TY - JOUR ID - 5145 TI - Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins JO - Iranian Journal of Basic Medical Sciences JA - IJBMS LA - en SN - 2008-3866 AU - Askari, Mahdi AU - Sahebkar, Amirhossein AU - Iranshahi, Mehrdad AD - Department of Pharmacognosy, Biotechnology Research Center, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran Y1 - 2009 PY - 2009 VL - 12 IS - 2 SP - 63 EP - 69 KW - Auraptene KW - Herniarin KW - 7- Isopentenyloxycoumarin KW - 7-Prenyloxycoumarins KW - Synthesis KW - Umbelliprenin DO - 10.22038/ijbms.2009.5145 N2 - Objective(s) 7-prenyloxycoumarins including 7-isopentenyloxycoumarin, auraptene and umbelliprenin, and herniarin have been widely recognized as bioactive coumarins. This paper presents the ways to synthesis these compounds. Materials and Methods 7-prenyloxycoumarins were synthesized by reaction between 7-hydroxycoumarin (' M) and relevant prenyl bromides (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 reduced pressure. The compounds were purified by column chromatography. Results Three bioactive 7-prenyloxycoumarins, namely, umbelliprenin, auraptene and 7-isopentenyloxycoumarin, together with herniarin were synthesized from 7-hydroxycoumarin under alkaline conditions (DBU) and then purified by column chromatography. The structures of the products were characterized by NMR spectroscopic method including 1H- and 13C-NMR experiments. Conclusion The method of synthesis for 7-prenyloxycoumarins and herniarin which is presented here has not been reported yet. Moreover, for the first time, umbelliprenin was chemically prepared in this work. UR - https://ijbms.mums.ac.ir/article_5145.html L1 - https://ijbms.mums.ac.ir/article_5145_2ad17899ddd6c0e50591f7bf6a3ac8d9.pdf ER -