The first sorbicillinoid alkaloids, the antileukemic sorbicillactones A and B, from a sponge-derived Penicillium chrysogenum strain

Tetrahedron

Volumn 61, Issue 30, 2005, Pages 7252-7265

  Bringmann, Gerhard ^a   Lang, Gerhard ^a   Gulder, Tobias A M ^a   Tsuruta, Hideyuki ^a   Mühlbacher, Jörg ^a,e   Maksimenka, Katja ^a   Steffens, Stefan ^b   Schaumann, Karsten ^b   Stöhr, Rüdiger ^c   Wiese, Jutta ^c   Imhoff, Johannes F ^c   Perovic̈ Ottstadt, Sanja ^d   Boreiko, Olexandra ^d   Müller, Werner E G ^d  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b ALFRED WEGENER INSTITUTE FOR POLAR AND MARINE RESEARCH   (Germany)

^c GEOMAR HELMHOLTZ CENTRE FOR OCEAN RESEARCH KIEL   (Germany)

^d JOHANNES GUTENBERG UNIVERSITY   (Germany)

^e NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Alkaloids; Antileukemic activity; Biosynthetic feeding experiments; Circular dichroism; Marine natural products; Penicillium chrysogenum; Quantum chemical CD calculations; Sorbicillin

Indexed keywords

ACETIC ACID; ALANINE; ALKALOID DERIVATIVE; ANTILEUKEMIC AGENT; BISVERTINOLONE; CARBON; MELEAGRINE; METHIONINE; NITROGEN; O ACETYLSORBIVINETONE; OXOSORBICILLINOL; ROQUEFORTINE; SEA WATER; SORBICILLACTONE A; SORBICILLACTONE A METHYL ESTER; SORBICILLACTONE B; SORBICILLIN; SORBICILLINOL; SORBIVINETOL; SORBIVINETONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CALCULATION; CIRCULAR DICHROISM; CYTOTOXICITY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; FUNGAL STRAIN; FUNGUS CULTURE; FUNGUS ISOLATION; HELA CELL; HUMAN; HUMAN CELL; LEUKEMIA CELL; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PENICILLIUM CHRYSOGENUM; PHEOCHROMOCYTOMA CELL; PRIORITY JOURNAL; QUANTUM CHEMISTRY; RAT; SPONGE (PORIFERA);

BETULACEAE; IRCINIA FASCICULATA; PENICILLIUM CHRYSOGENUM;

EID: 20544462843     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.026     Document Type: Article

References (37)

