Parthenolide
| Parthenolide | |
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(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.- |
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| Identifiers | |
| CAS number | 20554-84-1  |
| PubChem | 5353864 |
| UNII | 2RDB26I5ZB  |
| ChEMBL | CHEMBL540445 |
| RTECS number | LY4220000 |
| Properties | |
| Molecular formula | C15H20O3 |
| Molar mass | 248.32 g mol−1 |
| Melting point |
113-115 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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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.
The plant is well known in natural medicine. Tablets and tinctures are used for the relief of migraine, to help prevent blood clots,[1] as an anti-inflammatory providing relief in cases of arthritis, to relieve some types of menstrual problems, and as a digestive aid. Parthenolide is the main active ingredient.
Many vendors of feverfew remedies specify the content of parthenolide in their products. Lack of solubility in water limits the benefits of parthenolide as a drug, and now motivates drug researchers to develop synthetic analogs that will be easier to absorb.
[edit] Biological activities
- It is a potential anticancer drug. It destroys acute myelogenous leukemia (AML) cells by inducing apoptosis, 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.[2] Parthenolide is under consideration as a potential cancer drug in combination with sulindac.
- Parthenolide is active against a parasite Leishmania amazonensis.[3]
- Microtubule-interfering activity of parthenolide.[4]
- Anti-inflammatory and anti-hyperalgesic effects of sesquiterpene lactones.[5]
- Parthenolide blocks lipopolysaccharide-induced osteolysis through the suppression of NF-κB activity.[6]
[edit] References
- ^ López-Franco, O; Hernández-Vargas, P; Ortiz-Muñoz, G; Sanjuán, G; Suzuki, Y; Ortega, L; Blanco, J; Egido, J et al (2006). "Parthenolide modulates the NF-kappaB-mediated inflammatory responses in experimental atherosclerosis". Arteriosclerosis, thrombosis, and vascular biology 26 (8): 1864–70. doi:10.1161/01.ATV.0000229659.94020.53. PMID 16741149.
- ^ Guzman, ML; Rossi, RM; Karnischky, L; Li, X; Peterson, DR; Howard, DS; Jordan, CT (2005). "The sesquiterpene lactone parthenolide induces apoptosis of human acute myelogenous leukemia stem and progenitor cells". Blood 105 (11): 4163–9. doi:10.1182/blood-2004-10-4135. PMC 1895029. PMID 15687234. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1895029.
- ^ Tiuman, TS; Ueda-Nakamura, T; Garcia Cortez, DA; Dias Filho, BP; Morgado-Díaz, JA; De Souza, W; Nakamura, CV (2005). "Antileishmanial Activity of Parthenolide, a Sesquiterpene Lactone Isolated from Tanacetum parthenium". Antimicrobial agents and chemotherapy 49 (1): 176–82. doi:10.1128/AAC.49.11.176-182.2005. PMC 538891. PMID 15616293. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=538891.
- ^ Miglietta, A; Bozzo, F; Gabriel, L; Bocca, C (2004). "Microtubule-interfering activity of parthenolide". Chemico-biological interactions 149 (2–3): 165–73. doi:10.1016/j.cbi.2004.07.005. PMID 15501437.
- ^ Feltenstein, MW; Schühly, W; Warnick, JE; Fischer, NH; Sufka, KJ (2004). "Anti-inflammatory and anti-hyperalgesic effects of sesquiterpene lactones from Magnolia and Bear's foot". Pharmacology, biochemistry, and behavior 79 (2): 299–302. doi:10.1016/j.pbb.2004.08.008. PMID 15501305.
- ^ Yip, KH; Zheng, MH; Feng, HT; Steer, JH; Joyce, DA; Xu, J (2004). "Sesquiterpene lactone parthenolide blocks lipopolysaccharide-induced osteolysis through the suppression of NF-kappaB activity". Journal of Bone and Mineral Research 19 (11): 1905–16. doi:10.1359/JBMR.040919. PMID 15476591.
[edit] External links
- Parthenolide from Fermentek, the source of the original content
- Orally bioavailable parthenolide analog eradicates leukemia stem cells Will Boggs, MD, Reuters Health, October 26, 2007
- Zunino, SJ; Ducore, JM; Storms, DH (2007). "Parthenolide induces significant apoptosis and production of reactive oxygen species in high-risk pre-B leukemia cells". Cancer letters 254 (1): 119–27. doi:10.1016/j.canlet.2007.03.002. PMID 17470383.
- Guzman, ML; Jordan, CT (2005). "Feverfew: weeding out the root of leukaemia". Expert opinion on biological therapy 5 (9): 1147–52. doi:10.1517/14712598.5.9.1147. PMID 16120045.
- Daisies lead scientists down path to new leukemia drug, 10-02-2007
- DNC NEWS: Feverfew, Stem cells and the treatment of Cancer, June 29, 2005
- Headache herb may boost cancer survival, Indiana University Research and Creative Activity, Fall 2006
