2-dehydro-3-epi-20-hydroxyecdysone from Froelichia florida
Introduction
Froelichia floridana (Nutt.) Moq., widely known as “Florida snake-cotton” or “Cottontails” is a herbaceous annual, native to the U.S.A. and has become naturalised in Australia[1]. This species has not been investigated phytochemically before. As part of our continuing search for new phytoecdysteroids and also for new plant sources for phytoecdysteroids2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, we now report on the isolation and identification of a novel phytoecdysteroid, 2-dehydro-3-epi-20-hydroxyecdysone (1), as well as the known ecdysteroid 20-hydroxyecdysone (2) from the seeds of F. floridana.
Section snippets
Results and discussion
Ecdysteroid agonist/antagonist bioassay[14]- and ecdysteroid-specific RIA[15]-guided, and photodiode-array detector-assisted HPLC analyses of a methanol extract of the seeds of F. floridana yielded a novel phytoecdysteroid, 2-dehydro-3-epi-20-hydroxyecdysone (1) and a known one, 20-hydroxyecdysone (20E)[16]. 20E was readily identified by direct comparison of its HPLC and spectroscopic characteristics with those published in the literature and with a sample previously isolated in our
Experimental
UV MeOH; NMR: on a Bruker AVANCE DRX400 instrument using standard Bruker microprograms. The chemical shifts are expressed in ppm; LSIMS (−ve ion mode); glycerol matrix using a Cs+ primary ion beam on a VG Quattro triple quadrupole mass spectrometer (VG Biotech, Altrincham); Sep-Pak Vac 35 cc (10 g) C18 cartridge (Waters) were used for initial fractionation of extract. HPLC: (a) preparative/semipreparative — Gilson model 806 HPLC coupled with Gilson UV-Visible detector, (b) analytical-Gilson model
Acknowledgements
This research was supported by a grant from the Biotechnology and Biological Sciences Research Council. We thank Professor J. Koolman for antisera, Mark Prescott for assistance with mass spectrometry, and Perisri Whiting and Tamara Savchenko for valuable assistance.
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2021, Bioorganic ChemistryCitation Excerpt :The three TOCSY correlations of the OCH protons of both 5 (4.02/2.85, 1.76, 2.74) and 6 (4.34/2.18, 1.81, 2.66) suggested that 5 and 6 were the 2-dehydro analogs of 1. Based on the good match between our 1H and 13C NMR data and those reported by Savchenko et al. in the same solvent [46] and to those reported by Sarker et al. in a different solvent [47] the minor component, 6 was unambiguously assigned as the 2-dehydro-3α-OH derivative of 1 (Fig. 1). The analysis of the TOCSY, HSQC and HMBC (Figs. S13-14) data with the 1H and 13C assignments of 6 at hand, strengthened further the identical constitution of 5 and 6 and showed that the structural differences between these compounds concerned ring A only.
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2015, Studies in Natural Products ChemistryCitation Excerpt :Hydroxyl groups may often occur in C-2β, C-3β, C-14α, C-20R, and C-22R positions, which together give rise to the highly biologically active ponasterone A (25-deoxy-20E) (2). The less hydroxylated sites are C-1α (e.g., integristerone A, 12), C-1β (e.g., 1-epi-integristerone A), C-2α (e.g., paristerone, 13), C-3α (e.g., 3-epi-2-deoxyecdysone), C-5α (e.g., 5α-polypodine B), C-5β (e.g., polypodine B, 14), C-9 (e.g., viperidinone, 15), C-11α (e.g., turkesterone, 16), C-12β (e.g., 22-dehydro-12-hydroxycyasterone), C-19 (e.g., sogdisterone, 17), C-21 (e.g., 22-deoxy-20,21-dihydroxyecdysone), C-22S (e.g., 22-epi-20E), C-24S (e.g., pterosterone, 18), C-24R (e.g., 24-epi-pterosterone), C-25 (e.g., 20E) (5), C-26R/S (e.g., inokosterone, 19), C-28 (e.g., makisterone D, 20), and/or C-29 (e.g., amarasterone B) positions (Fig. 3) but rarely C-23 [18–22]. The hydroxyl group can take part in a variety of ecdysteroid conjugates (Fig. 4) through the formation of ester (acetate, benzoate, cinnamate, 3-p-coumarate, crotonate (2-deoxy-20E-3-crotonate), 3-hydroxybutanoate (venustone), pyrrole 2-carboxylate (canescensterone), sulfate), ether (methoxy; e.g., polypodoaurein), isopropylidene (2,3- or 20,22-monoacetonide), and/or glycosidic (galactoside, glucoside, xyloside) bond [12,23,24].
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