Oxirapentyns F-K from the marine-sediment-derived fungus Isaria felina KMM 4639

Journal of Natural Products

Volumn 77, Issue 6, 2014, Pages 1321-1328

  Yurchenko, Anton N ^a   Smetanina, Olga F ^a   Kalinovsky, Anatoly I ^a   Pushilin, Michael A ^b   Glazunov, Valeriy P ^a   Khudyakova, Yuliya V ^a   Kirichuk, Natalya N ^a   Ermakova, Svetlana P ^a   Dyshlovoy, Sergey A ^a,c   Yurchenko, Ekaterina A ^a   Afiyatullov, Shamil Sh ^a  

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^b INSTITUTE OF CHEMISTRY   (Russian Federation)

^c FAR EASTERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACREMINE S; BENZOFURAN DERIVATIVE; CHROMENE DERIVATIVE; CISPLATIN; CYCLODEPSIPEPTIDE; FUNGAL EXTRACT; ISARIDIN E; ISARIKETIDE; ISOISARIIN B; OXIRAPENTYN DERIVATIVE; OXIRAPENTYN F; OXIRAPENTYN G; OXIRAPENTYN H; OXIRAPENTYN I; OXIRAPENTYN J; OXIRAPENTYN K; POLYKETIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CONTROLLED STUDY; CRYSTALLIZATION; DRUG CYTOTOXICITY; FUNGAL STRAIN; FUNGUS; HL 60 CELL LINE; HUMAN; HUMAN CELL; ISARIA FELINA; LIPOPHILICITY; MOLECULAR WEIGHT; NONHUMAN; SEDIMENT; X RAY CRYSTALLOGRAPHY;

ALKYNES; ANTINEOPLASTIC AGENTS; BENZOPYRANS; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; DEPSIPEPTIDES; DRUG SCREENING ASSAYS, ANTITUMOR; GEOLOGIC SEDIMENTS; HL-60 CELLS; HUMANS; HYPOCREALES; MARINE BIOLOGY; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OCEANS AND SEAS;

EID: 84903641376     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np500014m     Document Type: Article

References (34)

