Spiroaspertrione A, a Bridged Spirocyclic Meroterpenoid, as a Potent Potentiator of Oxacillin against Methicillin-Resistant Staphylococcus aureus from Aspergillus sp. TJ23

Journal of Organic Chemistry

Volumn 82, Issue 6, 2017, Pages 3125-3131

  He, Yan ^a   Hu, Zhengxi ^a   Sun, Weiguang ^a   Li, Qin ^a   Li, Xiao Nian ^b   Zhu, Hucheng ^a   Huang, Jinfeng ^a   Liu, Junjun ^a   Wang, Jianping ^a   Xue, Yongbo ^a   Zhang, Yonghui ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ASPERGILLUS; BIOASSAY; DICHROISM; KETONES; SINGLE CRYSTALS; SPECTROSCOPIC ANALYSIS; X RAY DIFFRACTION;

ABSOLUTE CONFIGURATION; ASPERGILLUS SP; CARBOCYCLIC SKELETON; ELECTRONIC CIRCULAR DICHROISM; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MINIMAL INHIBITORY CONCENTRATION; POLYKETIDES; SINGLE CRYSTAL X-RAY DIFFRACTION;

BACTERIA;

ANDICONIN B; ANTIINFECTIVE AGENT; NATURAL PRODUCT; OXACILLIN; POLYKETIDE; SPIROASPERTRIONE A; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; ASPERGILLUS; BINDING SITE; BIOASSAY; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; DRUG ISOLATION; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGAL STRAIN; HETERONUCLEAR MULTIPLE BOND CORRELATION; HYDROGEN BOND; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION; CHEMISTRY; DRUG EFFECT; MICROBIAL SENSITIVITY TEST; PROCEDURES; SPECTROSCOPY;

ANTI-BACTERIAL AGENTS; ASPERGILLUS; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TESTS; OXACILLIN; SPECTRUM ANALYSIS;

EID: 85015645746     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.7b00056     Document Type: Article

References (35)

