Imperatorin
Names
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.893 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3 checkY
    Key: OLOOJGVNMBJLLR-UHFFFAOYSA-N checkY
  • InChI=1/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3
    Key: OLOOJGVNMBJLLR-UHFFFAOYAQ
  • O=C/3Oc2c(OC\C=C(/C)C)c1occc1cc2\C=C\3
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).
☒N verify (what is checkY☒N ?)

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

References

  1. ^ Sigurdsson S, Ogmundsdottir HM, Gudbjarnason S (July–August 2004). "Antiproliferative effect of Angelica archangelica fruits". Zeitschrift für Naturforschung C. 4th. 59 (7–8): 523–527. doi:10.1515/znc-2004-7-813. PMID 15813373. S2CID 20991241.
  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, Wang Y (July 2011). "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. 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. doi:10.4268/cjcmm20101214. 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". Journal of Natural Medicines. 65 (2): 370–374. doi:10.1007/s11418-010-0485-7. PMID 21082271. S2CID 21188255.
  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. doi:10.4268/cjcmm20100112. PMID 20349717.
  7. ^ Bafi-Yeboa NF, Arnason JT, Baker J, Smith ML (May 2005). "Antifungal constituents of northern prickly ash, Zanthoxylum americanum mill". Phytomedicine. 12 (5): 370–377. doi:10.1016/j.phymed.2003.12.005. PMID 15957372.
  8. ^ F. M. Dean Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963.
  9. ^ Keshab Ghosh (2004). "A furocoumarin, Imperatorin isolated from Urena lobata L. (Malvaceae)". Molecular Diversity Preservation International. M382. Archived from the original on 2005-04-06.
  10. ^ Ivey FD, Wang L, Demirbas D, Allain C, Hoffman CS (January 2008). "Development of a fission yeast-based high-throughput screen to identify chemical regulators of cAMP phosphodiesterases". J Biomol Screen. 13 (1): 62–71. doi:10.1177/1087057107312127. PMC 2851203. PMID 18227226.
  11. ^ a b 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. PMC 8418334. PMID 32450530.
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