Lactucopicrin

Last updated
Lactucopicrin
Lactucopicrin.png
Names
Preferred IUPAC name
[(3aR,4S,9aS,9bR)-4-Hydroxy-6-methyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-b]furan-9-yl]methyl (4-hydroxyphenyl)acetate
Other names
Intybin
Identifiers
3D model (JSmol)
ChemSpider
MeSH Intybin
PubChem CID
UNII
  • InChI=1S/C23H22O7/c1-11-7-16(25)20-12(2)23(28)30-22(20)21-14(9-17(26)19(11)21)10-29-18(27)8-13-3-5-15(24)6-4-13/h3-6,9,16,20-22,24-25H,2,7-8,10H2,1H3/t16-,20+,21-,22-/m0/s1
    Key: QCDLLIUTDGNCPO-AEMJNJESSA-N
  • InChI=1/C23H22O7/c1-11-7-16(25)20-12(2)23(28)30-22(20)21-14(9-17(26)19(11)21)10-29-18(27)8-13-3-5-15(24)6-4-13/h3-6,9,16,20-22,24-25H,2,7-8,10H2,1H3/t16-,20+,21-,22-/m0/s1
    Key: QCDLLIUTDGNCPO-AEMJNJESBM
  • CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)COC(=O)Cc4ccc(cc4)O
Properties
C23H22O7
Molar mass 410.422 g·mol−1
Pharmacology
Oral, Smoked
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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Common chicory is a somewhat woody, perennial herbaceous plant of the family Asteraceae, usually with bright blue flowers, rarely white or pink. Native to the Old World, it has been introduced to North America and Australia. Many varieties are cultivated for salad leaves, chicons, or roots, which are baked, ground, and used as a coffee substitute and food additive. In the 21st century, inulin, an extract from chicory root, has been used in food manufacturing as a sweetener and source of dietary fiber.

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Lactuca virosa is a plant in the Lactuca (lettuce) genus, often ingested for its mild analgesic and sedative effects. It is related to common lettuce, and is often called wild lettuce, bitter lettuce, laitue vireuse, opium lettuce, poisonous lettuce, tall lettuce, great lettuce or rakutu-karyumu-so.

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References

  1. Wesołowska, A; Nikiforuk, A; Michalska, K; Kisiel, W; Chojnacka-Wójcik, E (Sep 2006). "Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice". Journal of Ethnopharmacology. 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 (Sep 2000). "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. 275 (35): 26877–84. doi: 10.1074/jbc.M000244200 . PMID   10858433.
  3. Bischoff, TA; Kelley, CJ; Karchesy, Y; Laurantos, M; Nguyen-Dinh, P; Arefi, AG (2004). "Antimalarial activity of lactucin and lactucopicrin: sesquiterpene lactones isolated from Cichorium intybus L.". Journal of Ethnopharmacology. 95 (2–3): 455–7. doi:10.1016/j.jep.2004.06.031. PMID   15507374.
  4. Rollinger, JM; Mocka, P; Zidorn, C; Ellmerer, EP; Langer, T; Stuppner, H (2005). "Application of the in combo screening approach for the discovery of non-alkaloid acetylcholinesterase inhibitors from Cichorium intybus". Current Drug Discovery Technologies. 2 (3): 185–93. doi:10.2174/1570163054866855. PMID   16472227.