Regio- and stereoselective intermolecular oxidative phenol coupling in kotanin biosynthesis by Aspergillus niger

ChemBioChem

Volumn 8, Issue 5, 2007, Pages 521-529

  Hüttel, Wolfgang ^a,b   Müller, Michael ^a,b  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

^b UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Atropisomerism; Biaryls; Coumarins; Filamentous fungi; Isotopic labeling

Indexed keywords

8,8' BICOUMARIN DERIVATIVE; COUMARIN DERIVATIVE; DEMETHYLKOTANIN; DIMER; KOTANIN; MONOMER; ORLANDIN; PHENOL; SIDERIN; UNCLASSIFIED DRUG; COUMARIN; OXYGEN; UMBELLIFERONE DERIVATIVE;

ARTICLE; ASPERGILLUS NIGER; BIOSYNTHESIS; DEMETHYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NONHUMAN; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; CHEMICAL MODEL; CHEMISTRY; CIRCULAR DICHROISM; METABOLISM; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; THIN LAYER CHROMATOGRAPHY;

ASPERGILLUS NIGER; FUNGI;

ASPERGILLUS NIGER; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; CIRCULAR DICHROISM; COUMARINS; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; MODELS, CHEMICAL; OXYGEN; PHENOL; STEREOISOMERISM; UMBELLIFERONES;

EID: 34447626841     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200600434     Document Type: Article

References (60)

