Back to Search
Start Over
Arylnaphthalene Lignans with Anti-SARS-CoV-2 and Antiproliferative Activities from the Underground Organs of Linum austriacum and Linum perenne .
- Source :
-
Journal of natural products [J Nat Prod] 2023 Apr 28; Vol. 86 (4), pp. 672-682. Date of Electronic Publication: 2023 Mar 01. - Publication Year :
- 2023
-
Abstract
- Diphyllin ( 1 ) and justicidin B ( 2 ) are arylnaphthalene lignans with antiviral and antiproliferative effects. Compound 1 is also known as an effective inhibitor of the Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). To evaluate the in vitro antiviral and cytotoxic potency of both lignans in SARS-CoV-2 -infected cells and various cancer cell lines, respectively, 1 and 2 were isolated from the underground organs of Linum austriacum and Linum perenne . Two previously undescribed arylnaphthalene lignans, denominated linadiacin A and B ( 3 and 4 ), were also isolated and identified. In acidic media, 3 was converted by a two-step reaction into 2 via the intermediate 4 . Optimum acid treatment conditions were determined to isolate lignans by one-step preparative high-performance liquid chromatography (HPLC). The results of the conversion, HPLC-tandem mass spectrometry, nuclear magnetic resonance spectroscopy, and molecular modeling studies allowed complete structure analysis. Compounds 1 and 2 were the most effective against SARS-CoV-2 with a 3-log reduction in the viral copy number at a 12.5 μM concentration. Ten human cancer cell lines showed sensitivity to at least one of the isolated lignans.
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 86
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 36857518
- Full Text :
- https://doi.org/10.1021/acs.jnatprod.2c00580