Helenalin

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Helenalin
Helenalin.svg
Identifiers
CAS number 6754-13-8 YesY
PubChem 23205
ChemSpider 21713 N
UNII 4GUY9L896T N
KEGG C09473 YesY
ChEMBL CHEMBL338474 N
Jmol-3D images Image 1
Properties
Molecular formula C15H18O4
Molar mass 262.30 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Helenalin is a sesquiterpene lactone found in Arnica montana and Arnica chamissonis foliosa. Helenalin is a highly toxic compound, with hepatic and lymphatic tissues particularly vulnerable to its effects.[1] It is believed to be responsible for the toxicity and skin irritation associated with Arnica.[2][3] If enough of the plant is ingested, the helenalin produces severe gastroenteritis and internal bleeding of the digestive tract.[4]

Pharmacology[edit]

Helenalin has a variety of observed effects in vitro including anti-inflammatory and antitumor activities.[5]

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.[6] In vitro, it is also a potent, selective inhibitor of human telomerase[7]—which may partially account for its antitumor effects—has anti-trypanosomal activity,[8][9] and is toxic to Plasmodium falciparum.[10]

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.[11]

References[edit]

  1. ^ Chapman, Dennis E.; Roberts, G.B.; Reynolds, D.J.; Grippo, Anne A.; Holbrook, David J.; Hall, Iris H.; Chaney, Stephen G.; Chang, J. et al. (1988). "Acute Toxicity of Helenalin in BDF1 Mice". Toxicological Sciences 10 (2): 302. doi:10.1093/toxsci/10.2.302. 
  2. ^ Rudzki, Edward; Grzywa, Zdzislawa (1977). "Dermatitis from Arnica montana". Contact Dermatitis 3 (5): 281–2. doi:10.1111/j.1600-0536.1977.tb03682.x. PMID 145351. 
  3. ^ "Poisonous Plants: Arnica montana". Ces.ncsu.edu. 
  4. ^ Gregory L. Tilford. Edible and Medicinal Plants of the West. ISBN 0-87842-359-1. 
  5. ^ Powis G, Gallegos A, Abraham RT, Ashendel CL, Zalkow LH, Grindey GB, Bonjouklian R (1994). "Increased intracellular Ca2+ signaling caused by the antitumor agent helenalin and its analogues". Cancer Chemother. Pharmacol. 34 (4): 344–350. doi:10.1007/BF00686043. PMID 8033301. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ 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. 
  11. ^ 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.