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

Deadline for manuscript submissions: closed (10 March 2018) | Viewed by 96626

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Prof. Dr. Jun-ichi Kadokawa

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Department of Chemistry, Biotechnology, and Chemical Engineering, Graduate School of Science and Engineering, Kagoshima University, 1-21-40 Korimoto, Kagoshima 890-0065, Japan
Interests: polysaccharides; supramolecules; nanostructures; enzymatic synthesis; ionic liquids
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Dear Colleagues,

Polysaccharides are widely distributed and exhibit specific functions in nature. They are composed of a wide variety of monosaccharide residues through glycosidic linkages with highly stereo- and regio-controlled arrangements. Such diverse structures of natural polysaccharides contribute to showing a wide range of properties and natures, which provide to be employed as components in functional materials. Although natural polysaccharides often show poor solubilities in common solvents, leading to difficulty in proccessability, dissolution media, such as ionic liquids, have been found to efficiently dissolve polysaccharides. Synthesis of non-natural polysaccharides has also attracted a great deal of attention to obtain new polysaccharide-based functional materials. Owing to complicated structures, chemical synthesis of polysaccharides is one of challenging research topics in glycoscience. Efficient synthetic methods with highly stereo- and regio-construction of glycosidic linkages, such as enzymatic approach, recently, have been developed to produce well-defined polysaccharides.

This Special Issue aims at covering all fields concerning polysaccharide-based materials, including synthetic method, new functions, supramolecular and hierarchically controlled structures, environmentally benign and biomedical applications, and so on. Researchers in these fields are, therefore, warmly invited to propose relevant reviews, perspectives, and research papers to be published in this Special Issue of Molecules.

Prof. Dr. Jun-ichi Kadokawa
Guest Editor

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Keywords

New synthetic methods
Derivatization and modification, functional materials
Supramolecules
Hierarchically controlled structures
Environmentally benign materials
Biomedical applications

Related Special Issue

Polysaccharide-Based Materials II in Molecules (1 article)

Published Papers (13 papers)

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14 pages, 8545 KiB

Open AccessArticle

Stomatal Complex Development and F-Actin Organization in Maize Leaf Epidermis Depend on Cellulose Synthesis

by Emmanuel Panteris, Theonymphi Achlati, Gerasimos Daras and Stamatis Rigas

Molecules 2018, 23(6), 1365; https://doi.org/10.3390/molecules23061365 - 6 Jun 2018

Cited by 6 | Viewed by 4330

Abstract

Cellulose microfibrils reinforce the cell wall for morphogenesis in plants. Herein, we provide evidence on a series of defects regarding stomatal complex development and F-actin organization in Zea mays leaf epidermis, due to inhibition of cellulose synthesis. Formative cell divisions of stomatal complex ontogenesis were delayed or inhibited, resulting in lack of subsidiary cells and frequently in unicellular stomata, with an atypical stomatal pore. Guard cells failed to acquire a dumbbell shape, becoming rounded, while subsidiary cells, whenever present, exhibited aberrant morphogenesis. F-actin organization was also affected, since the stomatal complex-specific arrays were scarcely observed. At late developmental stages, the overall F-actin network was diminished in all epidermal cells, although thick actin bundles persisted. Taken together, stomatal complex development strongly depends on cell wall mechanical properties. Moreover, F-actin organization exhibits a tight relationship with the cell wall. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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13 pages, 4868 KiB

Open AccessArticle

Preparation and Characterization of Quaternized Chitosan Derivatives and Assessment of Their Antioxidant Activity

by Fang Luan, Lijie Wei, Jingjing Zhang, Wenqiang Tan, Yuan Chen, Fang Dong, Qing Li and Zhanyong Guo

Molecules 2018, 23(3), 516; https://doi.org/10.3390/molecules23030516 - 26 Feb 2018

Cited by 61 | Viewed by 5991

Abstract

Chitosan (CS) is an abundant and renewable polysaccharide that is reported to exhibit a great variety of beneficial properties. However, the poor solubility of chitosan in water limits its applications. In this paper, we successfully synthesized single N-quaternized (QCS) and double N-diquaternized (DQCS) chitosan derivatives, and the resulting quaternized materials were water-soluble. The degree of quaternization (DQ) of QCS and DQCS was 0.8 and 1.3, respectively. These derivatives were characterized by FTIR, ¹H NMR, ¹³C NMR, TGA, and SEM. Moreover, the antioxidant activity of the chitosan was evaluated by free radical scavenging ability (against DPPH-radical, hydroxyl-radical, and superoxide-radical) and ferric reducing power. Our results suggested that the antioxidant abilities were in the order of DQCS > QCS > CS, which was consistent with the number of quaternized groups. These data demonstrate that the number of quaternized groups of chitosan derivatives contributes to their antioxidant activity. Therefore, DQCS, with a higher number of quaternized groups and higher positive charge density, is endowed with high antioxidant activity, and can be used as a candidate material in food and pharmaceutical industries. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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12 pages, 2165 KiB

