Special Issue "Carbohydrate-Containing Marine Compounds of Mixed Biogenesis"

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: 25 August 2021.

Special Issue Editors

Prof. Dr. Valentin A. Stonik
E-Mail Website
Guest Editor
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100-let Vladivostoku, Vladivostok 690022, Russia
Interests: marine natural product chemistry; secondary metabolites; marine invertebrates; glycoconjugates; steroids; terpenoids; uncommon glycolipds; biochemistry; cell biology; pharmacology
Special Issues and Collections in MDPI journals
Dr. Natalia V. Ivanchina
E-Mail Website
Guest Editor
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100-let Vladivostoku, Vladivostok 690022, Russia
Interests: marine natural product chemistry; secondary metabolites; starfish polyhydroxysteroids and their glycoconjugates; biological activities; metabolomics; biosynthesis Portrait
Special Issues and Collections in MDPI journals

Special Issue Information

Dear Colleagues,

Researchers studying secondary metabolites typically classify these compounds into isoprenoids, polyketides, peptides, shikimate derivatives, etc., taking into account their biogenetic origin. However, there are many other classes of natural compounds derived by mixed biogenesis, including combinations of the acetate-malonate, acetate-mevalonate, shikimic acid, and other biosynthetic pathways. Although the biosynthesis of such compounds requires additional metabolic energy, they usually lead to metabolites with high physiological and/or environmental activities. Organisms living in aquatic—including marine—environments often produce water-soluble natural compounds that embody carbohydrate fragments as their hydrophilic components. Glycoconjugates of this type are widely represented in diverse marine organisms. These include steroid and terpenoid glycosides, a variety of glycolipids, lipopoly- and lipooligosaccharides, glycosides of polyphenolic metabolites, glycosylated peptides and polyketides, and many other structural groups of marine natural compounds.

Recently, we were operating as Editors of the Special Issue “Marine Glycoconjugates” (https://www.mdpi.com/journal/marinedrugs/special_issues/Marine_Glycoconjugates_Trends_Perspectives), but in this generally successful Issue, there were no articles on many of the above-mentioned groups of marine metabolites. In accordance with invitation and sponsor support of the international scientific journal Marine Drugs, we have decided to continue this work. As a result, a Special Issue of this journal “Carbohydrate-Containing Marine Compounds of Mixed Biogenesis” will be prepared.

Prof. Dr. Valentin A. Stonik
Dr. Natalia V. Ivanchina
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Marine Drugs is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2400 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • marine secondary metabolites
  • marine glycoconjugates
  • drug discovery
  • steroid and terpenoid marine glycosides
  • lipopoly- and oligoglycosides
  • glycolipids
  • structures
  • syntheses
  • biological activities

Published Papers (6 papers)

