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| Item type: | Article | ||||
|---|---|---|---|---|---|
| Journal or Publication Title: | Planta medica | ||||
| Publisher: | Thieme | ||||
| Volume: | 69 | ||||
| Number of Issue or Book Chapter: | 3 | ||||
| Page Range: | pp. 202-206 | ||||
| Date: | 2003 | ||||
| Additional Information (public): | 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) | ||||
| Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) | ||||
| Identification Number: |
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| 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 Decimal Classification: | 500 Science > 570 Life sciences 500 Science > 540 Chemistry & allied sciences | ||||
| Status: | Published | ||||
| Refereed: | Yes, this version has been refereed | ||||
| Created at the University of Regensburg: | No | ||||
| Item ID: | 17214 |
Abstract
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), ...
Abstract
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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