Open AccessArticle

Comparison of Structural and Functional Properties of Starches from the Rhizome and Bulbil of Chinese Yam (Dioscorea opposita Thunb.)

by Biao Zhang, Ke Guo, Lingshang Lin and Cunxu Wei

Molecules 2018, 23(2), 427; https://doi.org/10.3390/molecules23020427 - 15 Feb 2018

Cited by 22 | Viewed by 4895

Abstract

Chinese yam is an important edible starch plant and widely cultivated in China. Its rhizome and bulbil are starch storage tissues below and above ground, respectively. In this paper, starches were isolated from the rhizome and bulbil of Chinese yam, and their structural and functional properties were compared. Both starches had an oval shape with an eccentric hilum and a C_A-type crystalline structure. Their short-range ordered structure and lamellar structure had no significant difference. However, the rhizome starch had a significantly bigger granule size and lower amylose content than the bulbil starch. The swelling power and water solubility were significantly lower in the rhizome starch than in the bulbil starch. The onset and peak gelatinization temperatures were significantly higher in the rhizome starch than in the bulbil starch. The rhizome starch had a significantly higher breakdown viscosity and a lower setback viscosity than the bulbil starch. The thermal stability was lower in the rhizome starch than in the bulbil starch. The rhizome starch had a significantly lower resistance to hydrolysis and in vitro digestion than the bulbil starch. The above results provide important information for the utilization of rhizome and bulbil starches of Chinese yam. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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14 pages, 2546 KiB

Open AccessArticle

Preliminary Characterization, Antioxidant and Hepatoprotective Activities of Polysaccharides from Taishan Pinus massoniana Pollen

by Changming Zhou, Shaojie Yin, Zhongfang Yu, Yuxiang Feng, Kai Wei, Weiming Ma, Lijiang Ge, Zhengui Yan and Ruiliang Zhu

Molecules 2018, 23(2), 281; https://doi.org/10.3390/molecules23020281 - 30 Jan 2018

Cited by 19 | Viewed by 4564

Abstract

The objectives of the present study were to characterize the chemical composition, antioxidant activity and hepatoprotective effect of the polysaccharides from Taishan Pinus massoniana pollen (TPPPS). HPLC analysis showed that TPPPS was an acidic heteropolysaccharide with glucose and arabinose as the main component monosaccharides (79.6%, molar percentage). Fourier transform-infrared spectroscopy (FT-IR) analysis indicated that the spectra of TPPPS displayed infrared absorption peaks characteristic of polysaccharides. In in vitro assays TPPPS exhibited different degrees of dose-dependent antioxidant activities , and this was further verified by suppression of CCl₄-induced oxidative stress in the liver with three tested doses of TPPPS (100, 200, and 400 mg/kg bw) in rats. Pretreatment with TPPPS significantly decreased the levels of alanine aminotransferase (AST), aspartate aminotransferase (ALT), alkaline phosphatase (ALP), lactic dehydrogenase (LDH) and malondialdehyde (MDA) against CCl₄ injuries, and elevated the activities of superoxide dismutase (SOD) as well as glutathione peroxidase (GSH-Px). Histopathological observation further confirmed that TPPPS could protect the liver tissues from CCl₄-induced histological alternation. These results suggest that TPPPS has strong antioxidant activities and significant protective effect against acute hepatotoxicity induced by CCl₄. The hepatoprotective effect may partly be related to its free radical scavenging effect, increasing antioxidant activity and inhibiting lipid peroxidation. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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15 pages, 282 KiB

Open AccessArticle

Effects of Chitosan–PVA and Cu Nanoparticles on the Growth and Antioxidant Capacity of Tomato under Saline Stress

by Hipólito Hernández-Hernández, Susana González-Morales, Adalberto Benavides-Mendoza, Hortensia Ortega-Ortiz, Gregorio Cadenas-Pliego and Antonio Juárez-Maldonado

Molecules 2018, 23(1), 178; https://doi.org/10.3390/molecules23010178 - 16 Jan 2018

