{{chembox | Verifiedfields = changed | verifiedrevid = 443870625 | ImageFile=Imperatorin Structural Formula V.1.svg | ImageSize=200px | PIN=9-[(3-Methylbut-2-en-1-yl)oxy]-7''H''-furo[3,2-''g''][1]benzopyran-7-one | OtherNames=Ammidin<br />Marmelosin<br />Pentosalen<br />8-Isoamylenoxypsoralen<br />8-Isopentenyloxypsoralene |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 9797 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C09269 | 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 | InChIKey = OLOOJGVNMBJLLR-UHFFFAOYAQ | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 453805 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OLOOJGVNMBJLLR-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo=482-44-0 | PubChem=10212 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = K713N25C78 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 5885 | SMILES=O=C/3Oc2c(OC\C=C(/C)C)c1occc1cc2\C=C\3 }} |Section2={{Chembox Properties | Formula=C<sub>16</sub>H<sub>14</sub>O<sub>4</sub> | MolarMass=270.28 g/mol | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} }} '''Imperatorin''' is a furocoumarin and a phytochemical that has been isolated from ''Urena lobata'' L. (Malvaceae), ''Angelica archangelica'',<ref>{{cite journal |vauthors=Sigurdsson S, Ogmundsdottir HM, Gudbjarnason S |date=July–August 2004 |title=Antiproliferative effect of Angelica archangelica fruits. |journal=Zeitschrift für Naturforschung C |volume=59 |series=4th |issue=7–8 |pages=523–527 |pmid=15813373 |doi=10.1515/znc-2004-7-813|s2cid=20991241 |doi-access=free}}</ref> ''Angelica dahurica'',<ref>{{cite journal |vauthors=Xie Y, Zhao W, Zhou T, Fan G, Wu Y |date=September–October 2010 |title=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 |journal=Phytochemical Analysis |volume=21 |issue=5 |pages=473–82 |pmid=20931624 |doi=10.1002/pca.1222}}</ref> ''Glehnia littoralis'',<ref>{{cite journal |vauthors=Liu M, Shi X, Yang W, Liu S, Wang N, Shi R, Qiao S, Wang Q, Wang Y |title=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 |journal=Biomed. Chromatogr. |volume=25 |issue=7 |pages=783–793 |date=July 2011 |pmid=20878664 |doi=10.1002/bmc.1517}}</ref> ''Saposhnikovia divaricata'',<ref>{{cite journal |vauthors=Zhao B, Yang X, Yang X, Zhang L |date=June 2010 |trans-title=Chemical constituents of roots of Saposhnikovia divaricata |journal=Zhongguo Zhong Yao Za Zhi |volume=35 |series=2nd |issue=12 |pages=1569–72 |pmid=20815209 |language=zh|title=Chemical constituents of roots of Saposhnikovia divaricata |doi=10.4268/cjcmm20101214}}</ref> ''Cnidium monnieri'',<ref>{{cite journal |last=Shin |first=Eunjin |author2=Lee, Chul |author3=Sung, Sang Hyun |author4=Kim, Young Choong |author5=Hwang, Bang Yeon |author6=Lee, Mi Kyeong |date=2010-11-17 |title=Antifibrotic activity of coumarins from Cnidium monnieri fruits in HSC-T6 hepatic stellate cells |journal=Journal of Natural Medicines |volume=65| pmid=21082271 |doi=10.1007/s11418-010-0485-7 |issue=2 |pages=370–374| s2cid=21188255}}</ref> ''Incarvillea younghusbandii'',<ref>{{cite journal |vauthors=Fu Y, Bai Y, Dawa Z, Bai B, Ding L |date=January 2010 |trans-title=Chemical constituents of Incarvillea younghusbandii |journal=Zhongguo Zhong Yao Za Zhi |volume=35 |series=2nd |issue=1 |pmid=20349717 |title=Chemical constituents of Incarvillea younghusbandii |pages=58–62| doi=10.4268/cjcmm20100112}}</ref> and ''Zanthoxylum americanum mill''.<ref>{{cite journal |vauthors=Bafi-Yeboa NF, Arnason JT, Baker J, Smith ML |date=May 2005 |title=Antifungal constituents of northern prickly ash, Zanthoxylum americanum mill |journal=Phytomedicine |volume=12 |issue=5 |pmid=15957372 |pages=370–377 |doi=10.1016/j.phymed.2003.12.005}}</ref> It is biosynthesized from umbelliferone, a coumarin derivative.<ref>F. M. Dean ''Naturally Occurring Oxygen Ring Compounds'', Butterworths, London, 1963.</ref>
== 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.<ref>{{cite web |title=A furocoumarin, Imperatorin isolated from Urena lobata L. (Malvaceae) |author=Keshab Ghosh |date=2004 |id=M382 |publisher=Molecular Diversity Preservation International |url=http://www.mdpi.net/molbank/molbank2004/m0382.htm |archive-date=2005-04-06|archive-url=https://web.archive.org/web/20050406031843/http://www.mdpi.net/molbank/molbank2004/m0382.htm}}</ref>
== 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.<ref>{{cite journal |vauthors=Ivey FD, Wang L, Demirbas D, Allain C, Hoffman CS |title=Development of a fission yeast-based high-throughput screen to identify chemical regulators of cAMP phosphodiesterases |journal=J Biomol Screen |volume=13 |issue=1 |pages=62–71 |date=January 2008 |pmid=18227226 |pmc=2851203 |doi=10.1177/1087057107312127}}</ref> Imperatorin has been shown to have anti-inflammatory activity in chondrocytes.<ref name="Ahmad Ansari Bano Haqqi 2020">{{Cite journal |last=Ahmad |first=Nashrah |last2=Ansari |first2=Mohammad Y. |last3=Bano |first3=Shabana |last4=Haqqi |first4=Tariq M. |date=August 2020 |title=Imperatorin suppresses IL-1β-induced iNOS expression via inhibiting ERK-MAPK/AP1 signaling in primary human OA chondrocytes |journal=International Immunopharmacology |volume=85 |article-number=106612 |doi=10.1016/j.intimp.2020.106612 |issn=1878-1705 |pmc=8418334 |pmid=32450530}}</ref> Imperatorin treatment inhibits the expression of iNOS and suppresses the production of NO in osteoarthritic chondrocytes.<ref name="Ahmad Ansari Bano Haqqi 2020"/>
== See also == *Psoralen, the parent furocoumarin.
== References == {{Reflist}} {{coumarin}}
Category:Furanocoumarins Category:Terpeno-phenolic compounds Category:Phenol ethers