Diphyllin () and justicidin B () are arylnaphthalene lignans with antiviral and antiproliferative effects. Compound is also known as an effective inhibitor of the Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). To evaluate the antiviral and cytotoxic potency of both lignans in SARS-CoV-2 -infected cells and various cancer cell lines, respectively, and were isolated from the underground organs of and . Two previously undescribed arylnaphthalene lignans, denominated linadiacin A and B ( and ), were also isolated and identified. In acidic media, was converted by a two-step reaction into via the intermediate . 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 and 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.
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http://dx.doi.org/10.1021/acs.jnatprod.2c00580 | DOI Listing |
Molecules
November 2024
Department of Biotechnologies and Biosciences, University of Milano-Bicocca, 20126 Milan, Italy.
The screening of plant-derived compounds with anti-cancer properties is a promising strategy to meet the growing need for new, safe and effective anti-cancer drugs. Justicidin B is a plants secondary metabolite that displays anti-cancer properties in several tumor cells. Therefore, it represents a good candidate.
View Article and Find Full Text PDFChem Biodivers
January 2025
State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, South Beijing Road 40-1, Urumqi, Xinjiang, 830011, PR China.
Four undescribed compounds including a pair of enantiomers of a dihydroarylnaphthalene lignan [(±)-1], an arylnaphthalene lignan (2), and an indoleacetic acid ester (3), together with four known compounds (4-7), were isolated from the seeds of Lepidium sativum. Their structures were identified by HRMS and NMR spectroscopic data, and the absolute configuration of these compounds were assigned by ECD data in combination with quantum chemical calculations. Compound (-)-1 had weak inhibitory activity against HeLa cell line with an IC value of 60.
View Article and Find Full Text PDFPhytomedicine
November 2024
Department of Advanced Toxicology Research, Korea Institute of Toxicology, Daejeon 34114, South Korea. Electronic address:
J Org Chem
March 2024
Department of Chemistry and Biochemistry, Brigham Young University, C-100 BNSN, Provo, Utah 84602, United States.
Polycyclic aryl naphthalene and tetralin dihydro arylnaphthalene lactone lignans possess anticancer and antibiotic activity. Related furo[3,4-]pyranones, typified by the sequester-terpenoid isobolivianine, show similar antiproliferative bioactivity. Efficient syntheses of compounds featuring these polycyclic cores have proven challenging due to low yields and poor stereoselectivity.
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