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

Deadline for manuscript submissions: closed (31 May 2019) | Viewed by 43174

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Dr. Hidenori Tanaka

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Center for Highly Advanced Integration of Nano and Life Sciences (G- CHAIN), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
Special Issues, Collections and Topics in MDPI journals

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Dear Colleagues,

Carbohydrates, also called saccharides, are the most abundant biomolecules in nature and are found in all living organisms. Although well known as a source of energy and cell wall components, they act as the bioactive compounds “glycoconjugates”, in which mono- or oligosaccharide is covalently attached to proteins, lipids and other biomolecules. Glycoconjugates play pivotal roles in numerous biological events such as cell adhesion and immune response, and have therefore been attracting interest from not only biologists but also chemists. Carbohydrate chemistry has contributed to providing natural and non-natural products as powerful tools for the elucidation of their biological functions, leading to drug discovery.

This Special Issue of Molecules focuses on carbohydrate chemistry. We encourage authors to submit research papers describing new synthetic methodologies in oligosaccharide synthesis, including glycosylation and protection strategies. The development of glycosylation methods, protecting groups of carbohydrates, and the synthesis of carbohydrate-based compounds such as glycosidase inhibitors are also welcome.

Dr. Hidenori Tanaka
Guest Editor

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Keywords

oligosaccharide
glycosylation
protecting group
carbohydrate-based compound
inhibitor

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Published Papers (10 papers)

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Research

17 pages, 2967 KiB

Open AccessArticle

Advanced Glycation End Products of Bovine Serum Albumin Suppressed Th1/Th2 Cytokine but Enhanced Monocyte IL-6 Gene Expression via MAPK-ERK and MyD88 Transduced NF-κB p50 Signaling Pathways

by Chieh-Yu Shen, Cheng-Han Wu, Cheng-Hsun Lu, Yu-Min Kuo, Ko-Jen Li, Song-Chou Hsieh and Chia-Li Yu

Molecules 2019, 24(13), 2461; https://doi.org/10.3390/molecules24132461 - 4 Jul 2019

Cited by 16 | Viewed by 4897

Abstract

Advanced glycation end products (AGE), the most known aging biomarker, may cause “inflamm-aging” (i.e., chronic low-grade inflammation that develops with aging) in both aged and diabetes groups. However, the molecular bases of inflamm-aging remain obscure. We prepared AGE by incubating BSA (0.0746 mmol/L) + glucose (0.5 mol/L) at 37 °C in 5% CO₂–95% air for 1–180 days. The lysine glycation in BSA–AGE reached 77% on day 30 and 100% after day 130, whereas the glycation of arginine and cysteine was minimal. The N^ε-(carboxymethyl)-lysine content in BSA–AGE was also increased with increasing number of incubation days. The lectin-binding assay revealed that the glycation of BSA not only altered the conformational structure, but lost binding capacity with various lectins. An immunological functional assay showed that BSA–AGE > 8 μg/mL significantly suppressed normal human Th1 (IL-2 and IFN-γ) and Th2 (IL-10) mRNA expression, whereas AGE > 0.5 μg/mL enhanced monocyte IL-6 production irrelevant to cell apoptosis. The AGE-enhanced monocyte IL-6 production was via MAPK–ERK and MyD88-transduced NF-κBp50 signaling pathways. To elucidate the structure–function relationship of BSA–AGE-enhanced IL-6 production, we pre-preincubated BSA–AGE with different carbohydrate-degrading, protein-degrading, and glycoprotein-degrading enzymes. We found that trypsin and carboxypeptidase Y suppressed whereas β-galactosidase enhanced monocyte IL-6 production. In conclusion, BSA–AGE exerted both immunosuppressive and pro-inflammatory effects that are the molecular basis of inflamm-aging in aged and diabetes groups. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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11 pages, 1469 KiB

Open AccessCommunication

A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations

by Clara Uriel, Rebeca Sola-Llano, Jorge Bañuelos, Ana M. Gomez and J. Cristobal Lopez

Molecules 2019, 24(11), 2050; https://doi.org/10.3390/molecules24112050 - 29 May 2019

