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Natural Polysaccharides: Chemistry, Bioactivity and Analysis

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

Deadline for manuscript submissions: closed (10 January 2012) | Viewed by 117807

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Prof. Dr. Shaoping Li

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State Key Laboratory for Quality Research in Chinese Medicine, University of Macau, Macao, China
Interests: herbal glyco-analysis; quality control methods and standards development of Chinese medicines; study of edible and medicinal mushroom
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Special Issue Information

Dear Colleagues,

Although their ubiquitous role in biological processes, polysaccharides are still the "sleeping giant" of research in herbal medicine. In last decade, technological advances in glycobiology and glycochemistry are paving the way for a new era in developing sweet solutions to sticky situations. In order to present the developments in polysaccharide-related research in herbal medicine, a special issue, Polysaccharides: Organic Chemistry, Bioactivity and Analysis, including those from Medicinal Plants and Fungi, of Molecules was published in 2008.

This year (2011), a same topic, Natural Polysaccharides: Chemistry, Bioactivity and Analysis, will be published under Molecules aims to present the latest developments in polysaccharide-related research, including structure, properties, modification, analysis and application of polysaccharides from natural resources such as medicinal plants, microorganisms and mushrooms. This work will improve the multidisciplinary expertise from industry, academia and research institutions to communicate their knowledge in polysaccharide science and to exchange information on basic and applied research for the development of innovative products composed and derived of polysaccharides.

Contributions for this issue, both in form of original research and review articles, may cover all aspects of polysaccharides science from natural resources, chemistry, bioactivity and analysis, e.g. isolation, purification and characterization of polysaccharides from natural materials, development of new protocols and methods based on chemical or biological systems for the evaluation of in vivo and in vitro biological activities of polysaccharides; pharmacodynamics and pharmacokinetics of polysaccharides; qualitative and quantitative analysis of polysaccharides; innovative techniques and protocols for the extraction, isolation, structural characterization of polysaccharides will be welcomed.

Prof. Dr. Shao-ping Li
Guest Editor

Keywords

analysis
biomaterials
bioassay
chemistry
chemical characteristic
Chinese medicine
fungus
glycobiology
glycoinformatics
glycomics
herb
herbal medicine
medicinal plant
mushroom
pharmacological activity

Published Papers (14 papers)

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Research

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704 KiB

Open AccessArticle

The Potential Biotechnological Applications of the Exopolysaccharide Produced by the Halophilic Bacterium Halomonas almeriensis

by Inmaculada Llamas, Hakima Amjres, Juan Antonio Mata, Emilia Quesada and Victoria Béjar

Molecules 2012, 17(6), 7103-7120; https://doi.org/10.3390/molecules17067103 - 12 Jun 2012

Cited by 96 | Viewed by 7303

Abstract

We have studied the extracellular polysaccharide (EPS) produced by the type strain, M8^T, of the halophilic bacterium Halomonas almeriensis, to ascertain whether it might have any biotechnological applications. All the cultural parameters tested influenced both bacterial growth and polysaccharide production. EPS production was mainly growth-associated and under optimum environmental and nutritional conditions M8^T excreted about 1.7 g of EPS per litre of culture medium (about 0.4 g of EPS per gram of dry cell weight). Analysis by anion-exchange chromatography and high-performance size-exclusion chromatography indicated that the exopolysaccharide was composed of two fractions, one of 6.3 × 10⁶ and another of 1.5 × 10⁴ Daltons. The monosaccharide composition of the high-molecular-weight fraction was mannose (72% w/w), glucose (27.5% w/w) and rhamnose (0.5% w/w). The low-molecular-weight fraction contained mannose (70% w/w) and glucose (30% w/w). The EPS has a substantial protein fraction (1.1% w/w) and was capable of emulsifying several hydrophobic substrates, a capacity presumably related to its protein content. The EPS produced solutions of low viscosity with pseudoplastic behaviour. It also had a high capacity for binding some cations. It contained considerable quantities of sulphates (1.4% w/w), an unusual feature in bacterial polysaccharides. All these characteristics render it potentially useful as a biological agent, bio-detoxifier and emulsifier. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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592 KiB

Open AccessArticle

Influence of Chemical Extraction Conditions on the Physicochemical and Functional Properties of Polysaccharide Gum from Durian (Durio zibethinus) Seed

by Hamed Mirhosseini and Bahareh Tabatabaee Amid

Molecules 2012, 17(6), 6465-6480; https://doi.org/10.3390/molecules17066465 - 29 May 2012

