Quinofuracins A-E, produced by the fungus staphylotrichum boninense PF1444, show p53-dependent growth suppression

Journal of Natural Products

Volumn 78, Issue 2, 2015, Pages 188-195

  Tatsuda, Daisuke ^a   Momose, Isao ^a   Someno, Tetsuya ^a   Sawa, Ryuichi ^b   Kubota, Yumiko ^b   Iijima, Masatomi ^a   Kunisada, Takao ^c   Watanabe, Takumi ^b   Shibasaki, Masakatsu ^b   Nomoto, Akio ^a,b  

^a Institute of Microbial Chemistry (BIKAKEN) Numazu   (Japan)

^b INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

^c MEIJI SEIKA KAISHA LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGLYCONE; ANTHRAQUINONE DERIVATIVE; CARBENE; CARBONYL DERIVATIVE; FUNGAL EXTRACT; NUTLIN 3; PROTEIN P53; PROTON; QUINOFURACIN A; QUINOFURACIN B; QUINOFURACIN C; QUINOFURACIN D; QUINOFURACIN E; UNCLASSIFIED DRUG; 5'-OXOAVERANTIN; ANTINEOPLASTIC AGENT; VERSICOLORIN C;

ARTICLE; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL DEATH; CELL VIABILITY; CIRCULAR DICHROISM; CYTOTOXICITY; DRUG STRUCTURE; FUNGAL STRAIN; FUNGUS; GLIOBLASTOMA CELL LINE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HUMAN; HUMAN CELL; IC50; METHANOLYSIS; MTT ASSAY; NUCLEAR OVERHAUSER EFFECT; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOTRICHUM BONINENSE; WILD TYPE; ASCOMYCETES; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; GLIOBLASTOMA; ISOLATION AND PURIFICATION; JAPAN; METABOLISM; NUCLEAR MAGNETIC RESONANCE;

FUNGI;

ANTHRAQUINONES; ANTINEOPLASTIC AGENTS; ASCOMYCOTA; CELL DEATH; DRUG SCREENING ASSAYS, ANTITUMOR; GLIOBLASTOMA; HUMANS; JAPAN; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; TUMOR SUPPRESSOR PROTEIN P53;

EID: 84924057533     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np500581m     Document Type: Article

References (30)

