Versixanthones A-F, Cytotoxic Xanthone-Chromanone Dimers from the Marine-Derived Fungus Aspergillus versicolor HDN1009

Journal of Natural Products

Volumn 78, Issue 11, 2015, Pages 2691-2698

  Wu, Guangwei ^a   Yu, Guihong ^a   Kurtán, Tibor ^b   Mándi, Attila ^b   Peng, Jixing ^a   Mo, Xiaomei ^a   Liu, Ming ^a   Li, Hui ^a   Sun, Xinhua ^a   Li, Jing ^a   Zhu, Tianjiao ^a   Gu, Qianqun ^a   Li, Dehai ^a  

^a OCEAN UNIVERSITY OF CHINA   (China)

^b UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; DIMER; DIMETHYL SULFOXIDE; DNA TOPOISOMERASE; SECALONIC ACID D; UNCLASSIFIED DRUG; VERSIXANTHONE A; VERSIXANTHONE B; VERSIXANTHONE C; VERSIXANTHONE D; VERSIXANTHONE E; VERSIXANTHONE F; XANTHONE DERIVATIVE; ANTINEOPLASTIC AGENT; CHROMONE DERIVATIVE; DNA TOPOISOMERASE INHIBITOR;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ASPERGILLUS VERSICOLOR; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DRUG CYTOTOXICITY; DRUG ISOLATION; ENZYME INHIBITION; FUNGUS CULTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; IC50; MANGROVE; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; ASPERGILLUS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG SCREENING; HUMAN; ISOLATION AND PURIFICATION; MARINE BIOLOGY; MICROBIOLOGY; RHIZOPHORACEAE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; ASPERGILLUS; CHROMONES; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MARINE BIOLOGY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; RHIZOPHORACEAE; TOPOISOMERASE I INHIBITORS; XANTHONES;

EID: 84948743881     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00636     Document Type: Article

References (36)

