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Triterpene Glycosides from Antarctic Sea Cucumbers. 1. Structure of Liouvillosides A(1), A(2), A(3), B-1, and B-2 from the Sea Cucumber Staurocucumis liouvillei: New Procedure for Separation of Highly Polar Glycoside Fractions and Taxonomic Revision

Pacific Institute of Bioorganic Chemistry of the Far East Division of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022, Vladivostok, Russian Federation.
Journal of Natural Products (Impact Factor: 3.8). 11/2008; 71(10):1677-85. DOI: 10.1021/np800173c
Source: PubMed

ABSTRACT

Five new triterpene glycosides, liouvillosides A1 (1), A2 (2), A3 (3), B1 (4), and B2 (5), have been isolated from the Antarctic sea cucumber Staurocucumis liouviellei along with the known liouvilloside A(6), isolated earlier from the same species, and hemoiedemosides A (7) and B (8), isolated earlier from the Patagonian sea cucumber Hemioedema spectabilis. The isolation was carried out using a new chromatographic procedure including application of ion-pair reversed-phase chromatography followed by chiral chromatography on a cyclodextrin ChiraDex column. The structures of the new glycosides were elucidated using extensive NMR spectroscopy (1H and 13C NMR spectrometry, DEPT, 1H-(1)H COSY, HMBC, HMQC, and NOESY), ESI-FTMS, and CID MS/MS, and chemical transformations. Glycosides 1-3 are disulfated tetraosides and glycosides 4 and 5 are trisulfated tetraosides. Glycosides 2 and 3 contain 3-O-methylquinovose, found for the first time as a natural monosaccharide in sea cucumber glycosides. On the basis of analyses of glycoside structures a taxonomic revision is proposed.

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    • "Carbohydrate chains of sea cucumber glycosides include 2–6 monosaccharide residues, namely xylose, quinovose, glucose, 3-O-methylglucose, and sometimes 3-O-methylxylose, 3-О-methylquinovose, 3-О-methylglucuronic acid, and also 6-О- acetylglucose. They may contain one, two or three sulfate groups [5] [6] [7] [8]. Due to their ability to form a complex with 5(6)-unsaturated sterols of cellular membranes, the glycosides demonstrate a wide spectrum of biological activities including hemolytic, antifungal, cytotoxic, and many other types of membranotropic activities [9]. "
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    ABSTRACT: In non-cytotoxic concentrations, frondoside A (1) from the sea cucumber Cucumaria okhotensis and cucumarioside A2-2 (2) from C. japonica, as well as their complexes with cholesterol block the activity of membrane transport P-glycoprotein in cells of the ascite form of mouse Ehrlich carcinoma. They prevent in this way an efflux of fluorescent probe Calcein from the cells. Since the blocking of P-glycoprotein activity results in decrease of multidrug resistance, these glycosides and their complexes with cholesterol may be considered as potential inhibitors of multidrug resistance of tumor cells.
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    • "The sugar chain of typicosides C 1 (4) and C 2 (5) has only been found in glycosides from representatives of the order Dendrochirotida, predominately from the family Cucumariidae [1] [10] [24], and only in one species from the family Psolidae, namely Psolus patagonicus [1]. "
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    ABSTRACT: Five new minor triterpene glycosides, typicosides A1 (1), A2 (2), B1 (3), C1 (4) and C2 (5), along with two known glycosides, intercedenside A and holothurin B3, have been isolated from the sea cucumber Actinocucumis typica. Structures of the glycosides were elucidated by 2D NMR spectroscopy andMS. Glycosides 1-5 are linear mono- and disulfated tetraosides differing from each other in both aglycone structures and monosaccharide composition of the carbohydrate chains. Typicosides A1 (1) and A2 (2) have identical monosulfated carbohydrate moieties with a xylose residue as the third monosaccharide unit and differ from each other in aglycon structures. Typicoside B1 (3) has glucose as the third monosaccharide residue. Typicosides C1 (4) and C2 (5) contain the same disulfated carbohydrate chains and differ from each other in structures of aglycone side chains. Antifungal activity of glycosides 1-5 against three species of fungi along with cytotoxic activity against mouse spleen lymphocytes and mouse Ehrlich carcinoma cells (ascite form), as well as hemolytic activities against mouse erythrocytes have been studied. All new glycosides, except for typicoside C1 (4), containing a hydroxy-group in the aglycone side chain, demonstrate rather strong hemolytic and cytotoxic activities.
    Full-text · Article · Mar 2013 · Natural product communications
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    • "Furthermore, as part of our investigations, previously unknown species for science have been described (Ballesteros & Avila, 2006; Ríos & Cristobo, 2006; Figuerola et al., in press), and new compounds have been isolated and described too (e.g. Antonov et al., 2008, 2009, 2011; Reyes et al., 2008; Carbone et al., 2009; Carbone et al., in prep). Also, we have extended the range of species from our previous analysis by studying Antarctic macroalgae, which are known to be prolific producers of secondary metabolites with pharmaceutical applications (e.g. "

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