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Carbohydrate-Containing Marine Compounds of Mixed Biogenesis

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

Deadline for manuscript submissions: closed (25 August 2021) | Viewed by 27242

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Prof. Dr. Valentin A. Stonik

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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
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Dr. Natalia V. Ivanchina

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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,

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://0-www-mdpi-com.brum.beds.ac.uk/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 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 secondary metabolites
marine glycoconjugates
drug discovery
steroid and terpenoid marine glycosides
lipopoly- and oligoglycosides
glycolipids
structures
syntheses
biological activities

Published Papers (11 papers)

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Editorial

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3 pages, 186 KiB

Open AccessEditorial

Carbohydrate-Containing Marine Compounds of Mixed Biogenesis

by Valentin A. Stonik and Natalia V. Ivanchina

Mar. Drugs 2021, 19(12), 694; https://0-doi-org.brum.beds.ac.uk/10.3390/md19120694 - 06 Dec 2021

Cited by 1 | Viewed by 1906

Abstract

Marine natural compounds, containing rare and enzymatically-modified monosaccharide residues [...] Full article

(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)

Research

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9 pages, 901 KiB

Open AccessArticle

Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge Oceanapia sp.

by Tatyana N. Makarieva, Natalia V. Ivanchina, Pavel S. Dmitrenok, Alla G. Guzii, Valentin A. Stonik, Doralyn S. Dalisay and Tadeusz F. Molinski

Mar. Drugs 2021, 19(11), 635; https://0-doi-org.brum.beds.ac.uk/10.3390/md19110635 - 12 Nov 2021

Cited by 7 | Viewed by 2293

Abstract

Oceanalin B (1), an α,ω-bipolar natural product belonging to a rare family of sphingoid tetrahydoisoquinoline β-glycosides, was isolated from the EtOH extract of the lyophilized marine sponge Oceanapia sp. as the second member of the series after oceanalin A (2) from the same animal. The compounds are of particular interest due to their biogenetically unexpected structures as well as their biological activities. The structure and absolute stereochemistry of 1 as a α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside was elucidated using NMR, CD and MS spectral analysis and chemical degradation. Oceanalin B exhibited in vitro antifungal activity against Candidaglabrata with a MIC of 25 μg/mL. Full article

(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)

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15 pages, 11431 KiB

Open AccessArticle

Combined Anticancer Effect of Sulfated Laminaran from the Brown Alga Alaria angusta and Polyhydroxysteroid Glycosides from the Starfish Protoreaster lincki on 3D Colorectal Carcinoma HCT 116 Cell Line

by Olesya S. Malyarenko, Timofey V. Malyarenko, Roza V. Usoltseva, Valerii V. Surits, Alla A. Kicha, Natalia V. Ivanchina and Svetlana P. Ermakova

Mar. Drugs 2021, 19(10), 540; https://0-doi-org.brum.beds.ac.uk/10.3390/md19100540 - 25 Sep 2021

Cited by 4 | Viewed by 1913

Abstract

Colorectal cancer is one of the most frequent types of malignancy in the world. The search for new approaches of increasing the efficacy of cancer therapy is relevant. This work was aimed to study individual, combined anticancer effects, and molecular mechanism of action of sulfated laminaran AaLs of the brown alga Alaria angusta and protolinckiosides A (PL1), B (PL2), and linckoside L1 (L1) of the starfish Protoreaster lincki using a 3D cell culture model. The 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS), soft agar, 3D spheroids invasion, and Western blotting assays were performed to determine the effect and mechanism of the action of investigated compounds or their combinations on proliferation, colony formation, and the invasion of 3D HCT 116 spheroids. AaLs, PL1, PL2, and L1 individually inhibited viability, colony growth, and the invasion of 3D HCT 116 spheroids in a variable degree with greater activity of linckoside L1. AaLs in combination with L1 exerted synergism of a combined anticancer effect through the inactivation of protein kinase B (AKT) kinase and, consequently, the induction of apoptosis via the regulation of proapoptotic/antiapoptotic proteins balance. The obtained data about the efficacy of the combined anticancer effect of a laminaran derivative of brown algae and polyhydroxysteroid glycosides of starfish open up prospects for the development of new therapeutic approaches for colorectal cancer treatment. Full article

(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)

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12 pages, 1907 KiB

Open AccessArticle

Structure of the 4-O-[1-Carboxyethyl]-d-Mannose-Containing O-Specific Polysaccharide of a Halophilic Bacterium Salinivibrio sp. EG9S8QL

by Elena N. Sigida, Ibrahim M. Ibrahim, Maxim S. Kokoulin, Hussein H. Abulreesh, Khaled Elbanna, Svetlana A. Konnova and Yulia P. Fedonenko

Mar. Drugs 2021, 19(9), 508; https://0-doi-org.brum.beds.ac.uk/10.3390/md19090508 - 07 Sep 2021

Cited by 2 | Viewed by 2306

Abstract

The moderately halophilic strain Salinivibrio sp. EG9S8QL was isolated among 11 halophilic strains from saline mud (Emisal Salt Company, Lake Qarun, Fayoum, Egypt). The lipopolysaccharide was extracted from dried cells of Salinivibrio sp. EG9S8QL by the phenol–water procedure. The OPS was obtained by mild acid hydrolysis of the lipopolysaccharide and was studied by sugar analysis along with ¹H and ¹³C NMR spectroscopy, including ¹H,¹H COSY, TOCSY, ROESY, ¹H,¹³C HSQC, and HMBC experiments. The OPS was found to be composed of linear tetrasaccharide repeating units of the following structure: →2)-β-Manp4Lac-(1→3)-α-ManpNAc-(1→3)-β-Rhap-(1→4)-α-GlcpNAc-(1→, where Manp4Lac is 4-O-[1-carboxyethyl]mannose. Full article

(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)

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18 pages, 949 KiB

Open AccessArticle

Unusual Structures and Cytotoxicities of Chitonoidosides A, A₁, B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides

by Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andrijaschenko, Roman S. Popov, Pavel S. Dmitrenok, Ekaterina A. Chingizova and Vladimir I. Kalinin

Mar. Drugs 2021, 19(8), 449; https://0-doi-org.brum.beds.ac.uk/10.3390/md19080449 - 05 Aug 2021

Cited by 5 | Viewed by 1987

Abstract

Six new triterpene tetra-, penta- and hexaosides, chitonoidosides A (1), A₁ (2), B (3), C (4), D (5), and E (6), containing one or two sulfate groups, have been isolated [...] Read more.

