Abstract
During the systematic screening of active compounds from marine-derived fungi, the extract of a strain of Aspergillus versicolor MF359 isolated from a marine sponge of Hymeniacidon perleve was identified for detailed chemical investigation. Three new secondary metabolites, named hemiacetal sterigmatocystin (1), acyl-hemiacetal sterigmatocystin (2), and 5-methoxydihydrosterigmatocystin (3), together with a known compound, aversin (4), were characterized. 1 represents a first structure of sterigmatocystin hemiacetal from nature. The antibacterial activities of these identified compounds were evaluated against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, Bacillus subtilis, and Pseudomonas aeruginosa. Compound 3 showed activity against S. aureus and B. subtilis with MIC values of 12.5 and 3.125 μg/mL, respectively.
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Asai F, Tosa H, Tanaka T, Iinuma M (1995) A xanthone from pericarps of Garcinia mangostana. Phytochemistry 39:943–944
Ashforth EJ, Fu C, Liu X, Dai H, Song F, Guo H, Zhang L (2010) Bioprospecting for antituberculosis leads from microbial metabolites. Nat Prod Reps 27:1709–1719
Ashley DL, Orti DL, Hill RH Jr (1987) Proton nuclear magnetic resonance evidence for two configurations of the hemiacetals of aflatoxin B1 and sterigmatocystin. J Agric Food Chem 35:782–785
Belofsky GN, Jensen PR, Renner MK, Fenical W (1998) New cytotoxic sesquiterpenoid nitrobenzoyl esters from a marine isolate of the fungus Aspergillus versicolor. Tetrahedron 54:1715–1724
Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2006) Marine natural products. Nat Prod Rep 23:26–78
Bugni TS, Ireland CM (2004) Marine-derived fungi: a chemically and biologically diverse group of microorganisms. Nat Prod Rep 21:143–163
Chen PN, Kingston DGI, Vercellotti JR (1977) Reduction of sterigmatocystin and versicolorin a hemiacetals with sodium borohydride. J Org Chem 42:3599–3605
Chen C, Song F, Wang Q, Abdel-Mageed WM, Guo H, Fu C, Hou W, Dai H, Liu X, Yang N, Xie F, Yu K, Chen R, Zhang L (2012) A marine-derived Streptomyces sp. MS449 produces high yield of actinomycin X2 and actinomycin D with potent anti-tuberculosis activity. Appl Microbiol Biotechnol 95:919–927
Chen C, Wang J, Guo H, Hou W, Yang N, Ren B, Liu M, Dai H, Liu X, Song F, Zhang L (2013) Three antimycobacterial metabolites identified from a marine-derived Streptomyces sp. MS100061. Appl Microbiol Biotechnol 97:3885–3892
Cole R, Cox R (1981) Handbook of Toxic Fungal Metabolites. Academic, New York
Felsenstein J (1985) Confidence limits on phylogenies: an approach using the bootstrap. Evolution 39:783–791
Fremlin LJ, Piggott AM, Lacey E, Capon RJ (2009) Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor. J Nat Prod 72:666–670
He F, Sun YL, Liu KS, Zhang XY, Qian PY, Wang YF, Qi SH (2012) Indole alkaloids from marine-derived fungus Aspergillus sydowii SCSIO 00305. J Antibiot (Tokyo) 65:109–111
Kato H, Yoshida T, Tokue T, Nojiri Y, Hirota H, Ohta T, Williams RM, Tsukamoto S (2007) Notoamides A–D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp. Angew Chem Int Ed 46:2254–2256
Kusunoki M, Misumi J, Shimada T, Aoki K, Matsuo N, Sumiyoshi H, Yamaguchi T, Yoshioka H (2011) Long-term administration of the fungus toxin, sterigmatocystin, induces intestinal metaplasia and increases the proliferative activity of PCNA, p53, and MDM2 in the gastric mucosa of aged Mongolian gerbils. Environ Health Prev Med 16:224–231
Liu XH, Miao FP, Li XD, Yin XL, Ji NY (2012) A new sesquiterpene from an endophytic Aspergillus versicolor strain. Nat Prod Commun 7:819–820
Matasyoh JC, Dittrich B, Schueffler A, Laatsch H (2011) Larvicidal activity of metabolites from the endophytic Podospora sp. against the malaria vector Anopheles gambiae. Parasitol Res 108:561–566
