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Mol. Cells 2013; 35(5): 410-420

Published online May 31, 2013

https://doi.org/10.1007/s10059-013-0031-z

© The Korean Society for Molecular and Cellular Biology

Relative Antioxidant Activities of Quercetin and Its Structurally Related Substances and Their Effects on NF-?B/CRE/AP-1 Signaling in Murine Macrophages

Byung-Hak Kim, Jung Sook Choi, Eun Hee Yi, Jin-Ku Lee, Cheolhee Won, Sang-Kyu Ye, and Myoung-Hwan Kim

1Department of Pharmacology, 2Neuro-Immune Information Storage Network Research Center, Seoul National University College of Medi-cine, Seoul 110-799, Korea, 3Department of Beauty and Aesthetic Sciences, Gyeongdo Provincial College, Yecheon 757-807, Korea, 4Ischemic/Hypoxic Disease Institute, 5Department of Physiology, Seoul National University College of Medicine, Seoul 110-799, Korea, 6Seoul National University Bundang Hospital, Seongnam 463-707, Korea

Received: January 29, 2013; Revised: February 27, 2013; Accepted: March 19, 2013

Abstract

Reactive oxygen species (ROS) and reactive nitrogen species (RNS) produced by the oxidative burst in activated macrophages and neutrophils cause oxidative stress-implicated diseases. Quercetin is flavonoid that occurs naturally in plants and is widely used as a nutritional supplement due to its antioxidant and anti-inflammatory properties. In this study, we investigated antioxidant activities and mechanisms of action in zymosan-induced macro- phages of quercetin and quercetin-related flavonoids such as quercitrin, isoquercitrin, quercetin 3-O-beta-(2''-galloyl)-rhamnopyranoside (QGR) and quercetin 3-O-beta-(2''-galloyl)-glucopyranoside (QGG) as well as gallic acid, a building moiety of QGR and QGG. QGR and QGG exhib-ited stronger antioxidant activities compared with quercetin, whereas quercitrin, isoquercitrin and gallic acid exhibited weak-to-no antioxidant activities, assessed by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging, superoxide production, superoxide scavenging, nitric oxide (NO) production, peroxynitrite (ONOO-) scavenging and myeloperoxidase (MPO) activity. Regarding mechanisms, the quercetin-containing flavonoids QGR and QGG differentially targeted compared with quercetin in the NF-kappaB signaling pathway that inhibited the DNA binding activity of the NF-kappaB complex without affecting the degradation and phosphorylation of IkappaBalpha and NF-kappaB phosphorylation. In addition, QGR and QGG inhibited CRE and activator protein (AP-1) transcriptional activity and JNK phosphorylation by inhibiting the cAMP/protein kinase A (PKA) and protein kinase C (PKC) signaling in a different manner than quercetin. Our results showed that although QGR and QGG exhibited stronger antioxidant activities than querce-tin in macrophages, their mechanisms of action in terms of the NF-kappaB, PKA and PKC signaling pathways were different.

Keywords antioxidant, NF-?B/CRE/AP-1, quercetin, ROS/RNS, structurally related compounds

Article

Research Article

Mol. Cells 2013; 35(5): 410-420

Published online May 31, 2013 https://doi.org/10.1007/s10059-013-0031-z

Copyright © The Korean Society for Molecular and Cellular Biology.

Relative Antioxidant Activities of Quercetin and Its Structurally Related Substances and Their Effects on NF-?B/CRE/AP-1 Signaling in Murine Macrophages

Byung-Hak Kim, Jung Sook Choi, Eun Hee Yi, Jin-Ku Lee, Cheolhee Won, Sang-Kyu Ye, and Myoung-Hwan Kim

1Department of Pharmacology, 2Neuro-Immune Information Storage Network Research Center, Seoul National University College of Medi-cine, Seoul 110-799, Korea, 3Department of Beauty and Aesthetic Sciences, Gyeongdo Provincial College, Yecheon 757-807, Korea, 4Ischemic/Hypoxic Disease Institute, 5Department of Physiology, Seoul National University College of Medicine, Seoul 110-799, Korea, 6Seoul National University Bundang Hospital, Seongnam 463-707, Korea

Received: January 29, 2013; Revised: February 27, 2013; Accepted: March 19, 2013

Abstract

Reactive oxygen species (ROS) and reactive nitrogen species (RNS) produced by the oxidative burst in activated macrophages and neutrophils cause oxidative stress-implicated diseases. Quercetin is flavonoid that occurs naturally in plants and is widely used as a nutritional supplement due to its antioxidant and anti-inflammatory properties. In this study, we investigated antioxidant activities and mechanisms of action in zymosan-induced macro- phages of quercetin and quercetin-related flavonoids such as quercitrin, isoquercitrin, quercetin 3-O-beta-(2''-galloyl)-rhamnopyranoside (QGR) and quercetin 3-O-beta-(2''-galloyl)-glucopyranoside (QGG) as well as gallic acid, a building moiety of QGR and QGG. QGR and QGG exhib-ited stronger antioxidant activities compared with quercetin, whereas quercitrin, isoquercitrin and gallic acid exhibited weak-to-no antioxidant activities, assessed by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging, superoxide production, superoxide scavenging, nitric oxide (NO) production, peroxynitrite (ONOO-) scavenging and myeloperoxidase (MPO) activity. Regarding mechanisms, the quercetin-containing flavonoids QGR and QGG differentially targeted compared with quercetin in the NF-kappaB signaling pathway that inhibited the DNA binding activity of the NF-kappaB complex without affecting the degradation and phosphorylation of IkappaBalpha and NF-kappaB phosphorylation. In addition, QGR and QGG inhibited CRE and activator protein (AP-1) transcriptional activity and JNK phosphorylation by inhibiting the cAMP/protein kinase A (PKA) and protein kinase C (PKC) signaling in a different manner than quercetin. Our results showed that although QGR and QGG exhibited stronger antioxidant activities than querce-tin in macrophages, their mechanisms of action in terms of the NF-kappaB, PKA and PKC signaling pathways were different.

Keywords: antioxidant, NF-?B/CRE/AP-1, quercetin, ROS/RNS, structurally related compounds

Mol. Cells
Sep 30, 2022 Vol.45 No.9, pp. 603~672
COVER PICTURE
The Target of Rapamycin Complex (TORC) is a central regulatory hub in eukaryotes, which is well conserved in diverse plant species, including tomato (Solanum lycopersicum). Inhibition of TORC genes (SlTOR, SlLST8, and SlRAPTOR) by VIGS (virus-induced gene silencing) results in early fruit ripening in tomato. The red/ orange tomatoes are early-ripened TORC-silenced fruits, while the green tomato is a control fruit. Top, left, control fruit (TRV2-myc); top, right, TRV2-SlLST8; bottom, left, TRV2-SlTOR; bottom, right, TRV2-SlRAPTOR(Choi et al., pp. 660-672).

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