Cited by 101 | Viewed by 6969

Abstract

Chitosan is a natural polymer, which has been used in agriculture to stimulate crop growth. Furthermore, it has been used for the encapsulation of nanoparticles in order to obtain controlled release. In this work, the effect of chitosan–PVA and Cu nanoparticles (Cu NPs) absorbed on chitosan–PVA on growth, antioxidant capacity, mineral content, and saline stress in tomato plants was evaluated. The results show that treatments with chitosan–PVA increased tomato growth. Furthermore, chitosan–PVA increased the content of chlorophylls a and b, total chlorophylls, carotenoids, and superoxide dismutase. When chitosan–PVA was mixed with Cu NPs, the mechanism of enzymatic defense of tomato plants was activated. The chitosan–PVA and chitosan–PVA + Cu NPs increased the content of vitamin C and lycopene, respectively. The application of chitosan–PVA and Cu NPs might induce mechanisms of tolerance to salinity. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

11 pages, 1915 KiB

Open AccessArticle

Biotinylated Cyclooligosaccharides for Paclitaxel Solubilization

by Eunae Cho and Seunho Jung

Molecules 2018, 23(1), 90; https://doi.org/10.3390/molecules23010090 - 2 Jan 2018

Cited by 10 | Viewed by 3984

Abstract

The poor water solubility of paclitaxel causes significant problems in producing cancer therapeutic formulations. Here, we aimed to solubilize paclitaxel using biocompatible cyclic carbohydrates. Generally recognized as safe, labeled β-cyclodextrin (β-CD), a cyclic α-1,4-glucan consisting of seven glucoses, was prepared, and bio-sourced cyclosophoraoses (CyS), which are unbranched cyclic β-1,2-glucans with 17–23 glucose units, were purified using various chromatographic methods from Rhizobium leguminosarum cultural broth. For effective targeting, CyS and β-CD were modified with a biotinyl moiety in a reaction of mono-6-amino CyS and mono-6-amino-β-CD with N-hydroxysuccinimide ester of biotinamidohexanoic acid. Interestingly, the aqueous solubility of paclitaxel was enhanced 10.3- and 3.7-fold in the presence of biotinyl CyS and biotinyl β-CD, respectively. These findings suggest that biotin-appended cyclooligosaccharides can be applied to improve the delivery of paclitaxel. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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3004 KiB

Open AccessArticle

Zinc Ion Removal on Hybrid Pectin-Based Beads Containing Modified Poly(Methyl Methacrylate) Waste

by Agata Jakóbik-Kolon, Adrianna Szybaj, Krzysztof Mitko and Joanna Bok-Badura

Molecules 2017, 22(12), 2274; https://doi.org/10.3390/molecules22122274 - 20 Dec 2017

Cited by 7 | Viewed by 4292

Abstract

A new hybrid sorbent in the form of round beads containing modified poly(methyl methacrylate) (PMMA) waste immobilized in pectin and crosslinked with calcium ions was prepared. A previously obtained and characterized powdered poly(methyl methacrylate)–based sorbent was used. Batch and column studies on the new material’s sorption-desorption properties were performed. Two kinetic models (pseudo-first- and pseudo-second-order) and three isotherms (Langmuir, Langmuir bisite and Freundlich) were used to describe the results. Breakthrough and elution curves were also obtained. Nitric, hydrochloric, and sulfuric acid of various concentrations were used in the desorption studies. Higher sorption affinity of zinc(II) ions to hybrid sorbent than to pectin alone, reflected by higher values of the Langmuir and Freundlich model parameters, was observed. The maximum sorption capacities, calculated based on the best-fitted models, were 50.2 mg/g (Langmuir bisite) and 42.2 mg/g (Langmuir) for hybrid and only pectin beads, respectively. The stripping of Zn ions using 0.1 M solutions of mineral acids was similarly effective in the case of both sorbents. The mass balance calculated for the column studies showed about 100% recovery of zinc in a sorption-desorption cycle. By applying the hybrid sorbent under the studied conditions it is possible to purify Zn in water to the level permitted by law and concentrate Zn(II) ions by about 60 times. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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2762 KiB

Open AccessArticle

Thermal and Antioxidant Properties of Polysaccharides Sequentially Extracted from Mulberry Leaves (Morus alba L.)

by Bu-Yan Liao, Dan-Ye Zhu, Kiran Thakur, Ling Li, Jian-Guo Zhang and Zhao-Jun Wei

Molecules 2017, 22(12), 2271; https://doi.org/10.3390/molecules22122271 - 20 Dec 2017

