Special Issue "Echinoderms Metabolites: Structure, Functions and Biomedical Perspectives"

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

Deadline for manuscript submissions: 20 October 2020.

Special Issue Editor

Dr. Vladimir I. Kalinin
Website
Guest Editor
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, 159 Prospect 100-letiya Vladivostoka, Vladivostok 690022, Russia
Interests: sea cucmber triterpene glycosides; chemotaxonomy; biological activities
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Special Issue Information

Dear Colleagues,

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 having 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 Special Issue “Echinoderm Metabolites: Structure, Functions, and Biomedical Perspectives” is 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 the obtaining of semi-synthetic derivatives of biologically active natural products.

Dr. Vladimir I. Kalinin
Guest Editor

Manuscript Submission Information

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Keywords


  • echinoderms
  • sea cucumbers
  • starfish
  • sea urchins
  • steroids
  • terpenoids
  • glycosides
  • naphtoquinones
  • glycolipids
  • polysaccharides
  • chemical structures
  • synthesis
  • biological activity

Published Papers (2 papers)

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Research

Open AccessArticle
New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity
Mar. Drugs 2020, 18(5), 260; https://doi.org/10.3390/md18050260 - 15 May 2020
Abstract
Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (14), were isolated from the deep-water Far Eastern starfish Ceramaster patagonicus. The structures of 14 were established by NMR and ESIMS techniques as well as chemical transformations. [...] Read more.
Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (14), were isolated from the deep-water Far Eastern starfish Ceramaster patagonicus. The structures of 14 were established by NMR and ESIMS techniques as well as chemical transformations. Unusual compounds 14 contain the same 5α-cholestane-3β,6β,15α,16β,26-pentahydroxysteroidal moiety and differ from each other in the fatty acid units: 5′Z,11′Z-octadecadienoic (1), 11′Z-octadecenoic (2), 5′Z,11′Z-eicosadienoic (3), and 7′Z-eicosenoic (4) acids. Previously, only one such steroid conjugate with a fatty acid was known from starfish. After 72 h of cell incubation, using MTS assay it was found that the concentrations of compounds 1, 2, and 3 that caused 50% inhibition of growth (IC50) of JB6 Cl41 cells were 81, 40, and 79 µM, respectively; for MDA-MB-231 cells, IC50 of compounds 1, 2, and 3 were 74, 33, and 73 µM, respectively; for HCT 116 cells, IC50 of compounds 1, 2, and 3 were 73, 31, and 71 µM, respectively. Compound 4 was non-toxic against tested cell lines even in three days of treatment. Compound 2 (20 µM) suppressed colony formation and migration of MDA-MB-231 and HCT 116 cells. Full article
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Open AccessArticle
Inspired by Sea Urchins: Warburg Effect Mediated Selectivity of Novel Synthetic Non-Glycoside 1,4-Naphthoquinone-6S-Glucose Conjugates in Prostate Cancer
Mar. Drugs 2020, 18(5), 251; https://doi.org/10.3390/md18050251 - 11 May 2020
Abstract
The phenomenon of high sugar consumption by tumor cells is known as Warburg effect. It results from a high glycolysis rate, used by tumors as preferred metabolic pathway even in aerobic conditions. Targeting the Warburg effect to specifically deliver sugar conjugated cytotoxic compounds [...] Read more.
The phenomenon of high sugar consumption by tumor cells is known as Warburg effect. It results from a high glycolysis rate, used by tumors as preferred metabolic pathway even in aerobic conditions. Targeting the Warburg effect to specifically deliver sugar conjugated cytotoxic compounds into tumor cells is a promising approach to create new selective drugs. We designed, synthesized, and analyzed a library of novel 6-S-(1,4-naphthoquinone-2-yl)-d-glucose chimera molecules (SABs)—novel sugar conjugates of 1,4-naphthoquinone analogs of the sea urchin pigments spinochromes, which have previously shown anticancer properties. A sulfur linker (thioether bond) was used to prevent potential hydrolysis by human glycoside-unspecific enzymes. The synthesized compounds exhibited a Warburg effect mediated selectivity to human prostate cancer cells (including highly drug-resistant cell lines). Mitochondria were identified as a primary cellular target of SABs. The mechanism of action included mitochondria membrane permeabilization, followed by ROS upregulation and release of cytotoxic mitochondrial proteins (AIF and cytochrome C) to the cytoplasm, which led to the consequent caspase-9 and -3 activation, PARP cleavage, and apoptosis-like cell death. These results enable us to further clinically develop these compounds for effective Warburg effect targeting. Full article
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