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词条 Parthenolide
释义

  1. Applications

  2. In vitro biological activities

  3. References

  4. External links

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 409336852
| ImageFile = Parthenolide.svg
| IUPACName = (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
|Section1={{Chembox Identifiers
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| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 20554-84-1
| EINECS =
| PubChem = 5420805
| RTECS = LY4220000
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 2RDB26I5ZB
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| ChEBI_Ref = {{ebicite|correct|EBI}}
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| ChEMBL = 540445
| KEGG_Ref = {{keggcite|correct|kegg}}
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 20126246
| SMILES = C/C/1=C\\CC[C@@]2([C@@H](O2)[C@@H]3[C@@H](CC1)C(=C)C(=O)O3)C
| InChI2 = 1/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1
| InChIKey = KTEXNACQROZXEV-SLXBATTEBY
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = KTEXNACQROZXEV-SLXBATTESA-N}}
|Section2={{Chembox Properties
| C=15|H=20|O=3
| Appearance =
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| MeltingPtC = 113 to 115
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|Section9={{Chembox Related
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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

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.{{mcn|date=April 2018}} 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.{{citation needed|date=April 2018}}

In vitro biological activities

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

  • Inhibition HDAC1 protein without affecting other class I/II HDACs, which leads to sustained DNA damage response in certain cells (required for apoptosis).[1]
  • Modulation of the NF-κB-mediated inflammatory responses in experimental atherosclerosis.[2]
  • intraneural or systemic application promotes axon regeneration in the peripheral nervous system [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]
  • Activity against 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 induces MITF M isoform downregulation and senescence in MITF-Mhigh melanoma cells[10]
  • Agonist of the adiponectin receptor 2 (AdipoR2).[11]
  • Inhibition of mammalian thioredoxin reductase [12]

References

1. ^{{cite journal | vauthors = Rajendran P, Ho E, Williams DE, Dashwood RH | title = Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells | journal = Clinical Epigenetics | volume = 3 | issue = 1 | pages = 4 | year = 2011 | pmid = 22247744 | pmc = 3255482 | doi = 10.1186/1868-7083-3-4 }}
2. ^{{cite journal | vauthors = López-Franco O, Hernández-Vargas P, Ortiz-Muñoz G, Sanjuán G, Suzuki Y, Ortega L, Blanco J, Egido J, Gómez-Guerrero C | title = Parthenolide modulates the NF-kappaB-mediated inflammatory responses in experimental atherosclerosis | journal = Arteriosclerosis, Thrombosis, and Vascular Biology | volume = 26 | issue = 8 | pages = 1864–70 | date = August 2006 | pmid = 16741149 | doi = 10.1161/01.ATV.0000229659.94020.53 }}
3. ^{{cite journal | vauthors = Gobrecht P, Andreadaki A, Diekmann H, Heskamp A, Leibinger M, Fischer D | title = Promotion of Functional Nerve Regeneration by Inhibition of Microtubule Detyrosination | journal = The Journal of Neuroscience | volume = 36 | issue = 14 | pages = 3890–902 | date = April 2016 | pmid = 27053198 | doi = 10.1523/JNEUROSCI.4486-15.2016 }}
4. ^{{cite journal | vauthors = Guzman ML, Rossi RM, Karnischky L, Li X, Peterson DR, Howard DS, Jordan CT | title = The sesquiterpene lactone parthenolide induces apoptosis of human acute myelogenous leukemia stem and progenitor cells | journal = Blood | volume = 105 | issue = 11 | pages = 4163–9 | date = June 2005 | pmid = 15687234 | pmc = 1895029 | doi = 10.1182/blood-2004-10-4135 }}
5. ^{{cite journal | vauthors = Tiuman TS, Ueda-Nakamura T, Garcia Cortez DA, Dias Filho BP, Morgado-Díaz JA, de Souza W, Nakamura CV | title = Antileishmanial activity of parthenolide, a sesquiterpene lactone isolated from Tanacetum parthenium | journal = Antimicrobial Agents and Chemotherapy | volume = 49 | issue = 1 | pages = 176–82 | date = January 2005 | pmid = 15616293 | pmc = 538891 | doi = 10.1128/AAC.49.11.176-182.2005 }}
6. ^{{cite journal | vauthors = Miglietta A, Bozzo F, Gabriel L, Bocca C | title = Microtubule-interfering activity of parthenolide | journal = Chemico-Biological Interactions | volume = 149 | issue = 2-3 | pages = 165–73 | date = October 2004 | pmid = 15501437 | doi = 10.1016/j.cbi.2004.07.005 }}
7. ^{{cite journal | vauthors = Feltenstein MW, Schühly W, Warnick JE, Fischer NH, Sufka KJ | title = Anti-inflammatory and anti-hyperalgesic effects of sesquiterpene lactones from Magnolia and Bear's foot | journal = Pharmacology Biochemistry and Behavior | volume = 79 | issue = 2 | pages = 299–302 | date = October 2004 | pmid = 15501305 | doi = 10.1016/j.pbb.2004.08.008 }}
8. ^{{cite journal | vauthors = Yip KH, Zheng MH, Feng HT, Steer JH, Joyce DA, Xu J | title = Sesquiterpene lactone parthenolide blocks lipopolysaccharide-induced osteolysis through the suppression of NF-kappaB activity | journal = Journal of Bone and Mineral Research | volume = 19 | issue = 11 | pages = 1905–16 | date = November 2004 | pmid = 15476591 | doi = 10.1359/JBMR.040919 }}
9. ^{{cite journal | vauthors = Zunino SJ, Ducore JM, Storms DH | title = Parthenolide induces significant apoptosis and production of reactive oxygen species in high-risk pre-B leukemia cells | journal = Cancer Letters | volume = 254 | issue = 1 | pages = 119–27 | date = August 2007 | pmid = 17470383 | doi = 10.1016/j.canlet.2007.03.002 }}
10. ^{{cite journal | vauthors = Hartman ML, Talar B, Sztiller-Sikorska M, Nejc D, Czyz M | title = Parthenolide induces MITF-M downregulation and senescence in patient-derived MITF-M(high) melanoma cell populations | journal = Oncotarget | volume = 7 | issue = 8 | pages = 9026–40 | date = February 2016 | pmid = 26824319 | pmc = 4891023 | doi = 10.18632/oncotarget.7030 }}
11. ^{{cite journal | vauthors = Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z | title = Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay | journal = PLOS One | volume = 8 | issue = 5 | pages = e63354 | year = 2013 | pmid = 23691032 | pmc = 3653934 | doi = 10.1371/journal.pone.0063354 }}
12. ^{{cite journal | vauthors = Duan D, Zhang J, Yao J, Liu Y, Fang J | title = Targeting Thioredoxin Reductase by Parthenolide Contributes to Inducing Apoptosis of HeLa Cells | journal = The Journal of Biological Chemistry | volume = 291 | issue = 19 | pages = 10021–31 | date = May 2016 | pmid = 27002142 | pmc = 4858956 | doi = 10.1074/jbc.M115.700591 }}

External links

  • {{cite journal | vauthors = Guzman ML, Jordan CT | title = Feverfew: weeding out the root of leukaemia | journal = Expert Opinion on Biological Therapy | volume = 5 | issue = 9 | pages = 1147–52 | date = September 2005 | pmid = 16120045 | doi = 10.1517/14712598.5.9.1147 }}
{{HDAC inhibitors}}{{Signaling peptide/protein receptor modulators}}

5 : Adiponectin receptor agonists|Epoxides|Histone deacetylase inhibitors|Sesquiterpene lactones|Oxygen heterocycles
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