Effects of plant alkylphenols on cytokine production, tyrosine nitration and inflammatory damage in the efferent phase of contact hypersensitivity.

Abstract

BACKGROUND AND PURPOSE:

The phenolic compounds isoprenylhydroquinone glucoside (IHG), 3,5-dicaffeoylquinic acid (DCA), and its methyl ester (DCE) have previously been shown to inhibit both contact hypersensitivity (CHS) and peroxynitrite reactivity. The present work seeks to establish a relationship between the anti-inflammatory effect and the release of cytokines and tyrosine nitration in skin.

EXPERIMENTAL APPROACH:

Murine CHS was developed by means of sensitization and challenge with dinitrofluorobenzene (DNFB) or oxazolone. Ear swelling was measured 24 and 96 h after challenge. Interleukin (IL)-1beta, IL-4, and tumour necrosis factor (TNF)-alpha were measured by ELISA; and the expression of inducible nitric oxide synthase (iNOS) was detected by Western blotting. Histological samples were analysed for 3-nitrotyrosine.

KEY RESULTS:

In the oxazolone model, DCE reduced the 24 h swelling by 54% whereas the effect of DCA was lower (40% inhibition). All the test compounds reduced IL-1beta values 24 h after challenge with DNFB or oxazolone, DCE particularly inhibited IL-4 production (74% and 78%, respectively; P<0.01). Tyrosine nitration was also markedly reduced by DCE. In general, the test compounds limited the presence of polymorphonuclear (PMN) leukocytes in the skin.

CONCLUSIONS AND IMPLICATIONS:

These results suggest that the effect of 3,5-dicaffeoylquinic esters on CHS is associated with a decrease in the production of interleukins, but not with the inhibition of iNOS expression. Moreover, esterification of the carboxyl group at C-1 enhanced protection against tyrosine nitration in the skin.

• Authors: A Olmos, R M Giner, M C Recio, J L Rios, J M Cerdá-Nicolás, S Máñez
• Journal: British journal of pharmacology (Br J Pharmacol) Vol. 152 Issue 3 Pg. 366-73 (Oct 2007) ISSN: 0007-1188 [Print] England
• PMID: 17660848 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 3,5-dicaffeoylquinic acid methyl ester
• Anti-Inflammatory Agents
• Glucosides
• Hydroquinones
• Interleukin-1beta
• Tumor Necrosis Factor-alpha
• isoprenylhydroquinone glucoside
• Interleukin-4
• Chlorogenic Acid
• 3-nitrotyrosine
• Tyrosine
• Nitric Oxide Synthase Type II
• 3,5-dicaffeoylquinic acid

Topics

• Animals
• Anti-Inflammatory Agents (pharmacology)
• Asteraceae (chemistry)
• Blotting, Western
• Chlorogenic Acid (analogs & derivatives, pharmacology)
• Dermatitis, Contact (drug therapy)
• Disease Models, Animal
• Enzyme-Linked Immunosorbent Assay
• Female
• Gene Expression Regulation (drug effects)
• Glucosides (pharmacology)
• Hydroquinones (pharmacology)
• Interleukin-1beta (drug effects, metabolism)
• Interleukin-4 (metabolism)
• Mice
• Neutrophils (drug effects, metabolism)
• Nitric Oxide Synthase Type II (metabolism)
• Random Allocation
• Skin (drug effects, pathology)
• Tumor Necrosis Factor-alpha (drug effects, metabolism)
• Tyrosine (analogs & derivatives, drug effects, metabolism)