1,4-Benzodioxane Lignans: An Efficient, Asymmetric Synthesis of Flavonolignans and Study of Neolignan Cytotoxicity and Antiviral Profiles
| Autor: | Lisa I. Pilkington, Jessica Wagoner, Stephen J. Polyak, Toni Kline, David Barker |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Stereochemistry
Pharmaceutical Science Antineoplastic Agents Hepacivirus 010402 general chemistry Antiviral Agents 01 natural sciences Lignans Analytical Chemistry Flavonolignans chemistry.chemical_compound Cell Line Tumor Drug Discovery Humans Moiety Cytotoxicity Pharmacology Biological Products Molecular Structure 010405 organic chemistry Chemistry Extramural Organic Chemistry Enantioselective synthesis Allylic alcohol 0104 chemical sciences Complementary and alternative medicine Silybin Molecular Medicine Eusiderin |
| Zdroj: | Journal of Natural Products. 81:2630-2637 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.8b00416 |
| Popis: | 1,4-Benzodioxane lignans are a class of bioactive compounds that have received much attention through the years. Herein research pertaining to both 1,4-benzodioxane flavonolignans and 1,4-benzodioxane neolignans is presented. A novel synthesis of both traditional 1,4-benzodioxane flavonolignans and 3-deoxyflavonolignans is described. The antiviral and cytotoxic activities of 1,4-benzodioxane neolignans were then investigated; eusiderins A, B, G, and M, deallyl eusiderin A, and nitidanin, which contain the 1,4-benzodioxane motif but lack the chromanone motif found in the known antiviral flavonolignans, were tested. Notably, it was found that all eusiderin 1,4-benzodioxane neolignans exhibited greater antiviral activity than the potent and well-known silybin flavonolignans. While most modifications of the C-1' side chain did not significantly alter the cytotoxicity or antiviral activity, eusiderin M and nitidanin, which contain an allylic alcohol side chain, had lower cytotoxicity. All the eusiderins had similar antiviral activities, with eusiderin B having the best selectivity index. These results show that the chromanone moiety of the flavonolignans is not essential for bioactivity. |
| Databáze: | OpenAIRE |
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