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Ecdysteroid Glycosides: Identification, Chromatographic Properties, and Biological Significance

Annick MariaLaboratoire d'Endocrinologie Moléculaire et Evolution, EA 3501 & IFR83, Université Pierre et Marie Curie, 7 Quai St. Bernard, Case 29, 75252 Paris 05, FranceJean‐Pierre GiraultUniversité René Descartes, Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, 45 rue des Saints-Pères, F-75270 Paris Cedex 05 FranceZ. SaatovInstitute of Chemistry of Plant Substances, 700170 Tashkent, UzbekistanJuraj HarmathaInstitute of Organic Chemistry and Biochemistry, Academy of Sciences, Flemingovo nám. 2, 166 10 Prague, Czech RepublicLaurence DinanHatherly Laboratories, Department of Biological Sciences, University of Exeter, Prince of Wales Road, Exeter, Devon EX4 4PS, U.KRené LafontLaboratoire d'Endocrinologie Moléculaire et Évolution, EA 3501 & IFR83, Université Pierre et Marie Curie, 7 Quai St. Bernard, Case 29, 75252 Paris 05, France
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Аннотация

Ecdysteroid glycosides are found in both animals and plants. The chromatographic behavior of these molecules is characteristic, as they appear much more polar than their corresponding free aglycones when analyzed by normal-phase high-performance liquid chromatography (HPLC), whereas the presence of glycosidic moieties has a very limited (if any) impact on polarity when using reversed-phase HPLC. Biological activity is greatly reduced because the presence of this bulky substituent probably impairs the interaction with ecdysteroid receptor(s). 2-Deoxy-20-hydroxyecdysone 22-O-beta-D-glucopyranoside, which has been isolated from the dried aerial parts of Silene nutans (Caryophyllaceae), is used as a model compound to describe the rationale of ecdysteroid glycoside purification and identification.

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