Decaspirones F-I, bioactive secondary metabolites from the saprophytic fungus Helicoma viridis

Journal of Natural Products

Volumn 69, Issue 12, 2006, Pages 1672-1675

  Hu, Hejiao ^a   Guo, Huijuan ^a,b   Li, Erwei ^a   Liu, Xingzhong ^a   Zhou, Yuguang ^a   Che, Yongsheng ^a  

^a INSTITUTE OF MICROBIOLOGY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; DECASPIRONE F; DECASPIRONE G; DECASPIRONE H; DECASPIRONE I; MONOBROMOBENZOIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE; PALMARUMYCIN DERIVATIVE; SPIROBISNAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG INHIBITION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS; FUNGUS CULTURE; HELICOMA VIRIDIS; LACTOCOCCUS LACTIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PSEUDOMONAS AERUGINOSA; X RAY CRYSTALLOGRAPHY;

ANTI-BACTERIAL AGENTS; CHINA; CRYSTALLOGRAPHY, X-RAY; FUNGI; LACTOCOCCUS LACTIS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NAPHTHALENES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PSEUDOMONAS AERUGINOSA; SPIRO COMPOUNDS;

DREPANOSPORA VIRIDIS; FUNGI; LACTOCOCCUS; PSEUDOMONAS AERUGINOSA;

EID: 33846433507     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0603830     Document Type: Article

References (19)

1. Weber, H. A.; Baenziger, N. C.; Gloer, J. B. J. Am. Chem. Soc. 1990, 112, 6718-6719.
2. Weber, H. A.; Gloer, J. B. J. Org. Chem. 1991, 56, 4355-4360.
3. Singh, S. B.; Zink, D. L.; Liesch, J. M.; Ball, R. G.; Goetz, M. A.; Bolessa, E. A.; Giacobbe, R. A.; Silverman, K. C.; Bills, G. F.; Pelaez, F.; Cascales, C.; Gibbs, J. B.; Lingham, R. B. J. Org. Chem. 1994, 59, 6296-6302.
4. Krohn, K.; Michel, A.; Flörke, U.; Aust, H. J.; Draeger, S.; Schulz, B. Liebigs Ann. Chem. 1994, 1099-1108.
5. Krohn, K.; Michel, A.; Flörke, U.; Aust, H. J.; Draeger, S.; Schulz, B. Liebigs Ann. Chem. 1994, 1093-1097.
6. Schlingmann, G.; West, R. R.; Milne, L.; Pearce, J.; Carter, G. T. Tetrahedron Lett. 1993, 34, 7225-7228.
7. Schlingmann, G.; Matile, S.; Berova, N.; Nakanishi, K.; Carter, G. T. Tetrahedron 1996, 52, 435-446.
8. Thiergardt, R.; Hug, P.; Rihs, G.; Peter, H. H. Tetrahedron Lett. 1994, 35, 1043-1046.
9. Thiergardt, R.; Rihs, G.; Hug, P.; Peter, H. H. Tetrahedron 1994, 51, 733-742.
10. Chu, M.; Truumees, I.; Patel, M. G.; Gullo, V. P.; Pai, J.-K.; Puar, M. S.; McPhail, A. T. J. Org. Chem. 1994, 59, 1222-1223.
11. McDonald, L. A.; Abbanat, D. R.; Barbieri, L. R.; Bernan, V. S.; Discafani, C. M.; Greenstein, M.; Janota, K.; Korshalla, J. D.; Lassota, P.; Tischler, M.; Carter, G. T. Tetrahedron Lett. 1999, 40, 2489-2492.
12. van der Sar, S. A.; Blunt, J. W.; Munro, M. H. G. Org. Lett. 2006, 8, 2059-2061.
13. Chu, M.; Patel, M. G.; Pai, J. K.; Das, P. R.; Puar, M. S. J. Antibiot. 2000, 53, 153-157.
14. Wipf, P.; Lynch, S. M.; Birmingham, A.; Tamayo, G.; Jiménez, A.; Campos, N.; Powis, G. Org. Biomol. Chem. 2004, 2, 1651-1658.
15. Upon nearing completion of the manuscript, we became aware that another group had independently isolated and characterized (from a different fungal source) a series of five other compounds that are very close analogues of those described here. Because of the similarities in the structures, a mutual decision was made to name them all as decaspirones and to submit the corresponding manuscripts simultaneously to J. Nat. Prod. (see ref 16).
16. Jiao, P.; Swenson, D. C.; Gloer, J. B.; Campbell, J.; Shearer, C. A. J. Nat. Prod., 2006, 69, 1667-1671.
17. Krohn, K.; Beckmann, K.; Aust, H. J.; Draeger, S.; Schulz, B.; Busemann, S.; Bringmann, G. Liebigs Ann. Chem. 1997, 2531-2534.
18. Crystallographic data for compound 1 have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC 616787). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
19. Wicklow, D. T.; Joshi, B. K.; Gamble, W. R.; Gloer, J. B.; Dowd, P. F. Appl. Environ. Microbiol. 1998, 64, 4482-448.