Tetramic Acids and Pyridone Alkaloids from the Endolichenic Fungus Tolypocladium cylindrosporum

Journal of Natural Products

Volumn 78, Issue 9, 2015, Pages 2155-2160

  Li, Xiao Bin ^a   Li, Lin ^a   Zhu, Rong Xiu ^a   Li, Wei ^a   Chang, Wen Qiang ^a   Zhang, Lu Lu ^b   Wang, Xiao Ning ^a   Zhao, Zun Tian ^b   Lou, Hong Xiang ^a  

^a SHANDONG UNIVERSITY   (China)

^b SHANDONG NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3,8 DIHYDROXY 4 (4 HYDROXYPHENYL) 6 METHYLCOUMARIN; ALKALOID DERIVATIVE; COUMARIN DERIVATIVE; CYTOTOXIC AGENT; DOXORUBICIN; F 14329; PENICILLENOL A2; PYRIDOXATIN; TETRAMIC ACID DERIVATIVE; TOLYPOCLADENOL A1; TOLYPOCLADENOL A2; TOLYPOCLADENOL B; TOLYPYRIDONE A; TOLYPYRIDONE B; UNCLASSIFIED DRUG; 2 PYRROLIDONE DERIVATIVE; ALKALOID; ANTINEOPLASTIC AGENT; PYRIDONE DERIVATIVE; TETRAMIC ACID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOASSAY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG ISOLATION; FEMALE; G1 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; IN VITRO STUDY; LICHEN (ORGANISM); MEDICINAL FUNGUS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; TOLYPOCLADIUM CYLINDROSPORUM; X RAY DIFFRACTION; CELL CYCLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; ISOLATION AND PURIFICATION; SYNTHESIS;

ALKALOIDS; ANTINEOPLASTIC AGENTS; CELL CYCLE; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; PYRIDONES; PYRROLIDINONES;

EID: 84942588341     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np501018w     Document Type: Article

References (33)

