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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Planta medica | ||||
| Verlag: | Thieme | ||||
| Band: | 69 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 3 | ||||
| Seitenbereich: | S. 202-206 | ||||
| Datum: | 2003 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 139:159442 1-3 Pharmacology 7782-44-7D (Oxygen); 9002-17-9 (Xanthine oxidase); 9007-43-6 (Cytochrome c) Role: BSU (Biological study, unclassified), BIOL (Biological study) (antioxidant activity of phloroglucinol derivs. from hypericum species); 11079-53-1 (Hyperforin); 256471-46-2 (Ialibinone A); 256471-47-3 (Ialibinone B); 256471-48-4 (Ialibinone C); 256471-49-5 (Ialibinone D); 256471-50-8 (Ialibinone E); 350027-98-4 (Papuaforin A); 350027-99-5 (Papuaforin B); 350028-00-1 (Papuaforin C); 350028-01-2 (Papuaforin D); 350028-02-3 (Papuaforin E); 350028-03-4 (Hyperguinone A); 350028-04-5 (Hyperguinone B); 350028-05-6 (Hyperpapuanone); 398119-01-2 (Enaimeone A); 398119-02-3 (Enaimeone B); 398119-03-4 (Enaimeone C); 398119-04-5 (1'-Hydroxyialibinone A); 398119-05-6 (1'-Hydroxyialibinone B); 398119-06-7 (1'-Hydroxyialibinone D); 398119-08-9 (Furonewguinone B) Role: NPO (Natural product occurrence), PAC (Pharmacological activity), THU (Therapeutic use), BIOL (Biological study), OCCU (Occurrence), USES (Uses) (antioxidant activity of phloroglucinol derivs. from hypericum species) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann) | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Antioxidants Cytotoxicity Hypericum Radical scavengers Structure-activity relationship (antioxidant activity of phloroglucinol derivs. from hypericum species) Reactive oxygen species Role: BSU (Biological study, unclassified), BIOL (Biological study) (antioxidant activity of phloroglucinol derivs. from hypericum species) Respiration (burst antioxidant activity of phloroglucinol derivs. from hypericum species) antioxidant phloroglucinol deriv hypericum structure activity | ||||
| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 570 Biowissenschaften, Biologie 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status: | Veröffentlicht | ||||
| Begutachtet: | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden: | Nein | ||||
| Dokumenten-ID: | 17214 |
Zusammenfassung
Twenty-one phloroglucinol derivs., belonging to 8 different carbon skeletons, were tested for their ability to influence the oxidative burst of polymorphonuclear cells (PMNs) after stimulation with N-formyl-methionyl-leucyl-phenylalanine (fMLP) or opsonized zymosan (OZ). Results revealed a strong redn. of oxygen prodn. by PMNs after stimulation with fMLP for the compds. ialibinone E (5), ...
Zusammenfassung
Twenty-one phloroglucinol derivs., belonging to 8 different carbon skeletons, were tested for their ability to influence the oxidative burst of polymorphonuclear cells (PMNs) after stimulation with N-formyl-methionyl-leucyl-phenylalanine (fMLP) or opsonized zymosan (OZ). Results revealed a strong redn. of oxygen prodn. by PMNs after stimulation with fMLP for the compds. ialibinone E (5), hyperguinone B (15) and hyperforin (21). The IC50 values obtained were 2.5 micro M (5), 3.3 micro M (15) and 1.8 micro M (21), resp. Slight modifications of the substituents or variation of the stereochem. resulted in a significant loss of activity. None of the active compds. showed antioxidative activity after stimulation with OZ. The influence of compds. 5, 15 and 21 on the prodn. of oxygen radicals in an H2O2/horseradish peroxidase system was investigated and revealed potent activity only for compd. 5 (IC50 1 micro M). The superoxide-scavenging properties of ialibinone E and hyperguinone B were addnl. tested in a cytochrome c assay and only ialibinone E was significantly active at lower micromolar concns. Ialibinone E was not active in a xanthine oxidase assay (urate formation) in concns. up to 100 micro M and its activity is therefore not attributable to the inhibition of this enzyme. It can be assumed that the activity of compds. 5 and 15 in the different cellular and enzymic assays, is most likely caused by different and maybe specific mechanisms and cannot be explained by a radical scavenger activity alone. None of the active phloroglucinols showed cytotoxic effects against the PMNs.
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