printed in Croatia A free online edition of this book is available at www.intechopen.com Additional hard copies can be obtained from orders@intechopen.com The Complex World of Polysaccharides, Edited by Desiree Nedra Karunaratne p. cm. ISBN 978-953-51-0819-1 Contents Preface IX Section 1 Sources and Biological Properties of Polysaccharides 1 Chapter 1 Is Chitosan a New Panacea? Areas of Application 3 Susana P. Miranda Castro and Eva G. Lizárraga Paulín Chapter 2 Yeast (Saccharomyces cerevisiae) Glucan Polysaccharides – Occurrence, Separation and Application in Food, Feed and Health Industries 47 Stefan Kwiatkowski and Stefan Edgar Kwiatkowski Chapter 3 Mechanisms of O-Antigen Structural Variation of Bacterial Lipopolysaccharide (LPS) 71 Rosa Eugenia Reyes, Carolina Romo González, Rafael Coria Jiménez, Maribel Ortiz Herrera and Alejandra Aquino Andrade Chapter 4 Exopolysaccharide Biosynthesis in Rhizobium leguminosarum: From Genes to Functions 99 Tanya V. Ivashina and Vladimir N. Ksenzenko Chapter 5 Capsular Polysaccharides Produced by the Bacterial Pathogen Burkholderia pseudomallei 127 Shauna L. Reckseidler-Zenteno Chapter 6 Polysaccharides from Larch Biomass 153 Natalya Nikolaevna Trofimova, Elena Nikolaevna Medvedeva, Nadezhda Viktorovna Ivanova, Yuriy Alekseevich Malkov and Vasiliy Anatolievich Babkin Chapter 7 Antiviral Levans from Bacillus spp. Isolated from Honey 195 Mona A. Esawy, Eman F. Ahmed, Wafaa A. Helmy, Nahla M. Mansour, Waled M. El-Senousy and Mounir M. El-Safty Chapter 8 Lichen Polysaccharides 215 Desiree Nedra Karunaratne, R.G.U. Jayalal and V. Karunaratne VI Contents Section 2 Physical and Chemical Characteristics of Polysaccharides 227 Chapter 9 The Molecular Structure and Conformational Dynamics of Chitosan Polymers: An Integrated Perspective from Experiments and Computational Simulations 229 Richard A. Cunha, Thereza A. Soares, Victor H. Rusu, Frederico J.S. Pontes, Eduardo F. Franca and Roberto D. Lins Chapter 10 Concept of Template Synthesis of Proteoglycans 257 Aleksandr N. Zimnitskii Chapter 11 Coupled Mass Spectrometric Strategies for the Determination of Carbohydrates at Very Low Concentrations: The Case of Polysaccharides Involved in the Molecular Dialogue Between Plants and Rhizobia 305 V. Poinsot, M.A. Carpéné and F. Couderc Chapter 12 Diatom Polysaccharides: Extracellular Production, Isolation and Molecular Characterization 345 Ranieri Urbani, Paola Sist, Galja Pletikapić, Tea Mišić Radić, Vesna Svetličić and Vera Žutić Chapter 13 Exopolysaccharides of the Biofilm Matrix: A Complex Biophysical World 371 Pierre Lembre, Cécile Lorentz and Patrick Di Martino Section 3 Applications in the Food Industry 393 Chapter 14 Polysaccharide-Protein Interactions and Their Relevance in Food Colloids 395 Amit K. Ghosh and Prasun Bandyopadhyay Chapter 15 Chitosan: A Bioactive Polysaccharide in Marine-Based Foods 409 Alireza Alishahi Chapter 16 Polysaccharides as Carriers and Protectors of Additives and Bioactive Compounds in Foods 429 Rosa M. Raybaudi-Massilia and Jonathan Mosqueda-Melgar Chapter 17 Dietary Fiber and Availability of Nutrients: A Case Study on Yoghurt as a Food Model 455 Marina Dello Staffolo, Alicia E. Bevilacqua, María Susana Rodríguez and Liliana Albertengo Chapter 18 Plant Biotechnology for the Development of Design Starches 491 María Victoria Busi, Mariana Martín and Diego F. Gomez-Casati Contents VII Section 4 Applications in the Pharmaceutical Industry 511 Chapter 19 Bioactive Polysaccharides of American Ginseng Panax quinquefolius L. in Modulation of Immune Function: Phytochemical and Pharmacological Characterization 513 Edmund M. K. Lui, Chike G. Azike, José A. Guerrero-Analco, Ahmad A. Romeh, Hua Pei, Sherif J. Kaldas, John T. Arnason and Paul A. Charpentier Chapter 20 Polysaccharides from Red Algae: Genesis of a Renaissance 535 María Josefina Carlucci, Cecilia Gabriela Mateu, María Carolina Artuso and Luis Alberto Scolaro Chapter 21 1,3- -Glucans: Drug Delivery and Pharmacology 555 Mohit S. Verma and Frank X. Gu Chapter 22 Complexes of Polysaccharides and Glycyrrhizic Acid with Drug Molecules − Mechanochemical Synthesis and Pharmacological Activity 573 A. V. Dushkin, T. G. Tolstikova, M. V. Khvostov and G. A. Tolstikov Chapter 23 The Chitosan as Dietary Fiber: An in vitro Comparative Study of Interactions with Drug and Nutritional Substances 603 Máira Regina Rodrigues, Alexandre de Souza e Silva and Fábio Vieira Lacerda Chapter 24 The Future of Synthetic Carbohydrate Vaccines: Immunological Studies on Streptococcus pneumoniae Type 14 617 Dodi Safari, Ger Rijkers and Harm Snippe Preface When I was invited by InTech Open Access Publisher to edit a book on polysaccharides, I accepted the challenge since to me polysaccharides constitute a wide variety of biological polymers with diverse composition, physical characteristics and biological activity and have been the focus of my research career. These naturally occurring entities have been studied for their chemical and physical properties and more recently for bioactivity. They have been used in the food industry for functions