Cited by 6 | Viewed by 3056

Abstract

A concise synthetic route from methylmalonate to a tetravalent aliphatic scaffold has been developed. The ensuing tetra-tethered derivative is equipped with two hydroxyl groups, as well as orthogonal alkene and alkyne functionalities. The usefulness of the scaffold has been demonstrated with the preparation of two representative multivalent derivatives: (i) a tetravalent compound containing two D-mannose units, one fluorescent boron-dipyrromethene (BODIPY) dye and a suitably functionalized amino acid and (ii) by way of dimerization and saponification, a water-soluble tetramannan derivative containing two fluorescent BODIPY units. Additionally, photophysical measurements conducted on these derivatives support the viability of the herein designed single and double BODIPY-labeled carbohydrate-based clusters as fluorescent markers. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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13 pages, 2220 KiB

Open AccessArticle

Structural Characterization and Anti-Proliferation Activities Against Tumor Cells of an Arabinogalactan from Juniperus convallium

by Beibei Li, Mengxue Dong, Ji De, Li Ye, Daofeng Chen and Yan Lu

Molecules 2019, 24(10), 1850; https://doi.org/10.3390/molecules24101850 - 14 May 2019

Cited by 7 | Viewed by 3135

Abstract

As a hyperproliferative disorder, cancer has continued to be a major public health challenge. In the present study, a polysaccharide JC-PS1 was isolated and purified from Juniperus convallium. JC-PS1 is a heteropolysaccharide composed of Ara, Gal, GalA and Rha with the average molecular weight of 280 kDa. Based on the methylation and 2D NMR analysis, JC-PS1 was elucidated as a backbone of →5)-α-Araf-(1→ and →3,5)-α-Araf-(1→, and three kinds of branches attached to the O-3 position of →3,5)-α-Araf-(1→, including β-GalpA-(1→3)-β-Galp-(1→, α-Araf-(1→3)-α-Rhap-(1→ and α-Araf-(1→3)-β-Galp-(1→. Accordingly, the atomic force microscopy of JC-PS1 showed a linear filamentous structure with small proportion of branches. Furthermore, JC-PS1 exhibited significant anti-proliferation activities against PANC-1, A431, MDA-MB-231, U118MG and H1975 cells with the IC₅₀ values of 296.8, 477.9, 657.4, 686.7 and 862.1 μg/mL, respectively. This indicated that JC-PS1 could be a potential therapeutic agent for the treatment of cancer. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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16 pages, 4797 KiB

Open AccessArticle

¹H-NMR Metabolomics Analysis of the Effects of Sulfated Polysaccharides from Masson Pine Pollen in RAW264.7 Macrophage Cells

by Fangchen Su, Mengmeng Sun and Yue Geng

Molecules 2019, 24(9), 1841; https://doi.org/10.3390/molecules24091841 - 13 May 2019

Cited by 9 | Viewed by 3730

Abstract

Many polysaccharides have been shown to be bioactive, with the addition of sulfate often enhancing or altering this bioactivity. In previous studies, masson pine pollen polysaccharides, to include a sulfate derivative, have been shown to promote macrophage proliferation similarly to LPS. However, the exact metabolic mechanisms promoting this proliferation remain unclear. In this study, RAW264.7 macrophage cells were treated with a purified masson pine pollen polysaccharide (PPM60-D), a sulfate derivative (SPPM60-D), or LPS. Proliferation levels at a variety of concentrations were examined using MTT assay, with optimal concentration used when performing metabolomic analysis via ¹H nuclear magnetic resonance (¹H-NMR). This process resulted in the identification of thirty-five intracellular metabolites. Subsequent multivariate statistical analysis showed that both LPS and SPPM60-D promote RAW264.7 proliferation by promoting aerobic respiration processes and reducing processes associated with glycolysis. While some insight was gained regarding the mechanistic differences between SPPM60-D and LPS, the specific mechanisms governing the effect of SPPM60 on RAW264.7 cells will require further elucidation. These findings show that both LPS and SPPM60-D effectively promote RAW264.7 proliferation and may have beneficial uses in maintaining cellular vitality or inhibiting cancer. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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13 pages, 1893 KiB

Open AccessArticle

Adsorption of Tea Polyphenols using Microporous Starch: A Study of Kinetics, Equilibrium and Thermodynamics

by Xianchun Hu and Xianfeng Du

Molecules 2019, 24(8), 1449; https://doi.org/10.3390/molecules24081449 - 12 Apr 2019

