Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins
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...
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| Format: | Article |
| Language: | English |
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Mashhad University of Medical Sciences
2009-06-01
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| Series: | Iranian Journal of Basic Medical Sciences |
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| Online Access: | http://www.mums.ac.ir/shares/basic_medical/basicmedjou/88/summer/Askari.pdf |
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| author | Mahdi Askari, Amirhossein Sahebkar, Mehrdad Iransahi Amirhossein Sahebkar Mehrdad Iranshahi |
| author_facet | Mahdi Askari, Amirhossein Sahebkar, Mehrdad Iransahi Amirhossein Sahebkar Mehrdad Iranshahi |
| author_sort | Mahdi Askari, Amirhossein Sahebkar, Mehrdad Iransahi |
| collection | DOAJ |
| description | 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 |
| first_indexed | 2024-12-22T11:37:02Z |
| format | Article |
| id | doaj.art-2c89f4a4196c4807b7ae65f7ed8dcfbc |
| institution | Directory Open Access Journal |
| issn | 2008-3866 2008-3874 |
| language | English |
| last_indexed | 2024-12-22T11:37:02Z |
| publishDate | 2009-06-01 |
| publisher | Mashhad University of Medical Sciences |
| record_format | Article |
| series | Iranian Journal of Basic Medical Sciences |
| spelling | doaj.art-2c89f4a4196c4807b7ae65f7ed8dcfbc2022-12-21T18:27:24ZengMashhad University of Medical SciencesIranian Journal of Basic Medical Sciences2008-38662008-38742009-06-011242Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural CoumarinsMahdi Askari, Amirhossein Sahebkar, Mehrdad IransahiAmirhossein SahebkarMehrdad IranshahiObjective(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,Umbellipreninhttp://www.mums.ac.ir/shares/basic_medical/basicmedjou/88/summer/Askari.pdfAurapteneHerniarin7- Isopentenyloxycoumarin7-PrenyloxycoumarinsSynthesis |
| spellingShingle | Mahdi Askari, Amirhossein Sahebkar, Mehrdad Iransahi Amirhossein Sahebkar Mehrdad Iranshahi Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins Iranian Journal of Basic Medical Sciences Auraptene Herniarin 7- Isopentenyloxycoumarin 7-Prenyloxycoumarins Synthesis |
| title | Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins |
| title_full | Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins |
| title_fullStr | Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins |
| title_full_unstemmed | Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins |
| title_short | Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins |
| title_sort | synthesis and purification of 7 prenyloxycoumarins and herniarin as bioactive natural coumarins |
| topic | Auraptene Herniarin 7- Isopentenyloxycoumarin 7-Prenyloxycoumarins Synthesis |
| url | http://www.mums.ac.ir/shares/basic_medical/basicmedjou/88/summer/Askari.pdf |
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