Phenolic substances from Phagnalon rupestre protect against 2,4,6-trinitrochlorobenzene-induced contact hypersensitivity.

Abstract

2-isoprenylhydroquinone-1-glucoside (1), 3,5-dicaffeoylquinic acid (2), and 3,5-dicaffeoylquinic acid methyl ester (3), isolated from Phagnalon rupestre, improved the contact hypersensitivity response to 2,4,6-trinitrochlorobenzene in mice. These phenolics reduced ear swelling and IL-1β content by 50% 24 h after challenge; in addition, 2 inhibited tumor necrosis factor-α by 53%. All three compounds also reduced interleukin-2 content by 50% 72 h after challenge. Both 2 and 3 inhibited metalloproteinase-9 levels in the skin lesions by 66% and 41%, respectively, and lowered cyclooxygenase-2 expression by 44% and 49%, respectively, at 24 h. Moreover, 2 was effective against atopic dermatitis induced by repeated application of 2,4,6-trinitrochlorobenzene; it attenuated edema by over 40% from day 7 and inhibited inflammatory cell infiltration by 44% at day 22. In addition, 1-3 reduced metalloproteinase-9 expression in a dose-dependent manner in macrophages RAW 264.7 stimulated with lipopolysaccharide. Thus, compounds 2 and 3 were found to exhibit a greater activity against contact hypersensitivity than 1.

• Authors: Elisa Giner, Mariya El Alami, Salvador Máñez, M Carmen Recio, José-Luis Ríos, Rosa M Giner
• Journal: Journal of natural products (J Nat Prod) Vol. 74 Issue 5 Pg. 1079-84 (May 27 2011) ISSN: 1520-6025 [Electronic] United States
• PMID: 21469692 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Cyclooxygenase 2 Inhibitors
• Interleukin-1beta
• Interleukin-2
• Lipopolysaccharides
• Phenols
• Tumor Necrosis Factor-alpha
• Picryl Chloride

Topics

• Animals
• Cyclooxygenase 2 Inhibitors (pharmacology)
• Dermatitis, Contact (pathology)
• Disease Models, Animal
• Dose-Response Relationship, Drug
• Ear (pathology)
• Edema (chemically induced)
• Interleukin-1beta (analysis, metabolism)
• Interleukin-2 (analysis)
• Lipopolysaccharides (pharmacology)
• Macrophages (drug effects)
• Mice
• Phenols (chemistry, isolation & purification, pharmacology)
• Picryl Chloride (pharmacology)
• Skin (drug effects)
• Tumor Necrosis Factor-alpha (analysis, metabolism)