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Marine Drugs
Special Issues
Carbohydrate-Containing Marine Compounds of Mixed Biogenesis II
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Carbohydrate-Containing Marine Compounds of Mixed Biogenesis II

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

Deadline for manuscript submissions: closed (31 July 2023) | Viewed by 6094

Special Issue Editors

Prof. Dr. Valentin A. Stonik

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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; glycosides; glycoconjugates; steroids; terpenoids; uncommon glycolipids; other marine metabolites; structures; bioactivities; chemistry; biochemistry; cell biology; pharmacology
Special Issues, Collections and Topics in MDPI journals
Dr. Natalia V. Ivanchina

E-Mail Website
Guest Editor
G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far East Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia
Interests: marine natural product chemistry; secondary metabolites; starfish polar steroids and lipids; biological activities; metabolomics; biosynthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

There are many classes of natural compounds, possessing monosaccharide or oligosaccharide moieties, that are derived from mixed biogenesis. Carbohydrate-containing marine natural products represent one of biggest groups among such compounds. They are isolated from marine vertebrate and invertebrate animals, algae, fungi, and bacteria and include steroid and terpenoid glycosides, glycolipids, lipopoly- and lipooligosaccharides, glycosides of polyphenolic metabolites, glycosylated peptides, and polyketides, for example, glycosylated antibiotics, and so on. The inclusion of carbohydrate fragments in their structures usually leads to high physiological and/or environmental activities. Organisms living in the marine environment often produce water-soluble natural compounds that embody carbohydrate fragments as their hydrophilic components. These compounds often also contain a hydrophobic fragment which facilitates their interaction with cellular membrane and membrane proteins. Motivated by the success of the recent Special Issue “Carbohydrate-containing marine compounds of mixed biogenesis” (https://www.mdpi.com/journal/marinedrugs/special_issues/Carbohydrate-Containing) in the journal Marine Drugs, we have decided to pursue a follow-up Special Issue, “Carbohydrate-containing marine compounds of mixed biogenesis II”. We welcome your submissions to the Special Issue.

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 submissions that pass pre-check are 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 2900 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 natural product chemistry
  • glycosides
  • glycoconjugates
  • steroids
  • terpenoids
  • uncommon glycolipids
  • other marine carbohydrate-containing metabolites
  • structures
  • bioactivities
  • syntheses
  • bioactivities

Published Papers (4 papers)

