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{{chembox
{{chembox
| Verifiedfields = changed
| verifiedrevid = 409747857
| verifiedrevid = 443870625
|ImageFile=Imperatorin.png
| ImageFile=Imperatorin Structural Formula V.1.svg
|ImageSize=200px
| ImageSize=200px
|IUPACName=9-(3-Methylbut-2-enoxy)-7-furo[3,2-g]chromenone
| 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
| OtherNames=Ammidin<br>Marmelosin<br>Pentosalen<br>8-Isoamylenoxypsoralen<br>8-Isopentenyloxypsoralene
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OLOOJGVNMBJLLR-UHFFFAOYSA-N
| StdInChIKey = OLOOJGVNMBJLLR-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=482-44-0
| CASNo=482-44-0
|PubChem=10212
| PubChem=10212
| UNII_Ref = {{fdacite|correct|FDA}}
|UNII = K713N25C78
| UNII = K713N25C78
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 5885
| SMILES=O=C/3Oc2c(OC\C=C(/C)C)c1occc1cc2\C=C\3
| SMILES=O=C/3Oc2c(OC\C=C(/C)C)c1occc1cc2\C=C\3
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
|Formula=C<sub>16</sub>H<sub>14</sub>O<sub>4</sub>
| Formula=C<sub>16</sub>H<sub>14</sub>O<sub>4</sub>
|MolarMass=270.28 g/mol
| MolarMass=270.28 g/mol
|Appearance=
| Appearance=
|Density=
| Density=
|MeltingPt=
| MeltingPt=
|BoilingPt=
| BoilingPt=
|Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
|MainHazards=
| MainHazards=
|FlashPt=
| FlashPt=
| AutoignitionPt =
|Autoignition=
}}
}}
}}
}}
'''Imperatorin''' is a [[Furanocoumarin|furocoumarin]] and a [[phytochemical]] that has been isolated from ''[[Urena lobata]]'' L. ([[Malvaceae]]), ''[[Angelica archangelica]]'',<ref name=Sigurdsson_et_al_2004>{{cite journal |author=Sigurdsson S, Ogmundsdottir HM, Gudbjarnason S. |year=2004 |month=July-August |title=Antiproliferative effect of Angelica archangelica fruits. |journal=Zeitschrift für Naturforschung C |volume=59 |series=4th |issue=7–8 |pages=523–7 |pmid=15813373}}</ref> ''[[Angelica dahurica]]'',<ref name=Xie_et_al_2010>{{cite journal |author=Xie Y, Zhao W, Zhou T, Fan G, Wu Y. |year=2010 |month=September-October |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 |url=http://onlinelibrary.wiley.com/doi/10.1002/pca.1222/full |accessdate=2010-11-27 }}</ref> ''[[Glehnia littoralis]]'',<ref name=Liu_et_al_2010>{{cite journal |author=Liu, M., Shi, X., Yang, W., Liu, S., Wang, N., Shi, R., Qiao, S., Wang, Q. and Wang, Y. |date=2010-09-27 |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=Biochemical Chromatography |volume=[Epub ahead of print] |pmid=20878664 |doi=10.1002/bmc.1517 |url=http://onlinelibrary.wiley.com/doi/10.1002/bmc.1517/full |accessdate=2010-11-27 |pages=n/a–n/a}}</ref> ''[[Saposhnikovia divaricata]]'',<ref name=Zhao_et_al_2010>{{cite journal |author=Zhao B, Yang X, Yang X, Zhang L. |year=2010 |month=June |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=Chinese |accessdate=2010-11-27 |title=Chemical constituents of roots of Saposhnikovia divaricata}}</ref> ''[[Cnidium monnieri]]'',<ref name=Shin_et_al_2010>{{cite journal | last = Shin | first = Eunjin | coauthors = Lee, Chul; Sung, Sang Hyun; Kim, Young Choong; Hwang, Bang Yeon; and 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 = [Epub ahead of print] | series = 2nd | pmid = 21082271 | doi = 10.1007/s11418-010-0485-7 | url = http://www.springerlink.com/content/uj881g010mt00287/fulltext.pdf | accessdate = 2010-11-27 | issue = 2 | pages = 370–374}}</ref> ''[[Incarvillea younghusbandii]]'',<ref name=Fu_et_al_2010>{{cite journal | last = Fu | first = Y | coauthors = Bai Y, Dawa Z, Bai B, Ding L. | year = 2010 | month = January | 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}}</ref> and ''[[Zanthoxylum americanum mill]]''.<ref name=Bafi_Yeboa_et_al_2005>{{cite journal | last=Bafi-Yeboa | first=N. F. | coauthors=Arnason JT, Baker J, Smith ML. | year=2005 | month=May | title=Antifungal constituents of northern prickly ash, Zanthoxylum americanum mill | journal=Phytomedicine | volume=12 | issue=5 | pmid=15957372 | pages=370–7}}</ref> It is biosynthesized from [[umbelliferone]], a [[coumarin]] derivative.<ref>F. M. Dean ''Naturally Occurring Oxygen Ring Compounds'', Butterworths, London, 1963.</ref>
'''Imperatorin''' is a [[Furanocoumarin|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 [[solvent extraction|extracting]] under [[reflux]] with [[benzene]] the air-dried and pulverised roots followed by separation by [[column chromatography]].<ref>A furocoumarin, Imperatorin isolated from Urena lobata L. (Malvaceae) Keshab Ghosh [[Molbank]] 2004, M382 [http://www.mdpi.net/molbank/molbank2004/m0382.htm] [[Open access (publishing)|open access]] publication</ref>


==See also==
== Isolation ==
⚫
The procedure for the isolation of imperatorin from ''[[Urena lobata]]'' involves exhaustively [[solvent extraction|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 |url-status=dead |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 |pages=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.
*[[Psoralen]], the parent furocoumarin.


==References==
== References ==
{{Reflist}}
{{Reflist}}
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[[Category:Furanocoumarins]]
[[Category:Furanocoumarins]]
[[Category:Terpeno-phenolic compounds]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]

[[fr:Impératorine]]
[[it:Imperatorina]]

Latest revision as of 09:11, 14 April 2023

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

[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] 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

[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): 523–527. 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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