Abstract
Ecdysteroids, molting hormones of insects, can exert several mild, non-hormonal bioactivities in mammals, including humans. In a previous study, we have found a significant effect of certain derivatives on the ABCB1 transporter mediated multi-drug resistance of a transfected murine leukemia cell line. In this paper, we present a structure-activity relationship study focused on the apolar dioxolane derivatives of 20-hydroxyecdysone. Semi-synthesis and bioactivity of a total of 32 ecdysteroids, including 20 new compounds, is presented, supplemented with their complete 1H- and 13C-NMR signal assignment.
Highlights
Ecdysteroids represent a large family of steroid hormones that play a crucial role in arthropods’physiology
Compounds containing similar number of carbon atoms are presented in one table, and compounds with the highest structural similarity are presented in neighbouring columns
T-cell lymphoma cells (ECACC catalog no. 87111908, U.S FDA, Silver Spring, MD, USA); and a multi-drug resistant (MDR) cell line derived from PAR by transfection with pHa MDR1/A retrovirus [11]
Summary
Ecdysteroids represent a large family of steroid hormones that play a crucial role in arthropods’. The most abundant representative of these compounds, 20-hydroxyecdysone (20E), regulates the reproduction, embryogenesis, diapause and molting of arthropods [1] Their role in plants is still to be fully understood, but it had been suggested that they have high importance in several plants as defensive agents against non-adapted herbivores [2]. Ecdysteroids generally retain the cholesterol-originated side-chain, typically contain 27–29 carbon atoms and are substituted with 4–8 hydroxyl groups Their A/B ring junction is usually cis, and a characteristic 7-en-6-one (α,β-unsaturated ketone) chromophore group is present in their B-ring [4]. Due to their significantly different structure as compared to the vertebrate steroid hormones, these compounds have no hormonal effects in humans [5]. In the study reported we present the synthesis, structure elucidation and MDR-modulating activity of 32 ecdysteroid dioxolanes, including 20 new derivatives, and provide further insights on the structure-activity relationships of these compounds
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