Elsevier

Phytochemistry

Volume 49, Issue 8, 20 December 1998, Pages 2311-2314
Phytochemistry

2-dehydro-3-epi-20-hydroxyecdysone from Froelichia florida

https://doi.org/10.1016/S0031-9422(98)00447-6Get rights and content

Abstract

A new phytoecdysteroid, 2-dehydro-3-epi-20-hydroxyecdysone, together with 20-hydroxyecdysone have been isolated by bioassay/RIA-directed HPLC analyses of a methanol extract of the seeds of Froelichia floridana. The structure of the novel ecdysteroid was determined unambiguously by UV, LSIMS, and a combination of 1D and 2D NMR techniques. The biological activity in the Drosophila melanogaster BII cell bioassay (ED50=4.0×10−7 M) is considerably lower than that of 20-hydroxyecdysone (ED50=7.5×10−9 M).

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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