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Research

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Article
EPS364, a Novel Deep-Sea Bacterial Exopolysaccharide, Inhibits Liver Cancer Cell Growth and Adhesion
Mar. Drugs 2021, 19(3), 171; https://doi.org/10.3390/md19030171 - 22 Mar 2021
Viewed by 499
Abstract
The prognosis of liver cancer was inferior among tumors. New medicine treatments are urgently needed. In this study, a novel exopolysaccharide EPS364 was purified from Vibrio alginolyticus 364, which was isolated from a deep-sea cold seep of the South China Sea. Further research [...] Read more.
The prognosis of liver cancer was inferior among tumors. New medicine treatments are urgently needed. In this study, a novel exopolysaccharide EPS364 was purified from Vibrio alginolyticus 364, which was isolated from a deep-sea cold seep of the South China Sea. Further research showed that EPS364 consisted of mannose, glucosamine, gluconic acid, galactosamine and arabinose with a molar ratio of 5:9:3.4:0.5:0.8. The relative molecular weight of EPS364 was 14.8 kDa. Our results further revealed that EPS364 was a β-linked and phosphorylated polysaccharide. Notably, EPS364 exhibited a significant antitumor activity, with inducing apoptosis, dissipation of the mitochondrial membrane potential (MMP) and generation of reactive oxygen species (ROS) in Huh7.5 liver cancer cells. Proteomic and quantitative real-time PCR analyses indicated that EPS364 inhibited cancer cell growth and adhesion via targeting the FGF19-FGFR4 signaling pathway. These findings suggest that EPS364 is a promising antitumor agent for pharmacotherapy. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)
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Article
Determination of the Extraction, Physicochemical Characterization, and Digestibility of Sulfated Polysaccharides in Seaweed—Porphyra haitanensis
Mar. Drugs 2020, 18(11), 539; https://doi.org/10.3390/md18110539 - 28 Oct 2020
Viewed by 622
Abstract
The aim of the study was to extract Porphyra haitanensis polysaccharides (PHPs) using the water extraction and alcohol precipitation methods and explore their antioxidant activity and physicochemical properties. The single-factor and Box-Behnken response surface methodologies were used to optimize the extraction of polysaccharides [...] Read more.
The aim of the study was to extract Porphyra haitanensis polysaccharides (PHPs) using the water extraction and alcohol precipitation methods and explore their antioxidant activity and physicochemical properties. The single-factor and Box-Behnken response surface methodologies were used to optimize the extraction of polysaccharides from Porphyra haitanensis. Our results showed that the polysaccharide yield was as high as 20.48% with a raw material to water ratio of 0.04, and extraction time of 3 h at 80 °C. The extraction rate observed was similar to the actual extraction rate, thus proving the reliability of the optimization model. The extracted polysaccharides primarily consisted of galactose, glucose, and fucose in the molar ratio 76.2:2.1:1, respectively. The high performance gel permeation chromatography (HPGPC) results showed that the molecular weight of the PHPs obtained was 6.3 × 105 Da, and the sulfate content was 2.7 mg/mL. Fourier infrared spectroscopy was used to analyze the functional groups and structures of the polysaccharides. The effect of concentration, temperature, and pH on the apparent viscosity of the PHPs solution were studied using rheology experiments, which revealed that PHPs were a “non-Newtonian fluid” with shear-thinning behavior. The viscosity of the PHPs gradually increased with increasing sugar concentration, and decreased with increasing temperature, acidity, and alkalinity. Detection of the antioxidant activity of OH*, DPPH*, and ABTS* revealed that the scavenging activity of ABTS* was higher than that of OH* and DPPH* in the concentration range of 1–5 mg/mL. In the experiments of simulating gastric juice and alpha amylase in vitro, it was found that PHPs can better resist digestion of alpha amylase, and have better resistance than fructooligosaccharide (FOS), so PHPs have potential prebiotic activity. These findings demonstrate the potential of PHPs for use in the food and cosmetic industries. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)
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Article
Cloning and Characterization of a New β-Galactosidase from Alteromonas sp. QD01 and Its Potential in Synthesis of Galacto-Oligosaccharides
Mar. Drugs 2020, 18(6), 312; https://doi.org/10.3390/md18060312 - 14 Jun 2020
Cited by 3 | Viewed by 934
Abstract
As prebiotics, galacto-oligosaccharides (GOSs) can improve the intestinal flora and have important applications in medicine. β-galactosidases could promote the synthesis of GOSs in lactose and catalyze the hydrolysis of lactose. In this study, a new β-galactosidase gene (gal2A), which belongs to [...] Read more.
As prebiotics, galacto-oligosaccharides (GOSs) can improve the intestinal flora and have important applications in medicine. β-galactosidases could promote the synthesis of GOSs in lactose and catalyze the hydrolysis of lactose. In this study, a new β-galactosidase gene (gal2A), which belongs to the glycoside hydrolase family 2, was cloned from marine bacterium Alteromonas sp. QD01 and expressed in Escherichia coli. The molecular weight of Gal2A was 117.07 kDa. The optimal pH and temperature of Gal2A were 8.0 and 40 °C, respectively. At the same time, Gal2A showed wide pH stability in the pH range of 6.0–9.5, which is suitable for lactose hydrolysis in milk. Most metal ions promoted the activity of Gal2A, especially Mn2+ and Mg2+. Importantly, Gal2A exhibited high transglycosylation activity, which can catalyze the formation of GOS from milk and lactose. These characteristics indicated that Gal2A may be ideal for producing GOSs and lactose-reducing dairy products. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)
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Article
Structure and In Vitro Bioactivity against Cancer Cells of the Capsular Polysaccharide from the Marine Bacterium Psychrobacter marincola
Mar. Drugs 2020, 18(5), 268; https://doi.org/10.3390/md18050268 - 19 May 2020
Cited by 2 | Viewed by 844
Abstract
Psychrobacter marincola KMM 277T is a psychrophilic Gram-negative bacterium that has been isolated from the internal tissues of an ascidian Polysyncraton sp. Here, we report the structure of the capsular polysaccharide from P. marincola KMM 277T and its effect on the [...] Read more.
Psychrobacter marincola KMM 277T is a psychrophilic Gram-negative bacterium that has been isolated from the internal tissues of an ascidian Polysyncraton sp. Here, we report the structure of the capsular polysaccharide from P. marincola KMM 277T and its effect on the viability and colony formation of human acute promyelocytic leukemia HL-60 cells. The polymer was purified by several separation methods, including ultracentrifugation and chromatographic procedures, and the structure was elucidated by means of chemical analysis, 1-D, and 2-D NMR spectroscopy techniques. It was found that the polysaccharide consists of branched hexasaccharide repeating units containing two 2-N-acetyl-2-deoxy-d-galacturonic acids, and one of each of 2-N-acetyl-2-deoxy-d-glucose, d-glucose, d-ribose, and 7-N-acetylamino-3,5,7,9-tetradeoxy-5-N-[(R)-2-hydroxypropanoylamino]- l-glycero-l-manno-non-2-ulosonic acid. To our knowledge, this is the first finding a pseudaminic acid decorated with lactic acid residue in polysaccharides. The biological analysis showed that the capsular polysaccharide significantly reduced the viability and colony formation of HL-60 cells. Taken together, our data indicate that the capsular polysaccharide from P. marincola KMM 277T is a promising substance for the study of its antitumor properties and the mechanism of action in the future. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)
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Review