such as thickeners and protective coatings. Industrial uses of polysaccharides in cosmetics, textiles and medicines are based on rheological, emulsifying and stabilizing properties of polysaccharides. Even though carbohydrates have a long history of chemical and physical study, properties of polysaccharides with relation to structure activity/function has not been an area of in depth study. Polysaccharides of bacterial origin however gained interest in the 1980’s due to their potential as vaccine formulations. Therefore the detailed chemical structures of capsular polysaccharides, LPS and exopolysaccharides were elucidated leading to discovery of new naturally occurring sugars. The plant derived polysaccharides such as the hemicelluloses and starch and other specific polysaccharides such as inulin, beta glucans, alginates and pectins are very well documented and have been studied over a longer period of time. Other than the chemical and physical properties of the polysaccharides, the genetic involvements of the biosynthetic processes which imparts specificity to the structure and thereby its action, have also warranted much study leading to a better understanding of the structure activity relationship. Thus the areas of study of polysaccharides cover several disciplines. In compiling this book, the contributions on polysaccharides from diverse sources such as animals, plants and microorganisms were received and sectioned according to their properties and applications. The first section deals with sources of polysaccharides and their biological properties. A wide range of polysaccharides from bacterial origin to plants and lichens are presented along with their biological applications. The many applications of chitosan, the most abundant polysaccharide of animal origin, in areas from food, medicine, agriculture, pharmacy and other industries is revisited in the first chapter. The second chapter focusses on glucan polysaccharides, abundantly produced by microorganisms, having properties valuable in food uses. Here the yeast cell wall derived glucans and their products with applications in the food and health industries are presented. X Preface Biosynthesis of Bacterial polysaccharides occurs through elaborate mechanisms. The biosynthetic mechanisms leading to various structural changes in the O-antigens of bacterial polysaccharides are discussed in chapter 3. Variations in structure of the polysaccharides are shown to affect the biological properties and hence pathogenicity. Chapter 4 considers the genetic control of the biosynthesis of exopolysacchrides of Rhizobium leguminosarum. It is shown that diversity of the exopolysaccharides biosynthesized results from genetic rearrangements of the glycosyl transferase genes and other genes involved in translocation of the repeating units. The next chapter is devoted to the study of virulence and pathogenesis due to the capsular polysaccharides of Burkholderia pseudomallei . Several studies have been performed on bacterial polysaccharides as candidates for vaccines and it has been shown that virulence is due to changes in the capsular polysaccharide. Plant polysaccharides may be used for specific applications. However, the extraction of polysaccharides from plant waste products in timber industries with conversion of these polysaccharides into useful byproducts is a novel application. Chapter 6 addresses this showing that biomass obtained from large scale processing of Larch wood can be converted into valuable materials with many biological applications. The biological applications of the fructose rich levan polymer found abundantly in honey is discussed in the next chapter. The section ends with a lesser studied polysaccharide source: Lichens composed of a symbiotic relation between algae and fungi yielding polysaccharides which have been investigated for biological significance indicating antitumour, immunomodulatry and anti-inflammatory activities. Chemical and physical characterizations are important aspects when dealing with understanding the uses of polysaccharides in relation to their properties. The second section discusses methods required for characterization and estimation of spatial arrangement and results obtained therefrom. The five chapters in this section deal with physical properties, methods of characterization and chemical analysis techniques useful for structure determination of a range of polysaccharides from the animal world (chitosan) to polysaccharides from microbes (diatoms). The structural dynamics of chitosan, its conformation and its interactions with biological materials starts off this section. The importance of conformation and molecular modelling is known with drug design studies. Likewise the structural dynamics of polysaccharides are useful for identifying interactions between polysaccharides and biological entities as well as nanoparticles. The use of Quantum chemical methods to explain the template synthesis of proteoglycans is described in the next chapter. Chapter 11 in this section deals with some methods which are essential for elucidating the structure of a polysaccharide. The focus is on the use of mass spectral analysis for determining structures at very low concentration. Other than the basic techniques for chemical characterization, the application of physico-chemical techniques such as laser light scattering and atomic force microscopy is described in the characterization of diatom polysaccharides. The final chapter on biofilm matrices deals with problems encountered in isolation of the biofilm polysaccharides and reviews the chemical and physical methods available. [...]