Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins

Abstract

Objective(s)7-prenyloxycoumarins including 7-isopentenyloxycoumarin, auraptene and umbelliprenin, and herniarinhave been widely recognized as bioactive coumarins. This paper presents the ways to synthesis thesecompounds.Materials and Methods7-prenyloxycoumarins were synthesized by reaction between 7-hydroxycoumarin (1 M) and relevant prenylbromides (1.5 M) in acetone at room temperature. The reaction was carried out in the presence of DBU(1, 8-diazabicyclo [5.4.0] undec-7-ene) (2 M). After 24 hr, the mixture was concentrated under reducedpressure. The compounds were purified by column chromatography.ResultsThree bioactive 7-prenyloxycoumarins, namely, umbelliprenin, auraptene and 7-isopentenyloxycoumarin,together with herniarin were synthesized from 7-hydroxycoumarin under alkaline conditions (DBU) and thenpurified by column chromatography. The structures of the products were characterized by NMRspectroscopic method including 1H- and 13C-NMR experiments.ConclusionThe method of synthesis for 7-prenyloxycoumarins and herniarin which is presented here has not beenreported yet. Moreover, for the first time, umbelliprenin was chemically prepared in this work.Keywords: Auraptene, Herniarin, 7- Isopentenyloxycoumarin, 7-Prenyloxycoumarins, Synthesis,Umbelliprenin

Keywords

• Auraptene
• Herniarin
• 7- Isopentenyloxycoumarin
• 7-Prenyloxycoumarins
• Synthesis