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Lactucopicrin

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.

Lactucopicrin
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
  • 6466-74-6 (3aR,4S,9bS)
3D model (JSmol)
  • Interactive image
ChemSpider
  • 152483 (3aR,4S,9bS)
MeSH Intybin
  • 174863 (3aR,4S,9bS)
UNII
  • SKG846KJ3G Y
  • DTXSID90983277
  • 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).

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 edit

References edit

  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.


lactucopicrin, intybin, bitter, substance, that, sedative, analgesic, effect, acting, central, nervous, system, sesquiterpene, lactone, component, lactucarium, derived, from, plant, lactuca, virosa, wild, lettuce, well, being, found, some, related, plants, suc. 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 Lactucopicrin 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 CAS Number 6466 74 6 3aR 4S 9bS 3D model JSmol Interactive image ChemSpider 152483 3aR 4S 9bS MeSH Intybin PubChem CID 174863 3aR 4S 9bS UNII SKG846KJ3G Y CompTox Dashboard EPA DTXSID90983277 InChI 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 s1Key QCDLLIUTDGNCPO AEMJNJESSA NInChI 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 s1Key QCDLLIUTDGNCPO AEMJNJESBM SMILES 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 Chemical formula C 23H 22O 7 Molar mass 410 422 g mol 1 Pharmacology Routes ofadministration Oral Smoked Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references 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 editLactucinReferences edit Wesolowska A Nikiforuk A Michalska K Kisiel W Chojnacka Wojcik 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 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 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 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 Retrieved from https en wikipedia org w index php title Lactucopicrin amp oldid 1107518413, wikipedia, wiki, book, books, library,

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