Tyrosyl-DNA Phosphodiesterase i Inhibitors from the Australian Plant Macropteranthes leichhardtii

Journal of Natural Products

Volumn 78, Issue 7, 2015, Pages 1756-1760

  Tian, Li Wen ^a,d   Feng, Yunjiang ^a   Tran, Trong D ^a   Shimizu, Yoko ^b   Pfeifer, Tom ^b   Forster, Paul I ^c   Quinn, Ronald J ^a  

^a GRIFFITH UNIVERSITY   (Australia)

^b Centre for Drug Research and Development   (Canada)

^c QUEENSLAND HERBARIUM   (Australia)

^d SOUTHERN MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

MACROPTERANTHES LEICCHARDTII EXTRACT; MACROPTERANTHOL; PHOSPHODIESTERASE INHIBITOR; PLANT EXTRACT; TYROSYL DNA PHOSPHODIESTERASE 1 INHIBITOR; UNCLASSIFIED DRUG; GLUCOSIDE; PHENYLPROPIONIC ACID DERIVATIVE; PHOSPHODIESTERASE; TYROSYL-DNA PHOSPHODIESTERASE;

ARTICLE; AUSTRALIA; DRUG ISOLATION; DRUG PURIFICATION; DRUG SCREENING; DRUG STRUCTURE; ENZYME INHIBITION; IC50; MACROPTERANTHES LEICHHARDTII; MASS SPECTROMETRY; MEDICINAL PLANT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; COMBRETACEAE; DRUG EFFECTS; ISOLATION AND PURIFICATION; STRUCTURE ACTIVITY RELATION;

AUSTRALIA; COMBRETACEAE; GLUCOSIDES; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHENYLPROPIONATES; PHOSPHODIESTERASE INHIBITORS; PHOSPHORIC DIESTER HYDROLASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84937784151     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00211     Document Type: Article

References (24)

1. Interthal, H.; Pouliot, J. J.; Champoux, J. J. Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 12009 10.1073/pnas.211429198
2. Debéthune, L.; Kohlhagen, G.; Grandas, A.; Pommier, Y. Nucleic Acids Res. 2002, 30, 1198 10.1093/nar/30.5.1198
3. Takashima, H.; Boerkoel, C. F.; John, J.; Saifi, G. M.; Salih, M. A. M.; Armstrong, D.; Mao, Y.; Quiocho, F. A.; Roa, B. B.; Nakagawa, M.; Stockton, D. W.; Lupski, J. R. Nat. Genet. 2002, 32, 267 10.1038/ng987
4. Hirano, R.; Interthal, H.; Huang, C.; Nakamura, T.; Deguchi, K.; Choi, K.; Bhattacharjee, M. B.; Arimura, K.; Umehara, F.; Izumo, S.; Northrop, J. L.; Salih, M. A. M.; Inoue, K.; Armstrong, D. L.; Champoux, J. J.; Takashima, H.; Boerkoel, C. F. EMBO J. 2007, 26, 4732 10.1038/sj.emboj.7601885
5. Katyal, S.; El-Khamisy, S. F.; Russell, H. R.; Li, Y.; Ju, L.; Caldecott, K. W.; McKinnon, P. J. EMBO J. 2007, 26, 4720 10.1038/sj.emboj.7601869
6. Das, B. B.; Antony, S.; Gupta, S.; Dexheimer, T. S.; Redon, C. E.; Garfield, S.; Shiloh, Y.; Pommier, Y. EMBO J. 2009, 28, 3667 10.1038/emboj.2009.302
7. Barthelmes, H. U.; Habermeyer, M.; Christensen, M. O.; Mielke, C.; Interthal, H.; Pouliot, J. J.; Boege, F.; Marko, D. J. Biol. Chem. 2004, 279, 55618 10.1074/jbc.M405042200
8. Ganesan, A. Curr. Opin. Chem. Biol. 2008, 12, 306 10.1016/j.cbpa.2008.03.016
9. Liao, Z.; Thibaut, L.; Jobson, A.; Pommier, Y. Mol. Pharmacol. 2006, 70, 366 10.1124/mol.105.021865
10. Sirivolu, V. R.; Vernekar, S. K. V.; Marchand, C.; Naumova, A.; Chergui, A.; Renaud, A.; Stephen, A. G.; Chen, F.; Sham, Y. Y.; Pommier, Y.; Wang, Z. J. Med. Chem. 2012, 55, 8671 10.1021/jm3008773
11. Wei, K.; Li, W.; Koike, K.; Liu, L.; Fu, X.; Lin, L.; Chen, Y.; Nikaido, T. Chem. Pharm. Bull. 2004, 52, 776 10.1248/cpb.52.776
12. Zhou, Y.; Chen, H.-b.; Wang, B.; Liang, H.; Zhao, Y.-y.; Zhang, Q.-y. Planta Med. 2011, 77, 1944 10.1055/s-0031-1280093
13. Zou, J.; Mi, Y.; Chen, W.; Liu, Q.; Wang, J.; Lou, L.; Zhao, W. Planta Med. 2006, 72, 533 10.1055/s-2006-931559
14. Kikuzaki, H.; Sato, A.; Mayahara, Y.; Nakatani, N. J. Nat. Prod. 2000, 63, 749 10.1021/np9906121
15. Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J.; Rosini, C. Org. Lett. 2002, 4, 4595 10.1021/ol0201714
16. Srebro, M.; Govind, N.; Autschbach, J.; de Jong, W. A. J. Phys. Chem. A 2011, 115, 10930 10.1021/jp2055409
17. Yang, X. W.; Peng, K.; Liu, Z.; Zhang, G. Y.; Li, J.; Wang, N.; Steinmetz, A.; Liu, Y. J. Nat. Prod. 2013, 76, 2360-2363 10.1021/np400923c
18. Leyte-Lugo, M.; Gonzáles-Andrade, M.; Gonzalez, M. D. C.; Glenn, A. E.; Cerda-Garcia-Rojas, C. M.; Mata, R. J. Nat. Prod. 2012, 75, 1571-1577 10.1021/np300327y
19. Nakahashi, A.; Yaguchi, Y.; Miura, N.; Emura, M.; Monde, K. J. Nat. Prod. 2011, 74, 707 10.1021/np1007763
20. Stephens, P. J.; Pan, J. J.; Devlin, F. J.; Cheeseman, J. R. J. Nat. Prod. 2008, 71, 285 10.1021/np070502r
21. Kikuzaki, H.; Hara, S.; Kawai, Y.; Nakatani, N. Phytochemistry 1999, 52, 1307 10.1016/S0031-9422(99)00406-9
22. Dean, R. A.; Fam, H. K.; An, J.; Choi, K.; Shimizu, Y.; Jones, S. J. M.; Boerkoel, C. F.; Interthal, H.; Pfeifer, T. A. J. Biomol. Screening 2014, 19, 1372-1382 10.1177/1087057114546551
23. MacroModel, Version 9.9 ed.; Schrödinger, LCC: New York, 2012.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; J. E, P.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; R. Cammi, C. P.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.