Sterol and Sphingoid Glycoconjugates from Microalgae

Microalgae are well known as primary producers in the hydrosphere. As sources of natural products, microalgae are attracting major attention due to the potential of their practical applications as valuable food constituents, raw material for biofuels, drug candidates, and components of drug delivery systems. This paper presents a short review of a low-molecular-weight steroid and sphingolipid glycoconjugates, with an analysis of the literature on their structures, functions, and bioactivities. The discussed data on sterols and the corresponding glycoconjugates not only demonstrate their structural diversity and properties, but also allow for a better understanding of steroid biogenesis in some echinoderms, mollusks, and other invertebrates which receive these substances from food and possibly from their microalgal symbionts. In another part of this review, the structures and biological functions of sphingolipid glycoconjugates are discussed. Their role in limiting microalgal blooms as a result of viral infections is emphasized

Carbohydrate-Containing Low Molecular Weight Metabolites of Microalgae

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

Marine Excitatory Amino Acids: Structure, Properties, Biosynthesis and Recent Approaches to Their Syntheses

This review considers the results of recent studies on marine excitatory amino acids, including kainic acid, domoic acid, dysiherbaine, and neodysiherbaine A, known as potent agonists of one of subtypes of glutamate receptors, the so-called kainate receptors. Novel information, particularly concerning biosynthesis, environmental roles, biological action, and syntheses of these marine metabolites, obtained mainly in last 10–15 years, is summarized. The goal of the review was not only to discuss recently obtained data, but also to provide a brief introduction to the field of marine excitatory amino acid research

Carbohydrate-Containing Marine Compounds of Mixed Biogenesis

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

Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms

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

Carbohydrate-Containing Marine Compounds of Mixed Biogenesis

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

Marine Glycoconjugates: Trends and Perspectives

The books described marine glycoconjugates. Two articles concern microalgal metabolites such as steroid and sphingoid glycoconjugates, and a glycoprotein from a sea cucumber with interesting biological activities, respectively. One article discusses the fatty acid composition and thermotropic behavior of glycolipids and other membrane lipids of green macrophyte Ulva lactuca. Three articles cover lectin subjects. One review article analyzes perspectives of marine and freshwater lectins’ application in experimental oncology and the therapy of oncological diseases; another article describes the use of a sponge lectin in the construction of a recombinant virus. The third article concerns the function of the immunity of a lectin in producing this compound crinoid. Two articles concern steroid glycosides from star?sh, and two others concern triterpene glycosides from sea cucumbers. One article describes the e?ect of a glycosaminoglycan from the sea cucumber Apostichopus japonicus on hyperglycemia in the liver of insulin-resistant mice. One article concerns the isolation of 10 new triterpene glycosides from a fungus associated with a sea cucumber. The article by Dworaczek et al. characterizes the O-speci?c polysaccharide (O-antigen) of a bacterial pathogen of common carp by chemical and immunochemical methods. In total, the Special Issue comprises14 articles, including the editorial and two reviews

Asterosaponins: Structures, Taxonomic Distribution, Biogenesis and Biological Activities

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

Anticancer and Cancer Preventive Properties of Marine Polysaccharides: Some Results and Prospects

Many marine-derived polysaccharides and their analogues have been reported as showing anticancer and cancer preventive properties. These compounds demonstrate interesting activities and special modes of action, differing from each other in both structure and toxicity profile. Herein, literature data concerning anticancer and cancer preventive marine polysaccharides are reviewed. The structural diversity, the biological activities, and the molecular mechanisms of their action are discussed