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Review
Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms
Mar. Drugs 2021, 19(6), 327; https://doi.org/10.3390/md19060327 - 05 Jun 2021
Viewed by 325
Abstract
In this review, we discuss structural diversity, taxonomic distribution, biological activities, biogenesis, and synthesis of a rare group of terpenoids, the so-called malabaricane and isomalabaricane triterpenoids, as well as some compounds derived from them. Representatives of these groups were found in some higher [...] Read more.
In this review, we discuss structural diversity, taxonomic distribution, biological activities, biogenesis, and synthesis of a rare group of terpenoids, the so-called malabaricane and isomalabaricane triterpenoids, as well as some compounds derived from them. Representatives of these groups were found in some higher and lower terrestrial plants, as well as in some fungi, and in a relatively small group of marine sponges. The skeletal systems of malabaricanes and isomalabaricanes are similar to each other, but differ principally in the stereochemistry of their tricyclic core fragments, consisting of two six-membered and one five-membered rings. Evolution of these triterpenoids provides variety of rearranged, oxidized, and glycoconjugated products. These natural compounds have attracted a lot of attention for their biosynthetic origin and biological activity, especially for their extremely high cytotoxicity against tumor cells as well as promising neuroprotective properties in nanomolar concentrations. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)
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Review
Asterosaponins: Structures, Taxonomic Distribution, Biogenesis and Biological Activities
Mar. Drugs 2020, 18(12), 584; https://doi.org/10.3390/md18120584 - 24 Nov 2020
Cited by 3 | Viewed by 669
Abstract
Asterosaponins are a class of steroid oligoglycosides isolated from starfish with characteristic structures and diverse biological activities. In this review, we have attempted to combine the most important data concerning asterosaponins and give a list of these secondary metabolites with their structural peculiarities. [...] Read more.
Asterosaponins are a class of steroid oligoglycosides isolated from starfish with characteristic structures and diverse biological activities. In this review, we have attempted to combine the most important data concerning asterosaponins and give a list of these secondary metabolites with their structural peculiarities. The purpose of this review is to provide a brief but as complete as possible principal information about their chemical structures, taxonomic distribution in the marine environment, distribution in different geographical areas and depths, some properties, biological activities, and functions. Some other rare steroid metabolites from starfish, closely related in structures and probably biogenesis to asterosaponins, are also discussed. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)
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