Chemistry:Imperatorin
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| Preferred IUPAC name
9-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one | |
| Other names
Ammidin
Marmelosin Pentosalen 8-Isoamylenoxypsoralen 8-Isopentenyloxypsoralene | |
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3D model (JSmol)
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| Properties | |
| C16H14O4 | |
| Molar mass | 270.28 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Imperatorin is a furocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae), Angelica archangelica,[1] Angelica dahurica,[2] Glehnia littoralis,[3] Saposhnikovia divaricata,[4] Cnidium monnieri,[5] Incarvillea younghusbandii,[6] and Zanthoxylum americanum mill.[7] It is biosynthesized from umbelliferone, a coumarin derivative.[8]
Isolation
The procedure for the isolation of imperatorin from Urena lobata involves exhaustively extracting under reflux with benzene the air-dried and pulverised roots followed by separation by column chromatography.[9]
Biochemical activity
Imperatorin was identified from a Bioactive Molecules library in a high throughput screening experiment for inhibitors of the phosphodiesterase PDE4. It displays a significant preference for PDE4B over PDE4A.[10] Imperatorin has been shown to have anti-inflammatory activity in chondrocytes.[11] Imperatorin treatment inhibits the expression of iNOS and suppresses the production of NO in osteoarthritic chondrocytes.[11]
See also
- Psoralen, the parent furocoumarin.
References
- ↑ "Antiproliferative effect of Angelica archangelica fruits.". Zeitschrift für Naturforschung C. 4th 59 (7–8): 523–527. July–August 2004. doi:10.1515/znc-2004-7-813. PMID 15813373.
- ↑ "An efficient strategy based on MAE, HPLC-DAD-ESI-MS/MS and 2D-prep-HPLC-DAD for the rapid extraction, separation, identification and purification of five active coumarin components from Radix Angelicae Dahuricae". Phytochemical Analysis 21 (5): 473–82. September–October 2010. doi:10.1002/pca.1222. PMID 20931624.
- ↑ "Quantitative analysis of nine coumarins in rat urine and bile after oral administration of Radix Glehniae extract by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry". Biomed. Chromatogr. 25 (7): 783–793. July 2011. doi:10.1002/bmc.1517. PMID 20878664.
- ↑ "Chemical constituents of roots of Saposhnikovia divaricata" (in zh). Zhongguo Zhong Yao Za Zhi. 2nd 35 (12): 1569–72. June 2010. doi:10.4268/cjcmm20101214. PMID 20815209.
- ↑ Shin, Eunjin; Lee, Chul; Sung, Sang Hyun; Kim, Young Choong; Hwang, Bang Yeon; Lee, Mi Kyeong (2010-11-17). "Antifibrotic activity of coumarins from Cnidium monnieri fruits in HSC-T6 hepatic stellate cells". Journal of Natural Medicines 65 (2): 370–374. doi:10.1007/s11418-010-0485-7. PMID 21082271.
- ↑ "Chemical constituents of Incarvillea younghusbandii". Zhongguo Zhong Yao Za Zhi. 2nd 35 (1): 58–62. January 2010. doi:10.4268/cjcmm20100112. PMID 20349717.
- ↑ "Antifungal constituents of northern prickly ash, Zanthoxylum americanum mill". Phytomedicine 12 (5): 370–377. May 2005. doi:10.1016/j.phymed.2003.12.005. PMID 15957372.
- ↑ F. M. Dean Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963.
- ↑ Keshab Ghosh (2004). "A furocoumarin, Imperatorin isolated from Urena lobata L. (Malvaceae)". Molecular Diversity Preservation International. http://www.mdpi.net/molbank/molbank2004/m0382.htm.
- ↑ "Development of a fission yeast-based high-throughput screen to identify chemical regulators of cAMP phosphodiesterases". J Biomol Screen 13 (1): 62–71. January 2008. doi:10.1177/1087057107312127. PMID 18227226.
- ↑ 11.0 11.1 Ahmad, Nashrah; Ansari, Mohammad Y.; Bano, Shabana; Haqqi, Tariq M. (August 2020). "Imperatorin suppresses IL-1β-induced iNOS expression via inhibiting ERK-MAPK/AP1 signaling in primary human OA chondrocytes". International Immunopharmacology 85: 106612. doi:10.1016/j.intimp.2020.106612. ISSN 1878-1705. PMID 32450530.
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