Parthenolide

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Parthenolide
Parthenolide.svg
Identifiers
CAS number 20554-84-1 YesY
PubChem 5420805
ChemSpider 20126246 N
UNII 2RDB26I5ZB N
ChEMBL CHEMBL540445 N
RTECS number LY4220000
Jmol-3D images Image 1
Properties
Molecular formula C15H20O3
Molar mass 248.32 g mol−1
Melting point 113 to 115 °C (235 to 239 °F; 386 to 388 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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 ailments. 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[edit]

Parthenolide has a variety of reported in vitro biological activities, including:

References[edit]

  1. ^ Parthenolide from Fermentek
  2. ^ Will Boggs. "Orally Bioavailable Parthenolide Analog Eradicates Leukemia Stem Cells". Reuters Health. 
  3. ^ López-Franco, O; Hernández-Vargas, P; Ortiz-Muñoz, G; Sanjuán, G; Suzuki, Y; Ortega, L; Blanco, J; Egido, J; Gómez-Guerrero, C (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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 

External links[edit]