Contribution of cage-shaped structure of physalins to their mode of action in inhibition of NF-κB activation

ACS Medicinal Chemistry Letters

Volumn 4, Issue 8, 2013, Pages 730-735

  Ozawa, Masaaki ^a,b   Morita, Masaki ^a,c   Hirai, Go ^a,b   Tamura, Satoru ^a,d   Kawai, Masao ^e,f   Tsuchiya, Ayako ^a   Oonuma, Kana ^a,b   Maruoka, Keiji ^c   Sodeoka, Mikiko ^a,b,d  

^a RIKEN   (Japan)

^b RIKEN Center for Sustainable Resource Science   (Japan)

^c KYOTO UNIVERSITY   (Japan)

^d JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^e NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

^f National Museum of Nature and Science   (Japan)

Author keywords

highly oxygenated steroid; NF B; physalin; Physalis plants; SAR; synthetic analogues; withanolide

Indexed keywords

ANTIINFLAMMATORY AGENT; DIMER; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; PHYSALIN A; PHYSALIN B; PHYSALIN C; PHYSALIN F; PHYSALIN G; PHYSALIN N; PHYSALIN O; STEROID; TRANSCRIPTION FACTOR RELA; UNCLASSIFIED DRUG; WITHANOLIDE;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; DNA BINDING; DRUG CYTOTOXICITY; ENZYME ACTIVATION; ENZYME DEGRADATION; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; NONHUMAN; OLEFINATION; OXYGENATION; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

PHYSALIS;

EID: 84881433683     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400144e     Document Type: Article

References (22)

1. Matsuura, T.; Kawai, M. Bitter principles of Physalis alkekengi var. francheti: structure of physalin B Tetrahedron Lett. 1969, 10, 1765-1766
2. Makino, B.; Kawai, M.; Yamamura, H.; Araki, S.; Butsugan, Y. Tautomerism between exomethylene type physalins and oxymethylene-bridged physalins Pharmazie 2002, 57, 215-216
3. Antoun, M. D.; Abramson, D.; Tyson, R. L.; Chang, C. J.; McLaughlin, J. L.; Peck, G.; Cassady, J. M. Potential antitumor agents. XVII. Physalin B and 25,26-epidihydrophysalin C from Witheringia coccoloboides J. Nat. Prod. 1981, 44, 579-585
4. Damu, A. G.; Kuo, P. C.; Su, C. R.; Kuo, T. H.; Chen, T. H.; Bastow, K. F.; Lee, K. H.; Wu, T. S. Isolation, structures, and structure-cytotoxic activity relationships of withanolides and physalins from Physalis angulata J. Nat. Prod. 2007, 70, 1146-1152
5. Vieira, A. T.; Pinho, V.; Lepsch, L. B.; Scavone, C.; Ribeiro, I. M.; Tomassini, T.; Ribeiro-dos-Santos, R.; Soares, M. B. P.; Teixeira, M. M.; Souza, D. G. Mechanism of the anti-inflammatory effects of the natural secosteroids physalins in a model of intestinal ischaemia and reperfusion injury Br. J. Pharmacol. 2005, 146, 244-251
6. Jacobo-Herrera, N. J.; Bremner, P.; Márquez, N.; Gupta, M. P.; Gibbons, S.; Muñoz, E.; Heinrich, M. Physalins from Witheringia solanacea as modulators of the NF-κB cascade J. Nat. Prod. 2006, 69, 328-331
7. Wu, S. Y.; Leu, Y. L.; Chang, Y. L.; Wu, T. S.; Kuo, P. C.; Liao, Y. R.; Teng, C. M.; Pan, S. L. Physalin F induces cell apoptosis in human renal carcinoma cells by targeting NF-kappaB and generating reactive oxygen species PLoS One 2012, 7, e40727
8. Hosoya, T.; Arai, M. A.; Koyano, T.; Kowithayakorn, T.; Ishibashi, M. Naturally occurring small-molecule inhibitors of Hedgehog/GLI-mediated transcription ChemBioChem 2008, 9, 1082-1092
9. Vandenberghe, I.; Créancier, L.; Vispé, S.; Annereau, J. P.; Barret, J. M.; Pouny, I.; Samson, A.; Aussagues, Y.; Massiot, G.; Ausseil, F.; Bailly, C.; Kruczynski, A.; Physalin, B. A novel inhibitor of the ubiquitin-proteasome pathway, triggers NOXA-associated apoptosis Biochem. Pharmacol. 2008, 76, 453-462
10. Kawai, M.; Makino, B.; Yamamura, H.; Araki, S.; Butsugan, Y.; Ohya, J. Cytotoxic activity of physalins and related compounds against HeLa cells Pharmazie 2002, 57, 348-350
11. Ohkubo, M.; Hirai, G.; Sodeoka, M. Synthesis of DFGH ring system of type B physalins: highly oxygenated, cage-shaped molecules Angew. Chem., Int. Ed. 2009, 48, 3862-3866
12. Morita, M.; Hirai, G.; Ohkubo, M.; Koshino, H.; Hashizume, D.; Maruoka, K.; Sodeoka, M. Kinetically controlled one-pot formation of DEFGH-rings of type B physalins through domino-type transformations Org. Lett. 2012, 14, 3434-3437
13. Hoffmann, A.; Baltimore, D. Circuitry of nuclear factor κB signaling Immunol. Rev. 2006, 210, 171-186
14. Fang, S. T.; Liu, J. K.; Li, B. Ten new withanolides from Physalis peruviana Steroids 2012, 77, 36-44
15. Hayden, M. S.; Ghosh, S. Shared principles in NF-κB signaling Cell 2008, 132, 344-362
16. Karin, M.; Ben-Neriah, Y. Phosphorylation meets ubiquitination: the control of NF-κB activity Annu. Rev. Immunol. 2000, 18, 621-663
17. Huang, B.; Yang, X. D.; Lamb, A.; Chen, L. F. Posttranslational modifications of NF-κB: another layer of regulation for NF-κB signaling pathway Cell Signaling 2010, 22, 1282-1290
18. Ji, L.; Yuan, Y.; Luo, L.; Chen, Z.; Ma, X.; Ma, Z.; Cheng, L. Physalins with anti-inflammatory activity are present in Physalis alkekengi var. franchetii and can function as Michael reaction acceptors Steroids 2012, 77, 441-447
19. Vanden Berghe, W.; Sabbe, L.; Kaileh, M.; Haegeman, G.; Heyninck, K. Molecular insight in the multifunctional activities of Withaferin A Biochem. Pharmacol. 2012, 84, 1282-1291
20. Kaileh, M.; Vanden Berghe, W.; Heyerick, A.; Horion, J.; Piette, J.; Libert, C.; De Keukeleire, D.; Essawi, T.; Haegeman, G. Withaferin A strongly elicits IκB kinase β hyperphosphorylation concomitant with potent inhibition of its kinase activity J. Biol. Chem. 2007, 282, 4253-4264
21. Grover, A.; Shandilya, A.; Punetha, A.; Bisaria, V. S.; Sundar, D. Inhibition of the NEMO/IKKβ association complex formation, a novel mechanism associated with the NF-κB activation suppression by Withania somnifera's key metabolite withaferin A BMC Genomics 2010, 11, S25
22. Falsey, R. R.; Marron, M. T.; Gunaherath, G. M.; Shirahatti, N.; Mahadevan, D.; Gunatilaka, A. A.; Whitesell, L. Actin microfilament aggregation induced by withaferin A is mediated by annexin II Nat. Chem. Biol. 2006, 2, 33-38