Six new triterpene tetra-, penta- and hexaosides, chitonoidosides A (1), A₁ (2), B (3), C (4), D (5), and E (6), containing one or two sulfate groups, have been isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near Bering Island (Commander Islands) from the depth of 100–150 m. Three of the isolated compounds (1, 3 and 6) are characterized by the unusual aglycone of new type having 18(20)-ether bond and lacking a lactone in contrast with wide spread holostane derivatives. Another unexpected finding is 3-O-methylxylose residue as a terminal unit in the carbohydrate chains of chitonoidosides B (3), C (4), and E (6), which has never been found before in the glycosides from holothurians belonging to the Psolidae family. Moreover, this monosaccharide is sulfated in the compound 4 into unprecedented 3-O-methylxylose 4-O-sulfate residue. Chitonoidoside C (4) is characterized by tetrasaccharide moiety lacking a part of the bottom semi-chain, but having disaccharide fragment attached to C-4 of Xyl1. Such architecture is not common in sea cucumber glycosides. Cytotoxic activities of the compounds 1–5 against mouse and human erythrocytes and human cancer cell lines: adenocarcinoma HeLa, colorectal adenocarcinoma DLD-1, and leukemia promyeloblast HL-60 cells were studied. The cytotoxic effect of chitonoidoside d (5) was the most significant in this series due to the presence of pentasaccharide disulfated sugar chain in combination with holostane aglycone. Surprisingly, the glycosides 1 and 3, comprising the new aglycone without γ-lactone, demonstrated similar activity to the known compounds with holostane aglycones. Chitonoidoside C (4) was less cytotoxic due to the different architecture of the carbohydrate chain compared to the other glycosides and probably due to the presence of a sulfate group at C-4 in 3-O-MeXyl4. Full article

(This article belongs to the Special Issue Carbohydrate-Containing Marine Compounds of Mixed Biogenesis)

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17 pages, 4846 KiB

Open AccessArticle

EPS364, a Novel Deep-Sea Bacterial Exopolysaccharide, Inhibits Liver Cancer Cell Growth and Adhesion

by Yun Wang, Ge Liu, Rui Liu, Maosheng Wei, Jinxiang Zhang and Chaomin Sun

Mar. Drugs 2021, 19(3), 171; https://0-doi-org.brum.beds.ac.uk/10.3390/md19030171 - 22 Mar 2021

Cited by 19 | Viewed by 3023

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 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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21 pages, 3425 KiB

Open AccessArticle

Determination of the Extraction, Physicochemical Characterization, and Digestibility of Sulfated Polysaccharides in Seaweed—Porphyra haitanensis

by Mingshuang Dong, Yanhui Jiang, Chun Wang, Qian Yang, Xiaolu Jiang and Changliang Zhu

Mar. Drugs 2020, 18(11), 539; https://0-doi-org.brum.beds.ac.uk/10.3390/md18110539 - 28 Oct 2020

Cited by 16 | Viewed by 2508

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 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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13 pages, 2789 KiB

Open AccessFeature PaperArticle

Cloning and Characterization of a New β-Galactosidase from Alteromonas sp. QD01 and Its Potential in Synthesis of Galacto-Oligosaccharides

by Dandan Li, Shangyong Li, Yanhong Wu, Mengfei Jin, Yu Zhou, Yanan Wang, Xuehong Chen and Yantao Han

Mar. Drugs 2020, 18(6), 312; https://0-doi-org.brum.beds.ac.uk/10.3390/md18060312 - 14 Jun 2020

Cited by 17 | Viewed by 3973

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 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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17 pages, 4539 KiB

Open AccessArticle

Structure and In Vitro Bioactivity against Cancer Cells of the Capsular Polysaccharide from the Marine Bacterium Psychrobacter marincola

by Maxim S. Kokoulin, Alexandra S. Kuzmich, Lyudmila A. Romanenko, Irina V. Chikalovets and Oleg V. Chernikov

Mar. Drugs 2020, 18(5), 268; https://0-doi-org.brum.beds.ac.uk/10.3390/md18050268 - 19 May 2020

Cited by 8 | Viewed by 3020

Abstract

Psychrobacter marincola KMM 277^T 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 277^T 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 277^T 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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40 pages, 15087 KiB

Open AccessReview

Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms

by Valentin A. Stonik and Sophia A. Kolesnikova

Mar. Drugs 2021, 19(6), 327; https://0-doi-org.brum.beds.ac.uk/10.3390/md19060327 - 05 Jun 2021

Cited by 14 | Viewed by 3255

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 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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30 pages, 55305 KiB

Open AccessReview

Asterosaponins: Structures, Taxonomic Distribution, Biogenesis and Biological Activities

by Valentin A. Stonik, Alla A. Kicha, Timofey V. Malyarenko and Natalia V. Ivanchina

Mar. Drugs 2020, 18(12), 584; https://0-doi-org.brum.beds.ac.uk/10.3390/md18120584 - 24 Nov 2020

Cited by 25 | Viewed by 2815

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. 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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