Helenalin

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Helenalin

IUPAC name	(3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8- dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a- octahydroazuleno[6,5-b]furan-2,5-dione
Identifiers
CAS number	[6754-13-8]
PubChem	23205
KEGG	C09473
SMILES	CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2
Properties
Molecular formula	C₁₅H₁₈O₄
Molar mass	262.3 g mol^-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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.^[1] In vitro, it is also a potent, selective inhibitor of human telomerase^[2]—which may partially account for its antitumor effects—, has anti-trypanosomal activity,^[3]^[4] and is toxic to Plasmodium falciparum.^[5]

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.^[6]

Helenalin is a highly toxic compound.

[edit] References

^ 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. PMID 9837931.
^ 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.
^ 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. PMID 15856894.
^ 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.
^ 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.
^ 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.