Helenin

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Helenin
Alantolactone
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • Alantolactone: 208-899-3
KEGG
UNII
  • 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
  • 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
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).
Close

In 1895 the German scientists Julius Bredt and Wilhelm Posh extracted helenin from Inula helenium and determined its physical and chemical properties.[1]

Natural sources

Alantolactone occurs in the roots of Inula helenium and other Inula species.[2] Helenin discovered in Stevia lucida for the first time, showcasing potential links within the Asteraceae family. [3]

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.[4]

Biological activity

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

Toxicity

Certain individuals have experienced contact dermatitis when exposed to alantolactone.[10]

References

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