Cited by 89 | Viewed by 7569

Abstract

Durian seed is an agricultural biomass waste of durian fruit. It can be a natural plant source of non-starch polysaccharide gum with potential functional properties. The main goal of the present study was to investigate the effect of chemical extraction variables (i.e., the decolouring time, soaking temperature and soaking time) on the physicochemical properties of durian seed gum. The physicochemical and functional properties of chemically-extracted durian seed gum were assessed by determining the particle size and distribution, solubility and the water- and oil-holding capacity (WHC and OHC). The present work revealed that the soaking time should be considered as the most critical extraction variable affecting the physicochemical properties of crude durian seed gum. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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843 KiB

Open AccessCommunication

Immunostimulatory Effect of Laminarin on RAW 264.7 Mouse Macrophages

by Ji Young Lee, Young-Jin Kim, Hyun Joo Kim, Yoon-Sang Kim and Wansu Park

Molecules 2012, 17(5), 5404-5411; https://doi.org/10.3390/molecules17055404 - 08 May 2012

Cited by 79 | Viewed by 8314

Abstract

This study investigated the immunostimulatory effects of laminarin with respect to inflammatory mediators such as hydrogen peroxide, calcium, nitric oxide, various cytokines, transcription factors, and immune response gene in RAW 264.7 mouse macrophages. Laminarin did not reduce the cell proliferation of RAW 264.7 mouse macrophages at concentrations up to 500 µg/mL. Laminarin significantly increased the release of hydrogen peroxide, calcium, nitric oxide, monocyte chemotactic protein-1, vascular endothelial growth factor, leukemia inhibitory factor, and granulocyte-colony stimulating factor with enhancing expression of Signal Transducer and Activator of Transcription 1 (STAT1), STAT3, c-Jun, c-Fos, and cyclooxygenase-2 mRNA in RAW 264.7 cells. The results suggest that laminarin has immunostimulatory properties, strengthening immune reactions via the transcription factor pathway in macrophages. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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336 KiB

Open AccessArticle

MALDI-TOF MS Analysis of Native and Permethylated or Benzimidazole-Derivatized Polysaccharides

by Wei-Ting Hung, Shwu-Huey Wang, Yi-Ting Chen, Hui-Ming Yu, Chung-Hsuan Chen and Wen-Bin Yang

Molecules 2012, 17(5), 4950-4961; https://doi.org/10.3390/molecules17054950 - 30 Apr 2012

Cited by 34 | Viewed by 10021

Abstract

MALDI-TOF MS provides rapid and sensitive analyses of larger biomolecules. However, MS analyses of polysaccharide have been reported to have lower sensitivity compared to peptides and proteins. Here, we investigated some polysaccharides chemically derivatized by permethylation and ortho-phenylene diamine (OPD) tagging. Methylated glycan is obviously able to improve the sensitivity for mass spectrometry detection. Oxidative condensation by UV-activation tagging to saccharides by OPD and peptide-OPD also improve the sensitivity of MALDI-TOF MS analyses. Polysaccharides including dextran, glucomannan, arabinoxylan, arabinogalactan and beta-1,3-glucan, isolated from nutritional supplements of Ganoderma lucidum and Saccharomyces pastorianus were measured using MALDI-TOF MS with 2,5-dihydroxybenzoic acid (2,5-DHB) as the matrix. These glycans were also derivatized to methylated and benzimidazole-tagged glycans by chemical transformation for molecular weight analysis. The derivatized polysaccharides showed excellent MALDI-TOF MS signal enhancement in the molecular weight range from 1 to 5 kDa. Here, we demonstrate an efficient method to give glycan-benzimidazole (glycan-BIM) derivatives for polysaccharide determination in MALDI-TOF MS. Therefore, permethylated or benzimidazole-derivatized polysaccharides provide a new option for polysaccharide analysis using MALDI-TOF MS. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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2239 KiB

Open AccessArticle

Extraction and Characterization of Chitin from the Beetle Holotrichia parallela Motschulsky

by Shaofang Liu, Jie Sun, Lina Yu, Chushu Zhang, Jie Bi, Feng Zhu, Mingjing Qu, Chen Jiang and Qingli Yang

Molecules 2012, 17(4), 4604-4611; https://doi.org/10.3390/molecules17044604 - 17 Apr 2012

Cited by 269 | Viewed by 15799

Abstract

Insect chitin was isolated from adult Holotrichia parallela by treatment with 1 M HCl and 1 M NaOH, following by 1% potassium permanganate solution for decolorization. The yield of chitin from this species is 15%. This insect chitin was compared with the commercial a-chitin from shrimp, by infrared spectroscopy, X-ray diffraction, scanning electron microscopy, and elemental analysis. Both chitins exhibited similar chemical structures and physicochemical properties. Adult H. parallela is thus a promising alternative source of chitin. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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276 KiB

