Parthenolide
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| Names | |
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| IUPAC name
(1aR,7aS,10aS,10bS)-1a,5-dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
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| Other names
4xi-Germacra-1(10), 11(13)-dien-12-oic acid, 4,5-epoxy-6.alpha.-
hydroxy-, gamma-lactone |
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| Identifiers | |
20554-84-1  |
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| ChEMBL | ChEMBL540445  |
| ChemSpider | 20126246 |
| Jmol 3D model | Interactive image |
| PubChem | 5420805 |
| RTECS number | LY4220000 |
| UNII | 2RDB26I5ZB |
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| Properties | |
| C15H20O3 | |
| Molar mass | 248.32 g·mol−1 |
| Melting point | 113 to 115 °C (235 to 239 °F; 386 to 388 K) |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named. It is found in highest concentration in the flowers and fruit. Feverfew is used in herbalism and is purportedly useful for a variety of aliments. Many vendors of feverfew remedies specify the content of parthenolide in their products, because it is believed to be the primary chemical constituent responsible for biological activity.[1]
Lack of solubility in water and bioavailability limits the potential of parthenolide as a drug. Drug researchers are trying to develop synthetic analogs instead that will be absorbed to a more useful extent.[2]
In vitro biological activities
Parthenolide has a variety of reported in vitro biological activities, including:
- Modulation of the NF-κB-mediated inflammatory responses in experimental atherosclerosis.[3]
- Inducing apoptosis in acute myelogenous leukemia (AML) cells, leaving normal bone marrow cells relatively unscathed. Moreover, the compound may get at the root of the disease because it also kills stem cells that give rise to AML.[4] Parthenolide is under consideration as a potential cancer drug in combination with sulindac.[citation needed]
- Activity against a parasite Leishmania amazonensis.[5]
- Microtubule-interfering activity.[6]
- Anti-inflammatory and anti-hyperalgesic effects.[7]
- Blocking lipopolysaccharide-induced osteolysis through the suppression of NF-κB activity.[8]
- inducing apoptosis and production of reactive oxygen species in high-risk pre-B leukemia cells.[9]
Parthenolide has been found to act as an agonist of the adiponectin receptor 2 (AdipoR2).[10]
References
- ↑ Parthenolide from Fermentek
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External links
- Lua error in package.lua at line 80: module 'strict' not found.
- Headache herb may boost cancer survival, Indiana University Research and Creative Activity, Fall 2006