Cited by 62 | Viewed by 7200

Abstract

Polysaccharides from natural plant products are gaining considerable attention due to their multi-faceted health effects, as well their functional applications in food production. We reported the sequential extraction of mulberry leaf polysaccharides (MLPs) with hot buffer (HBSS), chelating agent (CHSS), dilute alkali (DASS) and concentrated alkali (CASS), in order to obtain polysaccharide fractions. Monosaccharide analysis proved that galactose (27.07%) and arabinose (25.99%) were the major sugars in HBSS, whereas arabinose (30.55%) was the major sugar in CHSS, and glucose was the major sugar in DASS (24.96%) and CASS (27.51%). The molecular weights of the polysaccharide fractions were 7.812 × 10³ (HBSS), 3.279 × 10³ (CHSS), 6.912 × 10³ (DASS), and 1.408 × 10³ kDa (CASS). HBSS and CASS showed the largest peak temperature and the highest endothermic enthalpy, respectively. Different antioxidant assays showed that the MLPs possessed appreciable antioxidant activities in a dose-dependent manner. At 5 mg/mL, HBSS and DASS possessed the largest 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) radical scavenging activity (96.82%). HBSS exhibited the highest reducing power, and DASS rendered the strongest ABTS radical scavenging activity (99.69%). CHSS performed the best hydroxyl radical scavenging activity (64.22%) and Fe²⁺-chelating ability (96.36%). Our results suggested that MLPs could be a promising source of natural antioxidants for use in the food, pharmaceutical, and cosmetic industries. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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4142 KiB

Open AccessArticle

Evaluation of Inulin Replacing Chitosan in a Polyurethane/Polysaccharide Material for Pb²⁺ Removal

by Angel Ramon Hernández-Martínez, Gustavo A. Molina, Luis Fernando Jiménez-Hernández, Adrian Hendrik Oskam, Gerardo Fonseca and Miriam Estevez

Molecules 2017, 22(12), 2093; https://doi.org/10.3390/molecules22122093 - 29 Nov 2017

Cited by 12 | Viewed by 5469

Abstract

Downstream waste from industry and other industrial processes could increase concentration of heavy metals in water. These pollutants are commonly removed by adsorption because it is an effective and economical method. Previously, we reported adsorption capacity of a chitosan/polyurethane/titanium dioxide (TiO₂) composite for three ions in a dynamic wastewater system. There, increasing the chitosan concentration in composite increased the cation removal as well; however, for ratios higher than 50% of chitosan/TiO₂, the manufacturing cost increased significantly. In this work, we address the manufacturing cost problem by proposing a new formulation of the composite. Our hypothesis is that inulin could replace chitosan in the composite formulation, either wholly or in part. In this exploratory research, three blends were prepared with a polyurethane matrix using inulin or/and chitosan. Adsorption was evaluated using a colorimetric method and the Langmuir and Freundlich models. Fourier-transform infrared spectroscopy (FTIR) spectra, scanning electron microscopy (SEM) micrographs, differential scanning calorimetry and thermogravimetric analysis curves were obtained to characterize blends. Results indicate that blends are suitable for toxic materials removal (specifically lead II, Pb²⁺). Material characterization indicates that polysaccharides were distributed in polyurethane’s external part, thus improving adsorption. Thermal degradation of materials was found above 200 °C. Comparing the blends data, inulin could replace chitosan in part and thereby improve the cost efficiency and scalability of the production process of the polyurethane based-adsorbent. Further research with different inulin/chitosan ratios in the adsorbent and experiments with a dynamic system are justified. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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8819 KiB

Open AccessArticle

Effects of Polysaccharides from Platycodon grandiflorum on Immunity-Enhancing Activity In Vitro

by Xiaona Zhao, Yuge Wang, Peng Yan, Guodong Cheng, Cheng Wang, Na Geng, Xuepeng Wang and Jianzhu Liu

Molecules 2017, 22(11), 1918; https://doi.org/10.3390/molecules22111918 - 7 Nov 2017

Cited by 42 | Viewed by 5282

Abstract

The study is aimed at investigating the immunoenhancement activity of polysaccharides from Platycodon grandiflorum polysaccharides (PGPSs) in vitro. In this study, some research on lymphocyte proliferation, cell cycle, and the levels of CD4⁺ and CD8⁺ T cells were performed. Four different concentrations of PGPSs (PGPS_tc, PGPS_60c, PGPS_80c, and PGPS_tp) were harvested and added to peripheral blood T lymphocytes. We observed significant increases in T lymphocyte proliferation at PGPS_tc groups individually or synergistically with phytohemagglutinin (PHA) at most concentrations, and their lymphocyte proliferation rates were the highest. The active sites of PGPS_tc and PGPS_60c were subsequently chosen. Then, we utilized flow cytometry to determine lymphocyte cell cycle distribution and levels of CD4⁺ and CD8⁺ T cells. At most time points, PGPS_tc could facilitate lymphocyte cell cycle progression from the G0/G1 phase to the S and G2/M phases and, simultaneously, increase the levels of CD4⁺ and CD8⁺ T cells. These results indicate that PGPS_tc enhances the immune functions, suggesting that PGPS_tc could be a potential immunopotentiator for further in vivo and clinical trial experiments. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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2661 KiB

