Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin.

Ernst, I. M. A., Palani, K., Esatbeyoglu, T., Schwarz, K. and Rimbach, Gerald (2013) Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin. Pharmacological Research, 70 (1). pp. 155-162. DOI 10.1016/j.phrs.2013.01.011.

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Numerous studies have reported a potent induction of Nuclear factor (erythroid-derived 2)-like 2 (Nrf2)-dependent gene expression by the isothiocyanate sulforaphane. However, little is known regarding the Nrf2-inducing activities of the lower structure-related sulforaphane homologues, such as iberverin, iberin and cheirolin, which exhibit different sulfur oxidation states. Therefore, in this study we synthesized the isothiocyanates iberverin, iberin and cheirolin with a high yield and purity and determined their Nrf2-inducing activity in NIH3T3 fibroblasts. Iberverin, iberin and cheirolin significantly induced Nrf2 nuclear translocation. The increase in nuclear Nrf2 levels was accompanied by a significant increase in heme oxygenase 1 (HO-1) and γ-glutamylcysteine synthetase (γGCS) mRNA and protein levels. Overall, iberverin, iberin and cheirolin exhibited a similar potency to sulforaphane in inducing Nrf2-dependent gene-expression. Furthermore, our data suggest that the induction of Nrf2 by iberverin, iberin and cheirolin may have occurred via an extracellular signal-related kinase (ERK)-dependent signal-transduction pathway.

Document Type: Article
Additional Information: Times Cited: 0 Ernst, Insa M. A. Palani, Kalpana Esatbeyoglu, Tuba Schwarz, Karin Rimbach, Gerald
Keywords: Iberverin, Iberin, Cheirolin, Chemical isothiocyanate Synthesis, Nrf2
Research affiliation: Kiel University
Kiel University > Kiel Marine Science
OceanRep > The Future Ocean - Cluster of Excellence
Refereed: Yes
Open Access Journal?: No
DOI etc.: 10.1016/j.phrs.2013.01.011
ISSN: 1043-6618
Projects: Future Ocean
Date Deposited: 08 Jul 2014 09:10
Last Modified: 24 Sep 2019 00:18

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