Helenalin

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IUPACName=(3a"S",4"S",4a"R",7a"R",8"R",9a"R")-4-hydroxy-4a,8-
dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-
octahydroazuleno [6,5-"b"] furan-2,5-dione
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CASNo=6754-13-8
PubChem=23205
KEGG=C09473
SMILES=CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2
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C=15|H=18|O=4
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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.cite journal |author=Lyss G, Knorre A, Schmidt TJ, Pahl HL, Merfort I |title=The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65 |journal=J Biol Chem |volume=273 |issue=50 |pages=33508–16 |year=1998 |pmid=9837931 |doi= |url=http://www.jbc.org/cgi/content/full/273/50/33508] "In vitro", it is also a potent, selective inhibitor of human telomerase [cite journal |author=Huang PR, Yeh YM, Wang TC |title=Potent inhibition of human telomerase by helenalin |journal=Cancer Lett |volume=227 |issue=2 |pages=169–74 |year=2005 |pmid=16112419 |doi=10.1016/j.canlet.2004.11.045] —which may partially account for its antitumor effects—, has anti-trypanosomal activity,cite journal |author=Jimenez-Ortiz V, Brengio SD, Giordano O, "et al." |title=The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes |journal=J Parasitol |volume=91 |issue=1 |pages=170–4 |year=2005 |pmid=15856894 |doi=] cite journal |author=Schmidt TJ, Brun R, Willuhn G, Khalid SA |title=Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones |journal=Planta Med |volume=68 |issue=8 |pages=750–1 |year=2002 |pmid=12221603 |doi=10.1055/s-2002-33799] and is toxic to "Plasmodium falciparum".cite journal |author=François G, Passreiter CM |title=Pseudoguaianolide sesquiterpene lactones with high activities against the human malaria parasite Plasmodium falciparum |journal=Phytother Res |volume=18 |issue=2 |pages=184–6 |year=2004 |pmid=15022176 |doi=10.1002/ptr.1376]

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.cite journal |author=Boulanger D, Brouillette E, Jaspar F, "et al." |title=Helenalin reduces Staphylococcus aureus infection in vitro and in vivo |journal=Vet Microbiol |volume=119 |issue=2–4 |pages=330–8 |year=2007 |pmid=17010538 |doi=10.1016/j.vetmic.2006.08.020]

Helenalin is a highly toxic compound.

References

External links

*http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/arn_0025.shtml