Helenalin
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| Names | |
|---|---|
| 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 | |
6754-13-8  | |
| 3D model (Jmol) | Interactive image |
| ChEMBL | ChEMBL338474  |
| ChemSpider | 21713 |
| KEGG | C09473 |
| PubChem | 23205 |
| UNII | 4GUY9L896T |
| |
| |
| Properties | |
| C15H18O4 | |
| Molar mass | 262.31 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| 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
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
- ↑ 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 (2): 302. doi:10.1093/toxsci/10.2.302.
- ↑ 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.
- ↑ "Poisonous Plants: Arnica montana". Ces.ncsu.edu.
- ↑ Gregory L. Tilford. Edible and Medicinal Plants of the West. ISBN 0-87842-359-1.
- ↑ Powis G, Gallegos A, Abraham RT, Ashendel CL, Zalkow LH, Grindey GB, Bonjouklian R; Gallegos; Abraham; Ashendel; Zalkow; Grindey; Bonjouklian (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.
- ↑ Lyss G, Knorre A, Schmidt TJ, Pahl HL, Merfort I; Knorre; Schmidt; Pahl; Merfort (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.
- ↑ Huang PR, Yeh YM, Wang TC; Yeh; Wang (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. doi:10.1645/GE-3373. PMID 15856894.
- ↑ Schmidt TJ, Brun R, Willuhn G, Khalid SA; Brun; Willuhn; Khalid (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; Passreiter (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.