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Celastrol

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Celastrol
Names
IUPAC name
3-Hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid
Other names
Tripterine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.266 Edit this at Wikidata
  • InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
    Key: KQJSQWZMSAGSHN-JJWQIEBTSA-N
  • InChI=1/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
    Key: KQJSQWZMSAGSHN-JJWQIEBTBS
  • CC1=C(C(=O)C=C2C1=CC=C3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@](CC5)(C)C(=O)O)C)C)C)C)O
Properties
C29H38O4
Molar mass 450.619 g·mol−1
Appearance Crystalline solid
Melting point 213 °C (415 °F; 486 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Celastrol (tripterine) is a chemical compound isolated from the root extracts of Tripterygium wilfordii (Thunder god vine) and Celastrus regelii. Celastrol is a pentacyclic triterpenoid and belongs to the family of quinone methides.

In in vitro and in vivo animal experiments, celastrol exhibits antioxidant,[2] anti-inflammatory,[3][4] anticancer,[5][6][7][8] and insecticidal [9] activities. It has been shown to have obesity-controlling effects in mice.[10]

References

  1. ^ Ryu, Y. B.; Park, S. J.; Kim, Y. M.; Lee, J. Y.; Seo, W. D.; Chang, J. S.; Park, K. H.; Rho, M. C.; Lee, W. S. (2010). "SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii". Bioorganic & Medicinal Chemistry Letters. 20 (6): 1873. doi:10.1016/j.bmcl.2010.01.152.
  2. ^ Allison, A. C.; Cacabelos, R.; Lombardi, V. R. M.; Alvarez, X. A.; Vigo, C. (2001). "Celastrol, a potent antioxidant and anti-inflammatory drug, as a possible treatment for Alzheimer's disease". Progress in Neuro-Psychopharmacology and Biological Psychiatry. 25 (7): 1341–1357. doi:10.1016/S0278-5846(01)00192-0. PMID 11513350.
  3. ^ Kim, D. H.; Shin, E. K.; Kim, Y. H.; Lee, B. W.; Jun, J. -G.; Park, J. H. Y.; Kim, J. -K. (2009). "Suppression of inflammatory responses by celastrol, a quinone methide triterpenoid isolated from Celastrus regelii". European Journal of Clinical Investigation. 39 (9): 819–827. doi:10.1111/j.1365-2362.2009.02186.x. PMID 19549173.
  4. ^ Venkatesha, S. H.; Yu, H.; Rajaiah, R.; Tong, L.; Moudgil, K. D. (2011). "Celastrus-derived Celastrol Suppresses Autoimmune Arthritis by Modulating Antigen-induced Cellular and Humoral Effector Responses". Journal of Biological Chemistry. 286 (17): 15138–15146. doi:10.1074/jbc.M111.226365. PMC 3083183. PMID 21402700.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  5. ^ Lee, J. H.; Choi, K. J.; Seo, W. D.; Jang, S. Y.; Kim, M.; Lee, B. W.; Kim, J. Y.; Kang, S.; Park, K. H.; Lee, Y. S.; Bae, S. (2011). "Enhancement of radiation sensitivity in lung cancer cells by celastrol is mediated by inhibition of Hsp90". International Journal of Molecular Medicine. 27 (3). doi:10.3892/ijmm.2011.601. PMID 21249311.
  6. ^ Tiedemann, R. E.; Schmidt, J.; Keats, J. J.; Shi, C. -X.; Zhu, Y. X.; Palmer, S. E.; Mao, X.; Schimmer, A. D.; Stewart, A. K. (2008). "Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF- B with antimyeloma activity in vitro and in vivo". Blood. 113 (17): 4027–4037. doi:10.1182/blood-2008-09-179796. PMID 19096011.
  7. ^ Zhu, H.; Liu, X. -W.; Cai, T. -Y.; Cao, J.; Tu, C. -X.; Lu, W.; He, Q. -J.; Yang, B. (2010). "Celastrol Acts as a Potent Antimetastatic Agent Targeting 1 Integrin and Inhibiting Cell-Extracellular Matrix Adhesion, in Part via the p38 Mitogen-Activated Protein Kinase Pathway". Journal of Pharmacology and Experimental Therapeutics. 334 (2): 489–499. doi:10.1124/jpet.110.165654. PMID 20472666.
  8. ^ Byun, J. -Y.; Kim, M. -J.; Eum, D. -Y.; Yoon, C. -H.; Seo, W. -D.; Park, K. H.; Hyun, J. -W.; Lee, Y. -S.; Lee, J. -S.; Yoon, M. -Y.; Lee, S. -J. (2009). "Reactive Oxygen Species-Dependent Activation of Bax and Poly(ADP-ribose) Polymerase-1 is Required for Mitochondrial Cell Death Induced by Triterpenoid Pristimerin in Human Cervical Cancer Cells". Molecular Pharmacology. 76 (4): 734–744. doi:10.1124/mol.109.056259. PMID 19574249.
  9. ^ Avilla, J. S.; Teixidò, A.; Velázquez, C.; Alvarenga, N.; Ferro, E.; Canela, R. (2000). "Insecticidal Activity of Maytenus Species (Celastraceae) Nortriterpene Quinone Methides against Codling Moth, Cydia pomonella (L.) (Lepidoptera: Tortricidae)". Journal of Agricultural and Food Chemistry. 48 (1): 88–92. doi:10.1021/jf990008w. PMID 10637057.
  10. ^ Liu, Junli; Lee, Jaemin; Salazar Hernandez, Mario Andres; Mazitschek, Ralph; Ozcan, Umut (May 2015). "Treatment of Obesity with Celastrol". Cell. 161 (5): 999–1011. doi:10.1016/j.cell.2015.05.011.
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