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Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II

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

Deadline for manuscript submissions: closed (31 May 2022) | Viewed by 17557

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Dr. Vladimir I. Kalinin

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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; sea cucumber triterpene glycosides; biological activities; evolution of biosynthesis; chemotaxonomy
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Dr. Alexanra S. Silchenko

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G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Interests: natural products chemistry; sea cucumbers; triterpene glycosides; biological activities; chemotaxonomy; biosynthesis; NMR spectroscopy
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Special Issue Information

Dear colleagues,

The present Special Issue is a continuation of a previous successful Special Issue entitled “Echinoderm Metabolites: Structure, Functions and Biomedical Perspectives” which is currently under preparation to be reprinted as a book.

Echinoderms are marine invertebrates belonging to the phylum Echinodermata (from the Ancient Greek words “echinos” (hedgehog) and “derma” (skin)). They have radial symmetry, a unique water vascular (ambulacral) system, and a limestone skeleton and include the classes Asteroidea (starfish), Ophiuroidea (brittle stars), Echinoidea (sea urchins), Holothuroidea (sea cucumbers), and Crinoidea (sea lilies). The skeleton of sea cucumbers is reduced by ossicles. Echinoderms have no freshwater or terrestrial representatives and are habitants of every ocean depth. The phylum contains more than 7000 living species. Echinoderms are unique sources of different metabolites with a wide spectrum of biological activities. All echinoderms possess a unique mechanism of decreasing the lever of free 5,6-unsaturated sterols in their cell membranes—sulfation of these food sterols. Moreover, sea cucumbers and starfish transform these 5,6-unsaturated sterols to stanols or 7,8-unsaturated sterols that allow them to synthesize and keep their own 5,6-sterol-depending membranolytic toxins, namely triterpene oligoglycosides for sea cucumbers and steroid olygoglycosides for starfish, which have protective significance for the producers.

Starfish and brittle stars have numerous polyhydoxysteroids and their sulfated and glycosylated derivatives, using them as food emulgators. All echinoderms contain carotenoids and naphthoquinone pigments. The latter are widely presented in sea urchins. The lipid composition of echinoderms is also uncommon and very interesting. For example, they contain cerebrosides and gangliosides characteristic of other deuterostomes, including Chordata, Hemichordata, and Tunicata, relatives of echinoderms. Echinoderms contain lectins, glycan-specific glycoproteins having immunity functions for the producers, and glycoseaminoglycans. Microorganisms associated with some echninoderms and adopted to their toxins may also produce very uncommon metabolites, such as diterpene glycosides synthesized by some fungi associated with sea cucumbers. All the listed as well as other classes of echinoderm metabolites possess significant biomedical potential revealing cytotoxic, antitumor, antifungal, immunomodulatory, antioxidant activity, anti-arthritic, and anti-diabetic action and may be also used as a food supplement for nutrition.

The main goal of this second version of the Special Issue “Echinoderm Metabolites: Structure, Functions, and Biomedical Perspectives II” is also to provide a convenient platform for discussion of all possible scientific aspects concerning low molecular weight and biopolymer metabolites from echinoderms and the microorganisms associated with them, including their isolation and chemical structures, taxonomical distribution and participation in food chains, methods of analysis, biological activities, biosynthesis and evolution, biological functions, and chemical syntheses, including obtaining semi-synthetic derivatives of biologically active natural products.

Dr. Vladimir I. Kalinin
Dr. Alexanra S. Silchenko
Guest Editors

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Keywords

Echinoderms
Sea cucumbers
Starfish
Sea urchins
Steroids
Terpenoids
Glycosides
Naphtoquinones
Glycolipids
Polysaccharides
Chemical structures
Synthesis
Biological activity

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Published Papers (9 papers)

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Editorial

Jump to: Research, Review

5 pages, 202 KiB

Open AccessEditorial

Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II

by Vladimir I. Kalinin and Alexandra S. Silchenko

Mar. Drugs 2022, 20(8), 492; https://doi.org/10.3390/md20080492 - 29 Jul 2022

Viewed by 1399

Abstract

Echinoderms belong to the phylum Echinodermata (from the Ancient Greek words “echinos” (hedgehog) and “derma” (skin)) [...] Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

