SYNTHESIS AND PURIFICATION OF 7-PRENYLOXYCOUMARINS AND HERNIARIN AS BIOACTIVE NATURAL COUMARINS

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ASKARI MAHDI; SAHEBKAR A.H.; IRANSHAHI MEHRDAD

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Journal Paper

Paper Information

Journal: Iranian Journal of Basic Medical Sciences Year:2009 | Volume:12 | Issue:2 (42) Page(s): 63-69

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Information Journal Paper

Title

SYNTHESIS AND PURIFICATION OF 7-PRENYLOXYCOUMARINS AND HERNIARIN AS BIOACTIVE NATURAL COUMARINS

Author(s)

ASKARI MAHDI | SAHEBKAR A.H. | IRANSHAHI MEHRDAD | Issue Writer Certificate

Keywords

AURAPTENE

HERNIARIN

7- ISOPENTENYLOXYCOUMARIN

7- PRENYLOXYCOUMARINS

SYNTHESIS

UMBELLIPRENIN

Abstract

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 (1 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.

Cites

ANTIHYPERTENSIVE EFFECT OF AURAPTENE, A MONOTERPENE COUMARIN FROM THE GENUS CITRUS, UPON CHRONIC ADMINISTRATION

References

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APA: Copy

ASKARI, MAHDI, SAHEBKAR, A.H., & IRANSHAHI, MEHRDAD. (2009). SYNTHESIS AND PURIFICATION OF 7-PRENYLOXYCOUMARINS AND HERNIARIN AS BIOACTIVE NATURAL COUMARINS. IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES, 12(2 (42)), 63-69. SID. https://sid.ir/paper/549516/en

Vancouver: Copy

ASKARI MAHDI, SAHEBKAR A.H., IRANSHAHI MEHRDAD. SYNTHESIS AND PURIFICATION OF 7-PRENYLOXYCOUMARINS AND HERNIARIN AS BIOACTIVE NATURAL COUMARINS. IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES[Internet]. 2009;12(2 (42)):63-69. Available from: https://sid.ir/paper/549516/en

IEEE: Copy

MAHDI ASKARI, A.H. SAHEBKAR, and MEHRDAD IRANSHAHI, “SYNTHESIS AND PURIFICATION OF 7-PRENYLOXYCOUMARINS AND HERNIARIN AS BIOACTIVE NATURAL COUMARINS,” IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES, vol. 12, no. 2 (42), pp. 63–69, 2009, [Online]. Available: https://sid.ir/paper/549516/en

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