Shornephine A: Structure, chemical stability, and P-glycoprotein inhibitory properties of a rare diketomorpholine from an Australian marine-derived Aspergillus sp.

Journal of Organic Chemistry

Volumn 79, Issue 18, 2014, Pages 8700-8705

  Khalil, Zeinab G ^a   Huang, Xiao Cong ^a   Raju, Ritesh ^a   Piggott, Andrew M ^a,b   Capon, Robert J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b MACQUARIE UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ASPERGILLUS; CHEMICAL STABILITY; DEGRADATION; SPECTROSCOPIC ANALYSIS; SUBMARINE GEOLOGY;

ASPERGILLUS SP; CHEMICAL DEGRADATION; DERIVATIZATIONS; DIKETOPIPERAZINES; HUMAN COLON CANCER CELLS; MARINE SEDIMENTS; P-GLYCOPROTEIN; STRUCTURE ELUCIDATION;

GLYCOPROTEINS;

15B BETA HYDROXY 5 N ACETYLADREEMIN; 15B BETA METHOXY 5 N ACETYLADREEMIN; 5 N ACETYLADREEMIN; DIKETOMORPHOLINE; GLYCOPROTEIN P INHIBITOR; MORPHOLINE DERIVATIVE; PIPERAZINEDIONE; SHORNEPHINE A; UNCLASSIFIED DRUG; MULTIDRUG RESISTANCE PROTEIN;

ALKYLATION; ARTICLE; ASPERGILLUS; AUSTRALIA; CANCER CELL LINE; DEGRADATION; DERIVATIZATION; DRUG ACTIVITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MARINE BACTERIUM; METHANOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; MARINE BIOLOGY; MULTIDRUG RESISTANCE; TUMOR CELL LINE;

ANIMALS; ASPERGILLUS; AUSTRALIA; CELL LINE, TUMOR; DIKETOPIPERAZINES; DRUG RESISTANCE, MULTIPLE; HUMANS; MARINE BIOLOGY; MOLECULAR STRUCTURE; MORPHOLINES; P-GLYCOPROTEIN;

EID: 84911862577     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501501z     Document Type: Article

References (18)

1. Mootz, H. D.; Marahiel, M. A. Curr. Opin. Chem. Biol. 1997, 1, 543-551.
2. Finefield, J. M.; Sherman, D. H.; Tsukamoto, S.; Williams, R. M. J. Org. Chem. 2011, 76, 5954-5958.
3. Guimaraes, D. O.; Borges, W. S.; Vieira, N. J.; De Oliveira, L. F.; Da Silva, C. H. T. P.; Lopes, N. P.; Dias, L. G.; Duran-Patron, R.; Collado, I. G.; Pupo, M. T. Phytochemistry 2010, 71, 1423-1429.
4. Little, P. R.; Hodge, A.; Watson, T. G.; Seed, J. A.; Maeder, S. J. N. Z. Vet. J. 2010, 58, 121-129.
5. Karwowski, J. P.; Jackson, M.; Rasmussen, R. R.; Humphrey, P. E.; Poddig, J. B.; Kohl, W. L.; Scherr, M. H.; Kadam, S.; McAlpine, J. B. J. Antibiot. 1993, 46, 374-379.
6. Hochlowski, J. E.; Mullally, M. M.; Spanton, S. G.; Whittern, D. N.; Hill, P.; McAlpine, J. B. J. Antibiot. 1993, 46, 380-386.
7. Li, S.; Finefield, J. M.; Sunderhaus, J. D.; McAfoos, T. J.; Williams, R. M.; Sherman, D. H. J. Am. Chem. Soc. 2012, 134, 788-791.
8. Kato, H.; Nakamura, Y.; Finefield, J. M.; Umaoka, H.; Nakahara, T.; Williams, R. M.; Tsukamoto, S. Tetrahedron Lett. 2011, 52, 6923-6926.
9. Finefield, J. M.; Greshock, T. J.; Sherman, D. H.; Tsukamoto, S.; Williams, R. M. Tetrahedron Lett. 2011, 52, 1987-1989.
10. Chen, M.; Shao, C.-L.; Fu, X.-M.; Xu, R.-F.; Zheng, J.-J.; Zhao, D.-L.; She, Z.-G.; Wang, C.-Y. J. Nat. Prod. 2013, 76, 547-553.
11. Hasumi, K.; Shinohara, C.; Iwanaga, T.; Endo, A. J. Antibiot. 1993, 46, 1782-1787.
12. Kagamizono, T.; Nishino, E.; Matsumoto, K.; Kawashima, A.; Kishimoto, M.; Sakai, N.; He, B.-M.; Chen, Z.-X.; Adachi, T.; et al. J. Antibiot. 1995, 48, 1407-1412.
13. Smelcerovic, A.; Yancheva, D.; Cherneva, E.; Petronijevic, Z.; Lamshoeft, M.; Herebian, D. J. Mol. Struct. 2011, 985, 397-402.
14. Suntornchashwej, S.; Chaichit, N.; Isobe, M.; Suwanborirux, K. J. Nat. Prod. 2005, 68, 951-955.
15. Wang, H.-j.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Nat. Prod. 1998, 61, 804-807.
16. Nakadate, S.; Nozawa, K.; Horie, H.; Fujii, Y.; Nagai, M.; Komai, S.-i.; Hosoe, T.; Kawai, K.-i.; Yaguchi, T.; Fukushima, K. Heterocycles 2006, 68, 1969-1972.
17. Huang, X.-c.; Sun, Y.-L.; Salim, A. A.; Chen, Z.-S.; Capon, R. J. Biochem. Pharmacol. 2013, 85, 1257-1268.
18. Hoye, T. R.; Jeffrey, C. S.; Shao, F. Nat. Protoc. 2007, 2, 2451-2458.