Detection of VM55599 and preparaherquamide from Aspergillus japonicus and Penicillium fellutanum: Biosynthetic implications

Journal of Natural Products

Volumn 71, Issue 9, 2008, Pages 1574-1578

  Ding, Yousong ^a   Gruschow, Sabine ^a   Greshock, Thomas J ^b   Finefield, Jennifer M ^b   Sherman, David H ^a   Williams, Robert M ^b,c  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Department of Environmental and Radiological Health Sciences   (United States)

^c UNIVERSITY OF COLORADO CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPERPARALINE A; BREAVIANAMIDE B; DRUG METABOLITE; MALBRANCHEAMIDE; MALBRANCHEAMIDE B; MARCFORTINE A; MARCFORTINE B; MARCFORTINE C; NATURAL PRODUCT; NOTOAMIDE A; NOTOAMIDE B; PARAHERQUAMIDE A; PREMALBRANCHEAMIDE; PREPARAHERQUAMIDE; SCLEROTIAMIDE; STEPHACIDIN B; UNCLASSIFIED DRUG; VM 55599;

ARTICLE; ASPERGILLUS; DIELS ALDER REACTION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS CULTURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PENICILLIUM; STEREOMETRY;

ASPERGILLUS; INDOLIZINES; MOLECULAR STRUCTURE; PENICILLIUM; SPIRO COMPOUNDS;

ASPERGILLUS JAPONICUS; PENICILLIUM FELLUTANUM;

EID: 54149105745     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np800292n     Document Type: Article

References (46)

