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Open AccessArticle

1-Carbomethoxy-β-Carboline, Derived from Portulaca oleracea L., Ameliorates LPS-Mediated Inflammatory Response Associated with MAPK Signaling and Nuclear Translocation of NF-κB

1
Immunoregulatory Material Research Center, Korea Research Institute of Biotechnology, 181 Ipsin-gil, Jeongeup-si, Jeonbuk 56212, Korea
2
Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Chonbuk National University, Iksan-si 570-752, Korea
*
Authors to whom correspondence should be addressed.
These authors equally contributed to this study.
Molecules 2019, 24(22), 4042; https://doi.org/10.3390/molecules24224042
Received: 2 October 2019 / Revised: 25 October 2019 / Accepted: 5 November 2019 / Published: 7 November 2019
(This article belongs to the Section Natural Products Chemistry)
Portulaca oleracea is as a medicinal plant known for its neuroprotective, hepatoprotective, antidiabetic, antioxidant, anticancer, antimicrobial, antiulcerogenic, and anti-inflammatory activities. However, the specific active compounds responsible for the individual pharmacological effects of P. oleracea extract (95% EtOH) remain unknown. Here, we hypothesized that alkaloids, the most abundant constituents in P. oleracea extract, are responsible for its anti-inflammatory activity. We investigated the phytochemical substituents (compounds 1–22) using nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESI-MS) and screened their effects on NO production in lipopolysaccharide (LPS)-induced macrophages. Compound 20, 1-carbomethoxy-β-carboline, as an alkaloid structure, ameliorated nitric oxide (NO) production, inducible nitric oxide synthase (iNOS), and proinflammatory cytokines associated with the mitogen-activated protein kinase (MAPK) pathways, p38, extracellular signal-regulated kinase (ERK), and c-Jun N-terminal kinase (JNK). Subsequently, we observed that compound 20 suppressed nuclear translocation of nuclear factor κB (NF-κB) using immunocytochemistry. Moreover, we recently reported that compound 8, trans-N-feruloyl-3’, 7’-dimethoxytyramine, was originally purified from P. oleracea extracts. Our results suggest that 1-carbomethoxy-β-carboline, the most effective anti-inflammatory agent among alkaloids in the 95% EtOH extract of P. oleracea, was suppressing the MAPK pathway and nuclear translocation of NF-κB. Therefore, P. oleracea extracts and specifically 1-carbomethoxy-β-carboline may be novel therapeutic candidates for the treatment of inflammatory diseases associated with the activation of MAPKs and NF-κB. View Full-Text
Keywords: Portulaca oleracea; 1-carbomethoxy-β-carboline; anti-inflammation; MAPKs; NF-κB Portulaca oleracea; 1-carbomethoxy-β-carboline; anti-inflammation; MAPKs; NF-κB
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Kim, K.-H.; Park, E.-J.; Jang, H.-J.; Lee, S.-J.; Park, C.S.; Yun, B.-S.; Lee, S.W.; Rho, M.-C. 1-Carbomethoxy-β-Carboline, Derived from Portulaca oleracea L., Ameliorates LPS-Mediated Inflammatory Response Associated with MAPK Signaling and Nuclear Translocation of NF-κB. Molecules 2019, 24, 4042.

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