Compuestos fenólicos de phagnalon rupestre activos en hipersensibilidad y liberación de mediadores inflamatorios
In the first part, the effect of pre- and post-challenge treatments with trifluoperazine and palmitoylcarnitine, two protein kinase C inhibitors, on the inflammation caused by delayed hyperensitivity to dinitrofluorobenzene (DNFB) and sheep red blood cells (SRBC) in mice is reported. The ability of trifluoperazine in inhibiting cutaneous DTH reaction, depending on the treatment schedule and the hapten challenge dose, has been determined.
Analysis of the methanolic extract of the aerial parts of Phagnalon rupestre (Asteraceae) had led to the isolation of fourteen phenolic compounds. Six have been identified on the basis of their NMR spectra as new natural compounds: four prenylhydroquinone glucosides 1-O-?-glucopyranosyl-1,4-dihydroxy-2-(3´,3´-dimethylallyl)-benzene, 1-O-?-glucopyranosyl-1,4-dihydroxy-2-(3´-hydroxymethyl-3´-methylallyl)-benzene, 1-O-(4´´-O-caffeoyl)-?-glucopyranosyl-1,4-dihydroxy-2-(3´,3´-dimethylallyl)-benzene and 1-O-?-glucopyranosyl-1,4-dihydroxy-2-(3´-hydroxy-3´-methylbutyl)-benzene; the lignan 7,7´-bis-(4-hydroxy-3,5-dimethoxyphenyl)-8,8´-dihydroxymethyl-tetrahydrofuran-4-O-?-glucopyranoside; and the acetophenone glucoside 12-O-?-glucopyranosyl-9?,12-dihyroxytremetone. The known flavonoids apigenin 7-O-?-glucopyranoside, luteolin 7-O-?-glucopyranoside, luteolin 7-O-?-glucuronide, the acetophenone picein and 3,5- and 4,5-di-O-caffeoylquinic acid methyl esters and their free carboxyl analogues were also isolated. Eight of them were tested for dinitrofluorobenzene-induced contact hypersensitivity inhibitory activity, being luteolin 7-O-?-glucopyranoside the most active.
In order to determine the antioxidant activity of the anti-inflammatory phenolic principles, we studied their effect on lipid peroxidation and superoxide free radical systems. The presence of the caffeoyl moiety is essential for both the antiperoxidative and radical scavenging activities, and the methylation of the quinic carboxyl group enhances the potency on xanthine oxidase inhibitory activity.
Finally, the last study undertake the assessment of the in vitro activity of the same compounds as above on the neutrophil, a biological system that allows the evaluation of some functions relative to the inflammatory process. The parameters measured were elastase release, myeloperoxidase activity and superoxide and leukotriene B4 production from polymorphonuclear leukocytes.
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Advisor:Mañez Aliño Salvador; Giner Pons Rosa Mª
School:Universitat de València
Source Type:Master's Thesis
Date of Publication:06/07/2002