||6-Shogaol is a pungent constituent of ginger similar to gingerol in chemical structure. It is an active compound isolated from Ginger (Zingiber officinale Rosc). It exhibits a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation. It has a very strong antitussive (anti-cough) effect. lt has been shown to induce apoptosis (kill) in human colorectal carcinoma cells via reactive oxygen species. It can also activate both TRPV1 and TRPA1 channels.
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1.Synthesis, evaluation, and metabolism of novel -shogaol derivatives as potent Nrf2 activators.
Zhu Y1, Wang P1, Zhao Y1, Yang C2, Clark A3, Leung T3, Chen X4, Sang S5. Free Radic Biol Med. 2016 Mar 25;95:243-254. doi: 10.1016/j.freeradbiomed.2016.03.026. [Epub ahead of print]
Oxidative stress is a central component of many chronic diseases. The Kelch-like ECH-associated protein 1 (Keap1)-nuclear factor erythroid 2 p45-related factor 2 (Nrf2) system is a major regulatory pathway of cytoprotective genes against oxidative and electrophilic stress. Activation of the Nrf2 pathway plays crucial roles in the chemopreventive effects of various inducers. In this study, we developed a novel class of potent Nrf2 activators derived from ginger compound, -shogaol (6S), using the Tg[glutathione S-transferase pi 1 (gstp1):green fluorescent protein (GFP)] transgenic zebrafish model. Investigation of structure-activity relationships of 6S derivatives indicates that the combination of an α,β-unsaturated carbonyl entity and a catechol moiety in one compound enhances the Tg(gstp1:GFP) fluorescence signal in zebrafish embryos. Chemical reaction and in vivo metabolism studies of the four most potent 6S derivatives showed that both α,β-unsaturated carbonyl entity and catechol moiety act as major active groups for conjugation with the sulfhydryl groups of the cysteine residues.