Parthenolide

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ImageFile = Parthenolide.svg
IUPACName = (1a"R",7a"S",10a"S")- 1a,5-dimethyl-8-methylene- 2,3,6,7,7a,8,10a,10b- octahydrooxireno [9,10] cyclodeca [1,2-b] furan-9(1a"H")-one
OtherNames = 4xi-Germacra-1(10), 11(13)-dien-12-oic acid, 4,5-epoxy-6.alpha.-
hydroxy-, gamma-lactone
Formula = C₁₅H₂₀O₃
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CASNo = 20554-84-1
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PubChem = 5353864
RTECS = LY4220000
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MolarMass = 248.317 g/mol
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OtherCpds = "Parthenolide" is a sesquiterpene lactone 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 [http://www.ncbi.nlm.nih.gov/pubmed/16741149] , 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.

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. [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. PMID 15687234. [http://www.bloodjournal.org/cgi/content/full/105/11/4163 Free full text] .] Parthenolide is under consideration as a potential cancer drug in combination with sulindac.
*Parthenolide is active against a parasite "Leishmania amazonensis". [Tiuman TS, Ueda-Nakamura T, Garcia Cortez DA, Dias Filho BP, Morgado-Diaz JA, de Souza W, Nakamura CV (2005). "Antileishmanial activity of parthenolide, a sesquiterpene lactone isolated from Tanacetum parthenium." "Antimicrob Agents Chemother" 49 (1): 176–82. PMID 15616293. PMC|538891.]
*Microtubule-interfering activity of parthenolide. [Miglietta A, Bozzo F, Gabriel L, Bocca C (2004). "Microtubule-interfering activity of parthenolide". "Chem Biol Interact" 149 (2-3): 165–73. PMID 15501437.]
*Anti-inflammatory and anti-hyperalgesic effects of sesquiterpene lactones. [Feltenstein MW, Schuhly W, Warnick JE, Fischer NH, Sufka KJ (2004). "Anti-inflammatory and anti-hyperalgesic effects of sesquiterpene lactones". "Pharmacol Biochem Behav" 79 (2): 299–302. PMID 15501305.]
*Parthenolide blocks lipopolysaccharide-induced osteolysis through the suppression of NF-κB activity. [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". "J Bone Miner Res" 19 (11): 1905–16. PMID 15476591.]

References

External links

* [http://www.fermentek.co.il/parthenolide.htm Parthenolide ] from Fermentek, the source of the original content
* [http://oncolink.upenn.edu/resources/article.cfm?c=3&s=8&ss=23&Year=2007&Month=10&id=14709 Orally bioavailable parthenolide analog eradicates leukemia stem cells] Will Boggs, MD, Reuters Health, October 26, 2007
* [http://www.ars.usda.gov/research/publications/Publications.htm?seq_no_115=189696 Parthenolide induces significant apoptosis and production of reactive oxygen species in high-risk pre-b leukemia cells] . 2007 Cancer Letters 254: 119-127., Zunino, S.J., Ducore, J.H., Storms, D.H.
* [http://www.expertopin.com/doi/abs/10.1517/14712598.5.9.1147?cookieSet=1&journalCode=ebt Feverfew: weeding out the root of leukaemia] , Monica L Guzman & Craig T Jordan, University of Rochester Medical Center; Expert Opinion on Biological Therapy, September 2005, Vol. 5, No. 9, Pages 1147-1152 (doi:10.1517/14712598.5.9.1147)
* [http://www.rockymountainbmt.com/news/Daisies-lead-scientists-down-path-to-new-leukemia-drug-17689.html Daisies lead scientists down path to new leukemia drug] , 10-02-2007
* [http://www.denvernaturopathic.com/news/feverfew.html DNC NEWS: Feverfew, Stem cells and the treatment of Cancer] , June 29, 2005
* [http://www.indiana.edu/~rcapub/v29n1/herb.shtml Headache herb may boost cancer survival] , Indiana University Research and Creative Activity, Fall 2006