Research

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12 pages, 895 KiB

Open AccessArticle

Unusual Ether Lipids and Branched Chain Fatty Acids in Sea Cucumber (Cucumaria frondosa) Viscera and Their Seasonal Variation

by Reem Abuzaytoun, Suzanne M. Budge, Wei Xia and Shawna MacKinnon

Mar. Drugs 2022, 20(7), 435; https://doi.org/10.3390/md20070435 - 29 Jun 2022

Cited by 12 | Viewed by 2026

Abstract

The sea cucumber, Cucumaria frondosa, is harvested primarily for its muscular bands and body wall. Development of a nutraceutical product based on lipid recovered from its viscera would give commercial value to the entire organism; however, such development requires knowledge of the lipid and fatty acid (FA) profiles of the viscera. Here, we describe the lipid and FA composition of viscera recovered from C. frondosa harvested in coastal waters in the northwest Atlantic, taking into account variation due to harvest season. We found highest lipid content at ~29% in winter, with diacylglyceryl ethers (DAGE) comprising ~55% of the total lipid mass and triacylglycerols (TAG), phospholipids (PL) and monoacylglycerol ethers (MAGE) at 5–25% each. The branched chain FA, 12-methyltetradecanoic acid (12-MTA), represented 42% of total FA mass in DAGE. In summer, lipid content was lower at 24% and TAG was the dominate lipid, with proportions more than double that found in winter (45% vs. 20%); DAGE in summer dropped to ~30% of total lipids. In TAG, 12-MTA was much lower than found in DAGE in winter, at only 10% but eicosapentaenoic acid (EPA) content was ~20%, which brought the total EPA% to 28% of total FA—the highest among all three seasons. There was little effect of season on MAGE or PL proportions. These data can help harvesters maximize catch efforts in terms of lipid yield and profile. Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

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13 pages, 2328 KiB

Open AccessArticle

Fucose-Rich Sulfated Polysaccharides from Two Vietnamese Sea Cucumbers Bohadschia argus and Holothuria (Theelothuria) spinifera: Structures and Anticoagulant Activity

by Nadezhda E. Ustyuzhanina, Maria I. Bilan, Andrey S. Dmitrenok, Eugenia A. Tsvetkova, Sofya P. Nikogosova, Cao Thi Thuy Hang, Pham Duc Thinh, Dinh Thanh Trung, Tran Thi Thanh Van, Alexander S. Shashkov, Anatolii I. Usov and Nikolay E. Nifantiev

Mar. Drugs 2022, 20(6), 380; https://doi.org/10.3390/md20060380 - 6 Jun 2022

Cited by 16 | Viewed by 2748

Abstract

Fucosylated chondroitin sulfates (FCSs) FCS-BA and FCS-HS, as well as fucan sulfates (FSs) FS-BA-AT and FS-HS-AT were isolated from the sea cucumbers Bohadschia argus and Holothuria (Theelothuria) spinifera, respectively. Purification of the polysaccharides was carried out by anion-exchange chromatography on DEAE-Sephacel column. Structural characterization of polysaccharides was performed in terms of monosaccharide and sulfate content, as well as using a series of non-destructive NMR spectroscopic methods. Both FCSs were shown to contain a chondroitin core [→3)-β-d-GalNAc-(1→4)-β-d-GlcA-(1→]_n bearing sulfated fucosyl branches at O-3 of every GlcA residue in the chain. These fucosyl residues were different in pattern of sulfation: FCS-BA contained Fuc2S4S, Fuc3S4S and Fuc4S at a ratio of 1:8:2, while FCS-HS contained these residues at a ratio of 2:2:1. Polysaccharides differed also in content of GalNAc4S6S and GalNAc4S units, the ratios being 14:1 for FCS-BA and 4:1 for FCS-HS. Both FCSs demonstrated significant anticoagulant activity in clotting time assay and potentiated inhibition of thrombin, but not of factor Xa. FS-BA-AT was shown to be a regular linear polymer of 4-linked α-L-fucopyranose 3-sulfate, the structure being confirmed by NMR spectra of desulfated polysaccharide. In spite of considerable sulfate content, FS-BA-AT was practically devoid of anticoagulant activity. FS-HS-AT cannot be purified completely from contamination of some FCS. Its structure was tentatively represented as a mixture of chains identical with FS-BA-AT and other chains built up of randomly sulfated alternating 4- and 3-linked α-L-fucopyranose residues. Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

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17 pages, 1977 KiB

Open AccessArticle

Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures

by Alla A. Kicha, Anatoly I. Kalinovsky, Timofey V. Malyarenko, Olesya S. Malyarenko, Svetlana P. Ermakova, Roman S. Popov, Valentin A. Stonik and Natalia V. Ivanchina

Mar. Drugs 2022, 20(3), 164; https://doi.org/10.3390/md20030164 - 24 Feb 2022

Cited by 6 | Viewed by 2027

Abstract

New steroidal 3β,21-disulfates (2–4), steroidal 3β,22-disulfate (5), and the previously known related steroidal 3β,21-disulfate (1) were isolated from the ethanolic extract of the Far Eastern starfish Pteraster marsippus, collected off Urup Island in the Sea of Okhotsk. The structures of these compounds were determined by intensive NMR and HRESIMS techniques as well as by chemical transformations. Steroids 2 and 3 have an oxo-group in the tetracyclic nucleus at position C-7 and differ from each other by the presence of the 5(6)-double bond. The Δ²⁴-22-sulfoxycholestane side chain of the steroid 5 has not been found previously in the starfish or ophiuroid steroids. The cytotoxic activities of 1, 4, 5, and the mixture of 2 and 3 were determined on the models of 2D and 3D cultures of human epithelial kidney cells (HEK293), melanoma cells (SK-MEL-28), small intestine carcinoma cells (HuTu80), and breast carcinoma cells (ZR-75-1). The mixture of 2 and 3 revealed a significant inhibitory effect on the cell viability of human breast carcinoma ZR-75-1 cells, but other tested compounds were less effective. Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

