2D 1H -13C Heteronuclear Shift Correlation Of 2a - Hydroxy Aiantolactone From Pulicaria Undulata C.A. Mey
Abstract
We have reported recently the isolation and characterization of several sesquiterpene lactones from Pulicaria undulata (1).
The lactones were isolated from an Et20 - Petrol (1:3) fraction by different chromatographic techniques including HPLC (RP 8, MeOH - H2O, 13:7).
In this way three eudesmanolides 1 - 3, a guaianolide 4, a nor -guaianolide 5, as well as the pseudoguaianolide 6 and the xanthanolide 7 were isolated. One of the eudesmanolides (2a - hydroxy aiantolactone), 1, was present as the main component.
Such lactones being known as biologically active substances, we have decided to describe for the first time a detailed interpretation of proton, 1H -NMR, 13C - NMR and 2D lH -13C - heteronuclear shift correlation spectra of 2a - hydroxy aiantolactone. The stereochemistry of C - 2 , C - 7 and C - 8 was determined by the NOESY experiments, H - 7 and H - 8 are in the a configuration and H - 2 is in the b configuration.
The lactones were isolated from an Et20 - Petrol (1:3) fraction by different chromatographic techniques including HPLC (RP 8, MeOH - H2O, 13:7).
In this way three eudesmanolides 1 - 3, a guaianolide 4, a nor -guaianolide 5, as well as the pseudoguaianolide 6 and the xanthanolide 7 were isolated. One of the eudesmanolides (2a - hydroxy aiantolactone), 1, was present as the main component.
Such lactones being known as biologically active substances, we have decided to describe for the first time a detailed interpretation of proton, 1H -NMR, 13C - NMR and 2D lH -13C - heteronuclear shift correlation spectra of 2a - hydroxy aiantolactone. The stereochemistry of C - 2 , C - 7 and C - 8 was determined by the NOESY experiments, H - 7 and H - 8 are in the a configuration and H - 2 is in the b configuration.
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