1. Part 7 in the series Novel Marine Natural Products, for part 6 see Ref. 17.
2. A.G. Kozlovskii, N.G. Vinokurova, and S.M. Ozerskaya Microbiology 67 1998 397 400
3. R.M. Williams, E.M. Stocking, and J.F. Sanz-Cervera Top. Curr. Chem. 209 2000 97 173
4. D.J. Cram, and M. Tishler J. Am. Chem. Soc. 70 1948 4238 4239
5. R. Andrade, W.A. Ayer, and P.P. Mebe Can. J. Chem. 70 1992 2526 2535
6. L.S. Trifonov, H. Hilpert, P. Floersheim, A.S. Dreiding, D.M. Rast, R. Skrivanova, and L. Hoesch Tetrahedron 42 1986 3157 3179
7. M. Kontani, Y. Sakagami, and S. Marumo Tetrahedron Lett. 35 1994 2577 2580
8. N. Abe, K. Yamamoto, and A. Hirota Biosci. Biotechnol. Biochem. 64 2000 620 622
9. S. Sperry, G.J. Samuels, and P. Crews J. Org. Chem. 63 1998 10011 10014
10. N. Abe, O. Sugimoto, K. Tanji, and A. Hirota J. Am. Chem. Soc. 122 2000 12606 12607
11. K.C. Nicolaou, R. Jautelat, G. Vassilikogiannakis, P.S. Baran, and K.B. Simonsen Chem. Eur. J. 5 1999 3651 3665
12. N. Abe, T. Murata, and A. Hirota Biosci. Biotechnol. Biochem. 62 1998 661 666
13. D. Barnes-Seeman, and E.J. Corey Org. Lett. 1 1999 1503 1504
14. K.C. Nicolaou, G. Vassilikogiannakis, K.B. Simonsen, P.S. Baran, Y.-L. Zhong, V.P. Vidali, E.N. Pitsinos, and E.A. Couladouros J. Am. Chem. Soc. 122 2000 3071 3079
15. G.A. Warr, J.A. Veitch, A.W. Walsh, G.A. Hesler, D.M. Pirnik, J.E. Leet, P.-F.M Lin, I.A. Medina, K.D. McBrien, S. Forenza, J.M. Clark, and K.S. Lam J. Antibiot. 49 1996 234 240
16. G. Bringmann, G. Lang, S. Steffens, E. Günther, and K. Schaumann Phytochemistry 63 2003 437 443
17. G. Bringmann, G. Lang, S. Steffens, and K. Schaumann J. Nat. Prod. 67 2004 311 315
18. G. Bringmann, and G. Lang W.E.G. Müller Marine Molecular Biotechnology Sponges (porifera) Vol. 1 2003 Springer Berlin 89 116
19. 26
20. Both, the constitution and the relative configuration of 1 were verified by a single-crystal X-ray analysis.
21. G. Bringmann, J. Mühlbacher, C. Repges, and J. Fleischhauer J. Comput. Chem. 22 2001 1273 1278
22. SYBYL: Tripos Associates, 169 Kanley Road, Suite 303, St. Louis, MO 63144.
23. L.S. Trifonov, J.H. Bieri, R. Prewo, A.S. Dreiding, L. Hösch, and D.M. Rast Tetrahedron 39 1983 4243 4256
24. H. Laatsch Antibase 2000, a Natural Products Database for Rapid Structure Determination, Chemical Concepts 2000 Weinheim Weinheim
25. N. Abe, T. Arakawa, K. Yamamoto, and A. Hirota Biosci. Biotechnol. Biochem. 66 2002 2090 2099
26. G. Bringmann, G. Lang, J. Mühlbacher, K. Schaumann, S. Steffens, P.G. Rytik, U. Hentschel, J. Morschhäuser, and R. Brun W.E.G. Müller Marine Molecular Biotechnology Sponges (porifera) Vol. 1 2003 Springer Berlin 231 253
27. Bringmann, G.; Lang, G.; Mühlbacher, J.; Schaumann, K.; Steffens, S.; Müller, W. E. G. German Patent Application DE 102 38 257.3, filed 21.08.2002; PCT/EP2003/007805 (17.7.2003); International Patent Number WO 2004/026854 A1 (1.4.2004).
28. Bringmann, G.; Lang, G.; Gulder, T.; Schaumann, K.; Steffens, S.; Imhoff, J. F.; Müller, W. E. G.; Perović, S. German Patent Application DE 10 2004 005 106.2, filed 02.02.2004; PCT/EP2003/007805 (07.17.2003); International Patent Number WO 2004/026854 A1, (04.01.2004).
29. R.J. Ogg, P.B. Kingsley, and J.S. Taylor J. Magn. Reson., Ser. B 104 1994 1 10
30. J. Del Bene, and H.H. Jaffe J. Chem. Phys. 48 1968 1807 1813
31. M.J.S. Dewar, E.G. Zoebisch, E. Healy, and J.J.P. Steward J. Am. Chem. Soc. 107 1985 3902 3909
32. Downing, J. W. Program Package BDZDO/MCDSPD; Department of Chemistry and Biochemistry, University of Colorado: Boulder, USA; modified by Fleischhauer, J.; Schleker, W.; Kramer, B.; ported to Linux by Gulden, K. -P.
33. L.J. Wickerham US Dept. Agric. Wash. D.C., Technol. Bull. 1029 1951 1 56
34. D.A. Scudiero, R.H. Shoemaker, K.D. Paull, A. Monks, S. Tierney, T.H. Nofziger, M.J. Currens, D. Seniff, and M.R. Boyd Cancer Res. 48 1988 4827 4833
35. R.I. Freshney Culture of Specific Cell Types Culture of Animal Cells. A Manual of Basic Technique 1987 A.R. Liss New York pp 257-288
36. S. Perovič, C. Schleger, G. Pergande, S. Iskric, H. Ushijima, P. Rytik, and W.E.G. Müller Eur. J. Pharmacol. (Mol. Pharmacol. Sec.) 288 1994 27 33
37. S. Perovič, M. Böhm, E. Meesters, A. Meinhardt, G. Pergande, and W.E.G. Müller Mech. Ageing Dev. 101 1998 1 19