One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor
| Autor: | Oliver Werz, Carlo Pergola, Konstantina Vougogiannopoulou, Amos B. Smith, Sylvie Michel, Christelle Lemus, Leandros Skaltsounis, Maria Halabalaki, Brigitte Deguin |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Stereochemistry
Iridoid Glucosides Anti-Inflammatory Agents Pharmaceutical Science Cyclopentane Monoterpenes Analytical Chemistry chemistry.chemical_compound Biosynthesis Glucosides Phenols Oleuropein Olea Drug Discovery 5-Lipoxygenase Inhibitor Oleocanthal Humans Iridoids Lipoxygenase Inhibitors Pyrans Pharmacology Aldehydes Inhibitory potential Arachidonate 5-Lipoxygenase biology Molecular Structure Plant Extracts Organic Chemistry Total synthesis biology.organism_classification Semisynthesis Plant Leaves Complementary and alternative medicine chemistry Molecular Medicine |
| Zdroj: | Journal of natural products. 77(3) |
| ISSN: | 1520-6025 |
| Popis: | The dialdehydes oleacein (2) and oleocanthal (4) are closely related to oleuropein (1) and ligstroside (3), the two latter compounds being abundant iridoids of Olea europaea. By exploiting oleuropein isolated from the plant leaf extract, an efficient procedure has been developed for a one-step semisynthesis of oleacein under Krapcho decarbomethoxylation conditions. Highlighted is the fact that 5-lipoxygenase is a direct target for oleacein with an inhibitory potential (IC50: 2 μM) more potent than oleocanthal (4) and oleuropein (1). This enzyme catalyzes the initial steps in the biosynthesis of pro-inflammatory leukotrienes. Taken together, the methodology presented here offers an alternative solution to isolation or total synthesis for the procurement of oleacein, thus facilitating the further development as a potential anti-inflammatory agent. |
| Databáze: | OpenAIRE |
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