Mori H, Sugie S, Yoshimi N, Kitamura J, Niwa M, Hamasaki T, Kawai K (1986) Genotoxic effects of a variety of sterigmatocystin-related compounds in the hepatocyte/DNA-repair test and the Salmonella microsome assay. Mutat Res 173:217–222
Rateb ME, Ebel R (2011) Secondary metabolites of fungi from marine habitats. Nat Prod Rep 28:290–344
Saitou N, Nei M (1987) The neighbor-joining method—a new method for reconstructing phylogenetic trees. Mol Biol Evol 4:406–425
Saleem M, Ali MSS, Hussain JA, Ashraf M, Lee YS (2007) Marine natural products of fungal origin. Nat Prod Rep 24:1142–1152
Shao C, She Z, Guo Z, Peng H, Cai X, Zhou S, Gu Y, Lin Y (2007) 1H and 13C NMR assignments for two anthraquinones and two xanthones from the mangrove fungus (ZSUH-36). Magn Reson Chem 45:434–438
Song F, Dai H, Tong Y, Ren B, Chen C, Sun N, Liu X, Bian J, Liu M, Gao H, Liu H, Chen X, Zhang L (2010) Trichodermaketones A-D and 7-O-methylkoninginin D from the marine fungus Trichoderma koningii. J Nat Prod 73:806–810
Song F, Liu X, Guo H, Ren B, Chen C, Piggott AM, Yu K, Gao H, Wang Q, Liu M, Liu X, Dai H, Zhang L, Capon RJ (2012a) Brevianamides with antitubercular potential from a marine-derived isolate of Aspergillus versicolor. Org Lett 14:4770–4773
Song F, Ren B, Yu K, Chen C, Guo H, Yang N, Gao H, Liu X, Liu M, Tong Y, Dai H, Bai H, Wang J, Zhang L (2012b) Quinazolin-4-one coupled with pyrrolidin-2-iminium alkaloids from marine-derived fungus Penicillium aurantiogriseum. Mar Drugs 10:1297–1306
Suda M, Mugishima T, Komatsu K, Sone T, Tanaka M, Mikami Y, Shiro M, Hirai M, Ohizumi Y, Kobayashi J (2003) Speradine A, a new pentacyclic oxindole alkaloid from a marine-derived fungus Aspergillus tamari. Tetrahedron 59:3227–3230
Tamura K, Dudley J, Nei M, Kumar S (2007) MEGA4: molecular evolutionary genetics analysis (MEGA) software version 4.0. Mol Biol Evol 24:1596–1599
Thompson JD, Higgins DG, Gibson TJ (1994) Clustal-W-improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673–4680
Toske SG, Jensen PR, Kauffman CA, Fenical W (1998) Aspergillamides A and B: modified cytotoxic tripeptides produced by a marine fungus of the genus Aspergillus. Tetrahedron 54:13459–13466
Trisuwan K, Rukachaisirikul V, Kaewpet M, Phongpaichit S, Hutadilok-Towatana N, Preedanon S, Sakayaroj J (2011) Sesquiterpene and xanthone derivatives from the sea fan-derived fungus Aspergillus sydowii PSU-F154. J Nat Prod 74(7):1663–1667
Wang Q, Song F, Xiao X, Huang P, Li L, Monte A, Abdel-Mageed WM, Wang J, Guo H, He W, Xie F, Dai H, Liu M, Chen C, Xu H, Liu M, Piggott AM, Liu X, Capon RJ, Zhang L (2013) Abyssomicins from the South China Sea deep-sea sediment Verrucosispora sp.: natural thioether michael addition adducts as antitubercular prodrugs. Angew Chem Int Edit 52:1231–1234
Wei MY, Wang CY, Liu QA, Shao CL, She ZG, Lin YC (2010) Five sesquiterpenoids from a marine-derived fungus Aspergillus sp. isolated from a gorgonian Dichotella gemmacea. Mar Drugs 8:941–949
Zhang Y, Li XM, Wang BG (2012) Anthraquinone derivatives produced by marine-derived fungus Aspergillus versicolor EN-7. Biosci Biotechnol Biochem 76:1774–1776
Acknowledgments
This work was supported in part by the National Program on Key Basic Research Project (973 program, 2013CB734000, 2012CB721000), the National Natural Science Foundation of China (30901849, 81102356, 81261120389, 81102369), the CAS Pillar Program (XDA04074000), the Ministry of Science and Technology of China (2011ZX11102-011-11), Genzyme, Sanofi company. L. Zhang is an Awardee of the National Distinguished Young Scholar Program in China.
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Song, F., Ren, B., Chen, C. et al. Three new sterigmatocystin analogues from marine-derived fungus Aspergillus versicolor MF359. Appl Microbiol Biotechnol 98, 3753–3758 (2014). https://doi.org/10.1007/s00253-013-5409-5
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DOI: https://doi.org/10.1007/s00253-013-5409-5