Structure elucidation of prenyl- and geranyl substituted coumarins in Gerbera piloselloides by NMR spectroscopy, electronic circular dichroism calculations, and single crystal X-ray crystallography
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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.
In: Molecules, Vol. 25, 1706, 08.04.2020.Research output: Contribution to journal › Journal article › Research › peer-review
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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