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Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo
Zitieren Sie bitte immer diese URN: urn:nbn:de:bvb:20-opus-215993
- Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)‐1 and (S)‐1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online byAlzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)‐1 and (S)‐1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC‐ECD coupling. (R)‐1 and (S)‐1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)‐enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short‐ and long‐term memory at low dosages.…
Autor(en): | Julian Hofmann, Shaimaa Fayez, Matthias Scheiner, Matthias Hoffmann, Sabrina Oerter, Antje Appelt‐Menzel, Pamela Maher, Tangui Maurice, Gerhard Bringmann, Michael Decker |
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URN: | urn:nbn:de:bvb:20-opus-215993 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Fakultät für Chemie und Pharmazie / Institut für Pharmazie und Lebensmittelchemie | |
Medizinische Fakultät / Lehrstuhl für Tissue Engineering und Regenerative Medizin | |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Chemistry – A European Journal |
Erscheinungsjahr: | 2020 |
Band / Jahrgang: | 26 |
Heft / Ausgabe: | 32 |
Erste Seite: | 7299 |
Letzte Seite: | 7308 |
Originalveröffentlichung / Quelle: | Chemistry – A European Journal 2020, 26(32):7299–7308. DOI: 10.1002/chem.202001264 |
DOI: | https://doi.org/10.1002/chem.202001264 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Freie Schlagwort(e): | Alzheimer′s disease; Eriodictyon californicum; chiral resolution; circular dichroism; flavonoids; sterubin |
Datum der Freischaltung: | 06.07.2021 |
Lizenz (Deutsch): | CC BY-NC-ND: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell, Keine Bearbeitungen 4.0 International |