Synthesis of Phenyl-1-benzoxepinols Isolated from Butcher's Broom and Analogous Benzoxepines

Herrmann, Josef M. and Untergehrer, Monika and Juergenliemk, Guido and Heilmann, Joerg and Koenig, Burkhard (2014) Synthesis of Phenyl-1-benzoxepinols Isolated from Butcher's Broom and Analogous Benzoxepines. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014 (15). pp. 3170-3181. ISSN 1434-193X, 1099-0690

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Abstract

Extracts of Ruscus aculeatus L., known as butcher's broom, are mainly used for the treatment of chronic venous insufficiency (CVI). In a recent study on the phenolic compounds of Rusci rhizoma, new phenyl-1-benzoxepinols were isolated. As the therapeutic effect of butcher's broom is ascribed to the pharmacological activity of the main constituents, steroidal saponins and their aglycones the ruscogenins, the role of the newly identified compounds was of interest. Owing to the low availability of the compounds by isolation, we synthesized them for pharmacological testing. In an ORAC-fluorescein assay they revealed a significant antioxidative activity, which may contribute to the anti-inflammatory properties of the phenolic fraction obtained from Rusci rhizoma extracts.

Item Type: Article
Uncontrolled Keywords: FRIEDEL-CRAFTS ACYLATION; CATALYZED ASYMMETRIC HYDROGENATION; ENANTIOSELECTIVE SYNTHESIS; REFORMATSKY REACTION; CARBOXYLIC-ACIDS; RUSCI-RHIZOMA; KAPPA-B; ESTERS; OXIDATION; METALS; Natural products; Oxygen heterocycles; Acylation; Antioxidants
Subjects: 500 Science > 540 Chemistry & allied sciences
600 Technology > 615 Pharmacy
Divisions: Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann)
Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 11 Nov 2019 10:09
Last Modified: 11 Nov 2019 10:09
URI: https://pred.uni-regensburg.de/id/eprint/10221

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