Imperatorin

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]

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
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 ?)
Infobox references

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. 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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