... The final section of the book is devoted to pharmaceutical applications involving polysaccharides The first two chapters deal with the use of polysaccharides as therapeutic agents The well- known medicinal properties of ginseng with emphasis on the activity of its polysaccharides, followed by the interaction of polysaccharides from red sea weed with virus, starts off this section The next three chapters... microbial cell membranes, altering their barrier properties, and thereby 16 The Complex World of Polysaccharides preventing the entry of nutrients or causing the leakage of intracellular contents [95-100] Another reported mechanism involves the penetration of low- molecular weight chitosan into the cell, binding to DNA and the subsequent inhibition of RNA and protein synthesis [101] Chitosan has also been... nanoparticles to enhance the property of the drug delivery vehicle Chapter 22 on the other hand presents the formation of supramolecular complexes for efficient delivery of poorly water soluble drugs On a different note, the effect of dietary fibre on availability of drugs with chitosan as the dietary fibre is evaluated in the next chapter In conclusion, the long standing debate on the use of polysaccharides. .. can inhibit the replication of bacteriophages by several mechanisms: it can (a) decrease the viability of cultured bacterial cells, (b) neutralize the infectivity of mature phage particles in the inoculum and/or daughter phage particles, and (c) block the replication of the virulent phage [114] The condition of the phage culture is known to be of paramount importance for the development of phage infection... but they came to the opposite conclusions [143] They noted that oral administration of LMW chitosan decreases the weight of the tumour [139, 142], although administration by intraperitoneal injection led to a higher inhibitory rate [142] It was reported the higher the MW of LMWC, the better the tumor inhibitory effect [139] The introduction of acidic groups as a result of chitosan oxidation has the. .. chapter distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses /by/ 3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited 4 The Complex World of Polysaccharides Why talk about the birth of the earth? This is because the chitin could be a constituent of the first living cell It... group When the degree of deacetylation of chitin reaches about 50% (depending on the origin of the polymer), it becomes soluble in aqueous acidic media and is called chitosan The solubilization occurs by protonation of the –NH2 function on the C-2 position of the D-glucosamine repeat unit, whereby the polysaccharide is converted to a polyelectrolyte in acidic media Chitosan is the only pseudonatural... to modify the surface of the material that already has excellent biofunctionality and bulk properties [71] Altering 12 The Complex World of Polysaccharides the physical and chemical properties of the chitosan in order to improve its medicinal quality will also influence its biocompatibility [69.70] The excellent biological properties of chitosan can be potentially improved with a variety of additional... and the future direction of carbohydrates as successful candidates is argued As evident from the diversity of the applications of polysaccharides presented in this book, study of carbohydrates brings us to a rare world where the abundance of sources and variety of structures is both mind boggling and intriguing Carbohydrates have been explored since the beginning of chemical investigations and polysaccharides. .. benefits The polysaccharides cellulose and hemicelluloses are recognized as dietary fibres The importance of dietary fibres for availability of nutrients is presented in the next chapter The section ends with the advantages of starch as a source of energy Modification of the properties of starch through biotechnological manipulation and production of high amylose starches is reviewed in this chapter The . THE COMPLEX WORLD OF POLYSACCHARIDES Edited by Desiree Nedra Karunaratne The Complex World of Polysaccharides http://dx.doi.org/10.5772/2947 Edited by Desiree Nedra Karunaratne. period of time. Other than the chemical and physical properties of the polysaccharides, the genetic involvements of the biosynthetic processes which imparts specificity to the structure and thereby. edition of this book is available at www.intechopen.com Additional hard copies can be obtained from orders@intechopen.com The Complex World of Polysaccharides, Edited by Desiree Nedra Karunaratne