Helenin

Last updated
Helenin
Alantolactone.svg
Alantolactone
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • Alantolactone:208-899-3
KEGG
PubChem CID
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
AppearanceCrystalline powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Contents

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

  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   978-1594778902.
  3. ↑ Chacón-Morales, Pablo A.; Dugarte, Carolina Santiago; Amaro-Luis, Juan M. (2021-11-02). "Helenin from Stevia lucida . The first report of this natural eudesmanolide mixture in Eupatorieae tribe" . Natural Product Research. 35 (21): 4139–4142. doi:10.1080/14786419.2020.1739677. ISSN   1478-6419. PMID   32189507.
  4. ↑ 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: 1–8. doi: 10.1155/2014/354618 .
  5. ↑ 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 (5): 199–226. doi:10.1002/jbt.21685. PMID   25597476. S2CID   10440798.
  6. ↑ Chun, J (1 Feb 2015). "Alantolactone selectively suppresses STAT3 activation and exhibits potent anticancer activity in MDA-MB-231 cells". Cancer Letters. 357 (1): 393–403. doi:10.1016/j.canlet.2014.11.049. PMID   25434800.
  7. ↑ 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 . PMID   25881570. S2CID   5196219.
  8. ↑ 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   11449472.
  9. ↑ O'Shea, S (2009). "In vitro activity of Inula helenium against clinical Staphylococcus aureus strains including MRSA". British Journal of Biomedical Science. 66 (4): 186–9. doi:10.1080/09674845.2009.11730271. PMID   20095126.
  10. ↑ 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 Dermatology. 99 (2): 163–9. doi:10.1111/j.1365-2133.1978.tb01977.x. PMID   698105. S2CID   73218116.
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