Browse > Article
http://dx.doi.org/10.7845/kjm.2013.3026

Isolation and Structure Determination of Metabolites from Cultures of Aspergillus protuberus  

Baek, So Yoon (School of Biotechnology, Yeungnam University)
Shim, Sang Hee (School of Biotechnology, Yeungnam University)
Publication Information
Korean Journal of Microbiology / v.49, no.2, 2013 , pp. 179-183 More about this Journal
Abstract
Marine-derived microbes have yielded a variety of metabolites so far. In the course of the project to find metabolites from marine microbes, an isolate of Aspergillus protuberus (SF 5767) was selected for chemical investigation. A large scale culture of this strain in PDA media was extracted with an organic solvent and the extract was fractionated by silica gel column chromatography. Repeated reverse phase HPLC of the fractions led to the isolation of three metabolites. Their chemical structures were elucidated as deoxybrevianamide E (1), brevianamide V (2), and ergosterol peroxide (3) on the basis of spectroscopic data including MS, NMR, and UV. To the best of our knowledge, chemical investigation of A. protuberus was conducted for the first time in this study.
Keywords
Aspergillus protuberus; brevianamide V; deoxybrevianamide E; metabolites;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Scott, P.M., Kennedy, B.P.C., Harwig, J., and Chen, Y.-K. 1974. Formation of diketopiperazines by Penicillium italicum isolated from oranges. Appl. Microbiol. 28, 892-894.
2 Sinha, S., Srivastava, R., de Clercq, E., and Singh, R.K. 2004. Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazapurine and diketopiperazine. Nucleos. Nucleot. Nucl. 23, 1815-1824.   DOI   ScienceOn
3 Song, F., Liu, X., Guo, H., Ren, B., Chen, C., Piggott, A.M., Yu, K., Gao, H., Wang, Q., Liu, M., and et al. 2012. Brevianamides with antitubercular potential from a marine-derived isolate of Aspergillus versicolor. Org. Lett. 14, 4770-4773.   DOI   ScienceOn
4 Park, S.H., Kim, D.S., Kim, W.G., Ryoo, I.J., Lee, D.H., Huh, C.H., Youn, S.W., Yoo, I.D., and Park, K.C. 2004. Terrein: a new melanogenesis inhibitor and its mechanism. Cell Mol. Life Sci. 61, 2878-2885.   DOI   ScienceOn
5 Stein, P.J. 1971. Austamide, a new toxic metabolite from Aspergillus ustus. Tetrahedron Lett. 36, 3331-3334.
6 Stein, P.J. 1973. The structures of five diketopiperazines from Aspergillus ustus. Tetrahedron 29, 107-120.   DOI   ScienceOn
7 van der Merwe, K.J., Steyn, P.S., Fourie, L., Scott, D.B., and Theron, J.J. 1965. Ochratoxin A, a toxic metabolite produced by Aspergillus ochraceus Wilh. Nature 205, 1112-1113.   DOI   ScienceOn
8 Van Middlesworth, F., Giacobbe, R.A., Lopez, M., Garrity, G., Bland, J.A., Bartizal, K., Fromtling, R.A., Polishook, J., Zweerink, M., and Edison, A.M. 1992. Sphingofungins A, B, C, and D; a new family of antifungal agents. I. Fermentation, isolation, and biological activity. J. Antibiot. 45, 861-867.   DOI
9 Wang, W., Lu, Z., Tao, H., Zhu, T., Fang, Y., Gu, Q., and Zhu, W. 2007. Isoechinulin-type alkaloids, variecolorins A-L, from halotolerant Aspergillus variecolor. J. Nat. Prod. 70, 1558-1564.   DOI   ScienceOn
10 Wijeratne, E.M., Turbyville, T.J., Zhang, Z., Bigelow, D., Pierson, L.S., VanEtten, H.D., Whitesell, L., Canfield, L.M., and Gunatilaka, A.A. 2003. Cytotoxic constituents of Aspergillus terreus from the rhizosphere of Opuntia versicolor of the Sonoran Desert. J. Nat. Prod. 66, 1567-1573.   DOI   ScienceOn
11 Codner, R.C., Sargeant, K., and Yeo, R. 1963. Production of aflatoxin by the culture of strains of Aspergillus flavus-oryzae on sterilized peanuts. Microbiol. Res. 5, 185-192.
12 Kato, H., Nakamura, Y., Finefield, J.M., Umaoka, H., Nakamura, T., Williams, R.M., and Tsukamoto, S. 2011. Study on the biosynthesis of the notoamides: pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E. Tetrahedron Lett. 52, 6923-6926.   DOI   ScienceOn
13 Hiort, J., Maksimenka, K., Reichert, M., Perovic-Ottstadt, S., Lin, W.H., Wray, V., Steube, K., Schaumann, K., Weber, H., Proksch, P., and et al. 2004. New natural products from the sponge-derived fungus Aspergillus niger. J. Nat. Prod. 67, 1532-1543.   DOI   ScienceOn
14 Houston, D.R., Synstad, B., Eijsink, V.G., Stark, M.J., Eggleston, I.M., and van Aalten, D.M. 2004. Structure-based exploration of cyclic dipeptide chitinase inhibitors. J. Med. Chem. 47, 5713-5720.   DOI   ScienceOn
15 Jin, W.B., Lermer, L., Chilton, J., Klingeman, H., and Towers, G.H. 1999. Antitumor sterols from the mycelia of Cordyceps sinensis. Phytochemistry 51, 891-898.   DOI   ScienceOn
16 Kim, M.-Y., Son, J.H., Jang, J.-H., Ahn, J.S., and Oh, H. 2012. Two new botcinin derivatives encountered in the studies of secondary metabolites from the marine-derived fungus Botryotinia sp. SF-5275. J. Antibiot. 65, 161-164.   DOI   ScienceOn
17 Kitamoto, K. 2002. Molecular Biology of the Koji Molds. Adv. Appl. Microbiol. 51, 129-153.   DOI
18 Kradin, R.L. and Mark, E.J. 2008. The pathology of pulmonary disorders due to Aspergillus spp. Arch. Pathol. Lab. Med. 132, 606-614.
19 Kwon, O.S., Park, S.H., Yun, B.S., Pyun, Y.R., and Kim, C.J. 2000. Cyclo(dehydroala-L-Leu), an ${\alpha}$-glucosidase inhibitor from Penicillium sp. F70614. J. Antibiot. 53, 954-958.   DOI   ScienceOn
20 Liu, Y., Li, X., Kim, S., Kang, J.S., Choi, H.D., Rho, J.R., and Son, B.W. 2004. Golmaenone, a new diketopiperazine alkaloid from the marine-derived fungus Aspergillus sp. Chem. Pharm. Bull. 52, 375-376.   DOI   ScienceOn
21 Nicholson, B., Lloyd, G.K., Miller, B.R., Palladino, M.A., Kiso, Y., Hayashi, Y., and Neuteboom, S.T. 2006. NPI-2358 is a tubulin-depolymerizing agent: In vitro evidence for activity as a tumor vascular-disrupting agent. Anti-Cancer Drugs 17, 25-31.   DOI   ScienceOn