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17 pages, 576 KiB

Open AccessArticle

Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides: Chemical Structures and Cytotoxicities of Chitonoidosides E₁, F, G, and H

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

Mar. Drugs 2021, 19(12), 696; https://doi.org/10.3390/md19120696 - 7 Dec 2021

Cited by 9 | Viewed by 2627

Abstract

Four new triterpene disulfated glycosides, chitonoidosides E₁ (1), F (2), G (3), and H (4), were isolated from the Far-Eastern sea cucumber Psolus chitonoides and collected near Bering Island (Commander Islands) at depths of 100–150 m. Among them there are two hexaosides (1 and 3), differing from each other by the terminal (sixth) sugar residue, one pentaoside (4) and one tetraoside (2), characterized by a glycoside architecture of oligosaccharide chains with shortened bottom semi-chains, which is uncommon for sea cucumbers. Some additional distinctive structural features inherent in 1–4 were also found: the aglycone of a recently discovered new type, with 18(20)-ether bond and lacking a lactone in chitonoidoside G (3), glycoside 3-O-methylxylose residue in chitonoidoside E₁ (1), which is rarely detected in sea cucumbers, and sulfated by uncommon position 4 terminal 3-O-methylglucose in chitonoidosides F (2) and H (4). The hemolytic activities of compounds 1–4 and chitonoidoside E against human erythrocytes and their cytotoxic action against the human cancer cell lines, adenocarcinoma HeLa, colorectal adenocarcinoma DLD-1, and monocytes THP-1, were studied. The glycoside with hexasaccharide chains (1, 3 and chitonoidoside E) were the most active against erythrocytes. A similar tendency was observed for the cytotoxicity against adenocarcinoma HeLa cells, but the demonstrated effects were moderate. The monocyte THP-1 cell line and erythrocytes were comparably sensitive to the action of the glycosides, but the activity of chitonoidosides E and E₁ (1) significantly differed from that of 3 in relation to THP-1 cells. A tetraoside with a shortened bottom semi-chain, chitonoidoside F (2), displayed the weakest membranolytic effect in the series. Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

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22 pages, 6601 KiB

Open AccessArticle

Structure-Activity Relationships of Holothuroid’s Triterpene Glycosides and Some In Silico Insights Obtained by Molecular Dynamics Study on the Mechanisms of Their Membranolytic Action

by Elena A. Zelepuga, Alexandra S. Silchenko, Sergey A. Avilov and Vladimir I. Kalinin

Mar. Drugs 2021, 19(11), 604; https://doi.org/10.3390/md19110604 - 25 Oct 2021

Cited by 15 | Viewed by 2266

Abstract

The article describes the structure-activity relationships (SAR) for a broad series of sea cucumber glycosides on different tumor cell lines and erythrocytes, and an in silico modulation of the interaction of selected glycosides from the sea cucumber Eupentacta fraudatrix with model erythrocyte membranes using full-atom molecular dynamics (MD) simulations. The in silico approach revealed that the glycosides bound to the membrane surface mainly through hydrophobic interactions and hydrogen bonds. The mode of such interactions depends on the aglycone structure, including the side chain structural peculiarities, and varies to a great extent. Two different mechanisms of glycoside/membrane interactions were discovered. The first one was realized through the pore formation (by cucumariosides A₁ (40) and A₈ (44)), preceded by bonding of the glycosides with membrane sphingomyelin, phospholipids, and cholesterol. Noncovalent intermolecular interactions inside multimolecular membrane complexes and their stoichiometry differed for 40 and 44. The second mechanism was realized by cucumarioside A₂ (59) through the formation of phospholipid and cholesterol clusters in the outer and inner membrane leaflets, correspondingly. Noticeably, the glycoside/phospholipid interactions were more favorable compared to the glycoside/cholesterol interactions, but the glycoside possessed an agglomerating action towards the cholesterol molecules from the inner membrane leaflet. In silico simulations of the interactions of cucumarioside A₇ (45) with model membrane demonstrated only slight interactions with phospholipid polar heads and the absence of glycoside/cholesterol interactions. This fact correlated well with very low experimental hemolytic activity of this substance. The observed peculiarities of membranotropic action are in good agreement with the corresponding experimental data on hemolytic activity of the investigated compounds in vitro. Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

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25 pages, 1064 KiB

Open AccessArticle

Triterpene Glycosides from the Far Eastern Sea Cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin): The Structures, Cytotoxicities, and Biogenesis of Kurilosides A₃, D₁, G, H, I, I₁, J, K, and K₁

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(4), 187; https://doi.org/10.3390/md19040187 - 27 Mar 2021

Cited by 6 | Viewed by 2131

Abstract

Nine new mono-, di-, and trisulfated triterpene penta- and hexaosides, kurilosides A₃ (1), D₁ (2), G (3), H (4), I (5), I₁ (6), J (7), K [...] Read more.

