Phagnalon rupestre as a Source of Compounds Active on Contact Hypersensitivity

Abstract

The effect of Phagnalon rupestre MeOH extract on dinitrofluorobenzene- and sheep red blood cells-induced hypersensitivity was investigated. Eight compounds were identified: three dimethylallyl-hydroquinone glucosides (1 - 3), 3,5- and 4,5-di-O-caffeoylquinic acid methyl esters (4 and 5), their free carboxyl analogues (6 and 7), and luteolin 7-O-β-glucoside (8). All were tested for dinitrofluorobenzene-induced contact hypersensitivity inhibitory activity. Flavonoid 8 was the most active (49 % and 79 % inhibition at 24 and 96 h, respectively). The hydroquinones 1, 2 and 3 were effective at 96 h after challenge (62 %, 73 % and 60 % inhibition, respectively), while some of the dicaffeoylquinic derivatives (4 and 7) produced slightly lower reduction of the inflammatory reaction.

References

• 1 Engler A. Syllabus der Pflanzenfamilien. Part II. Berlin; Gebrüder Bornträger 1964: 488-90
• 2 Font Quer  P. Plantas Medicinales. Vol. 3. Barcelona; Labor 1993: 788-9
• 3 Máñez S, Recio M C, Gil I, Gómez C, Giner R M, Waterman P G, Ríos J L. A glycosyl analogue of diacylglycerol and other anti-inflammatory constituents from Inula viscosa .  Journal of Natural Products. 1999;  62 601-4
• 4 Sala A, Recio M C, Máñez S, Giner R M, Ríos J L. New acetophenone glucosides isolated from extracts of Helichrysum italicum with anti-inflammatory activity.  Journal of Natural Products. 2001;  64 1360-2
• 5 Robert C, Kupper T S. Inflammatory skin diseases, T cells, and immune surveillance.  The New England Journal of Medicine. 1999;  341 1817-28
• 6 Góngora L, Giner R M, Máñez S, Recio M C, Ríos J L. New prenylhydroquinone glycosides from Phagnalon rupestre .  Journal of Natural Products. 2001;  64 1111-3
• 7 Pauli G F, Poetsch F, Nahrstedt A. Structure assignment of natural quinic acid derivatives using proton nuclear magnetic resonance techniques.  Phytochemical Analysis. 1998;  9 177-85
• 8 Timmermann B N, Hoffmann J J. Constituents of Chrysothamnus paniculatus 3: 3,4,5-tricaffeoylquinic acid (a new shikimate prearomatic) and 3,4-, 3,5- and 4,5-dicaffeoylquinic acids.  Journal of Natural Products. 1983;  46 365-8
• 9 Lu Y, Foo L Y. Flavonoid and phenolic glycosides from Salvia officinalis .  Phytochemistry. 2000;  55 263-7
• 10 Grabbe S, Schwarz T. Immunoregulatory mechanisms involved in elicitation of allergic contact hypersensitivity.  Immunology Today. 1998;  19 37-44
• 11 Halliday G M, Lucas A D. Protein kinase C transduces the signal for Langerhans’ cell migration from the epidermis.  Immunology. 1993;  79 621-6
• 12 Ferriola P C, Cody V, Middleton E  Jr. Protein kinase C inhibition by plant flavonoids. Kinetic mechanisms and structure-activity relationships.  Biochemical Pharmacology. 1989;  38 1617-24
• 13 Agullo G, Gamet-Payrastre L, Manenti S, Viala C, Rémésy C, Chap H, Payrastre B. Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: a comparision with tyrosine kinase and protein kinase C inhibition.  Biochemical Pharmacology. 1997;  53 1649-57
• 14 Gerritsen M E, Carley W W, Ranges G E, Shen C h-P, Phan S A, Ligon G F, Perry C A. Flavonoids inhibit cytokine-induced endothelial cell adhesion protein gene expression.  American Journal of Pathology. 1995;  147 278-92
• 15 Lepoittevin J P, Benezra C. Allergic contact dermatitis caused by naturally occurring quinones. Pharmaceutisch Weekblad.  Scientific Edition. 1991;  21 119-22
• 16 Ferrándiz M L, Sanz M J, Bustos G, Payá M, Alcaraz M J, De Rosa S. Avarol and avarone, two new anti-inflammatory agents of marine origin.  European Journal of Pharmacolgy. 1994;  253 75-82
• 17 Gil B, Sanz M J, Terencio M C, De Giulio A, De Rosa S, Alcaraz M J, Payá M. Effects of marine 2-polyprenyl-1,4-hydroquinones on phospholipase A₂ activity and some inflammatory responses.  European Journal of Pharmacology. 1995;  285 281-8
• 18 Lin L C, Kuo Y C, Chou C J. Immunomodulatory principles of Dichrocephala bicolor .  Journal of Natural Products. 1999;  62 405-8
• 19 Góngora L, Máñez S, Giner R M, Recio M C, Ríos J L. On the activity of trifluoperazine and palmitoylcarnitine in mice: delayed hypersensitivity models.  Life Sciences. 2000;  66 183-8