Ecdysteroid glycosides: identification, chromatographic properties, and biological significance.
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.
Maria
Annick
A
Laboratoire d'Endocrinologie Moléculaire et Evolution, EA 3501 & IFR83, Université Pierre et Marie Curie, 7 Quai St. Bernard, Case 29, 75252 Paris 05, France.
Girault
Jean-Pierre
JP
Saatov
Ziyadilla
Z
Harmatha
Juraj
J
Dinan
Laurence
L
Lafont
René
R
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D026461:Ecdysteroids / Q000032:analysis* / Q000737:chemistry; D006027:Glycosides / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D018402:Manduca / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D029751:Silene / Q000737:chemistry; D013256:Steroids / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification
C465597:2-deoxy-20-hydroxyecdysone-22-O-glucopyranoside; D026461:Ecdysteroids; D006027:Glycosides; D009005:Monosaccharides; D013256:Steroids