Lactucopicrin

From Wikipedia, the free encyclopedia
Lactucopicrin
Preferred IUPAC name

(4-Hydroxy-6-methyl-3-methylidene-2,7-dioxo-
4,5,9a,9b-tetrahydro-3aH-azuleno[8,7-b]furan-
9-yl)methyl 2-(4-hydroxyphenyl)acetate

Systematic name

{4-Hydroxy-6-methyl-3-methylidene-2,7-dioxo-
2H,3H,3aH,4H,5H,7H,8H,9bH-azuleno[4,5-b]
furan-9-yl}methyl 2-(4-hydroxyphenyl)acetate

Other names

{4-Hydroxy-6-methyl-3-methylidene-2,7-dioxo-
3aH,4H,5H,8H,9bH-azuleno[4,5-b]furan-9-yl}
methyl 2-(4-hydroxyphenyl)acetate
Intybin

Identifiers
CAS number 6466-74-6 (3aR,4S,9bS)
PubChem 174863 (3aR,4S,9bS) YesY
ChemSpider 152483 (3aR,4S,9bS) YesY
MeSH Intybin
Jmol-3D images Image 1
Properties
Molecular formula C23H22O7
Molar mass 410.42 g mol−1
Pharmacology
Routes of
administration		 Oral, Smoked
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Lactucopicrin (Intybin) is a bitter substance that has a sedative and analgesic effect,[1] acting on the central nervous system. It is a sesquiterpene lactone, and is a component of lactucarium, derived from the plant Lactuca virosa (wild lettuce), as well as being found in some related plants such as Cichorium intybus.[2] It is also found in dandelion coffee.

As well as their traditional use as sedatives and analgesics, these plants have also been used as antimalarials, and both lactucin and lactucopicrin have demonstrated antimalarial effects in vitro.[3] Lactucopicrin has also been shown to act as an acetylcholinesterase inhibitor.[4]

See also

References

  1. ↑ Wesołowska A, Nikiforuk A, Michalska K, Kisiel W, Chojnacka-Wójcik E. Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice. Journal of Ethnopharmacology. 2006 Sep 19;107(2):254-8. doi:10.1016/j.jep.2006.03.003 PMID 16621374
  2. ↑ Sessa RA, Bennett MH, Lewis MJ, Mansfield JW, Beale MH. Metabolite profiling of sesquiterpene lactones from Lactuca species. Major latex components are novel oxalate and sulfate conjugates of lactucin and its derivatives. Journal of Biological Chemistry. 2000 Sep 1;275(35):26877-84. PMID 10858433
  3. ↑ Bischoff TA, Kelley CJ, Karchesy Y, Laurantos M, Nguyen-Dinh P, Arefi AG. Antimalarial activity of lactucin and lactucopicrin: sesquiterpene lactones isolated from Cichorium intybus L. Journal of Ethnopharmacology. 2004 Dec;95(2-3):455-7. PMID 15507374
  4. ↑ Rollinger JM, Mocka P, Zidorn C, Ellmerer EP, Langer T, Stuppner H. Application of the in combo screening approach for the discovery of non-alkaloid acetylcholinesterase inhibitors from Cichorium intybus. Current Drug Discovery Technologies. 2005 Sep;2(3):185-93. PMID 16472227

External links

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.