Isolation of a new class of ecdysteroid conjugates (glucosyl-ferulates) using a combination of liquid chromatographic methods
Abstract
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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For sources containing ecdysteroid glycosides, aqueous alcohol provides good extraction yields; for sources containing non-polar conjugates, pure alcohol is more effective.
“For sources that contain ecdysteroid glycosides, aqueous alcohol provides good extraction yields, but for sources containing non-polar conjugates (acetates, acetonides, glucosylferulates; [109]), pure alcohol is more effective.”
From Ecdysteroids (2021) · cites this paper as [109]
Dacryhainansterone has a chromophore extended to a dienone with a maximum absorption at 298 nm (Log ε = 4.152).
“A couple of good examples of this are dacryhainansterone, where the chromphore is extended to a dienone, with a concommittant shift of the maximum absorption to 298 nm (Log ε = 4.152), and the glucopyranosyl ferulate conjugates [109], where the UV spectrum is a combination of the absorptions of the ferulyl group and the characteristic ecdysteroid absorption (Figure 11).”
From Ecdysteroids (2021) · cites this paper as [109]
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- Authors
- Ho, R., Girault, J.-P., Cousteau, P.-Y., Bianchini, J.-P., Raharivelomanana, P., & Lafont, R.
- Affiliations
- University of French Polynesia (PF)
- Centre National de la Recherche Scientifique (FR)
- Corresponding author
- Lafont, R.
- Venue
- Journal of Chromatographic Science
- Publisher
- Oxford University Press (OUP)
- Published
- 2008-02-01
- Volume
- 46
- Issue
- 2
- Pages
- 102-110
- ISSN
- 0021-9665 (ISSN-L)
- 1945-239X
- OpenAlex
- W2095880005
- Cited by
- 28
- References
- 19
- Citations by year
- 2026: 1 · 2022: 2 · 2021: 2 · 2020: 1 · 2018: 1 · 2016: 1 · 2015: 1 · 2013: 1 · 2012: 9
- FWCI
- 3.03
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Chromatographic Science (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Analytical Chemistry › Chromatography in Natural Products
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Keywords
- ecdysteroid conjugates, medicinal ferns, reversed-phase HPLC, normal-phase HPLC, chromatographic selectivity
- MeSH terms
- Chromatography, High Pressure Liquid, Mass Spectrometry, Nuclear Magnetic Resonance, Biomolecular, Ecdysteroids, Polypodiaceae
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