Bacillisporins D and E, New Oxyphenalenone Dimers from Talaromyces bacillisporus

Abstract

The oligophenalenone dimer duclauxin and two new analogues, bacillisporins D and E, were isolated from the fungus Talaromyces bacillisporus in addition to the previously reported bacillisporins A, B and C. Structures were established by spectroscopic studies. Duclauxin and bacillisporins A, B, C and E were evaluated for cytotoxicity against three human cancer cell lines. Bacillisporin A was strongly active against MCF-7 and NCI-H460 and moderately active against SF-268 while bacillisporins B, C and duclauxin were moderately active against all three cell lines.

References

• 1 Stolk A C, Samson R A. The genus Talaromyces: Studies on Talaromyces and related genera II. Studies in mycology No 2. Baarn; Centralbureau voor Schimmelcultures (CBS) 1972: p 1-65
• 2 Yamazaki M, Okuyama E. Isolation and structures of oxaphenalenone dimers from Talaromyces bacillosporus (sic!).  Chem Pharm Bull. 1980;  28 3649-55
• 3 Ishii K, Itoh T, Kobayashi K, Horie Y, Ueno Y. Isolation of a cytotoxic metabolite of Talaromyces bacillosporus (sic!).  Appl Envir Microbiol. 1995;  61 941-3
• 4 Shiojiri H, Nakamura T, Hissada K, Kawai K, Nozawa Y, Okuyama E. et al . The effect of bacillosporin A from Talaromyces bacillosporus (sic!) on mitochondrial respiration.  Mycotoxins. 1984;  20 17-9
• 5 Shibata S, Ogihara Y, Tokutake N, Tanaka O. Duclauxin, a metabolite of Penicillium duclauxii. Tetrahedron Lett 1965: 1287-8
• 6 Ogihara Y, Iitaka Y, Shibata S. X-Ray study of monobromoduclauxin. Tetrahedron Lett 1965: 1289-90
• 7 Kuhr I, Fuska J. Antitumor antibiotic produced by Penicillium stipitatum. Its identity with duclauxin.  J Antibiot. 1973;  26 535-6
• 8 Cooke R G, Edwards G M. Naturally occurring phenalenones and related compounds. In: Herz W, Grisebach H, Kirby GW, editors Progress in the chemistry of organic natural products. Wien; Springer Verlag 1981: p 153-90
• 9 Frisvad J C, Filtenborg O, Samson R A, Stolk A C. Chemotaxonomy of the genus Talaromyces .  Antonie van Leuwenhoek. 1990;  57 179-89
• 10 Fuskova A, Proksa B, Fuska J. In vitro effect of duclauxin and derivatives of coumarin on nucleic acid and protein synthesis in Ehrlich’s ascites carcinoma cells.  Pharmazie. 1977;  32 291
• 11 Kovac L, Bohmerova E, Fuska J. Inhibition of mitochondrial functions by the antibiotics bikaverin and duclauxin.  J Antibiot. 1978;  31 616-20
• 12 Kawai K, Nozwa Y, Ito T, Yamanaka N. Effects of xanthomegnin and duclauxin on culture cells of murine leukemia and Ehrlich ascites tumor.  Res Commun Chem Pathol Pharmacol. 1982;  3 29-38
• 13 Shiojiri H, Kawai K, Kato T, Ogihara Y, Nozawa Y. Cytotoxicities on culture cells and inhibitory effects on mitochondrial respiration by duclauxin and related compounds.  Mycotoxins. 1983;  18 38-41
• 14 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D. et al . New colorimetric cytotoxicity assay for anticancer drug screening.  J Natl Cancer Inst. 1990;  82 1107-12
• 15 Monks A, Scudiero D, Skehan P, Shoemaker R, Paul K, Vistica D. et al . Feasibility of a high-flux anticancer drug screening using a diverse panel of cultured human tumor cell lines.  J Natl Cancer Inst. 1991;  83 757-76