Helenin

Helenin

File:Alantolactone.svg Alantolactone
File:Isoalantolactone.svg Isoalantolactone
Names
IUPAC names Alantolactone: (3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one Isoalantolactone: (3aR,4aS,8aR,9aR)-8a-Methyl-3,5-bis(methylene)decahydronaphtho[2,3-b]furan-2(3H)-one
Other names Elecampane camphor, Inula camphor, Alant camphor
Identifiers
CAS Number	Alantolactone: 546-43-0 checkY isolantolactone: 470-17-7 checkY
3D model (JSmol)	Alantolactone: Interactive image isolantolactone: Interactive image
ChEBI	Alantolactone: CHEBI:2540 isolantolactone: CHEBI:5981
ChEMBL	Alantolactone: ChEMBL136356 isolantolactone: ChEMBL137803
ChemSpider	Alantolactone: 65564 isolantolactone: 66028
ECHA InfoCard
EC Number	Alantolactone: 208-899-3
E number
KEGG	Alantolactone: C09289 isolantolactone: C09484
PubChem CID	Alantolactone: 72724 isolantolactone: 73285
UNII	Alantolactone: M7GSN5Q1M6 checkY isolantolactone: BYH07P620U checkY
CompTox Dashboard (EPA)	Alantolactone: {{#property:P3117}}
InChI InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1 Key: PXOYOCNNSUAQNS-AGNJHWRGSA-N isolantolactone: InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1 Key: CVUANYCQTOGILD-QVHKTLOISA-N
SMILES Alantolactone: C[C@H]1CCC[C@]2(C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)C isolantolactone: C[C@]12CCCC(=C)[C@@H]1C[C@H]3[C@@H](C2)OC(=O)C3=C
Properties
Chemical formula	C15H20O2
Molar mass	232.323 g·mol−1
Appearance	Crystalline powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Helenin is a phytochemical mixture found in many plant species, including the Inula helenium (elecampane) of the family Asteraceae. It is a mixture of two isomeric sesquiterpene lactones, alantolactone and isoalantolactone.

In 1895 the German scientists Julius Bredt and Wilhelm Posh extracted helenin from Inula helenium and determined its physical and chemical properties.

Natural sources

Alantolactone occurs in the roots of Inula helenium and other Inula species. Helenin discovered in Stevia lucida for the first time, showcasing potential links within the Asteraceae family.

Properties

Helenin can be extracted from the roots of Inula helenium using alcohol or other non-polar solvents to produce a mixture with a composition of about 40% alantolactone and 60% isoalantolactone.

Biological activity

Alantolactone has a variety of in vitro biochemical properties, including:

• induces apoptosis and cell cycle arrest in lung squamous cancer cells
• suppresses STAT3 activation
• has antiinflammatory effects by inhibiting chemokine production and STAT1 phosphorylation
• anti-fungal
• anti-microbial

Toxicity

Certain individuals have experienced contact dermatitis when exposed to alantolactone.