Next Article in Journal
A Comparative Analysis of the Chemical Composition, Anti-Inflammatory, and Antinociceptive Effects of the Essential Oils from Three Species of Mentha Cultivated in Romania
Next Article in Special Issue
The Structure-Activity Relationship of Pterostilbene Against Candida albicans Biofilms
Previous Article in Journal
Betulinic Acid-Mediated Apoptosis in Human Prostate Cancer Cells Involves p53 and Nuclear Factor-Kappa B (NF-κB) Pathways
Previous Article in Special Issue
Phloretin Exerts Anti-Tuberculosis Activity and Suppresses Lung Inflammation
Article Menu
Issue 2 (February) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(2), 265; doi:10.3390/molecules22020265

Structure-Antioxidative and Anti-Inflammatory Activity Relationships of Purpurin and Related Anthraquinones in Chemical and Cell Assays

1
Department of Biological Science, Ajou University, Suwon 16499, Korea
2
Research Institute of Basic Sciences, Ajou University, Suwon 16499, Korea
3
STR Biotech. Ltd., Chuncheon 24232, Korea
4
Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, CA 94710, USA
*
Authors to whom correspondence should be addressed.
Academic Editor: Jean-Marc Sabatier
Received: 28 December 2016 / Revised: 6 February 2017 / Accepted: 8 February 2017 / Published: 10 February 2017
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)
View Full-Text   |   Download PDF [1307 KB, uploaded 10 February 2017]   |  

Abstract

Anthraquinone (9,10-anthraquinone) and several hydroxy derivatives, including purpurin (1,2,4-trihydroxyanthraquinone), anthrarufin (1,5-dihydroxyanthraquinone), and chrysazin (1,8-dihydroxyanthraquinone), were evaluated for antioxidative and anti-inflammatory activities in chemical assays and mammalian cells (murine macrophage RAW 264.7 cells). Several tests were used to assess their activities: 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical; ABTS radical cation; hydrogen peroxide scavenging; reduction of potassium ferricyanide; chelation of ferrous ions; inhibition of lipid peroxidation; inhibition of nitric oxide generation; scavenging of the intracellular hydroxyl radical; expression of NLRP3 polypeptide for inflammasome assembly; and quantitation of proinflammatory cytokine interleukin 1β (IL-1β) for inflammasome activation. The results show that purpurin, from the root of the madder plant (Rubia tinctorum L.), exhibited the highest antioxidative activity in both chemical and cultured cell antioxidant assays. The antioxidative activities of the other three anthraquinones were lower than that of purpurin. In addition, purpurin could down-regulate NLRP3 inflammasome assembly and activation, suggesting that it might protect foods against oxidative damage and prevent in vivo oxidative stress and inflammation. Structure-activity relationships and the significance of the results for food quality and human health are discussed. View Full-Text
Keywords: purpurin; anthraquinones; BHA; antioxidant tests; macrophage cells; reactive oxygen species; inflammasome activation; anti-inflammatory; cytokines; health benefits purpurin; anthraquinones; BHA; antioxidant tests; macrophage cells; reactive oxygen species; inflammasome activation; anti-inflammatory; cytokines; health benefits
Figures

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).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Nam, W.; Kim, S.P.; Nam, S.H.; Friedman, M. Structure-Antioxidative and Anti-Inflammatory Activity Relationships of Purpurin and Related Anthraquinones in Chemical and Cell Assays. Molecules 2017, 22, 265.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top