1. Rateb, M. E.; Ebel, R. Nat. Prod. Rep. 2011, 28, 290-344
2. Blunt, J. W.; Copp, B. R.; Keyzers, R. A.; Munro, M. H. G.; Prinsep, M. R. Nat. Prod. Rep. 2013, 30, 237-323
3. Hosoya, T.; Takagi, M.; Shin-ya, K. J. Antibiot. 2013, 66, 235-238
4. Asai, T.; Chung, Y. M.; Sakurai, H.; Ozeki, T.; Chang, F. R.; Yamashita, K.; Oshima, Y. Org. Lett. 2012, 14, 513-515
5. Morais-Urano, R. P.; Chagas, A. C. S.; Berlinck, R. G. S. Exp. Parasitol. 2012, 132, 362-366
6. Chung, Y. M.; El-Shazly, M.; Chuang, D. W.; Hwang, T. L.; Asai, T.; Oshima, Y.; Ashour, M. L.; Wu, Y. C.; Chang, F. R. J. Nat. Prod. 2013, 76, 1260-1266
7. Fujita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sasaki, S.; Toyama, R.; Chiba, K.; Hoshino, Y.; Okumoto, T. J. Antibiot. 1994, 47, 208-214
8. Furuya, T.; Hirotani, M.; Matsuzawa, M. Phytochemistry 1983, 22, 2509-2512
9. Zhang, Y.; Liu, S.; Liu, H.; Che, Y. J. Nat. Prod. 2009, 72, 1364-1367
10. Ma, C.; Li, Y.; Niu, S.; Zhang, H.; Liu, X.; Che, Y. J. Nat. Prod. 2011, 74, 32-37
11. Haritakun, R.; Strikitikulchai, P.; Khoyaiklang, P.; Isaka, M. J. Nat. Prod. 2007, 70, 1478-1480
12. Bunyapaiboonsri, T.; Yoiprommarat, S.; Intereya, K.; Rachtawee, P.; Hywel-Jones, N. L.; Isaka, M. J. Nat. Prod. 2009, 72, 756-759
13. Bunyapaiboonsri, T.; Yoiprommarat, S.; Srisanoh, U.; Choowong, W.; Tasanathai, K.; Hywel-Jones, N. L.; Luangsa-ard, J. J.; Isaka, M. Phytochem. Lett. 2011, 4, 283-286
14. Kikuchi, H.; Miyagawa, Y.; Sahashi, Y.; Inatomi, S.; Haganuma, A.; Nakahata, N.; Oshima, Y. Tetrahedron Lett. 2004, 45, 6225-6228
15. Kikuchi, H.; Miyagawa, Y.; Sahashi, Y.; Inatomi, S.; Haganuma, A.; Nakahata, N.; Oshima, Y. J. Org. Chem. 2004, 69, 352-356
16. Smetanina, O. F.; Yurchenko, A. N.; Afiyatullov, S. S.; Kalinovsky, A. I.; Pushilin, M. A.; Khudyakova, Y. V.; Slinkina, N. N.; Ermakova, S. P.; Yurchenko, E. A. Phytochem. Lett. 2012, 5, 165-169
17. Yurchenko, A. N.; Smetanina, O. F.; Khudyakova, Y. V.; Kirichuk, N. N.; Chaikina, E. L.; Anisimov, M. M.; Afiyatullov, S. S. Chem. Nat. Compd. 2013, 49, 857-860
18. Takahashi, S.; Itoh, Y.; Takeuchi, M.; Furuya, K.; Kodama, K.; Naito, A.; Haneishi, T.; Sato, S.; Tamura, C. J. Antibiot. 1983, 36, 1418-1420
19. Seto, H.; Furihata, K.; Otake, N.; Takahashi, S.; Haneishi, T.; Ohuchi, M. Tetrahedron Lett. 1984, 25, 337-340
20. Uhrín, D.; Batta, G.; Hruby, V. J.; Barlow, P.; Kover, K. J. Magn. Reson. 1998, 130, 155-161
21. Kuzumi, T.; Ooi, T.; Ohkubo, Y.; Yabuuchi, T. Bull. Chem. Soc. Jpn. 2006, 79, 965-980
22. Mashall, J. L. Carbon-Carbon and Carbon-Proton NMR Coupling; Verlag Chemie International: Deerfield Beach, 1983; pp 29-32.
23. Smetanina, O. F.; Yurchenko, A. N.; Kalinovskii, A. I.; Berdyshev, D. V.; Gerasimenko, A. V.; Pivkin, M. V.; Slinkina, N. N.; Dmitrenok, P. S.; Menzorova, N. I.; Kuznetsova, T. A.; Afiyatullov, S. S. Chem. Nat. Compd. 2011, 47, 385-390
24. Langenfeld, A.; Blond, A.; Gueye, S.; Herson, P.; Nay, B.; Dupont, J.; Prado, S. J. Nat. Prod. 2011, 74, 825-30
25. Kalinovskaya, N. I.; Kalinovsky, A. I.; Romanenko, L. A.; Dmitrenok, P. S.; Kuznetsova, T. A. Nat. Prod. Commun. 2010, 5, 597-602
26. Jimenez-Teja, D.; Hernandez-Galan, R.; Collado, I. G. Nat. Prod. Rep. 2006, 23, 108-116
27. Demyttenaere, J. C.; Willemen, H. M. Phytochemistry 1998, 47, 1029-1036
28. APEX2; Bruker AXS Inc.: Madison, WI, USA, 2005.
29. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122
30. Barltrop, J. A.; Owen, T. C.; Cory, A. H.; Cory, J. G. Bioorg. Med. Chem. Lett. 1991, 1, 611-614
31. Dyshlovoy, S. A.; Fedorov, S. N.; Kalinovsky, A. I.; Shubina, L. K.; Bokemeyer, C.; Stonik, V. A.; Honecker, F. Mar. Drugs 2012, 10, 1212-1224
32. Dyshlovoy, S. A.; Naeth, I.; Venz, S.; Preukschas, M.; Sievert, H.; Jacobsen, C.; Shubina, L. K.; Gesell Salazar, M.; Scharf, C.; Walther, R.; Krepstakies, M.; Priyadarshini, P.; Hauber, J.; Fedorov, S. N.; Bokemeyer, C.; Stonik, V. A.; Balabanov, S.; Honecker, F. J. Proteome Res. 2012, 11, 2316-2330
33. Freshney, R. I. Culture of Animal Cells: A Manual of Basic Technique; Wiley-Liss: New York, 1994.
34. Silchenko, A. S.; Kalinovsky, A. I.; Avilov, S. A.; Andryjaschenko, P. V.; Dmitrenok, P. S.; Yurchenko, E. A.; Dolmatov, I. Y.; Kalinin, V. I.; Stonik, V. A. Nat. Prod. Commun. 2013, 8, 1527-1534