Two New Drimane Sesquiterpenes, Fudecadiones A and B, from the Soil Fungus Penicillium sp. BCC 17468

Abstract

Two new drimane sesquiterpenoids, fudecadione A and fudecadione B (1, 2), together with the known brefeldin A (3) and fulvic acid (4), were isolated from the soil fungus Penicillium sp. BCC 17468. Chemical structures were determined based on spectroscopic evidence including 1D and 2D NMR and mass spectral data. The proposed relative stereochemistry of fudecadiones A and B was based upon NOESY spectral data and chemical means. Compounds 1 and 4 exhibited anticancer activity against MCF-7, KB, and NCI-H187, with IC₅₀ values in the range of 5.05–45.43 µg/mL, while compound 2 was inactive against these tumor cells. Brefeldin (3) also displayed antimalarial activity against Plasmodium falciparum (K1, multidrug-resistant strain), with an IC₅₀ value of 1.12 µg/mL.

Key words

drimane sesquiterpenes - antimalaria - Penicillium sp. - Trichocomaceae

References

• 1 Tabata N, Tomoda H, Masuma R, Iwai Y, Omura S. Fudecalone, a new anticoccidial agent produced by Penicillium sp. FO-2030.  J Antibiot (Tokyo). 1995;  48 53-58
• 2 Watanabe H, Yamaguchi T, Furuuchi T, Kitahara T. Synthesis and revision of the relative configuration of fudecalone.  Tetrahedron Lett. 2001;  42 917-919
• 3 Fujita K, Nagamine Y, Ping X, Taniguchi M. Mode of action of anhydrofulvic acid against Candida utilis ATCC 42402 under acidic condition.  J Antibiot (Tokyo). 1999;  52 628-634
• 4 Vurro M, Evidente A, Andolfi A, Zonno M C, Giordano F, Motta A. Brefeldin A and α,β-dehydrocurvularin, two phytotoxins from Alternaria zinniae, a biocontrol agent of Xanthium occidentale.  Plant Sci. 1998;  138 67-79
• 5 Wang F W, Jiao R H, Cheng A B, Tan S H, Song Y C. Antimicrobial potential of endophytic fungi residing in Quercus variabilis and brefeldin A obtained from Cladosporium sp.  World J Microbiol Biotechnol. 2007;  23 79-83
• 6 Capon R J, Stewart M, Ratnayake R, Lacey E, Gill J H. Citromycetins and bilains A–C: new aromatic polyketides and diketopiperazines from Australian marine-derived and terrestrial Penicillium spp.  J Nat Prod. 2007;  70 1746-1752
• 7 Sakaki T, Ichihara A, Sakamura S. Isolation of fulvic acid from Cercospora beticola.  Agric Biol Chem. 1981;  45 1275-1276
• 8 Desjardins R E, Canfield C J, Haynes J D, Chulay J D. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique.  Antimicrob Agents Chemother. 1979;  16 710-718
• 9 Changsen C, Franzblau S G, Palittapongarnpim P. Improved green fluorescent protein reporter gene-based microplate screening for antituberculosis compounds by utilizing an acetamidase promoter.  Antimicrob Agents Chemother. 2003;  47 3682-3687
• 10 O'Brien J, Wilson I, Orton T, Pognan F. Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity.  Eur J Biochem. 2000;  267 5421-5426