Molecular Insight into Gene Response of Diorcinol- and Rubrolide-Treated Biofilms of the Emerging Pathogen Stenotrophomonas maltophilia

Gudzuhn, Mirja; Alio, Ifey; Moll, Raphael; Vries, Jessica de; Boehlich, Jacob; Assmann, Maik; Janneschütz, Jasmin; Schützenmeister, Nina; Himmelbach, Axel; Daniel, Rolf; Streit, Wolfgang R.

doi:10.1128/spectrum.02582-21

Cited by 2 publications

(2 citation statements)

References 81 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Preparation of the The prenyl group plays an important role in the bioactivity of prenylated diresorcinols. For example, recent structural inspection and hierarchical clustering suggested that the prenyl group as a side chain substituent of diresorcinols is essential for the antibacterial activity [20].…”

Section: Resultsmentioning

confidence: 99%

Microwave-Assisted Cu-Catalyzed Diaryletherification for Facile Synthesis of Bioactive Prenylated Diresorcinols

Kang

Jung

2022

Molecules

View full text Add to dashboard Cite

Prenylated diresorcinols exhibit various bioactivities, including cytotoxic, antibacterial, and antifungal activities. Therefore, establishing facile and efficient synthetic routes for prenylated diresorcinols facilitates their development as chemical probes or drugs with a novel mode of action. In this study, microwave-assisted copper catalysis was explored as a cost-effective and environmentally friendly method for the cross-coupling of sterically hindered ortho-prenylated phenols and aryl halides to produce bioactive prenylated diresorcinols, diorcinol I and leotiomycene B. Notable advantages of microwave-assisted catalysis include not only operational simplicity and rapid heating but also shorter reaction times and higher chemical yields. In addition, highly regioselective prenylation of phenol was achieved for the preparation of ortho-prenyl phenol via directed lithiation and subsequent alkylation. This study provides valuable insights for the preparation of other bioactive prenylated diresorcinols. Furthermore, considering that prenylated benzenoids are biosynthetic precursors of various polycyclic natural products, this synthetic route could be expanded to more complex bioactive compounds possessing diaryl ethers.

show abstract

Section: Resultsmentioning

confidence: 99%

Microwave-Assisted Cu-Catalyzed Diaryletherification for Facile Synthesis of Bioactive Prenylated Diresorcinols

Kang

Jung

2022

Molecules

View full text Add to dashboard Cite

show abstract

“…demonstrated a loss of antibacterial activity associated with hydration of the C-5/C-6 butenolide exomethylene moiety in new rubrolides V and W recently isolated from a New Zealand Synoicum species . Barbosa et al evaluated rubrolides for herbicidal applications, while more recently, Gudzuhn et al evaluated rubrolides as biofilm inhibitors against the emerging MDR pathogen S. maltophilia associated with cystic fibrosis.…”

Section: Bioactive Metabolites From Algoa Bay Marine Ascidiansmentioning

confidence: 99%

A Quarter Century of Marine Biodiscovery in Algoa Bay, South Africa

2023

View full text Add to dashboard Cite

Algoa Bay, the largest crenulate bay on the southeastern coast of South Africa, is currently one of the most well-studied marine ecosystems in southern Africa. A plethora of endemic marine invertebrates inhabits the benthic reefs on the western edge of the Bay in close proximity to South Africa's sixth largest city. Over the past 25 years, South African marine natural products chemists, together with international collaborators from the US National Cancer Institute and other US institutions, have focused their attention on Algoa Bay's benthic marine invertebrates as a potential source of new anticancer compounds. This review commemorates a quarter of a century of marine biodiscovery in Algoa Bay and presents the structures and bioactivities of 49 new and 36 known specialized metabolites isolated from two molluscs, eight ascidians, and six sponges. Thirty-nine of these compounds were cytotoxic to cancer cells in vitro with 20 exhibiting moderate to potent cytotoxicity. Six other compounds exhibited antimicrobial activity. Foremost among the potential anticancer compounds is mandelalide A (38) from the Algoa Bay ascidian Lissoclinum species.

show abstract

Molecular Insight into Gene Response of Diorcinol- and Rubrolide-Treated Biofilms of the Emerging Pathogen Stenotrophomonas maltophilia

Cited by 2 publications

References 81 publications

Microwave-Assisted Cu-Catalyzed Diaryletherification for Facile Synthesis of Bioactive Prenylated Diresorcinols

Microwave-Assisted Cu-Catalyzed Diaryletherification for Facile Synthesis of Bioactive Prenylated Diresorcinols

A Quarter Century of Marine Biodiscovery in Algoa Bay, South Africa

Contact Info

Product

Resources

About