Total syntheses and antibacterial evaluations of cudraflavones A-C and related Flavones.

Staphylococcus aureus Anti-Bacterial Agents / pharmacology Flavones / pharmacology Bacteria Plant Extracts / pharmacology Microbial Sensitivity Tests
Antibacterial activity Natural product Prenylated flavone Total synthesis

Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
11 2023
Historique:
received: 04 06 2023
revised: 15 07 2023
accepted: 02 08 2023
medline: 18 9 2023
pubmed: 13 8 2023
entrez: 13 8 2023
Statut: ppublish

Résumé

The total syntheses of the natural prenylated flavones cudraflavones A-C (1-3), artoheterophyllin D (28) and artelasticin (29) are reported, along with the evaluations of their antibacterial activities. The key steps of the synthesis involved a Baker-Venkataraman rearrangement and an intramolecular cyclization for the construction of the flavone core and the regioselective formation of the pyran and isopentenyl scaffolds. The tested natural flavones 1-3 and 27-29 exhibited potent activity against S. aureus ATCC 29213, S. epidermidis ATCC 14990, E. faecalis ATCC 29212 and B. subtilis ATCC 6633 with MIC values ranging from 0.125 μg/mL to 16 μg/mL. Compound 3 displayed the strongest potency, with MIC values in the range between 0.125 and 1 μg/mL, as a potential candidate to combat G

Identifiants

DOI: 10.1016/j.bioorg.2023.106764 PMID: 37573609
pubmed: 37573609
pii: S0045-2068(23)00425-X
doi: 10.1016/j.bioorg.2023.106764
pii:
doi:

Substances chimiques

Anti-Bacterial Agents 0
Flavones 0
Plant Extracts 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

106764

Informations de copyright

Copyright © 2023 Elsevier Inc. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Hongbo Dong (H)

Engineering Research Center for Pharmaceuticals and Equipment of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China; Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China.

Li Liao (L)

Engineering Research Center for Pharmaceuticals and Equipment of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China; Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China.

Pei Yu (P)

Engineering Research Center for Pharmaceuticals and Equipment of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China.

Bin Long (B)

Engineering Research Center for Pharmaceuticals and Equipment of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China.

Yufei Che (Y)

Engineering Research Center for Pharmaceuticals and Equipment of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China.

Lan Lu (L)

Anti-infective Agent Creation Engineering Research Centre of Sichuan Province, School of Pharmacy, Chengdu University, Chengdu 610106, PR China.

Bing Xu (B)

Department of Pediatric Surgery, Sichuan Provincial People's Hospital, University of Electronic Science and Technology of China, Chengdu 610072, PR China. Electronic address: yourxubing@126.com.

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Classifications MeSH

questionsmedicales.fr › Bactéries › Bactéries à Gram positif › Cocci à Gram positif › Staphylococcaceae › Staphylococcus › Staphylococcus aureus › Total syntheses and antibacterial evaluations...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Anti-infectieux › Antibactériens › Total syntheses and antibacterial evaluations...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Benzopyranes › 4H-1-Benzopyran-4-ones › Flavonoïdes › Flavones › Total syntheses and antibacterial evaluations...
questionsmedicales.fr › Bactéries › Total syntheses and antibacterial evaluations...
questionsmedicales.fr › Préparations pharmaceutiques › Extraits de plantes › Total syntheses and antibacterial evaluations...
questionsmedicales.fr › Techniques d'investigation › Évaluation préclinique de médicament › Tests de sensibilité microbienne › Total syntheses and antibacterial evaluations...