Imperatorin

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Imperatorin
Imperatorin.png
Names
IUPAC name
9-(3-Methylbut-2-enoxy)-7-furo[3,2-g]chromenone
Other names
Ammidin
Marmelosin
Pentosalen
8-Isoamylenoxypsoralen
8-Isopentenyloxypsoralene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.893
KEGG
UNII
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).
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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[edit]

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[edit]

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]

See also[edit]

References[edit]

  1. ^ Sigurdsson S, Ogmundsdottir HM, Gudbjarnason S (July–August 2004). "Antiproliferative effect of Angelica archangelica fruits". Zeitschrift für Naturforschung C. 4th. 59 (7–8): 523–7. doi:10.1515/znc-2004-7-813. PMID 15813373. 
  2. ^ Xie Y, Zhao W, Zhou T, Fan G, Wu Y (September–October 2010). "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. doi:10.1002/pca.1222. PMID 20931624. 
  3. ^ Liu, M., Shi, X., Yang, W., Liu, S., Wang, N., Shi, R., Qiao, S., Wang, Q. and Wang, Y. (2010-09-27). "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". Biochemical Chromatography. 25: 783–93. doi:10.1002/bmc.1517. PMID 20878664. 
  4. ^ Zhao B, Yang X, Yang X, Zhang L (June 2010). "Chemical constituents of roots of Saposhnikovia divaricata" [Chemical constituents of roots of Saposhnikovia divaricata]. Zhongguo Zhong yao za zhi. 2nd (in Chinese). 35 (12): 1569–72. PMID 20815209. 
  5. ^ 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" (PDF). Journal of Natural Medicines. 65 (2): 370–374. doi:10.1007/s11418-010-0485-7. PMID 21082271. Retrieved 2010-11-27. 
  6. ^ Fu, Y; Bai Y; Dawa Z; Bai B; Ding L. (January 2010). "Chemical constituents of Incarvillea younghusbandii" [Chemical constituents of Incarvillea younghusbandii]. Zhongguo Zhong yao za zhi. 2nd. 35 (1): 58–62. PMID 20349717. 
  7. ^ Bafi-Yeboa, N. F.; Arnason JT; Baker J; Smith ML. (May 2005). "Antifungal constituents of northern prickly ash, Zanthoxylum americanum mill". Phytomedicine. 12 (5): 370–7. doi:10.1016/j.phymed.2003.12.005. PMID 15957372. 
  8. ^ F. M. Dean Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963.
  9. ^ A furocoumarin, Imperatorin isolated from Urena lobata L. (Malvaceae) Keshab Ghosh Molbank 2004, M382 [1] open access publication
  10. ^ Ivey F.D., Wang L., Demirbas D., Allain C., and Hoffman C.S. (2008). "Development of a fission yeast-based high throughput screen to identify chemical regulators of cAMP phosphodiesterases". J. Biomol. Screening. 13: 62–71. doi:10.1177/1087057107312127. PMID 18227226.