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Helenalin

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Helenalin
Names
IUPAC names (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-
dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-
octahydroazulenofuran-2,5-dione
Identifiers
CAS Number
3D model (JSmol)
KEGG
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2
Properties
Chemical formula C15H18O4
Molar mass 262.305 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Helenalin is a sesquiterpene lactone with potent anti-inflammatory and antitumor effects found in Arnica montana and Arnica chamissonis foliosa. It is the main compound responsible for the therapeutic effects of Arnica.

While it is not completely known how sesquiterpene lactones exert their anti-inflammatory effect, helenalin has been shown to selectively inhibit the transcription factor NF-κB, which plays a key role in regulating immune response, through a unique mechanism. In vitro, it is also a potent, selective inhibitor of human telomerase—which may partially account for its antitumor effects—has anti-trypanosomal activity, and is toxic to Plasmodium falciparum.

Animal and in vitro studies have also suggested that helenalin can reduce the growth of Staphylococcus aureus and reduce the severity of S. aureus infection.

Helenalin is a highly toxic compound, with hepatic and lymphatic tissues particularly vulnerable to its effects.

References

  1. Lyss G, Knorre A, Schmidt TJ, Pahl HL, Merfort I (1998). "The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65". J Biol Chem. 273 (50): 33508–16. doi:10.1074/jbc.273.50.33508. PMID 9837931.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
  2. Huang PR, Yeh YM, Wang TC (2005). "Potent inhibition of human telomerase by helenalin". Cancer Lett. 227 (2): 169–74. doi:10.1016/j.canlet.2004.11.045. PMID 16112419.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Jimenez-Ortiz V, Brengio SD, Giordano O; et al. (2005). "The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes". J Parasitol. 91 (1): 170–4. doi:10.1645/GE-3373. PMID 15856894. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  4. Schmidt TJ, Brun R, Willuhn G, Khalid SA (2002). "Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones". Planta Med. 68 (8): 750–1. doi:10.1055/s-2002-33799. PMID 12221603.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. François G, Passreiter CM (2004). "Pseudoguaianolide sesquiterpene lactones with high activities against the human malaria parasite Plasmodium falciparum". Phytother Res. 18 (2): 184–6. doi:10.1002/ptr.1376. PMID 15022176.
  6. Boulanger D, Brouillette E, Jaspar F; et al. (2007). "Helenalin reduces Staphylococcus aureus infection in vitro and in vivo". Vet Microbiol. 119 (2–4): 330–8. doi:10.1016/j.vetmic.2006.08.020. PMID 17010538. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  7. Chapman, Dennis E.; Roberts, G.B.; Reynolds, D.J.; Grippo, Anne A.; Holbrook, David J.; Hall, Iris H.; Chaney, Stephen G.; Chang, J.; Lee, K. H. (1988). "Acute Toxicity of Helenalin in BDF1 Mice". Toxicological Sciences. 10: 302. doi:10.1093/toxsci/10.2.302.
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