Secondary metabolites of Peucedanum tauricum fruits.
From the essential oil of fruits of Peucedanum tauricum Bieb., two guaiane type sesquiterpene hydrocarbons guaia-1(10),11-diene (1) and guaia-9,11-diene (2) were identified. The structures of 1 and 2 were assigned by 1D and 2D NMR analysis. The relative configurations of the compounds were established by 2D-NOESY experiments while the absolute configurations were deduced through chemical correlations with (+)-gamma-gurjunene (9) and capillary GC analysis using modified cyclodextrins as the stationary phases. From the dichloromethane extract of the less volatile fraction of the fruits, coumarins, viz. peucedanin (3), oxypeucedanin hydrate (4) and officinalin isobutyrate (5) were isolated. Compound 5 was confirmed to be 6-carbomethoxy-7-isobutyroxycoumarin by its 1D and 2D NMR data as well as by conversion into officinalin (7) by alkaline hydrolysis. Peuruthenicin, a positional isomer of officinalin, is assigned structure 8 on spectral basis. Bergapten (6) was identified by its mass spectrum. This is the first report on the isolation of compounds 4 and 5 from P. tauricum.
Tesso
Hailemichael
H
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany. michaeltesso@yahoo.com
König
Wilfried A
WA
Kubeczka
Karl-Heinz
KH
Bartnik
Magdalena
M
Glowniak
Kazimierz
K
D019661:Apiaceae / Q000737:chemistry*; D003374:Coumarins / Q000302:isolation & purification*; D005638:Fruit / Q000737:chemistry*; D015394:Molecular Structure; D045789:Sesquiterpenes, Guaiane / Q000302:isolation & purification*
D003374:Coumarins; D045789:Sesquiterpenes, Guaiane; C501248:guaia-1(10),11-diene; C501247:officinalin isobutyrate