1. Masters, K.; Bräse, S. Chem. Rev. 2012, 112, 3717-3776 10.1021/cr100446h
2. Wezeman, T.; Bräse, S.; Masters, K. Nat. Prod. Rep. 2015, 32, 6-28 10.1039/C4NP00050A
3. Zhang, W.; Krohn, K.; Ullah, Z.; Flörke, U.; Pescitelli, G.; Di Bari, L.; Antus, S.; Kurtán, T.; Rheinheimer, J.; Draeger, S.; Schulz, B. Chem.-Eur. J. 2008, 14, 4913-4923 10.1002/chem.200800035
4. Cai, S.; King, J. B.; Du, L.; Powell, D. R.; Cichewicz, R. H. J. Nat. Prod. 2014, 77, 2280-2287 10.1021/np5005449
5. Kikuchi, H.; Isobe, M.; Kurata, S.; Katou, Y.; Oshima, Y. Tetrahedron 2012, 68, 6218-6223 10.1016/j.tet.2012.05.064
6. El-Elimat, T.; Figueroa, M.; Raja, H. A.; Graf, T. N.; Swanson, S. M.; Falkinham, J. O., III; Wani, M. C.; Pearce, C. J.; Oberlies, N. H. Eur. J. Org. Chem. 2015, 2015, 109-121 10.1002/ejoc.201402984
7. Berova, N.; Polavarapu, P. L.; Nakanishi, K.; Woody, R. W. Comprehensive Chiroptical Spectroscopy: Applications in Stereochemical Analysis of Synthetic Compounds, Natural Products, and Biomolecules, Vol. 2; John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2012.
8. Du, L.; Liu, H.; Fu, W.; Li, D.; Pan, Q.; Zhu, T.; Geng, M.; Gu, Q. J. Med. Chem. 2011, 54, 5796-5810 10.1021/jm200511x
9. Li, L.; Li, D.; Luan, Y.; Gu, Q.; Zhu, T. J. Nat. Prod. 2012, 75, 920-927 10.1021/np3000443
10. Du, L.; Ai, J.; Li, D.; Zhu, T.; Wang, Y.; Knauer, M.; Bruhn, T.; Liu, H.; Geng, M.; Gu, Q.; Bringmann, G. Chem.-Eur. J. 2011, 17, 1319-1326 10.1002/chem.201001547
11. Ren, H.; Tian, L.; Gu, Q.; Zhu, W. Arch. Pharmacal Res. 2006, 29, 59-63 10.1007/BF02977469
12. Qin, T.; Johnson, R. P.; Porco, J. A., Jr. J. Am. Chem. Soc. 2011, 133, 1714-1717 10.1021/ja110698n
13. Bifulco, G.; Dambruoso, P.; Gomez-Paloma, L.; Riccio, R. Chem. Rev. 2007, 107, 3744-3779 10.1021/cr030733c
14. Bara, R.; Zerfass, I.; Aly, A. H.; Goldbach-Gecke, H.; Raghavan, V.; Sass, P.; Mándi, A.; Wray, V.; Polavarapu, P. L.; Pretsch, A.; Lin, W.; Kurtán, T.; Debbab, A.; Brötz-Oesterhelt, H.; Proksch, P. J. Med. Chem. 2013, 56, 3257-3272 10.1021/jm301816a
15. Zhang, Q.; Mándi, A.; Li, S.; Chen, Y.; Zhang, W.; Tian, X.; Zhang, H.; Li, H.; Zhang, W.; Zhang, S.; Ju, J.; Kurtán, T.; Zhang, C. Eur. J. Org. Chem. 2012, 2012, 5256-5262 10.1002/ejoc.201200599
16. Rönsberg, D.; Debbab, A.; Mándi, A.; Vasylyeva, V.; Böhler, P.; Stork, B.; Engelke, L.; Hamacher, A.; Sawadogo, R.; Diederich, M.; Wray, V.; Lin, W.; Kassack, M. U.; Janiak, C.; Scheu, S.; Wesselborg, S.; Kurtán, T.; Aly, A. H.; Proksch, P. J. Org. Chem. 2013, 78, 12409-12425 10.1021/jo402066b
17. Bringmann, G.; Hinrichs, J.; Henschel, P.; Kraus, J.; Peters, K.; Peters, E. Eur. J. Org. Chem. 2002, 2002, 1096-1106 10.1002/1099-0690(200203)2002:6<1096::AID-EJOC1096>3.0.CO;2-Z
18. Debbab, A.; Aly, A. H.; Edrada-Ebel, R.; Wray, V.; Pretsch, A.; Pescitelli, G.; Kurtan, T.; Proksch, P. Eur. J. Org. Chem. 2012, 2012, 1351-1359 10.1002/ejoc.201101442
19. Elsässer, B.; Krohn, K.; Flörke, U.; Root, N.; Aust, H.; Draeger, S.; Schulz, B.; Antus, S.; Kurtán, T. Eur. J. Org. Chem. 2005, 2005, 4563-4570 10.1002/ejoc.200500265
20. Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384-5427 10.1002/anie.200462661
21. Ducrot, P. H. C. R. C. R. Acad. Sci., Ser. IIc: Chim. 2001, 4, 273-283 10.1016/S1387-1609(01)01237-3
22. Parish, C. A.; Smith, S. K.; Calati, K.; Zink, D.; Wilson, K.; Roemer, T.; Jiang, B.; Xu, D.; Bills, G.; Platas, G.; Peláez, F.; Dáez, M. T.; Tsou, N.; McKeown, A. E.; Ball, R. G.; Powles, M. A.; Lai, Y.; Liberator, P.; Harris, G. J. Am. Chem. Soc. 2008, 130, 7060-7066 10.1021/ja711209p
23. Kurobane, I. M. W.; Vining, L. C.; Mcinnes, A. G.; Halifax, N. S. Germany patent DE3002671, 1980.
24. Chen, G.; Chen, Y.; Gao, H.; Shen, L.; Wu, Y.; Li, X.; Li, Y.; Guo, L.; Cen, Y.; Yao, X. J. Nat. Prod. 2013, 76, 702-709 10.1021/np400041y
25. Guo, Z.; She, Z.; Shao, C.; Wen, L.; Liu, F.; Zheng, Z.; Lin, Y. Magn. Reson. Chem. 2007, 45, 777-780 10.1002/mrc.2035
26. Ren, H. Pharm. Biol. 2011, 49 (8) 796-799 10.3109/13880209.2010.548817
27. Ren, H.; Tian, L.; Gu, Q. Q.; Zhu, W. M. Arch. Pharmacal Res. 2006, 29 (1) 59-63 10.1007/BF02977469
28. MacroModel; Schrödinger, LLC, 2012, http://www.schrodinger.com/MacroModel.
29. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799 10.1002/jcc.20495
30. Sun, P.; Xu, D.-X.; Mándi, A.; Kurtán, T.; Li, T. J.; Schulz, B.; Zhang, W. J. Org. Chem. 2013, 78, 7030-7047 10.1021/jo400861j
31. 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.; Peralta, J. E.; 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.; Cammi, R.; Pomelli, C.; 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, revision B.01; Gaussian, Inc.: Wallingford, CT, 2010.
32. Stephens, P. J.; Harada, N. Chirality 2010, 22, 229-233
33. Varetto, U. MOLEKEL, v. 5.4; Swiss National Supercomputing Centre: Manno, Switzerland, 2009.
34. Du, L.; Zhu, T. J.; Liu, H. B.; Fang, Y. C.; Zhu, W. M.; Gu, Q. Q. J. Nat. Prod. 2008, 71, 1837-1842 10.1021/np800303t
35. Gao, H.; Liu, W.; Zhu, T.; Mo, X.; Mándi, A.; Kurtán, T.; Li, J.; Ai, J.; Gu, Q.; Li, D. Org. Biomol. Chem. 2012, 10, 9501-9506 10.1039/c2ob26757h
36. Che, Q.; Zhu, T.; Qi, X.; Mándi, A.; Kurtán, T.; Mo, X.; Li, J.; Gu, Q.; Li, D. Org. Lett. 2012, 14 (13) 3438-3441 10.1021/ol301396h