New duclauxamide from Penicillium manginii YIM PH30375 and structure revision of the duclauxin family

Organic Letters

Volumn 17, Issue 5, 2015, Pages 1146-1149

  Cao, Pei ^a   Yang, Jing ^a   Miao, Cui Ping ^b   Yan, Yijun ^a   Ma, Ya Tuan ^a   Li, Xiao Nian ^a   Zhao, Li Xing ^b   Huang, Sheng Xiong ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b YUNNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CHROMONE DERIVATIVE; DUCLAUXAMIDE; DUCLAUXIN; POLYKETIDE;

CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG SCREENING; HL 60 CELL LINE; HUMAN; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; PENICILLIUM; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CHROMONES; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HL-60 CELLS; HUMANS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PENICILLIUM; POLYKETIDES;

EID: 84924269293     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00081     Document Type: Article

References (36)

1. Bérdy, J. J. Antibiot. 2005, 58, 1-26
2. Tan, R. X.; Zou, W. X. Nat. Prod. Rep. 2001, 18, 448-459
3. Strobel, G.; Daisy, B. Microbiol. Mol. Biol. Rev. 2003, 67, 491-502
4. Zhang, H. W.; Song, Y. C.; Tan, R. X. Nat. Prod. Rep. 2006, 23, 753-771
5. Strobel, G.; Daisy, B.; Castillo, U.; Harper, J. J. Nat. Prod. 2004, 67, 257-268
6. Gunatilaka, A. A. L. J. Nat. Prod. 2006, 69, 509-526
7. Zhang, D.; Ge, H.; Zou, J.-H.; Tao, X.; Chen, R.; Dai, J. Org. Lett. 2014, 16, 1410-1413
8. Gao, B.; Huang, L.; Liu, H.; Wu, H.; Zhang, E.; Yang, L.; Wu, X.; Wang, Z. Br. J. Pharmacol. 2014, 171, 214-223
9. Han, J.-B.; Hua, Y.-Q.; Chen, L.-Y.; Liu, L.-M. J. Chin. Integr. Med. 2012, 10, 256-263
10. Ng, T. B. J. Pharm. Pharmacol. 2006, 58, 1007-1019
11. Chan, R. Y. K.; Chen, W.-F.; Dong, A.; Guo, D.; Wong, M.-S. J. Clin. Endocrinol. Metab. 2002, 87, 3691-3695
12. Sankawa, U.; Taguchi, H.; Ogihara, Y.; Shibata, S. Tetrahedron Lett. 1966, 7, 2883-2886
13. Ayer, W. A.; Pedras, M. S.; Ward, D. E. Can. J. Chem. 1987, 65, 760-764
14. Elsebai, M. F.; Saleem, M.; Tejesvi, M. V.; Kajula, M.; Mattila, S.; Mehiri, M.; Turpeinen, A.; Pirttilä, A. M. Nat. Prod. Rep. 2014, 31, 628-645
15. Shibata, S.; Ogihara, Y.; Tokutake, N.; Tanaka, O. Tetrahedron Lett. 1965, 6, 1287-1288
16. Ogihara, Y.; Tanaka, O.; Shibata, S. Tetrahedron Lett. 1966, 7, 2867-2875
17. Kuhr, I.; Fuska, J.; Sedmera, P.; Podojil, M.; Vokoun, J.; Vaněk, Z. J. Antibiot. 1973, 26, 535-536
18. Bryant, F. O.; Cutler, H. G.; Jacyno, J. M. J. Pharm. Sci. 1993, 82, 1214-1217
19. Yamazaki, M.; Okuyama, E. Chem. Pharm. Bull. 1980, 28, 3649-3655
20. Dethoup, T.; Manoch, L.; Kijjoa, A.; Nascimento, M. S. J.; Puaparoj, P.; Silva, A. M. S.; Eaton, G.; Herz, W. Planta Med. 2006, 72, 957-960
21. Guo, Z.; Shao, C.; She, Z.; Cai, X.; Liu, F.; Vrijimoed, L. L. P.; Lin, Y. Magn. Reson. Chem. 2007, 45, 439-441
22. Wu, A.; Cremer, D.; Auer, A. A.; Gauss, J. J. Phys. Chem. A 2002, 106, 657-667
23. Ogihara, Y.; Iitaka, Y.; Shibata, S. Tetrahedron Lett. 1965, 6, 1289-1290
24. Ogihara, Y.; Iitaka, Y.; Shibata, S. Acta Crystallogr., Sect. B 1968, B24, 1037-1047
25. Bryant, F. O.; Cutler, H. G. Acta Crystallogr., Sect. C 1995, C51, 437-440
26. Mori, H.; Kawai, K.; Ohbayashi, F.; Kuniyasu, T.; Yamazaki, M.; Hamasaki, T.; Williams, G. M. Cancer Res. 1984, 44, 2918-2923
27. Kawai, K.; Shiojiri, H.; Nakamaru, T.; Nozawa, Y.; Sugie, S.; Mori, H.; Kato, T.; Ogihara, Y. Cell Biol. Toxicol. 1985, 1, 1-10
28. Lin, Z.; Zhu, T.; Fang, Y.; Gu, Q.; Zhu, W. Phytochemistry 2008, 69, 1273-1278
29. Wu, B.; Ohlendorf, B.; Oesker, V.; Wiese, J.; Malien, S.; Schmaljohann, R.; Imhoff, J. F. Mar. Biotechnol. 2015, 17, 110-119
30. Hooft, R. W. W.; Straver, L. H.; Spek, A. L. J. Appl. Crystallogr. 2008, 41, 96-103
31. Rychnovsky, S. D. Org. Lett. 2006, 8, 2895-2898
32. Dong, L.-B.; Wu, Y.-N.; Jiang, S.-Z.; Wu, X.-D.; He, J.; Yang, Y.-R.; Zhao, Q.-S. Org. Lett. 2014, 16, 2700-2703
33. Zhao, B.; Guengerich, F. P.; Bellamine, A.; Lamb, D. C.; Izumikawa, M.; Lei, L.; Podust, L. M.; Sundamoorthy, M.; Kalaitzis, J. A.; Reddy, L. M.; Kelly, S. L.; Stec, D.; Voehler, M.; Falck, J. R.; Moore, B. S.; Shimada, T.; Waterman, M. R. J. Biol. Chem. 2005, 280, 11599-11607
34. Aldemir, H.; Richarz, R.; Gulder, T. A. M. Angew. Chem., Int. Ed. 2014, 53, 8286-8293
35. Zmijewski, M. J., Jr.; Palaniswamy, V. A.; Gould, S. J. J. Chem. Soc., Chem. Commun. 1985, 18, 1261-1262
36. Rontein, D.; Nishida, I.; Tashiro, G.; Yoshioka, K.; Wu, W.-I.; Voelker, D. R.; Basset, G.; Hanson, A. D. J. Biol. Chem. 2001, 276, 35523-35529