Open AccessArticle

Cellulase-Assisted Extraction of Polysaccharides from White Hyacinth Bean: Characterization of Antioxidant Activity and Promotion for Probiotics Proliferation

by Guo-Wei Shu, Yun-Xia He, Ni Lei, Ji-Li Cao, He Chen and Li Chen

Molecules 2017, 22(10), 1764; https://doi.org/10.3390/molecules22101764 - 20 Oct 2017

Cited by 19 | Viewed by 4605

Abstract

Food-derived polysaccharides have advantages over synthetical compounds and have attracted interest globally for decades. In this study, we optimized the cellulase-assisted extraction of polysaccharides from white hyacinth bean (PWBs) with the aid of response surface methodology (RSM). The optimum extraction parameters were a pH of 7.79, a cellulase of 2.73%, and a ratio of water to material of 61.39, producing a high polysaccharide yield (3.32 ± 0.03)%. The scavenging ability of PWBs varied on three radicals (hydroxyl > 2,2-diphenyl-1-picrylhydrazyl (DPPH) > superoxide). Furthermore, PWBs contributed to the proliferation of three probiotic bacteria (Lactobacillus acidophilus LA5, Bifidobacterium bifidum BB01, and Lactobacillus bulgaricus LB6). These investigations of PWBs provide a novel bioresource for the exploitation of antioxidant and probiotic bacterial proliferation. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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2495 KiB

Open AccessArticle

Evaluation of the Molecular Structural Parameters of Normal Rice Starch and Their Relationships with Its Thermal and Digestion Properties

by Lingshang Lin, Qing Zhang, Long Zhang and Cunxu Wei

Molecules 2017, 22(9), 1526; https://doi.org/10.3390/molecules22091526 - 12 Sep 2017

Cited by 39 | Viewed by 5322

Abstract

The molecular structural parameters of six normal rice starches with different amylose contents were investigated through their iodine absorption spectra and gel permeation chromatography of fully branched and debranched starches. The thermal and digestion properties of starches were also determined and their relationships with molecular structural parameters were analyzed. Results showed that the molecular structural parameters of maximum absorption wavelength, blue value (BV), optical density 620 nm/550 nm (OD 620/550), amylose, intermediate component, and amylopectin, including its short branch-chains, long branch-chains, and branching degree, had high correlation in different determining methods. The intermediate component of starch was significantly positively related to amylose and negatively related to amylopectin, and the amylopectin branching degree was significantly positively related to amylopectin content and negatively related to amylose content. The gelatinization temperatures and enthalpy of native starch were significantly positively related to BV, OD 620/550, and amylose content and negatively related to amylopectin short branch-chains. The gelatinization temperatures and enthalpy of retrograded starch were significantly negatively related to amylopectin branching degree. The digestions of gelatinized and retrograded starches were significantly negatively related to the BV, OD 620/550, amylose, and intermediate component and positively related to amylopectin and its short branch-chains and branching degree. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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35 pages, 52977 KiB

Open AccessReview

Pectin and Pectin-Based Composite Materials: Beyond Food Texture

by Claudia Lara-Espinoza, Elizabeth Carvajal-Millán, René Balandrán-Quintana, Yolanda López-Franco and Agustín Rascón-Chu

Molecules 2018, 23(4), 942; https://doi.org/10.3390/molecules23040942 - 18 Apr 2018

Cited by 291 | Viewed by 32801

Abstract

Pectins are plant cell wall natural heteropolysaccharides composed mainly of α-1-4 d-galacturonic acid units, which may or may not be methyl esterified, possesses neutral sugars branching that harbor functional moieties. Physicochemical features as pH, temperature, ions concentration, and cosolute presence, affect directly the extraction yield and gelling capacity of pectins. The chemical and structural features of this polysaccharide enables its interaction with a wide range of molecules, a property that scientists profit from to form new composite matrices for target/controlled delivery of therapeutic molecules, genes or cells. Considered a prebiotic dietary fiber, pectins meetmany regulations easily, regarding health applications within the pharmaceutical industry as a raw material and as an agent for the prevention of cancer. Thus, this review lists many emergent pectin-based composite materials which will probably palliate the impact of obesity, diabetes and heart disease, aid to forestall actual epidemics, expand the ken of food additives and food products design. Full article

(This article belongs to the Special Issue Polysaccharide-based Materials)

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