NMR Structure Elucidation of Naphthoquinones from Quambalaria cyanescens
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- MeSH
- Anti-Infective Agents chemistry isolation & purification pharmacology MeSH
- Basidiomycota chemistry MeSH
- Magnetic Resonance Spectroscopy MeSH
- Magnetic Resonance Imaging MeSH
- Molecular Structure MeSH
- Naphthoquinones chemistry isolation & purification pharmacology MeSH
- Antineoplastic Agents chemistry isolation & purification pharmacology MeSH
- Hydrogen Bonding MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Anti-Infective Agents MeSH
- Naphthoquinones MeSH
- Antineoplastic Agents MeSH
Naphthoquinones isolated from Quambalaria cyanescens (quambalarines) are natural pigments possessing significant cytotoxic and antimicrobial properties. Determining the structure of naphthoquinone compounds is important for the understanding of their biological activities and the informed synthesis of related analogues. Identifying quambalarines is challenging, because they contain a hydroxylated naphthoquinone scaffold and have limited solubility. Here, we report a detailed structural study of quambalarine derivatives, which form strong intramolecular hydrogen bonds (IMHBs) that enable the formation of several tautomers; these tautomers may complicate structural investigation due to their fast interconversion. To investigate tautomeric equilibria and identify new quambalarines, we complemented the experimental NMR spectroscopy data with density functional theory (DFT) calculations.
Faculty of Science Charles University Hlavova 2030 8 128 43 Prague Czech Republic
Institute of Microbiology Czech Academy of Sciences Vídeňská 1083 142 20 Prague Czech Republic
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