Triterpene Glycosides from Antarctic Sea Cucumbers. 1. Structure of Liouvillosides A1, A2, A3, B1, and B2 from the Sea Cucumber Staurocucumis liouvillei: New Procedure for Separation of Highly Polar Glycoside Fractions and Taxonomic Revision
| Autor: | Evgeny V. Evtushenko, Alexey V. Smirnov, Valentin A. Stonik, Anatoly I. Kalinovsky, Stanislav D. Anastyuk, Pavel S. Dmitrenok, Manuel Ballesteros, Vladimir I. Kalinin, Sergi Taboada, Conxita Avila, Alexandr S. Antonov, Sergey A. Avilov |
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| Rok vydání: | 2008 |
| Předmět: |
Pharmacology
chemistry.chemical_classification biology Chemistry Stereochemistry Organic Chemistry Saponin Pharmaceutical Science Glycoside Nuclear magnetic resonance spectroscopy Carbon-13 NMR DEPT biology.organism_classification Analytical Chemistry Chiral column chromatography Sea cucumber Complementary and alternative medicine Triterpene Drug Discovery Molecular Medicine |
| Zdroj: | Journal of Natural Products. 71:1677-1685 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np800173c |
| Popis: | 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−1H 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 analys... |
| Databáze: | OpenAIRE |
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