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Valerenic acid

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withValeric acid.
Valerenic acid
Names
Preferred IUPAC name
(2E)-3-[(4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.112.154Edit this at Wikidata
UNII
  • InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+ checkY
    Key: FEBNTWHYQKGEIQ-DHZHZOJOSA-N checkY
  • InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+
  • Key: FEBNTWHYQKGEIQ-DHZHZOJOSA-N
  • C[C@@H]1CC[C@H](C2=C(CC[C@H]12)C)/C=C(\C)/C(=O)O
Properties
C15H22O2
Molar mass234.339 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Valerenic acid is asesquiterpenoid constituent of the essential oil of thevalerian plant.[1]

Valerian is used as a herbalsedative which may be helpful in the treatment ofinsomnia.[2] Valerenic acid may be at least partly responsible for valerian's sedative effects, in addition to the other valerenic acids hydroxyvalerenic acid and acetoxyvalerenic acid.[3][1] Valerian supplements are often standardized to contain a particular amount of valerenic acid by weight (often 0.8%).[3]

Valerenic acid acts as a subtype-selectiveGABAA receptor positive allosteric modulator via abinding site in thetransmembrane domain at the β+α− interface.[4] At receptors expressed inXenopusoocytes (frog eggs) it was shown that only assemblies incorporatingβ2 orβ3subunits were stimulated by valerenic acid. A study in mice demonstrated that a single amino acid substitution (N265M) in theβ3 subunit severely decreases the anxiolytic effect. Modulation of ion channel action was not significantly dependent on incorporation of α1, α2, α3 or α5 subunits.[5]

At the5-HT5A receptor valerenic acid acts as apartial agonist. Thisserotonin receptor subtype is distributed in thesuprachiasmatic nucleus, a tiny brain region implicated in thesleep-wake cycle.[6]

A study in 2006 found valerian extract as well as valerenic acid to inhibitNF-κB, a protein complex that controls thetranscription ofDNA, inHeLa (cultured human cancer) cells. This was measured with the IL-6 / Luc (interleukin-6luciferase) assay as a measurement tool. The study mentioned that such inhibition may be connected to the reportedanti-inflammatory action of the valerian plant.[7]

A small study with six human subjects found that valerenic acid peaked in concentration after about an hour and had an average half-life of 1.1 +/- 0.6 hours after oral ingestion of a commercially available valerian root supplement.[8] A later study from the same lab done with sixteen older women found similar values.[3]

See also

[edit]

References

[edit]
  1. ^abYuan CS, Mehendale S, Xiao Y, Aung HH, Xie JT, Ang-Lee MK (2004). "The gamma-aminobutyric acidergic effects of valerian and valerenic acid on rat brainstem neuronal activity".Anesth Analg.98 (2):353–8, table of contents.CiteSeerX 10.1.1.323.5518.doi:10.1213/01.ANE.0000096189.70405.A5.PMID 14742369.S2CID 14526474.
  2. ^Bent, Stephen; Padula, Amy; Moore, Dan; Patterson, Michael; Mehling, Wolf (2006)."Valerian for Sleep: A Systematic Review and Meta-Analysis".The American Journal of Medicine.119 (12). Elsevier BV:1005–1012.doi:10.1016/j.amjmed.2006.02.026.ISSN 0002-9343.PMC 4394901.PMID 17145239.
  3. ^abcAnderson, Gail D.; Elmer, Gary W.; Taibi, Diana M.; Vitiello, Michael V.; Kantor, Eric; Kalhorn, Thomas F.; Howald, William N.; Barsness, Suzanne; Landis, Carol A. (13 April 2010). "Pharmacokinetics of valerenic acid after single and multiple doses of valerian in older women".Phytotherapy Research.24 (10):1442–1446.doi:10.1002/ptr.3151.PMID 20878691.S2CID 21007272.
  4. ^Luger D, Poli G, Wieder M, Stadler M, Ke S, Ernst M, Hohaus A, Linder T, Seidel T, Langer T, Khom S, Hering S (2015)."Identification of the putative binding pocket of valerenic acid on GABAA receptors using docking studies and site-directed mutagenesis".Br. J. Pharmacol.172 (22):5403–13.doi:10.1111/bph.13329.PMC 4988470.PMID 26375408.
  5. ^Khom, S.; Baburin, I.; Timin, E.; Hohaus, A.; Trauner, G.; Kopp, B.; Hering, S. (2007). "Valerenic acid potentiates and inhibits GABAA receptors: Molecular mechanism and subunit specificity".Neuropharmacology.53 (1):178–187.doi:10.1016/j.neuropharm.2007.04.018.PMID 17585957.S2CID 7613630.
  6. ^Dietz, B.; Mahady, G.; Pauli, G.; Farnsworth, N. (2005)."Valerian extract and valerenic acid are partial agonists of the 5-HT receptor in vitro".Molecular Brain Research.138 (2):191–197.doi:10.1016/j.molbrainres.2005.04.009.PMC 5805132.PMID 15921820.
  7. ^Jacobo-Herrera, N. J.; Vartiainen, N.; Bremner, P.; Gibbons, S.; Koistinaho, J.; Heinrich, M. (2006). "F-κB modulators from Valeriana officinalis".Phytotherapy Research.20 (10):917–919.doi:10.1002/ptr.1972.PMID 16909443.S2CID 44352988.
  8. ^Anderson, Gail D.; Elmer, Gary W.; Kantor, Eric D.; Templeton, Ian E.; Vitiello, Michael V. (September 2005). "Pharmacokinetics of valerenic acid after administration of valerian in healthy subjects".Phytotherapy Research.19 (9):801–803.doi:10.1002/ptr.1742.PMID 16220575.S2CID 24684779.
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