Helenalin

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Structural formula
Structural formula of Helenalin
General
Surname Helenalin
other names

(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

Molecular formula C 15 H 18 O 4
External identifiers / databases
CAS number 6754-13-8
PubChem 23205
Wikidata Q387505
properties
Molar mass 262.3 g mol −1
safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301-311-331
P: 301 + 310-304 + 340-302 + 352-261-280-361-264-270-271-403 + 233-330-501-405-363
Toxicological data

125 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Helenalin is a natural anti-inflammatory agent with anti-tumor and anti-leukemic effects found in arnica and other Asteraceae . It suppresses the activation of an immune defense mediator and is toxic. Chemically, it is a sesquiterpene - lactone .

Mountain garnica ( Arnica montana ) contains helenalin.

In addition to the mountain garnica ( Arnica montana ), Helenalin is also found in other arnica (e.g. Arnica chamissonis ), water hemp ( Eupatorium perfoliatum ), the great nasturtium ( Tropaeolum majus ) - all in the herb - as well as in the common elephant ( Inula helenium ) - there also in the Root - proven.

While it is not certain how sesquiterpene lactones develop their anti-inflammatory effects, it has been proven with Helenalin that it selectively inhibits the transcription factor NF-κB , which plays a role in the control of the immune system. In vitro it is also a potent, selective inhibitor of telomerase in humans, and shows anti- trypanosomal activity.

It shows toxic effects on Plasmodium falciparum , and studies suggest that helenalin also inhibits the growth of Staphylococcus aureus and reduces the severity of S. aureus infection.

Helenaline is highly toxic and, as an allergen with a pronounced sensitization potential, is one of the main factors in an arnica allergy.

Individual evidence

  1. ↑ a b c ABCAM: ABCAM Safety Data Sheet , 2015, accessed on November 11, 2018
  2. ↑ Powis G, Gallegos A, Abraham RT, Ashendel CL, Zalkow LH, Grindey GB, Bonjouklian R: Increased intracellular Ca2 + signaling caused by the antitumor agent helenalin and its analogues . In: Cancer Chemother. Pharmacol. . 34, No. 4, 1994, pp. 344-350. doi : 10.1007 / BF00686043 . PMID 8033301 .
  3. ↑ Dirsch VM, Stuppner H, Vollmar AM: Cytotoxic sesquiterpene lactones mediate their death-inducing effect in leukemia T cells by triggering apoptosis. . In: Planta Med. . 67, No. 6, 2001, pp. 557-559. doi : 10.1055 / s-2001-16478 . PMID 11509981 .
  4. ^ Entry Helenalin. In: Liber Herbarum Mino. Retrieved October 29, 2008 .
  5. ^ G Lyss G, A. Knorre, TJ Schmidt, HL Pahl, I. Merfort: The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65 . In: J Biol Chem . 273, No. 50, 1998, pp. 33508-16. PMID 9837931 .
  6. ↑ PR Huang, YM Yeh, TC Wang: Potent inhibition of human telomerase by helenalin . In: Cancer Lett . 227, No. 2, 2005, pp. 169-174. doi : 10.1016 / j.canlet.2004.11.045 . PMID 16112419 .
  7. ^ V. Jimenez-Ortiz, SD Brengio, O. Giordano, et al .: The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes . In: J Parasitol . 91, No. 1, 2005, pp. 170-4. PMID 15856894 .
  8. ^ TJ Schmidt, R. Brun, G. Willuhn, SA Khalid: Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones . In: Planta Med . 68, No. 8, 2002, pp. 750-751. doi : 10.1055 / s-2002-33799 . PMID 12221603 .
  9. ↑ G. François, CM Pass Rider: Pseudoguaianolides sesquiterpene lactones with high activities against the human malaria parasite Plasmodium falciparum . In: Phytother Res . 18, No. 2, 2004, pp. 184-186. doi : 10.1002 / ptr.1376 . PMID 15022176 .
  10. ↑ D. Boulanger, E. Brouillette, F. Jaspar, et al .: Helenalin reduces Staphylococcus aureus infection in vitro and in vivo . In: Vet Microbiol . 119, No. 2-4, 2007, pp. 330-8. doi : 10.1016 / j.vetmic.2006.08.020 . PMID 17010538 .
  11. ↑ Roland Irion: Helenalin. Herbal type IV contact allergen. In: Everything about allergology. Retrieved October 29, 2008 .