Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships

Journal of Natural Products

Volumn 74, Issue 5, 2011, Pages 1126-1131

  Ayers, Sloan ^a   Graf, Tyler N ^a   Adcock, Audrey F ^b   Kroll, David J ^b   Matthew, Susan ^c   Carcache De Blanco, Esperanza J ^c   Shen, Qi ^d   Swanson, Steven M ^d   Wani, Mansukh C ^e   Pearce, Cedric J ^f   Oberlies, Nicholas H ^a  

^a UNIVERSITY OF NORTH CAROLINA AT GREENSBORO   (United States)

^b NORTH CAROLINA CENTRAL UNIVERSITY   (United States)

^c OHIO STATE UNIVERSITY   (United States)

^d UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^e RTI INTERNATIONAL   (United States)

^f Mycosynthetix Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

15 O DESMETHYL 7 OXOZEAENOL; 7 EPI ZEAENOL; 7 OXOZEAENOL; ALPHA ZEARALENOL; ALPHA ZERALANOL; ANTIBIOTIC AGENT; BETA ZEARALENOL; BETA ZERALANOL; CAMPTOTHECIN; CYTOTOXIC AGENT; HYPOTHEMYCIN; I KAPPA B; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LL Z 1640 1; RESORCYLIC ACID LACTONE DERIVATIVE; ROCAGLAMIDE; SODIUM BOROHYDRIDE; STAUROSPORINE; UNCLASSIFIED DRUG; ZEAENOL; ZEARALENONE;

ANTIBACTERIAL ACTIVITY; ARTICLE; ASTROCYTOMA; BACILLUS SUBTILIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; HUMAN CELL; LUNG NON SMALL CELL CANCER; MITOCHONDRIAL MEMBRANE POTENTIAL; MYCOBACTERIUM SMEGMATIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; FUNGI; HUMANS; HYDROXYBENZOIC ACIDS; LACTONES; MOLECULAR STRUCTURE; NF-KAPPA B; STRUCTURE-ACTIVITY RELATIONSHIP; ZEARALENONE;

FUNGI; PHOMA;

EID: 79957812702     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200062x     Document Type: Article

References (31)

