A New Lectin from Auricularia auricula Inhibited the Proliferation of Lung Cancer Cells and Improved Pulmonary Flora

Lectins are widely distributed in the natural world and are usually involved in antitumor activities. Auricularia auricula (A. auricula) is a medicinal and edible homologous fungus. A. auricula contains many active ingredients, such as polysaccharides, melanin, flavonoids, adenosine, sterols, alkaloids, and terpenes. In this study, we expected to isolate and purify lectin from A. auricula, determine the glycoside bond type and sugar-specific protein of A. auricula lectin (AAL), and finally, determine its antitumor activities. We used ammonium sulfate fractionation, ion exchange chromatography, and affinity chromatography to separate and purify lectin from A. auricula. The result was a 25 kDa AAL with a relative molecular mass of 18913.22. Protein identification results suggested that this lectin contained four peptide chains by comparing with the UniProt database. The FT-IR and β-elimination reaction demonstrated that the connection between the oligosaccharide and polypeptide of AAL was an N-glucoside bond. Analyses of its physical and chemical properties showed that AAL was a temperature-sensitive and acidic/alkaline-dependent glycoprotein. Additionally, the anticancer experiment manifested that AAL inhibited the proliferation of A549, and the I C 50 value was 28.19 ± 1.92 μ g / mL . RNA sequencing dataset analyses detected that AAL may regulate the expression of JUN, TLR4, and MYD88 to suppress tumor proliferation. Through the pulmonary flora analysis, the bacterial structure of each phylum in the lectin treatment group was more reasonable, and the colonization ability of the normal microflora was improved, indicating that lectin treatment could significantly improve the bacterial diversity characteristics.

Structure, Biological Activities and Metabolism of Flavonoid Glucuronides

Background: Flavonoid glucuronides are a kind of natural products which present a flavone linked directly with one or several glucuronides through O-glycoside bond. They had become of interest in natural product research in the past decades for their antioxidant, anti-inflammatory, and anti-bacteria activities. In particular, the compound breviscapine has a notable effect on cardio-cerebrovascular diseases. Several other compounds even have antitumor activity. Methods: Through searching the database and reading a large number of documents, we summarized the related findings of flavonoid glucuronides. Results: We summarized 211 naturally occurring flavonoid glucuronides in 119 references with their chemical structures, biological activities, and metabolism. A total of 220 references from 1953 to 2020 were cited in this paper according to literature databases such as CNKI, Weipu, Wanfang data, Elsevier, Springer, Wiley, NCBI, PubMed, EmBase, etc. Conclusion : Flavonoid glucuronides are a class of compounds with various chemical structures and a diverse range of biological activities. And they are thought to be potential candidates for drug discovery, but the specific study on their mechanisms is still limited until now. We hope this article can provide references for natural product researchers and draw more attention to flavonoid glucuronides’ biological activities and mechanisms.

Identification of Anthocyanins and Their Fouling Mechanisms during Non-Thermal Nanofiltration of Blueberry Aqueous Extracts

Organic fouling in the nanofiltration (NF) process, which is a non-thermal technology to recover active components, is a critical problem limiting its applications. This study seeks to identify the anthocyanins on the NF membrane and explore their fouling mechanisms during concentration of blueberry extracts. Seven kinds of monomeric anthocyanins in foulants—delphinidin-3-O-galactoside, delphinidin-3-O-glucoside, delphinidin-3-O-arabinoside, cyanidin-3-O-galactoside, petunidin-3-O-galactoside, peonidin-3-O-glucoside, and malvidin-3-O-glucoside—were identified. Moreover, chalcone, myricetin derivative, and an unknown substance with [M+H]+ at m/z 261.1309, which is the fragment ion corresponding to the break of glycoside bond of anthocyanins, were obtained. Interactions between anthocyanins and membrane made from polyamide were principally governed by the CH-π and π-π stacking of aromatic rings, the establishment of hydrogen bonds, and electrostatic interaction. This study will be helpful to further control fouling and choice of cleaning agents in concentration of anthocyanins-rich extracts.

Analisis Kadar Glukomanan Dari Biji Durian (Durio zeibethinus Murr) dengan Metode Spektrofotometri pada Berbagai Waktu dan Suhu Hidrolisis

Durian seeds are one type of seed that contains glucomannan. The aim is to determine glucomannan levels in the durian seed. The study was designed using a completely randomized design (CRD). The extracted glucomannan was determined by the spectrophotometry method at various temperature and hydrolysis time. The crude extract of glucomannan was hydrolyzed using 3 M HCl for 70, 80, 90, 100, and 110 minutes at 70, 80, 90, 100, and 110°C. The highest glucomannan concentration of 39.60% was obtained at a hydrolysis temperature of 100°C for 100 minutes. The analysis of the FTIR spectrophotometer shown that the vibration of the C-O-C functional group (glycoside bond) was obtained at the wavelength number of 1020.34 cm-1 which is a characteristic of glucomannan. Keywords: glucomannan, durian seed, hydrolysis, spectrophotometry

Azidophenylselenylation of glycals towards 2-azido-2-deoxy-selenoglycosides and their application in oligosaccharide synthesis

