Helenalin

Helenalin
Names
	IUPAC name (8αH)-6α-Hydroxy-4-oxo-10α-ambrosa-2,11(13)-dieno-12,8-lactone
	Systematic 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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL338474 ;
ChemSpider	21713 ;
KEGG	C09473 ;
PubChem CID	23205;
UNII	4GUY9L896T ;
CompTox Dashboard (EPA)	DTXSID50217868 ;
	InChI InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1 Key: ZVLOPMNVFLSSAA-XEPQRQSNSA-N ; InChI=1/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1 Key: ZVLOPMNVFLSSAA-XEPQRQSNBI;
	SMILES O=C/2O[C@@H]3C[C@H]([C@@H]1/C=C\C(=O)[C@@]1(C)[C@@H](O)[C@@H]3C\2=C)C;
Properties
Chemical formula	C15H18O4
Molar mass	262.305 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, or (-)-4-Hydroxy-4a,8-dimethyl-3,3a,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione, is a toxic sesquiterpene lactone which can be found in several plants such as Arnica montana and Arnica chamissonis Helenalin is responsible for the toxicity of the Arnica spp. Although toxic, helenalin possesses some in vitro anti-inflammatory and anti-neoplastic effects. Helenalin can inhibit certain enzymes, such as 5-lipoxygenase and leukotriene C4 synthase. For this reason the compound or its derivatives may have potential medical applications.^[1]^[2]

^ Cite error: The named reference Perry was invoked but never defined (see the help page).
^ Tornhamre, Susanne; Schmidt, Thomas J.; Näsman-Glaser, Barbro; Ericsson, Inger; Lindgren, Jan Åke (2001). "Inhibitory effects of helenalin and related compounds on 5-lipoxygenase and leukotriene C 4 synthase in human blood cells". Biochemical Pharmacology. 62 (7): 903–911. doi:10.1016/S0006-2952(01)00729-8. PMID 11543725.

[Perry-1] Cite error: The named reference Perry was invoked but never defined (see the help page).

[Tornhamre-2] Tornhamre, Susanne; Schmidt, Thomas J.; Näsman-Glaser, Barbro; Ericsson, Inger; Lindgren, Jan Åke (2001). "Inhibitory effects of helenalin and related compounds on 5-lipoxygenase and leukotriene C 4 synthase in human blood cells". Biochemical Pharmacology. 62 (7): 903–911. doi:10.1016/S0006-2952(01)00729-8. PMID 11543725.

[1]

[2]