Open AccessArticle

Chemical Characteristics and Antioxidant Properties of Crude Water Soluble Polysaccharides from Four Common Edible Mushrooms

by Jin-Zhe He, Qiao-Mei Ru, Dan-Dan Dong and Pei-Long Sun

Molecules 2012, 17(4), 4373-4387; https://doi.org/10.3390/molecules17044373 - 11 Apr 2012

Cited by 80 | Viewed by 9918

Abstract

Four crude water soluble polysaccharides, CABP, CAAP, CFVP and CLDP, were isolated from common edible mushrooms, including Agaricus bisporus, Auricularia auricula, Flammulina velutipes and Lentinus edodes, and their chemical characteristics and antioxidant properties were determined. Fourier Transform-infrared analysis showed that the four crude polysaccharides were all composed of β-glycoside linkages. The major monosaccharide compositions were D-galactose, D-glucose and D-mannose for CABP, CAAP and CLDP, while CFVP was found to consist of L-arabinose, D-galactose, D-glucose and D-mannose. The main molecular weight distributions of CABP and the other three polysaccharides were 66.0 × 10⁴ Da, respectively. Antioxidant properties of the four polysaccharides were evaluated in in vitro systems and CABP showed the best antioxidant properties. The studied mushroom species could potentially be used in part of well-balanced diets and as a source of antioxidant compounds. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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228 KiB

Open AccessArticle

Enhancement of Palmarumycin C₁₂and C₁₃ Production in Liquid Culture of the Endophytic Fungus Berkleasmium sp. Dzf12 by Oligosaccharides from Its Host Plant Dioscorea zingiberensis

by Yan Li, Tijiang Shan, Yan Mou, Peiqin Li, Jianglin Zhao, Wensheng Zhao, Youliang Peng, Ligang Zhou and Chunbang Ding

Molecules 2012, 17(4), 3761-3773; https://doi.org/10.3390/molecules17043761 - 26 Mar 2012

Cited by 13 | Viewed by 6734

Abstract

Three crude oligosaccharides were respectively prepared by acid hydrolysis of three polysaccharides, which were water-extracted polysaccharide (WEP), sodium hydroxide-extracted polysaccharide (SEP) and acid-extracted polysaccharide (AEP) from the rhizomes of Dioscorea zingiberensis. Among the three oligosaccharides, the crude oligosaccharide prepared by acid hydrolysis of WEP was found to be the most efficient elicitor to enhance the production of palmarumycins C₁₂ and C₁₃ in liquid culture of endophytic fungus Berkleasmium sp. Dzf12. When OW was applied to the medium at 300 mg/L on day 3 of culture, the maximal yields of palmarumycin C₁₂ (87.96 mg/L) and palmarumycin C₁₃ (422.28 mg/L) were achieved on day 15 of culture, which were 9.83 and 3.24-fold in comparison with those (8.95 and 130.43 mg/L) of control, respectively. The results indicate that addition of the oligosaccharides from the host plant D. zingiberensis should be an effective strategy for enhancing production of palmarumycins C₁₂ and C₁₃ in liquid culture of endophytic fungus Berkleasmium sp. Dzf12. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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242 KiB

Open AccessArticle

Isolation and Structural Characterisation of Okara Polysaccharides

by Bo Li, Fei Lu, Haijuan Nan and Yang Liu

Molecules 2012, 17(1), 753-761; https://doi.org/10.3390/molecules17010753 - 13 Jan 2012

Cited by 39 | Viewed by 8276

Abstract

Okara is a byproduct generated during tofu or soymilk production processes. Crude polysaccharide (yield 56.8%) was isolated by removing fat, protein and low molecular weight carbohydrates from initial okara. Crude okara polysaccharide was further divided into four soluble fractions and an insoluble residue fraction by extracting with 0.05 M EDTA + NH₄ oxalate, 0.05 M NaOH, 1 M NaOH and 4 M NaOH, with yields of 7.7%, 3.6%, 20.7%, 16.0% and 27.9%, respectively. Arabinose, galactose, galacturonic acid, xylose and glucose (only for the insoluble fraction) were the major constituent sugars. The primary sugar residues of okara polysaccharides were 1,4-linked β-galactopyranose, 1,5- and 1,3-linked α-arabinofuranose, 1,5-linked α-xylofuranose, 1,2-linked, 1,2,4-linked and terminal α-rhamnopyranose (or fucopyranose), and 1,4-linked β-glucopyranose (only for the insoluble fraction), indicating okara polysaccharides might contain galactan, arabinan, arabinogalactan, xylogalacturonan, rhamnogalacturonan, xylan, xyloglucan and cellulose. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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1126 KiB

