Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin
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Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin. / Wolf, Insa; Palani, Kalpana; Esatbeyoglu, Tuba; Schwarz, Karin; Rimbach, Gerald.
In: PHARMACOL RES, Vol. 70, No. 1, 01.04.2013, p. 155-62.Research output: SCORING: Contribution to journal › SCORING: Journal article › Research › peer-review
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T1 - Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin
AU - Wolf, Insa
AU - Palani, Kalpana
AU - Esatbeyoglu, Tuba
AU - Schwarz, Karin
AU - Rimbach, Gerald
N1 - Copyright © 2013 Elsevier Ltd. All rights reserved.
PY - 2013/4/1
Y1 - 2013/4/1
N2 - 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.
AB - 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.
KW - Active Transport, Cell Nucleus
KW - Animals
KW - Blotting, Western
KW - Cell Culture Techniques
KW - Cell Nucleus
KW - Cell Survival
KW - Chromatography, High Pressure Liquid
KW - Isothiocyanates
KW - Mice
KW - Molecular Structure
KW - NF-E2-Related Factor 2
KW - NIH 3T3 Cells
KW - Real-Time Polymerase Chain Reaction
KW - Signal Transduction
KW - Structure-Activity Relationship
KW - Sulfides
KW - Sulfones
U2 - 10.1016/j.phrs.2013.01.011
DO - 10.1016/j.phrs.2013.01.011
M3 - SCORING: Journal article
C2 - 23403058
VL - 70
SP - 155
EP - 162
JO - PHARMACOL RES
JF - PHARMACOL RES
SN - 1043-6618
IS - 1
ER -
