-
Something wrong with this record ?
NMR Structure Elucidation of Naphthoquinones from Quambalaria cyanescens
E. Procházková, O. Kucherak, E. Stodůlková, Z. Tošner, I. Císařová, M. Flieger, M. Kolařík, O. Baszczyňski
Language English Country United States
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
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
References provided by Crossref.org
- 000
- 00000naa a2200000 a 4500
- 001
- bmc22004669
- 003
- CZ-PrNML
- 005
- 20220127145055.0
- 007
- ta
- 008
- 220113s2021 xxu f 000 0|eng||
- 009
- AR
- 024 7_
- $a 10.1021/acs.jnatprod.0c00930 $2 doi
- 035 __
- $a (PubMed)33342211
- 040 __
- $a ABA008 $b cze $d ABA008 $e AACR2
- 041 0_
- $a eng
- 044 __
- $a xxu
- 100 1_
- $a Procházková, Eliška $u Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague, Czech Republic
- 245 10
- $a NMR Structure Elucidation of Naphthoquinones from Quambalaria cyanescens / $c E. Procházková, O. Kucherak, E. Stodůlková, Z. Tošner, I. Císařová, M. Flieger, M. Kolařík, O. Baszczyňski
- 520 9_
- $a 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.
- 650 _2
- $a antiinfekční látky $x chemie $x izolace a purifikace $x farmakologie $7 D000890
- 650 _2
- $a protinádorové látky $x chemie $x izolace a purifikace $x farmakologie $7 D000970
- 650 _2
- $a Basidiomycota $x chemie $7 D001487
- 650 _2
- $a vodíková vazba $7 D006860
- 650 _2
- $a magnetická rezonanční tomografie $7 D008279
- 650 _2
- $a magnetická rezonanční spektroskopie $7 D009682
- 650 _2
- $a molekulární struktura $7 D015394
- 650 _2
- $a naftochinony $x chemie $x izolace a purifikace $x farmakologie $7 D009285
- 655 _2
- $a časopisecké články $7 D016428
- 655 _2
- $a práce podpořená grantem $7 D013485
- 700 1_
- $a Kucherak, Oleksandr $u Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague, Czech Republic
- 700 1_
- $a Stodůlková, Eva $u Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, 142 20 Prague, Czech Republic
- 700 1_
- $a Tošner, Zdeněk $u Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague, Czech Republic
- 700 1_
- $a Císařová, Ivana $u Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague, Czech Republic
- 700 1_
- $a Flieger, Miroslav $u Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, 142 20 Prague, Czech Republic
- 700 1_
- $a Kolařík, Miroslav $u Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, 142 20 Prague, Czech Republic
- 700 1_
- $a Baszczyňski, Ondřej $u Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague, Czech Republic
- 773 0_
- $w MED00010055 $t Journal of natural products $x 1520-6025 $g Roč. 84, č. 1 (2021), s. 46-55
- 856 41
- $u https://pubmed.ncbi.nlm.nih.gov/33342211 $y Pubmed
- 910 __
- $a ABA008 $b sig $c sign $y p $z 0
- 990 __
- $a 20220113 $b ABA008
- 991 __
- $a 20220127145051 $b ABA008
- 999 __
- $a ok $b bmc $g 1751974 $s 1155818
- BAS __
- $a 3
- BAS __
- $a PreBMC
- BMC __
- $a 2021 $b 84 $c 1 $d 46-55 $e 20201219 $i 1520-6025 $m Journal of natural products $n J Nat Prod $x MED00010055
- LZP __
- $a Pubmed-20220113
