Helenin

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
CAS Number	546-43-0 Alantolactone 470-17-7 Isoalantolactone
3D model (Jmol)	Alantolactone: Interactive image Isoalantolactone: Interactive image
ChemSpider	65564 Alantolactone 66028 Isoalantolactone
ECHA InfoCard	100.008.091
SMILES Alantolactone: C[C@H]1CCC[C@]2(C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)C Isoalantolactone: C[C@]12CCCC(=C)[C@@H]1C[C@H]3[C@@H](C2)OC(=O)C3=C
Properties
Chemical formula	C15H20O2
Molar mass	232.32 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 Asteraceae family. It is a mixture of two isomeric sesquiterpene lactones, alantolactone and isoalantolactone.

In 1895 a 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]

Properties

The roots of Inula helenium can be extracted using alcohol or other non-polar solvents to produce helenin with a composition of about 40% alantolactone and 60% isoalantolactone.^[3]

Biological activity

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

• induces apoptosis and cell cycle arrest in lung squamous cancer cells^[4]
• suppresses STAT3 activation^[5]
• has antiinflammatory effects by inhibiting chemokine production and STAT1 phosphorylation^[6]
• anti-fungal^[7]
• anti-microbial^[8]

Toxicity

Certain individuals have experienced contact dermatitis when exposed to alantolactone.^[9]

References

1. Chemical Society (Great Britain) (1895). The collected works of Sir Humphry Davy ...: Discourses delivered before the Royal society. Elements of agricultural chemistry, pt. I. Smith, elder and Company. p. 555. Retrieved 31 July 2015.
2. Hoffmann, David (2003). Medical Herbalism:The Science and Practice of Herbal Medicine. Health & Fitness. ISBN 1594778906.
3. Xu, Renjie (2014). "Pharmacokinetic Comparison of Isoalantolactone and Alantolactone in Rats after Administration Separately by Optimization of an UPLC-MS2 Method". Journal of Chemistry. 2014: 8. doi:10.1155/2014/354618.
4. Zhao, Peng (19 Jan 2015). "Alantolactone Induces Apoptosis and Cell Cycle Arrest on Lung Squamous Cancer SK-MES-1 Cells". Journal of Biochemical and Molecular Toxicology. 29: 199–226. doi:10.1002/jbt.21685. Retrieved 1 August 2015.
5. Chun, J (1 Feb 2015). "Alantolactone selectively suppresses STAT3 activation and exhibits potent anticancer activity in MDA-MB-231 cells.". Cancer Letters. 357: 393–403. doi:10.1016/j.canlet.2014.11.049. PMID 25434800.
6. Hye, Sun Lim (17 Apr 2015). "Alantolactone from Saussurea lappa Exerts Antiinflammatory Effects by Inhibiting Chemokine Production and STAT1 Phosphorylation in TNF-α and IFN-γ-induced in HaCaT cells". Phytotherapy Research. 29 (7): 1088–1096. doi:10.1002/ptr.5354. Retrieved 2 August 2015.
7. Alejandro, Barreroa, (2000). "New sources and antifungal activity of sesquiterpene lactones". Fitoterapia. 66 (71): 60–64. doi:10.1016/s0367-326x(99)00122-7. PMID 20095126.
8. O'Shea, S (2009). "In vitro activity of Inula helenium against clinical Staphylococcus aureus strains including MRSA". British Journal of Medical Science. 66 (4): 186–9. doi:10.1016/s0367-326x(99)00122-7. PMID 20095126.
9. Stampf, J (August 1978). "Allergic contact dermatitis due to sesquiterpene lactones. A comparative study of human and animal sensitivity to alpha-methylene-gamma-butyrolactone and derivatives". The British Journal of Dermatilogy. 99 (2): 163–9. doi:10.1111/j.1365-2133.1978.tb01977.x. PMID 698105.