Nine new mono-, di-, and trisulfated triterpene penta- and hexaosides, kurilosides A₃ (1), D₁ (2), G (3), H (4), I (5), I₁ (6), J (7), K (8), and K₁ (9) and two desulfated derivatives, DS-kuriloside L (10), having a trisaccharide branched chain, and DS-kuriloside M (11), having hexa-nor-lanostane aglycone with a 7(8)-double bond, have been isolated from the Far-Eastern deep-water sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin) and their structures were elucidated based on 2D NMR spectroscopy and HR-ESI mass-spectrometry. Five earlier unknown carbohydrate chains and two aglycones (having a 16β,(20S)-dihydroxy-fragment and a 16β-acetoxy,(20S)-hydroxy fragment) were found in these glycosides. All the glycosides 1–9 have a sulfate group at C-6 Glc, attached to C-4 Xyl1, while the positions of the other sulfate groups vary in different groups of kurilosides. The analysis of the structural features of the aglycones and the carbohydrate chains of all the glycosides of T. kurilensis showed their biogenetic relationships. Cytotoxic activities of the compounds 1–9 against mouse neuroblastoma Neuro 2a, normal epithelial JB-6 cells, and erythrocytes were studied. The highest cytotoxicity in the series was demonstrated by trisulfated hexaoside kuriloside H (4), having acetoxy-groups at C(16) and C(20), the latter one obviously compensated the absence of a side chain, essential for the membranolytic action of the glycosides. Kuriloside I₁ (6), differing from 4 in the lacking of a terminal glucose residue in the bottom semi-chain, was slightly less active. The compounds 1–3, 5, and 8 did not demonstrate cytotoxic activity due to the presence of hydroxyl groups in their aglycones. Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

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Review

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34 pages, 1933 KiB

Open AccessReview

Application of MS-Based Metabolomic Approaches in Analysis of Starfish and Sea Cucumber Bioactive Compounds

by Roman S. Popov, Natalia V. Ivanchina and Pavel S. Dmitrenok

Mar. Drugs 2022, 20(5), 320; https://doi.org/10.3390/md20050320 - 12 May 2022

Cited by 15 | Viewed by 4362

Abstract

Today, marine natural products are considered one of the main sources of compounds for drug development. Starfish and sea cucumbers are potential sources of natural products of pharmaceutical interest. Among their metabolites, polar steroids, triterpene glycosides, and polar lipids have attracted a great deal of attention; however, studying these compounds by conventional methods is challenging. The application of modern MS-based approaches can help to obtain valuable information about such compounds. This review provides an up-to-date overview of MS-based applications for starfish and sea cucumber bioactive compounds analysis. While describing most characteristic features of MS-based approaches in the context of starfish and sea cucumber metabolites, including sample preparation and MS analysis steps, the present paper mainly focuses on the application of MS-based metabolic profiling of polar steroid compounds, triterpene glycosides, and lipids. The application of MS in metabolomics studies is also outlined. Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

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31 pages, 3866 KiB

Open AccessReview

Sphingolipids of Asteroidea and Holothuroidea: Structures and Biological Activities

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

Mar. Drugs 2021, 19(6), 330; https://doi.org/10.3390/md19060330 - 8 Jun 2021

Cited by 15 | Viewed by 4329

Abstract

Sphingolipids are complex lipids widespread in nature as structural components of biomembranes. Commonly, the sphingolipids of marine organisms differ from those of terrestrial animals and plants. The gangliosides are the most complex sphingolipids characteristic of vertebrates that have been found in only the Echinodermata (echinoderms) phylum of invertebrates. Sphingolipids of the representatives of the Asteroidea and Holothuroidea classes are the most studied among all echinoderms. In this review, we have summarized the data on sphingolipids of these two classes of marine invertebrates over the past two decades. Recently established structures, properties, and peculiarities of biogenesis of ceramides, cerebrosides, and gangliosides from starfishes and holothurians are discussed. The purpose of this review is to provide the most complete information on the chemical structures, structural features, and biological activities of sphingolipids of the Asteroidea and Holothuroidea classes. Full article

(This article belongs to the Special Issue Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives II)

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