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Organic synthesis and anti-influenza A virus activity of cyclobakuchiols A, B, C, and D
- Source :
- PLoS ONE, Vol 16, Iss 3, p e0248960 (2021), PLoS ONE
- Publication Year :
- 2021
- Publisher :
- Public Library of Science (PLoS), 2021.
-
Abstract
- Novel antiviral agents for influenza, which poses a substantial threat to humans, are required. Cyclobakuchiols A and B have been isolated from Psoralea glandulosa, and cyclobakuchiol C has been isolated from P. corylifolia. The structural differences between cyclobakuchiol A and C arise due to the oxidation state of isopropyl group, and these compounds can be derived from (+)-(S)-bakuchiol, a phenolic isoprenoid compound present in P. corylifolia seeds. We previously reported that bakuchiol induces enantiospecific anti-influenza A virus activity involving nuclear factor erythroid 2-related factor 2 (Nrf2) activation. However, it remains unclear whether cyclobakuchiols A–C induce anti-influenza A virus activity. In this study, cyclobakuchiols A, B, and C along with cyclobakuchiol D, a new artificial compound derived from cyclobakuchiol B, were synthesized and examined for their anti-influenza A virus activities using Madin-Darby canine kidney cells. As a result, cyclobakuchiols A–D were found to inhibit influenza A viral infection, growth, and the reduction of expression of viral mRNAs and proteins in influenza A virus-infected cells. Additionally, these compounds markedly reduced the mRNA expression of the host cell influenza A virus-induced immune response genes, interferon-β and myxovirus-resistant protein 1. In addition, cyclobakuchiols A–D upregulated the mRNA levels of NAD(P)H quinone oxidoreductase 1, an Nrf2-induced gene, in influenza A virus-infected cells. Notably, cyclobakuchiols A, B, and C, but not D, induced the Nrf2 activation pathway. These findings demonstrate that cyclobakuchiols have anti-influenza viral activity involving host cell oxidative stress response. In addition, our results suggest that the suitably spatial configuration between oxidized isopropyl group and phenol moiety in the structure of cyclobakuchiols is required for their effect.
- Subjects :
- RNA viruses
Myxovirus Resistance Proteins
0301 basic medicine
Viral Diseases
Chemistry Techniques, Synthetic
medicine.disease_cause
Biochemistry
Madin Darby Canine Kidney Cells
chemistry.chemical_compound
Medical Conditions
0302 clinical medicine
Image Processing, Computer-Assisted
NAD(P)H Dehydrogenase (Quinone)
Influenza A virus
Pathology and laboratory medicine
Bakuchiol
Staining
Multidisciplinary
Chemistry
H1N1
Cell Staining
Medical microbiology
Enzymes
Infectious Diseases
030220 oncology & carcinogenesis
Viruses
Host-Pathogen Interactions
RNA, Viral
Medicine
Pathogens
Oxidoreductases
Luciferase
Research Article
Gene Expression Regulation, Viral
Cell Survival
NF-E2-Related Factor 2
Science
Viral Structure
Research and Analysis Methods
Microbiology
Antiviral Agents
Virus
Viral Proteins
03 medical and health sciences
Dogs
Downregulation and upregulation
Cyclohexanes
Virology
medicine
Influenza viruses
Animals
RNA, Messenger
Gene
Medicine and health sciences
Biology and life sciences
Host Cells
Organisms
Viral pathogens
Proteins
Interferon-beta
Molecular biology
Influenza
Microbial pathogens
030104 developmental biology
Specimen Preparation and Treatment
Enzymology
NAD+ kinase
Viral Transmission and Infection
Isopropyl
Orthomyxoviruses
Subjects
Details
- Language :
- English
- ISSN :
- 19326203
- Volume :
- 16
- Issue :
- 3
- Database :
- OpenAIRE
- Journal :
- PLoS ONE
- Accession number :
- edsair.doi.dedup.....985eababdefa5e6cb783536060e637b2