Open AccessArticle

Comparison of Polysaccharides from Two Species of Ganoderma

by Jing Xie, Jing Zhao, De-Jun Hu, Jin-Ao Duan, Yu-Ping Tang and Shao-Ping Li

Molecules 2012, 17(1), 740-752; https://doi.org/10.3390/molecules17010740 - 13 Jan 2012

Cited by 50 | Viewed by 8013

Abstract

Ganoderma lucidum and Ganoderma sinense, known as Lingzhi in Chinese, are commonly used Chinese medicines with excellent beneficial health effects. Triterpenes and polysaccharides are usually considered as their main active components. However, the content of triterpenes differs significantly between the two species of Ganoderma. To date, a careful comparison of polysaccharides from the two species of Ganoderma has not been performed. In this study, polysaccharides from fruiting bodies of two species of Lingzhi collected from different regions of China were analyzed and compared based on HPSEC-ELSD and HPSEC-MALLS-RI analyses, as well as enzymatic digestion and HPTLC of acid hydrolysates. The results indicated that both the HPSEC-ELSD profiles and the molecular weights of the polysaccharides were similar. Enzymatic digestion showed that polyshaccharides from all samples of Lingzhi could be hydrolyzed by pectinase and dextranase. HPTLC profiles of their TFA hydrolysates colored with different reagents and their monosaccharides composition were also similar. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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203 KiB

Open AccessArticle

Enhancement of Diosgenin Production in Dioscorea zingiberensis Cell Cultures by Oligosaccharides from Its Endophytic Fungus Fusarium oxysporum Dzf17

by Peiqin Li, Ziling Mao, Jingfeng Lou, Yan Li, Yan Mou, Shiqiong Lu, Youliang Peng and Ligang Zhou

Molecules 2011, 16(12), 10631-10644; https://doi.org/10.3390/molecules161210631 - 19 Dec 2011

Cited by 42 | Viewed by 7031

Abstract

The effects of the oligosaccharides from the endophytic fungus Fusarium oxysporum Dzf17 as elicitors on diosgenin production in cell suspension cultures of its host Dioscorea zingiberensis were investigated. Three oligosaccharides, DP4, DP7 and DP10, were purified from the oligosaccharide fractions DP2-5, DP5-8 and DP8-12, respectively, which were prepared from the water-extracted mycelial polysaccharide of the endophytic fungus F. oxysporum Dzf17. When the cell cultures were treated with fraction DP5-8 at 20 mg/L on day 26 and harvested on day 32, the maximum diosgenin yield (2.187 mg/L) was achieved, which was 5.65-fold of control (0.387 mg/L). When oligosaccharides DP4, DP7 and DP10 were individually added to 26-day-old D. zingiberensis cell cultures at concentrations of 2, 4, 6, 8 and 10 mg/L in medium, DP7 at 6 mg/L was found to significantly enhance diosgenin production, with a yield of 3.202 mg/L, which was 8.27-fold of control. When the cell cultures were treated with DP7 twice on days 24 and 26, and harvested on day 30, both diosgenin content and yield were significantly increased and reached the maximums of 1.159 mg/g dw and 4.843 mg/L, both of which were higher than those of single elicitation, and were 9.19- and 12.38-fold of control, respectively. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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198 KiB

Open AccessArticle

Effects of Polysaccharide Elicitors from Endophytic Fusarium oxysporium Dzf17 on Growth and Diosgenin Production in Cell Suspension Culture of Dioscorea zingiberensis

by Peiqin Li, Yan Mou, Tijiang Shan, Jianmei Xu, Yan Li, Shiqiong Lu and Ligang Zhou

Molecules 2011, 16(11), 9003-9016; https://doi.org/10.3390/molecules16119003 - 26 Oct 2011

