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Molecules 2018, 23(12), 3241; https://doi.org/10.3390/molecules23123241

Structural Moieties Required for Cinnamaldehyde-Related Compounds to Inhibit Canonical IL-1β Secretion

Department of Food Science, Yuanpei University of Medical Technology, No. 306, Yuanpei Street, Hsinchu 300, Taiwan
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Author to whom correspondence should be addressed.
Academic Editor: Arduino A. Mangoni
Received: 7 November 2018 / Revised: 2 December 2018 / Accepted: 6 December 2018 / Published: 7 December 2018
(This article belongs to the Special Issue Anti-Inflammatory and Anti-Allergy Agents in Medicinal Chemistry-II)
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Abstract

Suppressing canonical NOD-like receptor protein 3 (NLRP3) inflammasome-mediated interleukin (IL)-1β secretion is a reliable strategy for the development of nutraceutical to prevent chronic inflammatory diseases. This study aimed to find out the functional group responsible for the inhibitory effects of cinnamaldehyde-related compounds on the canonical IL-1β secretion. To address this, the suppressing capacities of six cinnamaldehyde-related compounds were evaluated and compared by using the lipopolysaccharide (LPS)-primed and adenosine 5′-triphosphate (ATP)-activated macrophages. At concentrations of 25~100 μM, cinnamaldehyde and 2-methoxy cinnamaldehyde dose-dependently inhibited IL-1β secretion. In contrast, cinnamic acid, cinnamyl acetate, cinnamyl alcohol and α-methyl cinnamaldehyde did not exert any inhibition. Furthermore, cinnamaldehyde and 2-methoxy cinnamaldehyde diminished expressions of NLRP3 and pro-IL-1β. Meanwhile, cinnamaldehyde and 2-methoxy cinnamaldehyde prevented the ATP-induced reduction of cytosolic pro-caspase-1 and increase of secreted caspase-1. In conclusion, for cinnamaldehyde-related compounds to suppress NLRP3 inflammasome-mediated IL-1β secretion, the propenal group of the side chain was essential, while the substituted group of the aromatic ring played a modifying role. Cinnamaldehyde and 2-methoxy cinnamaldehyde exerted dual abilities to inhibit canonical IL-1β secretion at both stages of priming and activation. Therefore, there might be potential to serve as complementary supplements for the prevention of chronic inflammatory diseases. View Full-Text
Keywords: cinnamaldehyde; 2-methoxy cinnamaldehyde; NLRP3 inflammasome; IL-1β; sterile inflammation cinnamaldehyde; 2-methoxy cinnamaldehyde; NLRP3 inflammasome; IL-1β; sterile inflammation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Ho, S.-C.; Chang, Y.-H.; Chang, K.-S. Structural Moieties Required for Cinnamaldehyde-Related Compounds to Inhibit Canonical IL-1β Secretion. Molecules 2018, 23, 3241.

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