Cited by 22 | Viewed by 4051

Abstract

Microporous starch (MPS) granules were formed by the partial hydrolysis of starch using α–amylase and glucoamylase. Due to its biodegradability and safety, MPS was employed to adsorb tea polyphenols (TPS) based on their microporous characteristics. The influences of solution pH, time, initial concentration and temperature on the adsorptive capacity were investigated. The adsorption kinetics data conformed to the pseudo second–order kinetics model, and the equilibrium adsorption data were well described by the Langmuir isotherm model. According to the fitting of the adsorption isotherm formula, the maximum adsorption capacity of TPS onto MPS at pH 6.7 and T = 293 K was approximately 63.1 mg/g. The thermodynamic parameters suggested that the adsorption of TPS onto MPS was spontaneous and exothermic. Fourier transform infrared (FT–IR) analysis and the thermodynamics data were consistent with a physical adsorption mechanism. In addition, MPS-loaded TPS had better stability during long-term storage at ambient temperature. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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12 pages, 2362 KiB

Open AccessArticle

Antiviral Activity of Uridine Derivatives of 2-Deoxy Sugars against Tick-Borne Encephalitis Virus

by Ewelina Krol, Ilona Wandzik, Gabriela Brzuska, Luděk Eyer, Daniel Růžek and Boguslaw Szewczyk

Molecules 2019, 24(6), 1129; https://doi.org/10.3390/molecules24061129 - 21 Mar 2019

Cited by 8 | Viewed by 4144

Abstract

Tick-borne encephalitis virus (TBEV) is a causative agent of tick-borne encephalitis (TBE), one of the most important human infections involving the central nervous system. Although effective vaccines are available on the market, they are recommended only in endemic areas. Despite many attempts, there are still no specific antiviral therapies for TBEV treatment. Previously, we synthesized a series of uridine derivatives of 2-deoxy sugars and proved that some compounds show antiviral activity against viruses from the Flaviviridae and Orthomyxoviridae families targeting the late steps of the N-glycosylation process, affecting the maturation of viral proteins. In this study, we evaluated a series of uridine derivatives of 2-deoxy sugars for their antiviral properties against two strains of the tick-borne encephalitis virus; the highly virulent TBEV strain Hypr and the less virulent strain Neudoerfl. Four compounds (2, 4, 10, and 11) showed significant anti-TBEV activity with IC₅₀ values ranging from 1.4 to 10.2 µM and low cytotoxicity. The obtained results indicate that glycosylation inhibitors, which may interact with glycosylated membrane TBEV E and prM proteins, might be promising candidates for future antiviral therapies against TBEV. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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15 pages, 1835 KiB

Open AccessArticle

Properties and Digestibility of Octenyl Succinic Anhydride-Modified Japonica-Type Waxy and Non-Waxy Rice Starches

by Junhee No, Saehun Mun and Malshick Shin

Molecules 2019, 24(4), 765; https://doi.org/10.3390/molecules24040765 - 20 Feb 2019

Cited by 37 | Viewed by 3807

Abstract

Waxy and non-waxy rice starches from japonica type Korean rice varieties were esterified with different levels of octenyl succinic anhydride (OSA), and the molecular structure of amylopectin (AP), digestibility, and emulsion stability were investigated. As OSA levels increased, the degree of substitution, granule size, peak and final viscosities, emulsion stability, and short chain of AP increased. However, the gelatinization temperature and enthalpy, and digestibility decreased. All OSA esterified starches showed a new band at 1723 cm⁻¹, but maintained A-type crystallinity. The DP6-12 of AP in waxy rice starch (WRS) was higher than that in non-waxy rice starch (NRS) with increasing OSA levels. Because the amylose and long chain of AP accessed easily with OSA groups, the digestibility of NRS was lower than that of WRS. The emulsion stability was higher in WRS than in NRS. From the above results, it is suggested that amylose should have a higher affinity with OSA esterification than AP and that the emulsion stability should increase in WRS, but the digestibility should decrease in NRS after OSA modification. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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20 pages, 5075 KiB

Open AccessArticle

Photochemical Reactions in Dialdehyde Starch

by Marta Ziegler-Borowska, Katarzyna Wegrzynowska-Drzymalska, Dorota Chelminiak-Dudkiewicz, Jolanta Kowalonek and Halina Kaczmarek

Molecules 2018, 23(12), 3358; https://doi.org/10.3390/molecules23123358 - 18 Dec 2018