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Research

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15 pages, 3887 KiB  
Article
Structure of the Lipooligosaccharide from the Deep-Sea Marine Bacterium Idiomarina zobellii KMM 231T, Isolated at a Depth of 4000 Meters
by Maxim S. Kokoulin, Pavel S. Dmitrenok and Lyudmila A. Romanenko
Mar. Drugs 2022, 20(11), 700; https://doi.org/10.3390/md20110700 - 09 Nov 2022
Cited by 1 | Viewed by 1504
Abstract
The structural characterization of lipopolysaccharides has critical implications for some biomedical applications, and marine bacteria are an inimitable source of new glyco-structures potentially usable in medicinal chemistry. On the other hand, lipopolysaccharides of marine Gram-negative bacteria present certain structural features that can help [...] Read more.
The structural characterization of lipopolysaccharides has critical implications for some biomedical applications, and marine bacteria are an inimitable source of new glyco-structures potentially usable in medicinal chemistry. On the other hand, lipopolysaccharides of marine Gram-negative bacteria present certain structural features that can help the understanding of the adaptation processes. The deep-sea marine Gram-negative bacterium Idiomarina zobellii KMM 231T, isolated from a seawater sample taken at a depth of 4000 m, represents an engaging microorganism to investigate in terms of its cell wall components. Here, we report the structural study of the R-type lipopolysaccharide isolated from I. zobellii KMM 231T that was achieved through a multidisciplinary approach comprising chemical analyses, NMR spectroscopy, and MALDI mass spectrometry. The lipooligosaccharide turned out to be characterized by a novel and unique pentasaccharide skeleton containing a very short mono-phosphorylated core region and comprising terminal neuraminic acid. The lipid A was revealed to be composed of a classical disaccharide backbone decorated by two phosphate groups and acylated by i13:0(3-OH) in amide linkage, i11:0 (3-OH) as primary ester-linked fatty acids, and i11:0 as a secondary acyl chain. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis II)
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16 pages, 3105 KiB  
Article
Identification, Characteristics and Function of Phosphoglucomutase (PGM) in the Agar Biosynthesis and Carbon Flux in the Agarophyte Gracilariopsis lemaneiformis (Rhodophyta)
by Qionglin Chen, Xinlei Yu, Shixia Liu, Suya Luo, Xiaojiao Chen, Nianjun Xu and Xue Sun
Mar. Drugs 2022, 20(7), 442; https://doi.org/10.3390/md20070442 - 02 Jul 2022
Cited by 3 | Viewed by 2154
Abstract
Agar is widely applied across the food, pharmaceutical and biotechnology industries, owing to its various bioactive functions. To better understand the agar biosynthesis in commercial seaweed Gracilariopsis lemaneiformis, the activities of four enzymes participating in the agar biosynthesis were detected, and phosphoglucomutase [...] Read more.
Agar is widely applied across the food, pharmaceutical and biotechnology industries, owing to its various bioactive functions. To better understand the agar biosynthesis in commercial seaweed Gracilariopsis lemaneiformis, the activities of four enzymes participating in the agar biosynthesis were detected, and phosphoglucomutase (PGM) was confirmed as highly correlated with agar accumulation. Three genes of PGM (GlPGM1, GlPGM2 and GlPGM3) were identified from the G. lemaneiformis genome. The subcellular localization analysis validated that GlPGM1 was located in the chloroplast and GlPGM3 was not significantly distributed in the organelles. Both the GlPGM1 and GlPGM3 protein levels showed a remarkable consistency with the agar variations, and GlPGM3 may participate in the carbon flux between (iso)floridoside, floridean starch and agar synthesis. After treatment with the PGM inhibitor, the agar and floridean starch contents and the activities of floridean starch synthase were significantly decreased; products identified in the Calvin cycle, the pentose phosphate pathway, the Embden-Meyerhof-Parnas pathway and the tricarboxylic acid cycle were depressed; however, lipids, phenolic acids and the intermediate metabolites, fructose-1,6-phosphate were upregulated. These findings reveal the essential role of PGM in regulating the carbon flux between agar and other carbohydrates in G. lemaneiformis, providing a guide for the artificial regulation of agar accumulation. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis II)
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21 pages, 1007 KiB  
Article
Structures and Biologic Activity of Chitonoidosides I, J, K, K1 and L-Triterpene Di-, Tri- and Tetrasulfated Hexaosides from the Sea Cucumber Psolus chitonoides
by Alexandra S. Silchenko, Sergey A. Avilov, Pelageya V. Andrijaschenko, Roman S. Popov, Ekaterina A. Chingizova, Pavel S. Dmitrenok, Anatoly I. Kalinovsky, Anton B. Rasin and Vladimir I. Kalinin
Mar. Drugs 2022, 20(6), 369; https://doi.org/10.3390/md20060369 - 30 May 2022
Cited by 5 | Viewed by 1775
Abstract
Five new triterpene di-, tri- and tetrasulfated hexaosides (chitonoidosides I (1), J (2), K (3), K1 (4) and L (5)) were isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near [...] Read more.
Five new triterpene di-, tri- and tetrasulfated hexaosides (chitonoidosides I (1), J (2), K (3), K1 (4) and L (5)) were isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near Bering Island (Commander Islands) from a depth of 100–150 m. The structural variability of the glycosides concerned both the aglycones (with 7(8)- or 9(11)-double bonds) and carbohydrate chains differing from each other by the third sugar residue (Xyl or sulfated by C-6 Glc) and/or by the fourth—terminal in the bottom semi-chain—residue (Glc or sulfated by C-6 MeGlc) as well as by the positions of a sulfate group at C-4 or C-6 in the sixth—terminal in the upper semi-chain—residue (MeGlc). Hemolytic activities of these compounds 1–5 against human erythrocytes as well as cytotoxicity against human cancer cell lines, HeLa, DLD-1 and HL-60, were studied. The hexaosides, chitonoidosides K (3) and L (5) with four sulfate groups, were the most active against tumor cells in all the tests. Noticeably, the sulfate group at C-4 of MeGlc6 did not decrease the membranolytic effect of 5 as compared with 3, having the sulfate group at C-6 of MeGlc6. Erythrocytes were, as usual, more sensitive to the action of the studied glycosides than cancer cells, although the sensitivity of leukemia promyeloblast HL-60 cells was higher than that of other tumor cells. The glycosides 1 and 2 demonstrated some weaker action in relation to DLD-1 cells than against other tumor cell lines. Chitonoidoside K1 (4) with a hydroxyl at C 25 of the aglycone was not active in all the tests. The metabolic network formed by the carbohydrate chains of all the glycosides isolated from P. chitonoides as well as the aglycones biosynthetic transformations during their biosynthesis are discussed and illustrated with schemes. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis II)
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Review

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26 pages, 8186 KiB  
Review
Carbohydrate-Containing Low Molecular Weight Metabolites of Microalgae
by Valentin A. Stonik and Inna V. Stonik
Mar. Drugs 2023, 21(8), 427; https://doi.org/10.3390/md21080427 - 28 Jul 2023
Viewed by 1284
Abstract
Microalgae are abundant components of the biosphere rich in low molecular weight carbohydrate-containing natural products (glycoconjugates). Glycoconjugates take part in the processes of photosynthesis, provide producers with important biological molecules, influence other organisms and are known by their biological activities. Some of them, [...] Read more.
Microalgae are abundant components of the biosphere rich in low molecular weight carbohydrate-containing natural products (glycoconjugates). Glycoconjugates take part in the processes of photosynthesis, provide producers with important biological molecules, influence other organisms and are known by their biological activities. Some of them, for example, glycosylated toxins and arsenicals, are detrimental and can be transferred via food chains into higher organisms, including humans. So far, the studies on a series of particular groups of microalgal glycoconjugates were not comprehensively discussed in special reviews. In this review, a special focus is given to glycoconjugates’ isolation, structure determination, properties and approaches to search for new bioactive metabolites. Analysis of literature data concerning structures, functions and biological activities of ribosylated arsenicals, galactosylated and sulfoquinovosylated lipids, phosphoglycolipids, glycoside derivatives of toxins, and other groups of glycoconjugates was carried out and discussed. Recent studies were fundamental in the discovery of a great variety of new carbohydrate-containing metabolites and their biological activities in defining the role of microalgal viral infections in regulating microalgal blooms as well as in the detection of glycoconjugates with potent immunomodulatory properties. Those discoveries support growing interest in these molecules. Full article
(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis II)
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