Synthesis, Biological Investigation, and Structural Revision of Sielboldianin A
| Autor: | Marius Aursnes, Jørn Eivind Tungen, Renate Kristianslund, Carl Henrik Görbitz, Trond Vidar Hansen |
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| Rok vydání: | 2018 |
| Předmět: |
Antioxidant
Stereochemistry medicine.medical_treatment Pharmaceutical Science 010402 general chemistry 01 natural sciences Antioxidants Analytical Chemistry chemistry.chemical_compound Cell Line Tumor Drug Discovery medicine Humans Pharmacology chemistry.chemical_classification Reactive oxygen species Biological Products Natural product 010405 organic chemistry Chemistry Plant Extracts Terpenes Organic Chemistry Enantioselective synthesis Absolute configuration Total synthesis Stereoisomerism Hep G2 Cells 0104 chemical sciences Complementary and alternative medicine Molecular Medicine Specific rotation Lipid Peroxidation Enantiomer K562 Cells Reactive Oxygen Species |
| Zdroj: | Journal of natural products. 81(4) |
| ISSN: | 1520-6025 |
| Popis: | The two ar-bisabol sesquiterpenoids (+)-sielboldianin A (1) and (+)-sielboldianin B (2) were isolated from the stem bark of the plant Fraxinus sielboldiana and belong to a medicinally interesting class of natural products used in traditional Chinese medicine. Herein the total synthesis of the proposed structure of (+)-sielboldianin A (1) is reported using an organocatalyzed enantioselective bromolactonization protocol. X-ray analysis of a key intermediate together with specific rotation values and NOESY data of the synthesized product enabled the revision of the absolute configuration of the natural product (+)-sielboldianin A to (7R,10R). Studies on the antioxidant effects using two cell-based assays were conducted. These studies revealed that the enantiomer of 1 exhibited antioxidant effects with IC50 values of 18 ± 3 μM in a cellular lipid peroxidation antioxidant activity assay. Moreover, (−)-1 showed strong protective effects against reactive oxygen species in a cell-based antioxidant activity assay ... |
| Databáze: | OpenAIRE |
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