1. Arnold, A. E.; Henk, D. A.; Eells, R. L.; Lutzoni, F.; Vilgalys, R. Mycologia 2007, 99, 185-206 10.3852/mycologia.99.2.185
2. Li, X. B.; Zhou, Y. H.; Zhu, R. X.; Chang, W. Q.; Yuan, H. Q.; Gao, W.; Zhang, L. L.; Zhao, Z. T.; Lou, H. X. Chem. Biodiversity 2015, 12, 575-592 10.1002/cbdv.201400146
3. Li, G.; Wang, H. Y.; Zhu, R. X.; Sun, L. M.; Wang, L. N.; Li, M.; Li, Y. Y.; Liu, Y. Q.; Zhao, Z. T.; Lou, H. X. J. Nat. Prod. 2012, 75, 142-147 10.1021/np200614h
4. Li, W.; Li, X. B.; Li, L.; Li, R. J.; Lou, H. X. Phytochem. Lett. 2015, 12, 22-26 10.1016/j.phytol.2015.02.008
5. Scorsetti, A. C.; Elíades, L. A.; Stenglein, S. A.; Cabello, M. N.; Pelizza, S. A.; Saparrat, M. C. N. Rev. Biol. Trop. 2012, 60, 833-841 10.15517/rbt.v60i2.4006
6. Survase, S. A.; Kagliwal, L. D.; Annapure, U. S.; Singhal, R. S. Biotechnol. Adv. 2011, 29, 418-435 10.1016/j.biotechadv.2011.03.004
7. Bullough, D. A.; Jackson, C. G.; Henderson, P. J. F.; Beechey, R. B.; Linnett, P. E. FEBS Lett. 1982, 145, 258-262 10.1016/0014-5793(82)80178-6
8. Weiser, J.; Matha, V. J. Invertebr. Pathol. 1988, 51, 94-96 10.1016/0022-2011(88)90093-6
9. Gupta, S.; Krasnoff, S. B.; Roberts, D. W.; Renwick, J. A. A. J. Org. Chem. 1992, 57, 2306-2313 10.1021/jo00034a022
10. Du, L.; Risinger, A. L.; King, J. B.; Powell, D. R.; Cichewicz, R. H. J. Nat. Prod. 2014, 77, 1753-1757 10.1021/np500387h
11. Chu, M.; Truumees, I.; Mierzwa, R.; Patel, M.; Puar, M. S. J. Antibiot. 1997, 50, 1061-1063 10.7164/antibiotics.50.1061
12. Rainaldi, M.; Moretto, A.; Peggion, C.; Formaggio, F.; Mammi, S.; Peggion, E.; Galvez, J. A.; Díaz-de-Villegas, M. D.; Cativiela, C.; Toniolo, C. Chem.-Eur. J. 2003, 9, 3567-3576 10.1002/chem.200304756
13. Kanasaki, R.; Kobayashi, M.; Fujine, K.; Sato, I.; Hashimoto, M.; Takase, S.; Tsurumi, Y.; Fujie, A.; Hino, M.; Hashimoto, S.; Hori, Y. J. Antibiot. 2006, 59, 158-167 10.1038/ja.2006.23
14. Tsantrizos, Y. S.; Pischos, S.; Sauriol, F. J. Org. Chem. 1996, 61, 2118-2121 10.1021/jo951837t
15. Gräfe, U.; Ihn, W.; Tresselt, D.; Miosga, N.; Kaden, U.; Schlegel, B.; Bormann, E. J.; Sedmera, P.; Novák, J. Biol. Met. 1990, 3, 39-44 10.1007/BF01141176
16. Ihn, W.; Gräfe, U.; Dornberger, K.; Bormann, E. J.; Krebs, D.; Heidenbluth, K. H.; Rudat, W. R. Bundesrepublik Deutschland Patent DD292024, A5 19910718, 1991.
17. Gräfe, U.; Ihn, W.; Schlegel, B.; Hoefle, G.; Augustiniak, H.; Sandor, P. Pharmazie 1991, 46, 613-614
18. Yan, J. K.; Li, L.; Wang, Z. M.; Wu, J. Y. Carbohydr. Polym. 2010, 79, 125-130 10.1016/j.carbpol.2009.07.047
19. Jegorov, A.; Matha, V.; Hušák, M.; Kratochvíl, B.; Stuchlík, J.; Sedmera, P.; Havlíček, V. J. Chem. Soc., Dalton Trans. 1993, 1, 1287-1293 10.1039/dt9930001287
20. Mogensen, J. M.; Møller, K. A.; von Freiesleben, P.; Labuda, R.; Varga, E.; Sulyok, M.; Kubátová, A.; Thrane, U.; Andersen, B.; Nielsen, K. F. J. Ind. Microbiol. Biotechnol. 2011, 38, 1329-1335 10.1007/s10295-010-0916-1
21. Lin, J.; Chen, X. Y.; Cai, X. Y.; Yu, X. F.; Liu, X. Z.; Cao, Y.; Che, Y. S. J. Nat. Prod. 2011, 74, 1798-1804 10.1021/np200431k
22. Feng, Y. J.; Blunt, J. W.; Cole, A. L. J.; Munro, M. H. G. J. Nat. Prod. 2002, 65, 1681-1682 10.1021/np020160j
23. Aoki, S.; Higuchi, K.; Ye, Y.; Satari, R.; Kobayashi, M. Tetrahedron 2000, 56, 1833-1836 10.1016/S0040-4020(00)00092-2
24. Lin, Z. J.; Lu, Z. Y.; Zhu, T. J.; Fang, Y. C.; Gu, Q. Q.; Zhu, W. M. Chem. Pharm. Bull. 2008, 56, 217-221 10.1248/cpb.56.217
25. Kemami Wangun, H. V.; Hertweck, C. Org. Biomol. Chem. 2007, 5, 1702-1705 10.1039/b702378b
26. McBrien, K. D.; Gao, Q.; Huang, S.; Klohr, S. E.; Wang, R. R.; Pirnik, D. M.; Neddermann, K. M.; Bursuker, I.; Kadow, K. F.; Leet, J. E. J. Nat. Prod. 1996, 59, 1151-1153 10.1021/np960521t
27. Bailly, F.; Maurin, C.; Teissier, E.; Vezin, H.; Cotelle, P. Bioorg. Med. Chem. 2004, 12, 5611-5618 10.1016/j.bmc.2004.07.066
28. Takashi, N.; Mutsuo, N.; Hidetake, K.; Masaaki, T.; Isshin, T. In Jpn. Kokai Tokkyo Koho, JP 2007153840 A 20070621, 2007.
29. Teshima, Y.; Shin-ya, K.; Shimazu, A.; Furihata, K.; Chul, H. S.; Furihata, K.; Hayakawa, Y.; Nagai, K.; Seto, H. J. Antibiot. 1991, 44, 685-687 10.7164/antibiotics.44.685
30. Snider, B. B.; Lu, Q. J. Org. Chem. 1994, 59, 8065-8070 10.1021/jo00105a024
31. Tomoda, H.; Tabata, N.; Yang, D. J.; Takayanagi, H.; Omura, S. J. Antibiot. 1995, 48, 793-804 10.7164/antibiotics.48.793
32. Schroeder, F. C.; Gibson, D. M.; Churchill, A. C. L.; Sojikul, P.; Wursthorn, E. J.; Krasnoff, S. B.; Clardy, J. Angew. Chem., Int. Ed. 2007, 46, 901-904 10.1002/anie.200603821
33. Lee, H. J.; Chung, M. C.; Lee, C. H.; Chun, H. K.; Kim, H. M.; Kho, Y. H. J. Microbiol. Biotechnol. 1996, 6, 445-450