Meroterpenoids from Neosetophoma sp.: A Dioxa[4.3.3]propellane Ring System, Potent Cytotoxicity, and Prolific Expression

Organic Letters

Volumn 21, Issue 2, 2019, Pages 529-534

  El Elimat, Tamam ^a   Raja, Huzefa A ^b   Ayers, Sloan ^b   Kurina, Steven J ^c   Burdette, Joanna E ^c   Mattes, Zachary ^d   Sabatelle, Robert ^e   Bacon, Jeffrey W ^d   Colby, Aaron H ^e   Grinstaff, Mark W ^d,e   Pearce, Cedric J ^f   Oberlies, Nicholas H ^b  

^a JORDAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Jordan)

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

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d Boston University   (United States)

^e Boston University   (United States)

^f Mycosynthetix Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; TERPENE;

ASCOMYCETES; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; ASCOMYCOTA; HUMANS; MOLECULAR STRUCTURE; TERPENES;

EID: 85060051031     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.8b03769     Document Type: Article

References (17)

1. Matsuda, Y.; Awakawa, T.; Abe, I. Tetrahedron 2013, 69, 8199, 10.1016/j.tet.2013.07.029
2. Matsuda, Y.; Abe, I. Nat. Prod. Rep. 2016, 33, 26, 10.1039/C5NP00090D
3. Overy, D. P.; Berrue, F.; Correa, H.; Hanif, N.; Hay, K.; Lanteigne, M.; Mquilian, K.; Duffy, S.; Boland, P.; Jagannathan, R.; Carr, G. S.; Vansteeland, M.; Kerr, R. G. Mycology 2014, 5, 130, 10.1080/21501203.2014.931893
4. Hoffmann, T.; Krug, D.; Bozkurt, N.; Duddela, S.; Jansen, R.; Garcia, R.; Gerth, K.; Steinmetz, H.; Müller, R. Nat. Commun. 2018, 9, 803, 10.1038/s41467-018-03184-1
5. El-Elimat, T.; Figueroa, M.; Ehrmann, B. M.; Cech, N. B.; Pearce, C. J.; Oberlies, N. H. J. Nat. Prod. 2013, 76, 1709, 10.1021/np4004307
6. Mayerl, F.; Gao, Q.; Huang, S.; Klohr, S. E.; Matson, J. A.; Gustavson, D. R.; Pirnik, D. M.; Berry, R. L.; Fairchild, C.; Rose, W. C. J. Antibiot. 1993, 46, 1082, 10.7164/antibiotics.46.1082
7. Zhang, J.; Liu, L.; Wang, B.; Zhang, Y.; Wang, L.; Liu, X.; Che, Y. J. Nat. Prod. 2015, 78, 3058, 10.1021/acs.jnatprod.5b00969
8. Hoye, T. R.; Jeffrey, C. S.; Shao, F. Nat. Protoc. 2007, 2, 2451, 10.1038/nprot.2007.354
9. Ayers, S.; Zink, D. L.; Powell, J. S.; Brown, C. M.; Grund, A.; Bills, G. F.; Platas, G.; Thompson, D.; Singh, S. B. J. Nat. Prod. 2008, 71, 457, 10.1021/np070513k
10. Bunyapaiboonsri, T.; Veeranondha, S.; Boonruangprapa, T.; Somrithipol, S. Phytochem. Lett. 2008, 1, 204, 10.1016/j.phytol.2008.09.008
11. Vorrink, S. U.; Zhou, Y.; Ingelman-Sundberg, M.; Lauschke, V. M. Toxicol. Sci. 2018, 163, 655, 10.1093/toxsci/kfy058
12. Colby, A. H.; Oberlies, N. H.; Pearce, C. J.; Herrera, V. L. M.; Colson, Y. L.; Grinstaff, M. W. Wiley Interdiscip. Rev.: Nanomed. Nanobiotechnol. 2017, 9, e1451, 10.1002/wnan.1451
13. Hsiao, C.-J.; Hsiao, S.-H.; Chen, W.-L.; Guh, J.-H.; Hsiao, G.; Chan, Y.-J.; Lee, T.-H.; Chung, C.-L. Chem.-Biol. Interact. 2012, 197, 23, 10.1016/j.cbi.2012.03.004
14. Kaneko, M.; Matsuda, D.; Ohtawa, M.; Fukuda, T.; Nagamitsu, T.; Yamori, T.; Tomoda, H. Biol. Pharm. Bull. 2012, 35, 18, 10.1248/bpb.35.18
15. Dilmaç, A. M.; Spuling, E.; de Meijere, A.; Bräse, S. Angew. Chem., Int. Ed. 2017, 56, 5684, 10.1002/anie.201603951
16. Pihko, A. J.; Koskinen, A. M. P. Tetrahedron 2005, 61, 8769, 10.1016/j.tet.2005.06.013
17. Grinstaff, M. W.; Kaplan, H. M.; Kohn, J. ACS Biomater. Sci. Eng. 2018, 4, 3919, 10.1021/acsbiomaterials.7b00268