Imperatorin
{{chembox
| Verifiedfields = changed
| verifiedrevid = 443870625
| ImageFile=Imperatorin Structural Formula V.1.svg
| ImageSize=200px
| PIN=9-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one
| OtherNames=Ammidin
Marmelosin
Pentosalen
8-Isoamylenoxypsoralen
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=C16H14O4
| 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,{{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}} Angelica dahurica,{{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}} Glehnia littoralis,{{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}} Saposhnikovia divaricata,{{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}} Cnidium monnieri,{{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}} Incarvillea younghusbandii,{{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}} and Zanthoxylum americanum mill.{{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}} It is biosynthesized from umbelliferone, a coumarin derivative.F. M. Dean Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963.
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.{{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 |url-status=dead |archive-date=2005-04-06|archive-url=https://web.archive.org/web/20050406031843/http://www.mdpi.net/molbank/molbank2004/m0382.htm}}
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.{{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}} Imperatorin has been shown to have anti-inflammatory activity in chondrocytes.{{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 |pages=106612 |doi=10.1016/j.intimp.2020.106612 |issn=1878-1705 |pmc=8418334 |pmid=32450530}} Imperatorin treatment inhibits the expression of iNOS and suppresses the production of NO in osteoarthritic chondrocytes.
See also
- Psoralen, the parent furocoumarin.