Atlantinone A, a meroterpenoid produced by Penicillium ribeum and several cheese associated penicillium species

Metabolites

Volumn 2, Issue 1, 2012, Pages 214-220

  Dalsgaard, Petur W ^a   Petersen, Bent O ^b   Duus, Jens Ø ^c   Zidorn, Christian ^d   Frisvad, Jens C ^e   Christophersen, Carsten ^a   Larsen, Thomas O ^e  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b CARLSBERG LABORATORY   (Denmark)

^c not available   (Denmark)

^d UNIVERSITY OF INNSBRUCK   (Austria)

^e TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Andrastin; Atlantinone A; Cheese associated fungi; Penicillium ribeum; Psychrotolerant

Indexed keywords

ATLANTINONE A; FUNGAL PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; FUNGUS GROWTH; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PENICILLIUM; PROTEIN PURIFICATION; PROTEIN STRUCTURE;

EID: 84881170468     PISSN: None     EISSN: 22181989     Source Type: Journal    
DOI: 10.3390/metabo2010214     Document Type: Article

References (19)

1. Uchida, R.; Shiomi, K.; Inokoshi, J.; Sunazuka, T.; Tanaka, H.; Iwai, Y.; Takayanagi, H.; Omura, S. Andrastins A-C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929. II. Structure and biosynthesis. J. Antibiot. 1996, 49, 418-424.
2. Shiomi, K.; Tomoda, H.; Otoguro, K.; Omura, S. Meroterpenoids with various biological activities produced by fungi. Pure Appl. Chem. 1999, 71, 1059-1064.
3. Uchida, R.; Shiomi, K.; Inokoshi, J.; Tanaka, H.; Iwai, Y.; Omura, S. Andrastin D, novel protein farnesyltransferase inhibitor produced by Penicillium sp. FO-3929. J. Antibiot. 1996, 49, 1278-1280.
4. Kosemura, S. Meroterpenoids from Penicillium citreo-viride B. IFO 4692 and 6200 hybrid. Tetrahedron 2003, 59, 5055-5072.
5. Omura, S.; Inokoshi, J.; Uchida, R.; Shiomi, K.; Masuma, R.; Kawakubo, T.; Tanama, H.; Iwai, Y.; Kosemura, S.; Yamamura, S. Andrastins A-C, new protein farnesyltransferase inhibitors produced by Penicillium sp. FO-3929. I. Producing strain, fermentation, isolation, and biological activity. J. Antibiot. 1996, 49, 414-417.
6. Rho, M.-C.; Toyoshima, M.; Hayashi, M.; Uchida, R.; Shiomi, K.; Komiyama, K.; Omura, S. Enhancement of drug accumulation by andrastin A produced by Penicillium sp. FO-3929 in vincristine-resistant KB cells. J. Antibiot. 1998, 51, 68-72.
7. Pedretti, A.; Villa, L.; Vistoli, G. Modeling of binding modes and inhibition mechanism of some natural ligands of farnesyl transferase using molecular docking. J. Med. Chem. 2002, 45, 1460-1465.
8. Nielsen, K.F.; Dalsgaard, P.W.; Smedsgaard, J.; Larsen, T.O. Andrastins A-D, Penicillium roqueforti metabolites consistently produced in blue-mold-ripened cheese. J. Agric. Food Chem. 2005, 53, 2908-2913.
9. Fernández-Bodega, M.A.; Mauriz, E.; Gómez, A.; Martin, J.F. Proteolytic activity, mycotoxins and andrastin A in Penicillium roqueforti strains isolated from Cabrales, Valdeón and Bejes-Tresviso local varieties of blue-weined cheeses. Int. J. Food Microbiol. 2009, 136, 18-25.
10. Overy, D.P.; Larsen, T.O.; Dalsgaard, P.W.; Frydenvang, K.; Phipps, R., Munro, M.H.G.; Christophersen, C. Andrastin A and barceloneic acid metabolites, protein farnesyl transferase inhibitors from Penicillium albocoremium: Chemotaxonomic significance and pathological implications. Mycol. Res. 2005, 1243-1249.
11. Sonjak, S.; Frisvad, J.C.; Gunde-Cimerman, N. Comparison of secondary metabolite production by Penicillium crustosum strains, isolated from Arctic and other various ecological niches. FEMS Microbiol. Ecol. 2005, 53, 51-60.
12. Frisvad, J.C.; Larsen, T. O; Dalsgaard, P.W.; Seifert, K.A.; Louis-Seize, G.; Lyhne, E.K.; Jarvis, B.B.; Fettinger, J.C.; Overy, D.P. Four psychrotolerant species with high chemical diversity consistently producing cycloaspeptide A, Penicillium jamesonlandense sp. nov., Penicillium ribeum sp. nov., Penicillium soppi, and Penicillium lanosum. Int. J. Syst. Evol. Microbiol.2006, 56, 1427-1437.
13. Dalsgaard, P.W.; Larsen, T.O.; Frydenvang, K.; Christophersen, C. Psychrophilin A and cycloaspeptide D, novel cyclic peptides from the psychrotolerant fungus Penicillium ribeum. J. Nat. Prod. 2004, 67, 878-881.
14. Wang, X.; Sena Filho, J.G.; Hoover, A.R.; King, J.B.; Ellis, T.K.; Powell, D.R.; Cichewicz, R.H. Chemical epigenetics alters the secondary metabolite composition of guttate excreted by an atlantic-forest-soil-derived Penicillium citreonigrum. J. Nat. Prod. 2010, 73, 942-948.
15. Larsen, T.O.; Gareis, M.; Frisvad, J.C. Cell cytotoxicity and mycotoxin and secondary metabolite production by common penicillia on cheese agar. J. Agric. Food Chem. 2002, 50, 6148-6164.
16. Schroeckh, V.; Scherlach, K.; Nützmann, H.W.; Shelest, E.; Schmidt-Heck, W.; Schuemann, J.; Martin, K.; Hertweck, C.; Brakhage, A.A. Intimate bacterial-fungal interaction triggers biosynthesis of archetypal polyketides in Aspergillus nidulans. Proc. Natl. Acad. Sci. USA 2009, 106, 14558-14563.
17. Houbraken, J.; Samson, R.A. Phylogeny of Penicillium and the segregation of Trichocomaceae into three families. Stud. Mycol. 2011, 70, 1-51.
18. Rivera, K.G.; Seifert, K.A. A taxonomic and phylogenetic revision of the Penicillium sclerotiorum complex. Stud. Mycol. 2011, 70, 139-158.
19. Nielsen, M.L.; Nielsen, J.B.; Rank, C.; Klejnstrup, M.L.; Holm, D.K.; Brogaard, K.H.; Hansen, B.G.; Frisvad, J.C.; Larsen, T.O.; Mortensen, U.H. A genome-wide polyketide synthase deletion library uncovers novel genetic links to polyketides and meroterpenoids in Aspergillus nidulans. FEMS Microbiol. Lett. 2011, 321, 157-166.