1. a) G. Bringmann, C. Günther, M. Ochse, O. Schupp, S. Tasler, Prog. Chem. Org. Nat. Prod. 2001, 82, 1-249;
2. b) G. Bringmann, R. Walter, R. Weirich, Angew. Chem. 1990, 102, 1006-1019;
3. Angew. Chem. Int. Ed. Engl. 1990, 29, 977-991.
4. a) Binol: J. M. Brunel, Chem. Rev. 2005, 105, 857-898;
5. b) Binap: R. Noyori, Nobel Lecture, December 8, 2001, http://nobelprize.org/chemistry/laureates/2001/noyori-lecture.pdf.
6. a) G. Bringmann, A. J. Price Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518-5563;
7. Angew. Chem. Int. Ed. 2005, 44, 5384-5427;
8. b) I. Cepanec, Synthesis of Biaryls, Elsevier, Amsterdam, 2004, pp. 1-349.
9. Nonselective oxidative phenol coupling can be utilized to generate structural diversity, if the products can be separated: a) D. Drochner, W. Hüttel, M. Nieger, M. Müller, Angew. Chem. 2003, 115, 961-963;
10. Angew. Chem. Int. Ed. 2003, 42, 931-933;
11. b) D. Drochner, W. Hüttel, S. E. Bode, M. Müller, U. Karl, M. Nieger, W. Steglich, Eur. J. Org. Chem. 2007, DOI: 10.1002/ejoc.200600899;
12. c) M. Müller, Curr. Opin. Biotechnol. 2004, 15, 591-598.
13. a) For a review see ref. [3] and references therein;
14. b) T. Temma, S. Habaue, Tetrahedron Lett. 2005, 46, 5655-5657.
15. Salutaridin, Morphin: a) T. Amann, M. H, Zenk, Tetrahedron Lett. 1991, 32, 3675-3678;
16. b) R. Gerardy, M. H. Zenk, Phytochemistry 1993, 32, 79-86;
17. c) T. Amann, P. H. Roos, H. Huh, M. H. Zenk, Heterocycles 1995, 40, 425-440;
18. Berbamunin: d) M. H. Zenk, R. Gerardy, R. Stadler, J. Chem. Soc., Chem. Commun. 1989, 1725-1727;
19. e) R. Stadler, M. H. Zenk, J. Biol. Chem. 1993, 268, 823-831;
20. Isoandrocymbin, Colchicin: f) U. H. Maier, M. H. Zenk, Tetrahedron Lett. 1997, 38, 7357-7360;
21. g) E. McDonald, R. Ramage, R. N. Woodhouse, E. W. Underhill, L. R. Wetter, A. R. Battersby, J. Chem. Soc. Perkin Trans. 1 1998, 2979-2988;
22. Lunarin: h) S. Sagner, Z.-W. Shen, B. Deus-Neumann, M. H. Zenk, Phytochemistry 1998, 47, 375-387;
23. i) L. Nezbedová, M. Hesse, K. Drandarov, C. Werner, Tetrahedron Lett. 2000, 41, 7859-7862;
24. j) L. Nezbedová, M. Hesse, K. Drandarov, L. Bigler, C. Werner, Planta 2001, 213, 411-417;
25. Michellamin: k) J. Schlauer, M. Rückert, B. Wiesen, M. Herderich, L. Aké Assi, R. D. Haller, S. Bär, K.-U. Fröhlich, G. Bringmann, Arch. Biochem. Biophys. 1998, 350, 87-94;
26. Tellimagrandin II: l) R. Niemetz, G. Schilling, G. G. Gross, Chem. Commun. 2001, 35-36
27. Geodin (fungi): m) I. Fujii, H. Iijima, S. Tsukita, Y. Ebizuka, U. Sankawa, J. Biochem. 1987, 101, 11-18;
28. n) I. Fujii, Z. G. Chen, Y. Ebizuka, U. Sankawa, Biochem. Int. 1991, 25, 1043-1049;
29. o) I. Fujii, Y. Ebizuka, U. Sankawa, J. Biochem. 1988, 103, 878-883;
30. p) H.-H Park, T. Hakamatsuka, U. Sankawa, Y. Ebizuka, Phytochemistry 1995, 38, 373-380;
31. q) Z. G. Chen, I. Fujii, Y. Ebizuka, U. Sankawa, Arch. Microbiol. 1992, 158, 29-34;
32. r) K.-X. Huang, I. Fujii, Y. Ebizuka, K. Gomi, U. Sankawa, J. Biol. Chem. 1995, 270, 21 495-21 502.
33. L. B. Davin, H.-B. Wang, A. L. Crowell, D. L. Bedgar, D. M. Martin, S. Sarkanen, N. G. Lewis, Science 1997, 275, 362-367.
34. S. C. Halls, L. B. Davin, D. M. Kramer, N. G. Lewis, Biochemistry 2004, 43, 2587-2595.
35. a) Siderin (4): A. G. González, B. M. Fraga, M. G. Hernández, J. G. Luis, Phytochemistry 1972, 11, 2115-2116;
36. the structure was revised by: b) P. Venturella, A. Bellino, F. Piozzi, Tetrahedron Lett. 1974, 15, 979-981;
37. Kotanin (1), demethylkotanin (9): c) G. Büchi, D. H. Klaubert, R. C. Shank, S. M. Weinreb, G. N. Wogan, J. Org. Chem. 1971, 36, 1143-1147;
38. the fungus was erroneously classified as A. glaucus. Revised in: d) G. Büchi, K. Chun Luk, B. Kobbe, J. M. Townsend, J. Org. Chem. 1977, 42, 244-246;
39. Orlandin (10): e) H. G. Cutler, F. G. Crumley, R. H. Cox, O. Hernandez, R. J. Cole, J. W. Dorner, J. Agric. Food Chem. 1979, 27, 592-595;
40. Desertorin A-C (2, 13 and 14): f) K. Nozawa, H. Seyea, S. Nakajima, S.-I. Udagawa, K.-I. Kawai, J. Chem. Soc. Perkin Trans. 1 1987, 1735-1738;
41. Isokotanin A-C (3, 11 and 12): g) J. A. Laakso, E. D. Narske, J. B. Gloer, J. Nat. Prod. 1994, 57, 128-133;
42. h) K. Nozawa, S. Nakajima, K.-I. Kawai, S.-I. Udagawa, M. Miyaji, Phytochemistry 1994, 35, 1049-1051;
43. Aflavarin: i) M. R. TePaske, J. B. Gloer, D. T. Wicklow, P. F. Dowd, J. Nat. Prod. 1992, 55, 1080-1086; 7-O-Demethyl-3,8′- bisiderin (15): see ref. [10h].
44. Bicoumanigrin: j) J. Hiort, K. Maksimenka, M. Reichert, S. Perović-Ottstadt, W. H. Lin, V. Wray, K. Steube, K. Schaumann, H. Weber, P. Proksch, R. Ebel, W. E. G. Müller, G. Bringmann, J. Nat. Prod. 2004, 67, 1532-1543.
45. a) M. Müller, K. Lamottke, W. Steglich, S. Busemann, M. Reichert, G. Bringmann, P. Spiteller, Eur. J. Org. Chem. 2004, 4850-4855;
46. b) C. Elsworth, M. Gill, A. Giménez, N. M. Milanovic, E. Raudies, J. Chem. Soc. Perkin Trans. 1 1999, 119-125.
47. J. B. Stothers, A. Stoessl, Can. J. Chem. 1988, 66, 2816-2818.
48. W. Hüttel, M. Nieger, M. Müller, Synthesis 2003, 1803-1808 and ref. therein.
49. Findings of kotanin (1) and derivatives 9 and 10 are described in: a) R. A. Samson, J. A. M. P. Houbraken, A. F. A. Kuijpers, J. M. Frank, J. C. Frisvad, Stud. Mycol. 2004, 50, 45-61;
50. b) L. Pařenicová, P. Skouboe, J. Frisvad, R. A. Samson, L. Rossen, M. ten Hoor-Suykerbuyk, J. Visser, Appl. Environ. Microbiol. 2001, 67, 521-527;
51. K. F. Nielsen, S. Gravesen, P. A. Nielsen, B. Andersen, U. Thrane, J. C. Frisvad, Mycopathologia 1999, 145, 43-56; and ref. [9c, 9e, 9g, 9h].
52. A. M. Calvo, R. A. Wilson, J. W. Bok, N. P. Keller, Microbiol. Mol. Biol. Rev. 2002, 66, 447-459.
53. The yield was detected by weighing; however, the product fraction contained minor impurities.
54. The substrates were added two days after inoculation as for the earlier cultures. Initial growth, however, was slightly attenuated during this experiment.
55. a) K. A. Kumar, B. S. V. Kumar, B. Laxminarayana, S. Anathanarayanan, Stud. Surf. Sci. Catal. 1998, 113, 541-546;
56. b) H. Kasahara, M. Miyazawa, H. Kameoka, Phytochemistry 1997, 44, 1479-1482.
57. W. Hüttel, Dissertation, Universität Bonn (Germany), 2005.
58. 13C-feeding experiments: S. Bode, D. Drochner, M. Müller, unpublished results.
59. 13C-5 as a substrate were not successful.
60. J. Chiarello, M. M. Joullié, Tetrahedron 1988, 44, 41-48.