Coumarins from Seseli hartvigii.
Linear-type furocoumarins, 5-[(2"E,6"R)-6"-hydroxy-3",7"-dimethylocta-2",7"-dienyloxy]psoralen and 5-[(2"E,6"S)-6"-hydroxy-3",7"-dimethylocta-2",7"-dienyloxy]psoralen (1) were first isolated from whole plants of Seseli hartvigii together with one new natural product 6-(3'-methyl-2'-oxo-3'-butenyl)-7-methoxycoumarin (2), and four known compounds (tamarin, bergaptol, notoptol, and a mixture of beta-sitosterol and stigmasterol). The structure of 1 was elucidated by extensive spectroscopic analysis and chemical conversion. The modified Mosher's method and HPLC were applied to determine its stereochemistry. Both R- and S-configurations exist in 1; after modification by Mosher's reagent, they were effectively separated, and their ratio was deduced to be 59% and 41%, respectively.
Zhang
Lin
L
Shenyang Pharmaceutical University, Department of Traditional Medicine, 110000 Liaoning-Shenyang, PR China.
Tosun
Alev
A
Baba
Masaki
M
Okada
Yoshihito
Y
Wu
Lijun
L
Okuyama
Torn
T
D019661:Apiaceae / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D003374:Coumarins