Cited by 32 | Viewed by 6612

Abstract

In this study potato and corn starch were subjected to oxidation, using sodium periodate, to obtain dialdehyde starch (DAS) containing different amount of aldehyde groups. The obtained modified starch samples have been characterized with chemical analysis, scanning electron microscopy (SEM) and ATR-FTIR spectroscopy. Then, the samples were exposed to polychromatic UV radiation and the course of photochemical reaction has been monitored with ATR-FTIR spectroscopy. The surface properties of the native and dialdehyde starch before and after UV-irradiation have been determined by contact angle measurements and calculation of surface free energy. The crystallinity of the samples has been estimated with X-ray diffraction (XRD). It has been proved that the dialdehyded corn starch contained a higher amount of functional groups was more photostable than the oxidized potato starch. Sodium iodide(V), firmly bound to DAS macromolecules, has been found to have a significant effect on the photooxidative degradation of the tested systems. In addition, the mechanism of photoinduced reactions in the dialdehyde starch has been proposed. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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11 pages, 870 KiB

Open AccessArticle

Analysis of Targeted Metabolites and Molecular Structure of Starch to Understand the Effect of Glutinous Rice Paste on Kimchi Fermentation

by Duyun Jeong, Jong-Hee Lee and Hyun-Jung Chung

Molecules 2018, 23(12), 3324; https://doi.org/10.3390/molecules23123324 - 14 Dec 2018

Cited by 9 | Viewed by 4779

Abstract

Bachu (Chinese cabbage) kimchi, a Korean traditional fermented dish, were prepared with or without the addition of glutinous (waxy) rice paste and their characteristics including pH, total bacteria count, total starch content, sugar metabolites, and molecular structure of starch were examined periodically for 20 days to investigate the effect of adding glutinous rice paste to kimchi during fermentation. The pH and total bacteria count showed that the fermentation of kimchi added with glutinous rice paste (GRP kimchi) progressed a little more quickly than that of control kimchi without glutinous rice paste. The GRP kimchi had higher glucose content but lower fructose content than control kimchi. Interestingly, maltose was only detected in GRP kimchi during fermentation. The GRP kimchi contained much greater amount of mannitol throughout fermentation than control kimchi. Total starch content in GRP kimchi gradually decreased during fermentation, which might have contributed to its greater glucose content and the larger amount of maltose production. In GRP kimchi, peak height and area for all degrees of polymerization (DP) of starch decreased during fermentation and its average chain length decreased while the proportion of short chains increased as fermentation processed, indicating degradation of starch chains by enzymes presented in the kimchi. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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11 pages, 1694 KiB

Open AccessArticle

Hierarchical Structure, Gelatinization, and Digestion Characteristics of Starch from Longan (Dimocarpus longan Lour.) Seeds

by Ziman Hu, Lei Zhao, Zhuoyan Hu and Kai Wang

Molecules 2018, 23(12), 3262; https://doi.org/10.3390/molecules23123262 - 10 Dec 2018

Cited by 15 | Viewed by 3927

Abstract

Starch was isolated from longan seeds of three widely distributed cultivars (Chuliang, Shixia, and Caopu) in China. Comparisons of the multi-level structure of the starch of longan seeds among various cultivars were made, and the relations between these structural and property characteristics are discussed. The isolated starch, accounting for 44.9–49.5% (w/w) in longan seeds, had an oval or an irregular polygonal shape with a smooth surface. Their chain-length distributions (CLDs) varied with longan cultivar; Chuliang showed a larger proportion of longer amylopectin chains with a degree of polymerization (DP) 30~100. This is attributed to the slightly higher relative crystallinity of Chuliang longan seed starch. Apparent differences were also detected in amylose structure. Caopu showed a higher amylose content than Chuliang and Shixia, resulting in its lower gelatinization temperatures and enthalpy change. All longan seed starch had a typical A-type crystal structure with relative crystallinity ranging 28.6–28.9%. For raw starch, Caopu showed the lowest digestion rate, followed by Chuliang; Shixia showed the highest. This is because Caopu had the highest amylose content. Chuliang had a more intact structure than Shixia, as suggested by its higher crystallinity, although they had similar amylose content. After being fully gelatinized, all starch showed a similar digestion process, indicating that the digestibility of gelatinized starch does not differ with starch source or structure. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry)

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