1. Zhao, Y.; Bernard, D.; Wang, S. BioDiscovery 2013, 8, 1-15
2. Meek, D. W. Nat. Rev. Cancer 2009, 9, 714-723
3. Vassilev, L. T.; Vu, B. T.; Graves, B.; Carvajal, D.; Podlaski, F.; Filipovic, Z.; Kong, N.; Kammlott, U.; Lukacs, C.; Klein, C.; Fotouhi, N.; Liu, E. A. Science 2004, 303, 844-848
4. Ding, Q.; Zhang, Z.; Liu, J. J.; Jiang, N.; Zhang, J.; Ross, T. M.; Chu, X. J.; Bartkovitz, D.; Podlaski, F.; Janson, C.; Tovar, C.; Filipovic, Z. M.; Higgins, B.; Glenn, K.; Packman, K.; Vassilev, L. T.; Graves, B. J. Med. Chem. 2013, 56, 5979-5983
5. Tovar, C.; Graves, B.; Packman, K.; Filipovic, Z.; Higgins, B.; Xia, M.; Tardell, C.; Garrido, R.; Lee, E.; Kolinsky, K.; To, K. H.; Linn, M.; Podlaski, F.; Wovkulich, P.; Vu, B.; Vassilev, L. T. Cancer Res. 2013, 73, 2587-2597
6. Rew, Y.; Sun, D.; Gonzalez-Lopez De Turiso, F.; Bartberger, M. D.; Beck, H. P.; Canon, J.; Chen, A.; Chow, D.; Deignan, J.; Fox, B. M.; Gustin, D.; Huang, X.; Jiang, M.; Jiao, X.; Jin, L.; Kayser, F.; Kopecky, D. J.; Li, Y.; Lo, M. C.; Long, A. M.; Michelsen, K.; Oliner, J. D.; Osgood, T.; Ragains, M.; Saiki, A. Y.; Schneider, S.; Toteva, M.; Yakowec, P.; Yan, X.; Ye, Q.; Yu, D.; Zhao, X.; Zhou, J.; Medina, J. C.; Olson, S. H. J. Med. Chem. 2012, 55, 4936-4954
7. Yu, S.; Qin, D.; Shangary, S.; Chen, J.; Wang, G.; Ding, K.; McEachern, D.; Qiu, S.; Nikolovska-Coleska, Z.; Miller, R.; Kang, S.; Yang, D.; Wang, S. J. Med. Chem. 2009, 52, 7970-7973
8. Kojima, K.; Burks, J. K.; Arts, J.; Andreeff, M. Mol. Cancer Ther. 2010, 9, 2545-2557
9. Tabernero, J.; Dirix, L.; Schoffski, P.; Cervantes, A.; Lopez-Martin, J. A.; Capdevila, J.; van Beijsterveldt, L.; Platero, S.; Hall, B.; Yuan, Z.; Knoblauch, R.; Zhuang, S. H. Clin. Cancer Res. 2011, 17, 6313-6321
10. Van Meir, E. G.; Polverini, P. J.; Chazin, V. R.; Su Huang, H. J.; de Tribolet, N.; Cavenee, W. K. Nat. Genet. 1994, 8, 171-176
11. Birkinshaw, J. H.; Roberts, J. C.; Roffey, P. J. Chem. Soc. C 1966, 9, 855-857
12. Sakuno, E.; Yabe, K.; Nakajima, H. Appl. Environ. Microbiol. 2003, 69, 6418-6426
13. Sakuno, E.; Wen, Y.; Hatabayashi, H.; Arai, H.; Aoki, C.; Yabe, K.; Nakajima, H. Appl. Environ. Microbiol. 2005, 71, 2999-3006
14. Gorst-Allman, C. P.; Pachler, K. G. R.; Steyn, P. S.; Wessels, P. L.; Scott, D. B. J. Chem. Soc., Perkin Trans. 1 1977, 2181-2188
15. Castonguay, A.; Brassard, P. Can. J. Chem. 1977, 55, 1324-1332
16. Yabe, K.; Matsuyama, Y.; Ando, Y.; Nakajima, H.; Hamasaki, T. Appl. Environ. Microbiol. 1993, 59, 2486-2492
17. Padron, J. I.; Morales, E. Q.; Vázquez, J. T. J. Org. Chem. 1998, 63, 8247-8258
18. Yasuzawa, T.; Saitoh, Y.; Sano, H. J. Antibiot. 1990, 43, 336-343
19. Gorin, P. A. J.; Mazurek, M. Can. J. Chem. 1975, 53, 1212-1223
20. Ritchie, R. G. S.; Cry, N.; Korsch, B.; Koch, H. J.; Perlin, A. S. Can. J. Chem. 1975, 53, 1424-1433
21. Richards, M. R.; Bai, Y.; Lowary, T. L. Carbohydr. Res. 2013, 374, 103-114
22. Huang, H.; Wang, F.; Luo, M.; Chen, Y.; Song, Y.; Zhang, W.; Zhang, S.; Ju, J. J. Nat. Prod. 2012, 75, 1346-1352
23. Hamasaki, T.; Hatsuda, Y.; Terashima, N.; Renbutsu, M. Agric. Biol. Chem. 1965, 29, 166-167
24. Yabe, K.; Hamasaki, T. Appl. Environ. Microbiol. 1993, 59, 2493-2500
25. Nonaka, K.; Iwatsuki, M.; Shiomi, K.; Omura; Masuma, R.; Miyazaki, H.; Tomoda, H. Mycoscience 2012, 53, 312-318
26. Yabe, K.; Nakajima, H. Food Hyg. Saf. Sci. 2011, 52, 135-147
27. Kornsakulkarn, J.; Saepua, S.; Srichomthong, K.; Supothina, S.; Thongpanchang, C. Tetrahedron 2012, 68, 8480-8486
28. Running, E. W. J. Chem. Inf. Comput. Sci. 1993, 33, 934-935
29. Ayer, A. W.; Kawahara, N. Tetrahedron Lett. 1995, 36, 7953-7956
30. Magome, E.; Harimaya, K.; Gomi, S.; Koyama, M.; Chiba, N.; Ota, K.; Mikawa, T. J. Antibiot. 1996, 49, 599-602