Parthenolide

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Parthenolide
Parthenolide.svg
Names
IUPAC name
(3aS,9aR,10aS,10bS,E)-6,9a-dimethyl-3-methylene-3a,4,5,8,9,9a,10a,10b-octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-2(3H)-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.220.558
RTECS number LY4220000
UNII
Properties
C15H20O3
Molar mass 248.32 g·mol−1
Melting point 113 to 115 °C (235 to 239 °F; 386 to 388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.

Applications[edit]

Lack of solubility in water and bioavailability limits the potential of parthenolide as a drug, however synthetic analogs may be developed that could be absorbed to a more useful extent,[1] the feverfew plant is used in herbalism for a variety of aliments. Some vendors specify the content of parthenolide in their products, believing it to be the primary constituent responsible for its activity.[2]

In vitro biological activities[edit]

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

References[edit]

  1. ^ Will Boggs. "Orally Bioavailable Parthenolide Analog Eradicates Leukemia Stem Cells". Reuters Health. 
  2. ^ Parthenolide from Fermentek
  3. ^ Rajendran, P; Ho, E; Williams, DE; Dashwood, RH (2011). "Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells". Clin Epigenetics. 3: 4. doi:10.1186/1868-7083-3-4. PMC 3255482Freely accessible. PMID 22247744. 
  4. ^ 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. 
  5. ^ Gobrecht, P.; Andreadaki, A.; Diekmann, H.; Heskamp, A.; Leibinger, M.; Fischer, D. (6 April 2016). "Promotion of Functional Nerve Regeneration by Inhibition of Microtubule Detyrosination". Journal of Neuroscience. 36 (14): 3890–3902. doi:10.1523/JNEUROSCI.4486-15.2016. PMID 27053198. 
  6. ^ 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 1895029Freely accessible. PMID 15687234. 
  7. ^ 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 538891Freely accessible. PMID 15616293. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ 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. 
  11. ^ 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. 
  12. ^ Hartman, M. L.; Talar, B.; Sztiller-Sikorska, M.; Nejc, D.; Czyz, M. (2016). "Parthenolide induces MITF-M downregulation and senescence in patient-derived MITF-Mhigh melanoma cell populations". Oncotarget. 7 (8): 9026–9040. doi:10.18632/oncotarget.7030. 
  13. ^ Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z (2013). "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLoS ONE. 8 (5): e63354. doi:10.1371/journal.pone.0063354. PMC 3653934Freely accessible. PMID 23691032. 

External links[edit]

  1. ^ Gobrecht, P.; Andreadaki, A.; Diekmann, H.; Heskamp, A.; Leibinger, M.; Fischer, D. (6 April 2016). "Promotion of Functional Nerve Regeneration by Inhibition of Microtubule Detyrosination". Journal of Neuroscience. 36 (14): 3890–3902. doi:10.1523/JNEUROSCI.4486-15.2016. PMID 27053198.