1. Walsh, T. R.; Weeks, J.; Livermore, D. M.; Toleman, M. A. Lancet Infect. Dis. 2011, 11, 355-362 10.1016/S1473-3099(11)70059-7
2. Antibiotic Resistance Threats in the United States, 2013; Centers for Disease Control and Prevention, 2013. https://www.cdc.gov/drugresistance/threat-report-2013/.
3. Gonzales, P. R.; Pesesky, M. W.; Bouley, R.; Ballard, A.; Biddy, B. A.; Suckow, M. A.; Wolter, W. R.; Schroeder, V. A.; Burnham, C. D.; Mobashery, S.; Chang, M.; Dantas, G. Nat. Chem. Biol. 2015, 11, 855-861 10.1038/nchembio.1911
4. Fuda, C.; Hesek, D.; Lee, M.; Morio, K.; Nowak, T.; Mobashery, S. J. Am. Chem. Soc. 2005, 127, 2056-2057 10.1021/ja0434376
5. Otero, L. H.; Rojas-Altuve, A.; Llarrull, L. I.; Carrasco-López, C.; Kumarasiri, M.; Lastochkin, E.; Fishovitz, J.; Dawley, M.; Hesek, D.; Lee, M.; Johnson, J. W.; Fisher, J. F.; Chang, M.; Mobashery, S.; Hermoso, J. A. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 16808-16813 10.1073/pnas.1300118110
6. Long, S. W.; Olsen, R. J.; Mehta, S. C.; Palzkill, T.; Cernoch, P. L.; Perez, K. K.; Musick, W. L.; Rosato, A. E.; Musser, J. M. Antimicrob. Agents Chemother. 2014, 58, 6668-6674 10.1128/AAC.03622-14
7. van Hal, S. J.; Paterson, D. L.; Gosbell, I. B. Eur. J. Clin. Microbiol. Infect. Dis. 2011, 30, 603-610 10.1007/s10096-010-1128-3
8. Villegas-Estrada, A.; Lee, M.; Hesek, D.; Vakulenko, S. B.; Mobashery, S. J. Am. Chem. Soc. 2008, 130, 9212-9213 10.1021/ja8029448
9. Dilworth, T. J.; Sliwinski, J.; Ryan, K.; Dodd, M.; Mercier, R. C. Antimicrob. Agents Chemother. 2014, 58, 1028-1033 10.1128/AAC.01888-13
10. Banerjee, R.; Fernandez, M. G.; Enthaler, N.; Graml, C.; Greenwood-Quaintance, K. E.; Patel, R. Eur. J. Clin. Microbiol. Infect. Dis. 2013, 32, 827-833 10.1007/s10096-013-1817-9
11. Lee, S. H.; Jarantow, L. W.; Wang, H.; Sillaots, S.; Cheng, H.; Meredith, T. C.; Thompson, J.; Roemer, T. Chem. Biol. 2011, 18, 1379-1389 10.1016/j.chembiol.2011.08.015
12. Bush, K. Nat. Chem. Biol. 2015, 11, 832-833 10.1038/nchembio.1935
13. Gonzales, P. R.; Pesesky, M. W.; Bouley, R.; Ballard, A.; Biddy, B. A.; Suckow, M. A.; Wolter, W. R.; Schroeder, V. A.; Burnham, C. D.; Mobashery, S.; Chang, M.; Dantas, G. Nat. Chem. Biol. 2015, 11, 855-861 10.1038/nchembio.1911
14. He, Y.; Tian, J.; Chen, X.; Sun, W.; Zhu, H.; Li, Q.; Lei, L.; Yao, G.; Xue, Y.; Wang, J.; Li, H.; Zhang, Y. Sci. Rep. 2016, 6, 24291 10.1038/srep24291
15. Hu, Z.; Wang, J.; Bi, X.; Zhang, J.; Xue, Y.; Yang, Y.; Luo, Z.; Yao, G.; Zhang, Y. Tetrahedron Lett. 2014, 55, 6093-6095 10.1016/j.tetlet.2014.09.041
16. Zhu, H.; Chen, C.; Xue, Y.; Tong, Q.; Li, X. N.; Chen, X.; Wang, J.; Yao, G.; Luo, Z.; Zhang, Y. Angew. Chem., Int. Ed. 2015, 54, 13374-13378 10.1002/anie.201506264
17. Qi, C.; Bao, J.; Wang, J.; Zhu, H.; Xue, Y.; Wang, X.; Li, H.; Sun, W.; Gao, W.; Lai, Y.; Chen, J. G.; Zhang, Y. Chem. Sci. 2016, 7, 6563-6572 10.1039/C6SC02464E
18. Tang, Y.; Xue, Y.; Du, G.; Wang, J.; Liu, J.; Sun, B.; Li, X. N.; Yao, G.; Luo, Z.; Zhang, Y. Angew. Chem., Int. Ed. 2016, 55, 4069-4073 10.1002/anie.201600313
19. Hu, Z.; Wu, Y.; Xie, S.; Sun, W.; Guo, Y.; Li, X. N.; Liu, J.; Li, H.; Wang, J.; Luo, Z.; Xue, Y.; Zhang, Y. Org. Lett. 2017, 19, 258-261 10.1021/acs.orglett.6b03557
20. Flack, H. D.; Bernardinelli, G. Acta Crystallogr., Sect. A: Found. Crystallogr. 1999, 55, 908-915 10.1107/S0108767399004262
21. Matsuda, Y.; Wakimoto, T.; Mori, T.; Awakawa, T.; Abe, I. J. Am. Chem. Soc. 2014, 136, 15326-15336 10.1021/ja508127q
22. Simpson, T. J. J. Chem. Soc., Perkin Trans. 1 1979, 2118-2121 10.1039/p19790002118
23. Macías, F. A.; Varela, R. M.; Simonet, A. M.; Cutler, H. G.; Cutler, S. J.; Dugan, F. M.; Hill, R. A. J. Org. Chem. 2000, 65, 9039-9046 10.1021/jo0011078
24. Su, Z.; Yeagley, A. A.; Su, R.; Peng, L.; Melander, C. ChemMedChem 2012, 7, 2030-2039 10.1002/cmdc.201200350
25. Harris, T. L.; Worthington, R. J.; Melander, C. Angew. Chem., Int. Ed. 2012, 51, 11254-11257 10.1002/anie.201206911
26. Hu, L.; Zhu, H.; Li, L.; Huang, J.; Sun, W.; Liu, J.; Li, H.; Luo, Z.; Wang, J.; Xue, Y.; Zhang, Y.; Zhang, Y. Sci. Rep. 2016, 6, 27588 10.1038/srep27588
27. Chan, L. C.; Gilbert, A.; Basuino, L.; da Costa, T. M.; Hamilton, S. M.; dos Santos, K. R.; Chambers, H. F.; Chatterjee, S. S. Antimicrob. Agents Chemother. 2016, 60, 3934-3950 10.1128/AAC.00358-16
28. Berti, A. D.; Theisen, E.; Sauer, J. D.; Nonejuie, P.; Olson, J.; Pogliano, J.; Sakoulas, G.; Nizet, V.; Proctor, R. A.; Rose, W. E. Antimicrob. Agents Chemother. 2016, 60, 451-458 10.1128/AAC.02071-15
29. Bouley, R.; Kumarasiri, M.; Peng, Z.; Otero, L. H.; Song, W.; Suckow, M. A.; Schroeder, V. A.; Wolter, W. R.; Lastochkin, E.; Antunes, N. T.; Pi, H.; Vakulenko, S.; Hermoso, J. A.; Chang, M.; Mobashery, S. J. Am. Chem. Soc. 2015, 137, 1738-1741 10.1021/jacs.5b00056
30. Otero, L. H.; Rojas-Altuve, A.; Llarrull, L. I.; Carrasco-López, C.; Kumarasiri, M.; Lastochkin, E.; Fishovitz, J.; Dawley, M.; Hesek, D.; Lee, M.; Johnson, J. W.; Fisher, J. F.; Chang, M.; Mobashery, S.; Hermoso, J. A. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 16808-16813 10.1073/pnas.1300118110
31. Shimizu, M.; Shiota, S.; Mizushima, T.; Ito, H.; Hatano, T.; Yoshida, T.; Tsuchiya, T. Antimicrob. Agents Chemother. 2001, 45, 3198-3201 10.1128/AAC.45.11.3198-3201.2001
32. Santiago, C.; Pang, E. L.; Lim, K.; Loh, H.; Ting, K. N. BMC Complementary Altern. Med. 2015, 15, 178-184 10.1186/s12906-015-0699-z
33. CLSI Methods for Determining Bactericidal Activity of Antimicrobial Agents; Approved Guideline, document M26-A; Clinical and Laboratory Standards Institute, Wayne, PA, 1999.
34. 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.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; 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. J.; Cross, 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 C.01; Gaussian, Inc.: Wallingford CT, 2010.
35. Glendening, E. D.; Reed, A. E.; Carpenter, E. J.; Weinhold, F. NBO, version 3.1; Gaussian, Inc.: Wallingford, CT, 2009.