1. (a) Yamazaki, M.; Okuyama, E.; Kobayashi, M.; Inoue, H. Tetrahedron Lett. 1981, 22, 135-136.
2. (b) Ondeyka, J. G.; Goegelman, R. T.; Schaeffer, J. M.; Kelemen, L.; Zitano, L. J. Antibiot. 1990, 43, 1375-1379.
3. (c) Liesch, J. M.; Wichmann, C. F. J. Antibiot. 1990, 43, 1380-1386.
4. (d) Blanchflower, S. E.; Banks, R. M.; Everett, J. R.; Manger, B. R.; Reading, C. J. Antibiot. 1991, 44, 492-497.
5. (a) Hayashi, H.; Nishimoto, Y.; Nozaki, H. Tetrahedron Lett. 1997, 38, 5655-5658.
6. (b) Hayashi, H.; Nishimoto, Y.; Akiyama, K.; Nozaki, H. Biosci. Biotechnol. Biochem. 2000, 64, 111-115.
7. (c) Banks, R. M.; Blanchflower, S. E.; Everett, J. R.; Manger, B. R.; Reading, C. J. Antibiot. 1997, 50, 840-846.
8. (a) Qian-Cutrone, J.; Huang, S.; Shu, Y.-Z.; Vyas, D.; Fairchild, C.; Menendez, A.; Krampitz, K.; Dalterio, R.; Klohr, S. E.; Gao, Q. J. Am. Chem. Soc. 2002, 124, 14556-14557.
9. (b) Qian-Cutrone, J.; Krampitz, K.;. Shu, Y.-Z. Chang, L. P. U.S. Patent 6,291,461, 2001.
10. (a) Birch, A. J.; Wright, J. J. J. Chem. Soc., Chem Commun. 1969, 644-645.
11. (b) Birch, A. J.; Wright, J. J. Tetrahedron 1970, 26, 2329-2344.
12. (c) Birch, A. J.; Russell, R. A. Tetrahedron 1972, 28, 2999-3008.
13. (d) Bird, B. A.; Remaley, A. T.; Campbell, I. M. Appl. Environ. Microbiol. 1981, 42, 521-525.
14. (e) Bird, B. A.; Campbell, I. M. Appl. Environ. Microbiol. 1982, 43, 345-348.
15. (f) Robbers, J. E.; Straus, J. W. Lloydia 1975, 38, 355-356.
16. (g) Paterson, R. R. M.; Hawksworth, D. L. Trans. Br. Mycol. Soc. 1985, 85, 95-100.
17. (h) Wilson, B. J.; Yang, D. T. C.; Harris, T. M. Appl. Microbiol. 1973, 26, 633-635.
18. (i) Coeteer, J. Acta Crystallogr. 1974, B30, 2254-2256.
19. (a) Polonsky, J.; Merrien, M.-A.; Prange, T.; Pascard, C. J. Chem. Soc., Chem. Comm. 1980, 601-602.
20. (b) Prange, T.; Buillion, M-A.; Vuilhorgne, M.; Pascard, C.; Polonsky, J. Tetrahedron Lett. 1980, 22, 1977-1980.
21. (a) Kato, H.; Yoshida, T.; Tokue, T.; Nojiri, Y.; Hirota, H.; Ohta, T.; Williams, R. M.; Tsukamoto, S. Angew. Chem., Int. Ed. 2007, 46, 2254-2256.
22. Whyte, A. C.; Gloer, J. B. J. Nat. Prod. 1996, 59, 1093-1095.
23. (a) Martinez-Luis, S.; Rodriguez, R.; Acevedo, L.; Gonzalez, M. C.; Lira-Rocha, A.; Mata, R. Tetrahedron 2006, 62, 1817-1822.
24. (b) Figueroa, M.; del Carmen Gonzalez, M.; Mata, R. Nat. Prod. Res. 2008, 22, 709-714.
25. (c) Miller, K. A.; Welch, T. R.; Greshock, T. J.; Ding, Y.; Sherman, D. H.; Williams, R. M. J. Org. Chem. 2008, 73, 3116-3119.
26. (a) Stocking, E.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078-3115.
27. (b) Cox, R. J.; Williams, R. M. Acc. Chem. Res. 2003, 36, 127-139.
28. (c) Williams, R. M. Chem. Pharm. Bull. 2002, 50, 711-740.
29. (d) Williams, R. M.; Sanz-Cervera, J. F.; Stocking, E. In Topics in Current Chemistry, Volume on Biosynthesis-Terpenes and Alkaloids; Leeper, F., Vederas, J. C., Eds.; Springer-Verlag: Berlin, 2000; Vol. 209, pp 97-173.
30. Blanchflower, S. E.; Banks, R. M.; Everett, J. R.; Reading, C. J. Antibiot. 1993, 46, 1355-1363.
31. Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 2002, 124, 2556-2559.
32. (a) Stocking, E. M.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 1675-1683.
33. (b) Stocking, E. M.; Sanz-Cervera, J. F.; Williams, R. M. Angew. Chem., Int. Ed. 2001, 40, 1296-1298.
34. (a) Stocking, E.; Sanz-Cervera, J. F.; Williams, R. M.; Unkefer, C. J. J. Am. Chem. Soc. 1996, 118, 7008-7009.
35. (b) Stocking, E. M.; Martinez, R. A.; Silks, L. A.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 2001, 123, 3391-3392.
36. (c) Gray, C.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 2003, 125, 14692-14693.
37. (d) Stocking, E.; Sanz-Cervera, J. F.; Unkefer, C. J.; Williams, R. M. Tetrahedron 2001, 57, 5303-5320.
38. Both enantiomers of stephacidin A and notoamide B have recently been isolated from distinct Aspergillus spp.; see:Greshock, T. J.; Grubbs, A. W.; Jiao, P.; Wicklow, D. T.; Gloer, J. B.; Williams, R. M. Angew. Chem., Int. Ed. 2008, 47, 3573-3577.
39. Ding, Y.; Miller, K. A.; Greshock, T. J.; Sherman, D. H.; Williams, R. M. (unpublished results).
40. (a) Hayasaka, Y.; Wilkinson, K. L.; Elsey, G. M.; Raunkjaer, M.; Sefton, M. A. J. Agric Food Chem. 2007, 55, 9195-9201.
41. (b) Koh, H. L.; Wang, H.; Zhou, S.; Chan, E.; Woo, S. O. J. Pharm. Biomed. Anal. 2006, 40, 653-661.
42. (c) Ding, B.; Zhou, T.; Fan, G.; Hong, Z.; Wu, Y. J. Pharm. Biomed. Anal. 2007, 45, 219-226.
43. Nielsen, K. F.; Sumarah, M. W.; Frisvad, J. C.; Miller, J. D. J. Agric. Food Chem. 2006, 54, 3756-3763.
44. (a) Williams, R. M.; Cao, J.; Tsujishima, H.; Cox, R. J. J. Am. Chem. Soc. 2003, 125, 12172-12178.
45. (b) Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1993, 115, 9323-9324.
46. (c) Domingo, L. R.; Zaragozá, R. J.; Williams, R. M. J. Org. Chem. 2003, 68, 2895-2902.