Parthenolide

Last updated
Parthenolide
Parthenolide.svg
Names
IUPAC name
(1aR,4E,7aS,10aS,10bR)-2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.220.558 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
RTECS number
  • LY4220000
UNII
  • InChI=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 X mark.svgN
    Key: KTEXNACQROZXEV-SLXBATTESA-N X mark.svgN
  • Key: KTEXNACQROZXEV-SLXBATTEBY
  • InChI=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
  • C/C/1=C\CC[C@@]2([C@@H](O2)[C@@H]3[C@@H](CC1)C(=C)C(=O)O3)C
Properties
C15H20O3
Molar mass 248.322 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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Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew ( Tanacetum parthenium ), after which it is named, and in the closely related tansy ( Tanacetum vulgare ). [1] It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available. [2] [3]

Lack of solubility in water and bioavailability limits the potential of parthenolide as a drug.

In vitro research

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

References

  1. ↑ Onozato, Thelma; Nakamura, Celso Vataru; Garcia Cortez, Diógenes Aparício; Dias Filho, Benedito Prado; Ueda-Nakamura, Tânia (2009). "Tanacetum vulgare: antiherpes virus activity of crude extract and the purified compound parthenolide". Phytother Res. 23 (6): 791–6. doi: 10.1002/ptr.2638 . PMID   19152371. S2CID   3547899.
  2. ↑ Quick, Andrew; Rogers, Donald (1976). "Crystal and molecular structure of parthenolide [4,5-epoxygermacra-1(10),11(13)-dien-12,6-olactone]" . Journal of the Chemical Society, Perkin Transactions 2 (4): 465. doi:10.1039/p29760000465. ISSN   0300-9580.
  3. ↑ Long, Jing; Ding, Ya-Hui; Wang, Pan-Pan; Zhang, Quan; Chen, Yue (2013-10-18). "Protection-Group-Free Semisyntheses of Parthenolide and Its Cyclopropyl Analogue" . The Journal of Organic Chemistry. 78 (20): 10512–10518. doi:10.1021/jo401606q. ISSN   0022-3263. PMID   24047483.
  4. ↑ Rajendran P, Ho E, Williams DE, Dashwood RH (2011). "Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells". Clinical Epigenetics. 3 (1): 4. doi: 10.1186/1868-7083-3-4 . PMC   3255482 . PMID   22247744.
  5. ↑ López-Franco O, Hernández-Vargas P, Ortiz-Muñoz G, Sanjuán G, Suzuki Y, Ortega L, Blanco J, Egido J, Gómez-Guerrero C (August 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.
  6. ↑ Guzman ML, Rossi RM, Karnischky L, Li X, Peterson DR, Howard DS, Jordan CT (June 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.
  7. ↑ Tiuman TS, Ueda-Nakamura T, Garcia Cortez DA, Dias Filho BP, Morgado-Díaz JA, de Souza W, Nakamura CV (January 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.
  8. ↑ Miglietta A, Bozzo F, Gabriel L, Bocca C (October 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. ↑ 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. Bibcode:2013PLoSO...863354S. doi: 10.1371/journal.pone.0063354 . PMC   3653934 . PMID   23691032.
  10. ↑ Duan D, Zhang J, Yao J, Liu Y, Fang J (May 2016). "Targeting Thioredoxin Reductase by Parthenolide Contributes to Inducing Apoptosis of HeLa Cells". The Journal of Biological Chemistry. 291 (19): 10021–31. doi: 10.1074/jbc.M115.700591 . PMC   4858956 . PMID   27002142.
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