1. Kinghorn, A. D.; Carache de Blanco, E. J.; Chai, H. B.; Orjala, J.; Farnsworth, N. R.; Soejarto, D. D.; Oberlies, N. H.; Wani, M. C.; Kroll, D. J.; Pearce, C. J.; Swanson, S. M.; Kramer, R. A.; Rose, W. C.; Fairchild, C. R.; Vite, G. D.; Emanuel, S.; Jarjoura, D.; Cope, F. O. Pure Appl. Chem. 2009, 81, 1051-1063.
2. Orjala, J.; Oberlies, N. H.; Pearce, C. J.; Swanson, S. M.; Kinghorn, A. D. In Bioactive Compounds from Natural Sources, 2nd ed.; Tringali, C., Ed.; Taylor & Francis: London, accepted.
3. Hawksworth, D. L.; Rossman, A. Y. Phytopathology 1997, 87, 888-891.
4. Fleming, A. Penicillin, Its Practical Application; Butterworth & Co. Ltd.: London, 1946; p 380.
5. Dreyfus, M.; Harri, E.; Hofmann, H.; Pache, W.; Tscherter, H. Eur. J. Appl. Microbiol. 1976, 3, 125-133.
6. Brown, A. G.; Smale, T. C.; King, T. J.; Hasenkamp, R.; Thompson, R. H. J. Chem. Soc., Perkin Trans. 1 1976, 11, 1165-1170.
7. Brinkmann, V.; Billich, A.; Baumruker, T.; Heining, P.; Schmouder, R.; Francis, G.; Aradhye, S.; Burtin, P. Nat. Rev. Drug Discovery 2010, 9, 883-897.
8. Griffiths, R.; Richards, W.; Johnson, M.; McCann, U.; Jesse, R. J. Psychopharmacol. 2008, 22, 621-632.
9. Misiek, M.; Hoffmeister, D. Planta Med. 2007, 73, 103-115.
10. The use of the term "fungus" in titles of articles published in the Journal of Natural Products has increased steadily over the last 10 years, from appearing 12 times in 2000 to appearing 31 times in 2009; at the time of manuscript submission, the term was on target to increase to nearly 40 times in 2010.
11. Pearce, C.; Eckard, P.; Gruen-Wollny, I.; Hanske, F. G. In Natural Product Chemistry for Drug Discovery; Buss, A. D.; Butler, M. S., Eds.; The Royal Society of Chemistry: Cambridge, 2010; pp 215-244.
12. Alali, F. Q.; El-Elimat, T.; Li, C.; Qandil, A.; Alkofahi, A.; Tawaha, K.; Burgess, J. P.; Nakanishi, Y.; Kroll, D. J.; Navarro, H. A.; Falkinham, J. O., III; Wani, M. C.; Oberlies, N. H. J. Nat. Prod. 2005, 68, 173-178.
13. Li, C.; Lee, D.; Graf, T. N.; Phifer, S. S.; Nakanishi, Y.; Riswan, S.; Setyowati, F. M.; Saribi, A. M.; Soejarto, D. D.; Farnsworth, N. R.; Falkinham, J. O., III; Kroll, D. J.; Kinghorn, A. D.; Wani, M. C.; Oberlies, N. H. J. Nat. Prod. 2009, 72, 1949-1953.
14. These previous studies were retrieved from the Mycosynthetix database, which covers previous research on these organisms going back over 30 years.
15. Tatsuta, K.; Takano, S.; Sato, T.; Nakano, S. Chem. Lett. 2001, 172-173.
16. Dakas, P. Y.; Jogireddy, R.; Valot, G.; Barluenga, S.; Winssinger, N. Chemistry 2009, 15, 11490-11497.
17. Ellestad, G. A.; Lovell, F. M.; Perkinson, N. A.; Hargreaves, R. T.; McGahren, W. J. J. Org. Chem. 1978, 43, 2339-2343.
18. Sugawara, F.; Kim, K. W.; Kobayashi, K.; Uzawa, J.; Yoshida, S.; Murofushi, N.; Takahashi, N.; Strobel, G. A. Phytochemistry 1992, 31, 1987-1990.
19. Xu, L. X.; He, Z. X.; Xue, J. H.; Chen, X. P.; Wei, X. Y. J. Nat. Prod. 2010, 73, 885-889.
20. Winssinger, N.; Barluenga, S. Chem. Commun. 2007, 22-36.
21. Schulte, T. W.; Akinaga, S.; Soga, S.; Sullivan, W.; Stensgard, B.; Toft, D.; Neckers, L. M. Cell Stress Chaperones 1998, 3, 100-108.
22. Sharma, S. V.; Agatsuma, T.; Nakano, H. Oncogene 1998, 16, 2639-2645.
23. Schirmer, A.; Kennedy, J.; Murli, S.; Reid, R.; Santi, D. V. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 4234-4239.
24. Ninomiya-Tsuji, J.; Kajino, T.; Ono, K.; Ohtomo, T.; Matsumoto, M.; Shiina, M.; Mihara, M.; Tsuchiya, M.; Matsumoto, K. J. Biol. Chem. 2003, 278, 18485-18490.
25. Soule, H. D.; Vazguez, J.; Long, A.; Albert, S.; Brennan, M. J. Natl. Cancer Inst. 1973, 51, 1409-1416.
26. Carney, D. N.; Gazdar, A. F.; Bunn, P. A., Jr.; Guccion, J. G. Stem Cells 1982, 1, 149-164.
27. Rosenblum, M. L.; Gerosa, M. A.; Wilson, C. B.; Barger, G. R.; Pertuiset, B. F.; de Tribolet, N.; Dougherty, D. V. J. Neurosurg. 1983, 58, 170-176.
28. Fogh, J.; Trempe, G. In Human Tumor Cells In Vitro; Plenum: New York, 1975; pp 115-159.
29. Rae, J. M.; Creighton, C. J.; Meck, J. M.; Haddad, B. R.; Johnson, M. D. Breast Cancer Res. Treat. 2007, 104, 13-19.
30. Salim, A. A.; Pawlus, A. D.; Chai, H. B.; Farnsworth, N. R.; Douglas Kinghorn, A.; Carcache-Blanco, E. J. Bioorg. Med. Chem. Lett. 2007, 17, 109-112.
31. Deng, Y.; Balunas, M. J.; Kim, J. A.; Lantvit, D. D.; Chin, Y. W.; Chai, H.; Sugiarso, S.; Kardono, L. B.; Fong, H. H.; Pezzuto, J. M.; Swanson, S. M.; de Blanco, E. J.; Kinghorn, A. D. J. Nat. Prod. 2009, 72, 1165-1169.