Published:Journal of Chromatographic Science,
ISSN 0021-9665 Volume
46, Number 2, February 2008, pp. 102-110
Isolation of a New Class of Ecdysteroid Conjugates
(Glucosyl-ferulates) Using a Combination of Liquid Chromatographic
Methods
Raimana Ho[1], Jean-Pierre Girault[2], Pierre-Yves
Cousteau[1,3], Jean-Pierre Bianchini[1], Phila Raharivelomanana[1],
and René Lafont[1,3],
[1]Laboratoire de Chimie des Substances Naturelles, Université de
la Polynésie Française, B.P. 6570 Faaa, 98702 FAAA,
Tahiti, Polynésie Française;
[2]Laboratoire de
Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS
UMR 8601, Université Paris Descartes, 45 rue des Saints
Pères,
75270 Paris, Cedex 06, France; and
[3]Laboratoire de Biochimie
structurale et fonctionnelle des Protéines, CNRS FRE 2852,
Université Pierre et Marie Curie, Case 29, 7 Quai Saint
Bernard, 75252 Paris, Cedex 05, France
The Polynesian medicinal fern Microsorum membranifolium
contains very large amounts of ecdysteroids, including ecdysone,
20-hydroxyecdysone, 2-deoxy-20-hydroxyecdysone, and 2-deoxyecdysone.
It also contains large amounts of unusual ecdysteroids which
have been unambiguously identified by mass spectrometry and nuclear
magnetic resonance. A new class of ecdysteroid conjugates (3-glucosyl-ferulates
of 2-deoxyecdysone and 2-deoxy-20-hydroxyecdysone) is isolated,
together with a new glycoside (2-deoxyecdysone 25-rhamnoside).
The simultaneous presence of a sugar and an aromatic moiety results
in a very particular chromatographic behavior of these conjugates.
They behave like flavonoids and polyphenols when using the classical
purification on polyamide, aimed at removing the latter from
crude plant extracts, and would therefore be lost. They elute
as non-polar ecdysteroids on reversed-phase high-performance
liquid chromatography (RP-HPLC), whereas their behavior on normal-phase
(NP) HPLC is strongly dependent on the mobile phase composition.
Our data highlight the importance of selectivity in the choice
of HPLC methods used for ecdysteroid separations.
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