Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Standard

Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography. / Li, Tuo; Ma, Xue; Fedotov, Daniil; Kjaerulff, Louise; Frydenvang, Karla Andrea; Coriani, Sonia; Hansen, Paul Robert; Kongstad, Kenneth Thermann; Stærk, Dan.

I: Molecules, Bind 25, 1706, 08.04.2020.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Li, T, Ma, X, Fedotov, D, Kjaerulff, L, Frydenvang, KA, Coriani, S, Hansen, PR, Kongstad, KT & Stærk, D 2020, 'Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography', Molecules, bind 25, 1706. https://doi.org/10.3390/molecules25071706

APA

Li, T., Ma, X., Fedotov, D., Kjaerulff, L., Frydenvang, K. A., Coriani, S., Hansen, P. R., Kongstad, K. T., & Stærk, D. (2020). Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography. Molecules, 25, [1706]. https://doi.org/10.3390/molecules25071706

Vancouver

Li T, Ma X, Fedotov D, Kjaerulff L, Frydenvang KA, Coriani S o.a. Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography. Molecules. 2020 apr. 8;25. 1706. https://doi.org/10.3390/molecules25071706

Author

Li, Tuo ; Ma, Xue ; Fedotov, Daniil ; Kjaerulff, Louise ; Frydenvang, Karla Andrea ; Coriani, Sonia ; Hansen, Paul Robert ; Kongstad, Kenneth Thermann ; Stærk, Dan. / Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography. I: Molecules. 2020 ; Bind 25.

Bibtex

@article{4d58857c10234dfaa42bf4c877c112cc,
title = "Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography",
abstract = "Crude ethyl acetate extract of Gerbera piloselloides (L.) Cass. was investigated by dual high-resolution PTP1B/α-glucosidase inhibition profiling and LC-PDA-HRMS. This indicated the presence of a series of unprecedented prenyl- and geranyl substituted coumarin derivatives correlated with both α-glucosidase- and PTP1B inhibitory activity. Repeated chromatographic separation targeted these compounds led to isolation of 13 new compounds, of which ten could be isolated as both enantiomers after chiral separation. The structures of all isolated compounds were characterized by HRMS and extensive 1D and 2D NMR analysis. The absolute configurations of the isolated compounds were determined by comparison of experimental and calculated electronic circular dichroism spectra. Compounds 6 features a rare furan-oxepane 5/7 ring system, possibly formed through addition of a geranyl unit to C-3 of 5-methylcoumarin, representing a new type of geranyl-substituted coumarin skeleton. Compounds 19 and 24 are the first examples of dimeric natural products consisting of both coumarin and chromone moieties.",
author = "Tuo Li and Xue Ma and Daniil Fedotov and Louise Kjaerulff and Frydenvang, {Karla Andrea} and Sonia Coriani and Hansen, {Paul Robert} and Kongstad, {Kenneth Thermann} and Dan St{\ae}rk",
year = "2020",
month = apr,
day = "8",
doi = "10.3390/molecules25071706",
language = "English",
volume = "25",
journal = "Molecules",
issn = "1420-3049",
publisher = "M D P I AG",

}

RIS

TY - JOUR

T1 - Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography

AU - Li, Tuo

AU - Ma, Xue

AU - Fedotov, Daniil

AU - Kjaerulff, Louise

AU - Frydenvang, Karla Andrea

AU - Coriani, Sonia

AU - Hansen, Paul Robert

AU - Kongstad, Kenneth Thermann

AU - Stærk, Dan

PY - 2020/4/8

Y1 - 2020/4/8

N2 - Crude ethyl acetate extract of Gerbera piloselloides (L.) Cass. was investigated by dual high-resolution PTP1B/α-glucosidase inhibition profiling and LC-PDA-HRMS. This indicated the presence of a series of unprecedented prenyl- and geranyl substituted coumarin derivatives correlated with both α-glucosidase- and PTP1B inhibitory activity. Repeated chromatographic separation targeted these compounds led to isolation of 13 new compounds, of which ten could be isolated as both enantiomers after chiral separation. The structures of all isolated compounds were characterized by HRMS and extensive 1D and 2D NMR analysis. The absolute configurations of the isolated compounds were determined by comparison of experimental and calculated electronic circular dichroism spectra. Compounds 6 features a rare furan-oxepane 5/7 ring system, possibly formed through addition of a geranyl unit to C-3 of 5-methylcoumarin, representing a new type of geranyl-substituted coumarin skeleton. Compounds 19 and 24 are the first examples of dimeric natural products consisting of both coumarin and chromone moieties.

AB - Crude ethyl acetate extract of Gerbera piloselloides (L.) Cass. was investigated by dual high-resolution PTP1B/α-glucosidase inhibition profiling and LC-PDA-HRMS. This indicated the presence of a series of unprecedented prenyl- and geranyl substituted coumarin derivatives correlated with both α-glucosidase- and PTP1B inhibitory activity. Repeated chromatographic separation targeted these compounds led to isolation of 13 new compounds, of which ten could be isolated as both enantiomers after chiral separation. The structures of all isolated compounds were characterized by HRMS and extensive 1D and 2D NMR analysis. The absolute configurations of the isolated compounds were determined by comparison of experimental and calculated electronic circular dichroism spectra. Compounds 6 features a rare furan-oxepane 5/7 ring system, possibly formed through addition of a geranyl unit to C-3 of 5-methylcoumarin, representing a new type of geranyl-substituted coumarin skeleton. Compounds 19 and 24 are the first examples of dimeric natural products consisting of both coumarin and chromone moieties.

U2 - 10.3390/molecules25071706

DO - 10.3390/molecules25071706

M3 - Journal article

C2 - 32276427

VL - 25

JO - Molecules

JF - Molecules

SN - 1420-3049

M1 - 1706

ER -

ID: 238957537