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Molecules 2016, 21(9), 1206; doi:10.3390/molecules21091206

Anti-Inflammatory Effects and Mechanisms of Action of Coussaric and Betulinic Acids Isolated from Diospyros kaki in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

1
Research Institute of Pharmaceutical Sciences, Keimyung University, 1095 Dalgubeol-Daero, Daegu 42601, Korea
2
College of Pharmacy, Chosun University, Dong-Gu, Gwangju 61452, Korea
3
Institute of Pharmaceutical Research and Development, College of Pharmacy, Wonkwang University, Iksan 54538, Korea
*
Author to whom correspondence should be addressed.
Academic Editor: Norbert Latruffe
Received: 4 August 2016 / Revised: 6 September 2016 / Accepted: 7 September 2016 / Published: 9 September 2016
(This article belongs to the Special Issue Natural Products and Inflammation)
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Abstract

Diospyros kaki Thunb. is widely distributed in East Asian countries, its leaves being mainly used for making tea. In this study, coussaric acid (CA) and betulinic acid (BA), both triterpenoid compounds, were obtained from D. kaki leaf extracts through bioassay-guided isolation. CA and BA showed anti-inflammatory effects via inhibition of the nuclear factor-κB (NF-κB) pathway, providing important information on their anti-inflammatory mechanism. Furthermore, they markedly inhibited nitric oxide (NO) and prostaglandin E2 (PGE2) production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages, and suppressed tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and interleukin-1β (IL-1β) levels. Furthermore, they decreased protein expression of inducible nitric oxide synthase and cyclooxygenase-2. Pre-treatment with CA and BA inhibited LPS-induced NF-κB. We further examined the effects of CA and BA on heme oxygenase (HO)-1 expression in RAW 264.7 macrophages: BA induced HO-1 protein expression in a dose-dependent manner, while CA had no effect. We also investigated whether BA treatment induced nuclear translocation of Nrf2. BA inhibited LPS-induced NF-κB-binding activity, as well as pro-inflammatory mediator and cytokine production (e.g., NO, PGE2, TNF-α, IL-1β, IL-6), by partial reversal of this effect by SnPP, an inhibitor of HO-1. These findings further elucidate the anti-inflammatory mechanism of CA and BA isolated from D. kaki. View Full-Text
Keywords: Diospyros kaki Thunb.; coussaric acid (CA); betulinic acid (BA); anti-inflammation; nuclear factor-kappa B; heme oxygenase-1 Diospyros kaki Thunb.; coussaric acid (CA); betulinic acid (BA); anti-inflammation; nuclear factor-kappa B; heme oxygenase-1
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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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Kim, K.-S.; Lee, D.-S.; Kim, D.-C.; Yoon, C.-S.; Ko, W.; Oh, H.; Kim, Y.-C. Anti-Inflammatory Effects and Mechanisms of Action of Coussaric and Betulinic Acids Isolated from Diospyros kaki in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages. Molecules 2016, 21, 1206.

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