helenalin
Sign in to saveAlso known as 6alpha,8beta-dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone, Helenalin A, (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
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.
Research
258 papers- Helenalin - A Sesquiterpene Lactone with Multidirectional Activity.Current drug targets · 2019
- Recent Patents on Anti-Cancer Potential of Helenalin.Recent patents on anti-cancer drug discovery · 2020
- Helenalin Facilitates Reactive Oxygen Species-Mediated Apoptosis and Cell Cycle Arrest by Targeting Thioredoxin Reductase-1 in Human Prostate Cancer Cells.Medical science monitor : international medical journal of experimental and clinical research · 2021
- In vitro metabolism of helenalin and its inhibitory effect on human cytochrome P450 activity.Archives of toxicology · 2022
- Helenalin Analogues Targeting NF-κB p65: Thiol Reactivity and Cellular Potency Studies of Varied Electrophiles.ChemMedChem · 2018
via PubMed
Wikidata facts
- Mass
- 262.121
Show 6 more facts
- chemical formula
- C₁₅H₁₈O₄
- isomeric SMILES
- C[C@@H]1C[C@@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)O)C(=C)C(=O)O2
- canonical SMILES
- CC1CC2C(C(C3(C1C=CC3=O)C)O)C(=C)C(=O)O2
- subject has role
- platelet aggregation inhibitors
- has characteristic
- bitterness
- Commons category
- Helenalin
Sources (2)
via Wikidata · CC0
~7 min read
Encyclopedic overview
9 sectionsContents
- Structure and reactivity
- Chemical derivatives
- Some biochemical effects of helenalin
- Metabolism
- ''In vitro'' anti-inflammatory and anti-neoplastic effects
- Application
- Toxicity
- Pharmacology
- 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.
== Structure and reactivity ==
Excerpted from Wikipedia’s “helenalin” article, available under the CC BY-SA 4.0 licence.