Cited by 51 | Viewed by 6548

Abstract

Three polysaccharides, namely exopolysaccharide (EPS), water-extracted mycelial polysaccharide (WPS) and sodium hydroxide-extracted mycelial polysaccharide (SPS), were prepared from the endophytic fungus Fusarium oxysporium Dzf17 isolated from the rhizomes of Dioscorea zingiberensis. The effects of the time of addition and polysaccharide concentration on the growth and diosgenin accumulation in cell suspension culture of D. zingiberensis were studied. Among them, WPS was found to be the most effective polysaccharide. When WPS was added to the medium at 20 mg/L on the 25th day of culture, the cell dry weight was increased 1.34-fold, diosgenin content 2.85-fold, and diosgenin yield 3.83-fold in comparison to those of control. EPS and SPS showed moderate and relatively weak enhancement effects on cell growth and diosgenin accumulation, respectively. The dynamics of cell growth and diosgenin accumulation when WPS was added to the medium at 20 mg/L on the 25th day of culture were investigated, and results showed that dry weight of cells reached a maximum value on day 30 but the maximum diosgenin content was achieved on day 31. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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419 KiB

Open AccessArticle

Antibacterial Characteristics and Activity of Water-Soluble Chitosan Derivatives Prepared by the Maillard Reaction

by Ying-Chien Chung, Jan-Ying Yeh and Cheng-Fang Tsai

Molecules 2011, 16(10), 8504-8514; https://doi.org/10.3390/molecules16108504 - 11 Oct 2011

Cited by 77 | Viewed by 8023

Abstract

The antibacterial activity of water-soluble chitosan derivatives prepared by Maillard reactions against Staphylococcus aureus, Listeria monocytogenes, Bacillus cereus, Escherichia coli, Shigella dysenteriae, and Salmonella typhimurium was examined. Relatively high antibacterial activity against various microorganisms was noted for the chitosan-glucosamine derivative as compared to the acid-soluble chitosan. In addition, it was found that the susceptibility of the test organisms to the water-soluble chitosan derivative was higher in deionized water than in saline solution. Metal ions were also found to reduce the antibacterial activity of the water-soluble chitosan derivative on S. aureus. The marked increase in glucose level, protein content and lactate dehydrogenase (LDH) activity was observed in the cell supernatant of S. aureus exposed to the water-soluble chitosan derivative in deionized water. The results suggest that the water-soluble chitosan produced by Maillard reaction may be a promising commercial substitute for acid-soluble chitosan. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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Review

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398 KiB

Open AccessReview

Mixed Biopolymer Systems Based on Starch

by M. Abd Elgadir, Md. Jahurul Haque Akanda, Sahena Ferdosh, Amid Mehrnoush, Alias A. Karim, Takahiro Noda and Md. Zaidul Islam Sarker

Molecules 2012, 17(1), 584-597; https://doi.org/10.3390/molecules17010584 - 09 Jan 2012

Cited by 23 | Viewed by 6825

Abstract

A binary mixture of starch–starch or starch with other biopolymers such as protein and non-starch polysaccharides could provide a new approach in producing starch-based food products. In the context of food processing, a specific adjustment in the rheological properties plays an important role in regulating production processing and optimizing the applicability, stability, and sensory of the final food products. This review examines various biopolymer mixtures based on starch and the influence of their interaction on physicochemical and rheological properties of the starch-based foods. It is evident that the physicochemical and rheological characteristics of the biopolymers mixture are highly dependent on the type of starch and other biopolymers that make them up mixing ratios, mixing procedure and presence of other food ingredients in the mixture. Understanding these properties will lead to improve the formulation of starch–based foods and minimize the need to resort to chemically modified starch. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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377 KiB

Open AccessReview

Modulation of Animal and Human Hematopoiesis by β-Glucans: A Review

by Michal Hofer and Milan Pospíšil

Molecules 2011, 16(9), 7969-7979; https://doi.org/10.3390/molecules16097969 - 15 Sep 2011

Cited by 22 | Viewed by 6580

Abstract

β-Glucans are cell wall constituents of bacteria, yeast, fungi, and plants. They are not expressed in mammalian cells, but they are recognized by mammalian cells as pathogen-associated molecular patterns by pattern recognition receptors and thus act as biological response modifiers. This review summarizes data on the hematopoiesis-stimulating effects of β-glucans, as well as on their ability to enhance bone marrow recovery after an injury. β-Glucans have been shown to support murine hematopoiesis suppressed by ionizing radiation or cytotoxic anti-cancer therapy. They also enhance stem cell homing and engraftment. Basically, two forms of β-glucan preparations have been investigated, namely particulate and soluble ones. β-Glucans are generally well tolerated, the particulate forms showing a higher incidence of undesirable side effects. Taken together, the hematopoiesis-stimulating properties of β-glucans predetermine these biological response modifiers to ever increasing use in human medicinal practice. Full article

(This article belongs to the Special Issue Natural Polysaccharides: Chemistry, Bioactivity and Analysis)

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