Circumdatin A, B, and C: Three new benzodiazepine alkaloids isolated from a culture of the fungus Aspergillus ochraceus

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1689-1692

  Rahbæk, Lisa ^a   Breinholt, Jens ^b   Frisvad, Jens C ^c   Christophersen, Carsten ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b NOVO NORDISK A S   (Denmark)

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ASPERLICIN; BENZODIAZEPINE DERIVATIVE; CIRCUMDATIN A; CIRCUMDATIN B; CIRCUMDATIN C; DRUG METABOLITE; PENICILLIC ACID; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ASPERGILLUS OCHRACEUS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; EXTRACTION; NONHUMAN; NOTE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 0033525505     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981536u     Document Type: Note

References (25)

1. Medina, J. H.; Paladini, A. C.; Izquierdo, I. Behav. Brain Res. 1993, 58, 1-8.
2. (a) Kimura, Y.; Hamasaki, T.; Nakajima, H.; Isogai, A. Tetrahedron Lett. 1982, 23, 225-228.
3. (b) Ellestad, G. A.; Mirando, P.; Kunstmann, M. P. J. Org. Chem. 1973, 38, 4204-4205.
4. Barrow, C. J.; Sun, H. H. J. Nat. Prod. 1994, 57, 471-476.
5. (a) Liesch, J. M.; Hensens, O. D.; Springer, J. P.; Chang, R. S. L.; Lotti, V. J. J. Antibiot. 1985, 38, 1638-1641.
6. (b) Liesch, J. M.; Hensens, O. D.; Zink, D. L.; Goetz, M. A. J. Antibiot. 1988, 41, 878-881.
7. Dictionary of Natural Products on CD-ROM; Chapman & Hall: New York (version 6: 2), 1998.
8. (a) Frisvad, J. C.; Thrane, U. J. Chromatogr. 1987, 404, 195-214.
9. (b) Frisvad, J. C. Bot. J. Linn. Soc. 1989, 99, 81-95.
10. (a) Weigelt, J.; Otting, G. J. Magn. Reson. A 1995, 113, 128-130.
11. (b) Reif, B.; Köck, M.; Kerssebaum, R.; Kang, H.; Fenical, W.; Griesinger, C. J. Magn. Reson. A 1996, 118, 282-285.
12. (c) Meissner, A.; Moskau, D.; Nielsen, N. C.; Sørensen, O. W. J. Magn. Reson. 1997, 124, 245-249.
13. (d) Breinholt, J.; Gürtler, H.; Kjær, A.; Nielsen, S. E.; Olsen, C. E. Acta Chem. Scand. 1998, 52, 1040-1044.
14. 13C-pair, respectively.
15. Sun, H. H.; Barrow, C. J.; Sedlock, D. M.; Gillum, A. M.; Cooper, R. J. Antibiot. 1994, 47, 515-522.
16. Sun, H. H.; Byard, S. J.; Cooper, R. J. Antibiot. 1994, 47, 599-601.
17. Kalinowski, H. O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscsopy; John Wiley and Sons Ltd.: New York, 1988; p 506.
18. Boyes-Korkis, J. M.; Gurney, K. A.; Penn, J.; Mantle, P. G.; Bilton, J. N.; Sheppard, R. N. J. Nat. Prod. 1993, 56, 1707-1717.
19. Penn, J.; Mantle, P. G.; Bilton, J. N.; Sheppard, R. N. J. Chem. Soc., Perkin. Trans. 1 1992, 1495-1496.
20. See Supporting Information Available.
21. Advanced Chemistry Development (ACD version 2.51), Advanced Chemistry Department Inc.: 133 Richmond St. West, Suite 605, Toronto, ON M5H 2L3 Canada, 1994-1997.
22. Roos, W. Alkaloids (Academic Press) 1990, 39, 63-97.
23. Following isolates were examined: NRRL 5221, NRRL 3174, NRRL 5175, NRRL 5063, NRRL 5228, NRRL 2864, NRRL 5220, NRRL 402, NRRL 410, NRRL 5222, NRRL 6319, IBT 10136, CBS 263.67, CBS 108.08, CBS 420.80, CBS 624.78, CBS 748.7, RMF 7884, RMF 7943. NRRL = Northern Regional Research Laboratory, Peoria, IL. IBT = Department of Biotechnology, Technical University of Denmark. CBS = Centraalbureau voor Schimmelscultures, Baarn, Holland. RMF = Rocky Mountain Fungi, Department of Botany, University of Wyoming, Laramie.
24. Following strains were examined. A ostianus: CBS 103.07, CBS 101.23, CBS 311.80, NRRL 422, IMI 177964b, IMI 348937, CCRC 32240. A petrakii: CBS 105.57. For CBS and NRRL see ref 17. IMI = Commonwealth Agricultural Bureau International Mycological Institute, Kew, Great Britain. CCRC = Culture Collection and Research Center, Food Industry Research and Development Institute, Hsinchu, Taiwan.
25. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596.