Abstract2-Amino-2-deoxy-pyranosyl units are important structural components of cell-wall polymers in prokaryotes, fungi and mammals. With respect to the need for development of novel and efficient vaccines and tools for serodiagnosis of infectious diseases, of particular interest are the oligosaccharide cell-wall antigens of pathogenic bacteria and fungi, which comprise 2-amino-2-deoxy-D-glucopyranose and 2-amino-2-deoxy-D-galactopyranose units as α- or β-anomers. Synthesis of N-acylated α-GlcN and α-GalN containing oligosaccharides is a special challenge due to the presence of a participating group at C2 which favors the formation of β- rather than α-glycoside bond. Herein we overview the efficient two-step approach for preparation of 1,2-cis-glycosides of 2-amino-2-deoxy-D-glucopyranose and 2-amino-2-deoxy-D-galactopyranose, which was recently developed in our laboratory. In the first step, an efficient and straightforward azidophenylselenylation procedure of glycals gives phenyl 2-azido-2-deoxy-1-selenoglycosides as versatile glycosyl donors. In the second step, these donors can be efficiently transformed into α- or β-glycosides depending on the choice of the solvent. In acetonitrile, total β-stereocontrol was achieved, and the use of diethyl ether as a solvent favouring α-stereoselectivity of glycosylations with phenyl 2-azido-2-deoxy-1-selenoglycosides. Besides, it was shown, that low reactivity and nucleophilicity of glycosyl acceptors which are glycosylated with phenyl 2-azido-2-deoxy-1-selenogalactosides facilitated the formation of α-GalN derivatives. To date, homogenous azidophenylselenylation of glycals and glycosylation with phenyl 2-azido-2-deoxy-1-seleno-α-D-glycopyranosides can be regarded as most useful tool for introduction of 2-amino-2-deoxy-D-glycopyranoside residues into complex synthetic oligosaccharides.

Programmable Synthesis of 2-Deoxyglycosides

Control of glycoside bond stereochemistry is the central challenge in the synthesis of oligosaccharides. 2-Deoxyglycosides, which lack a C2 substituent to guide stereoselectivity, are among the most difficult classes of glycoside bond constructions. Here we present a method to synthesize 2-deoxysaccharides with specified glycoside bond stereochemistry using a nucleophilic carbohydrate residue and the synthetic equivalent of an alcohol electrophile. Because the configuration of the nucleophile can be precisely controlled, both α- and β-glycosides can be synthesized from the same starting material in nearly all cases examined. Stereoselectivities in these reactions are often greater than 50:1 and yields typically exceed 70%. This strategy is amenable to the stereocontrolled syntheses of trisaccharide diastereomers, and a tetrasaccharide. Our method offers a fundamentally new approach to O-glycoside synthesis to enable downstream biochemical and natural product applications.

Programmable Synthesis of 2-Deoxyglycosides

Control of glycoside bond stereochemistry is the central challenge in the synthesis of oligosaccharides. 2-Deoxyglycosides, which lack a C2 substituent to guide stereoselectivity, are among the most difficult classes of glycoside bond constructions. Here we present a method to synthesize 2-deoxysaccharides with specified glycoside bond stereochemistry using a nucleophilic carbohydrate residue and the synthetic equivalent of an alcohol electrophile. Because the configuration of the nucleophile can be precisely controlled, both α- and β-glycosides can be synthesized from the same starting material in nearly all cases examined. Stereoselectivities in these reactions are often greater than 50:1 and yields typically exceed 70%. This strategy is amenable to the stereocontrolled syntheses of trisaccharide diastereomers, and a tetrasaccharide. Our method offers a fundamentally new approach to O-glycoside synthesis to enable downstream biochemical and natural product applications.

Where to Next? Unsolved Questions

The first ten chapters of this book are a kind of snapshot that captures the current state of knowledge and proposes a scenario for life’s beginning that is based on the properties of RNA described by Harry Noller in the epigraph (Noller, 2012). Despite this progress, there are still enormous gaps in our understanding that remain to be filled. The purpose of this chapter is to make those gaps explicit for future investigators who might be attracted to the question of how life can begin. Because life is an interacting system of immense complexity, each component of which is essential to cellular function as a living system, the gaps have little in common. They can be presented as a set of questions related to sources and properties of organic compounds, mechanisms for capturing energy, polymerization and replication of nucleic acids, the origin of ribosomes, and the transmission of genetic information. For each question, I will discuss one or more papers that could provide clues to an answer and then add some ideas that might serve as guides to future research. A source of mononucleotides is a problem not just for the hypothesis being presented in this book but for any proposed pathway to the origin of life. Unlike amino acids, there is no obvious source of mononucleotides, for the following reasons: Three different molecular species must be present in an aqueous solution at concentrations sufficient for a reaction to occur. They must somehow, even in this mixture of organic solutes, form a specific ester bond between a phosphate and a ribose, then must form an N-glycoside bond between the ribose and a nucleobase (Fig. 11.1), and these reactions must occur spontaneously in a hydrothermal environment. Furthermore, it is not enough for one base to occur in the solution, all four (adenine, uracil, guanine, and cytosine) must be present.

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

To synthesize nucleoside and oligosaccharide derivatives, we often use a glycosylation reaction to form a glycoside bond. Coupling reactions between a nucleobase and a sugar donor in the former case, and the reaction between an acceptor and a sugar donor of in the latter are carried out in the presence of an appropriate activator. As an activator of the glycosylation, a combination of a Lewis acid catalyst and a hypervalent iodine was developed for synthesizing 4’-thionucleosides, which could be applied for the synthesis of 4’-selenonucleosides as well. The extension of hypervalent iodine-mediated glycosylation allowed us to couple a nucleobase with cyclic allylsilanes and glycal derivatives to yield carbocyclic nucleosides and 2’,3’-unsaturated nucleosides, respectively. In addition, the combination of hypervalent iodine and Lewis acid could be used for the glycosylation of glycals and thioglycosides to produce disaccharides. In this paper, we review the use of hypervalent iodine-mediated glycosylation reactions for the synthesis of nucleosides and oligosaccharide derivatives.