Abstract
The addition of metal bromides (NaBr and CaBr2) during fermentation of the marine-mudflat-derived fungus Aspergillus niger induced production of a new radical scavenging brominated naphthopyranone, 6,9-dibromoflavasperone (1); and three known naphtho-γ-pyranone monomers, flavasperone (2), TMC-256A1 (3), and fonsecin (4); and one naphtho-γ-pyranone dimer, aurasperone B (5). The structure of 6,9-dibromoflavasperone (1) was assigned through the combination of spectroscopic data analyses and comparison with the spectral data of flavasperone (2). Compounds 1–5 displayed potent radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl, with IC50 values of 21, 25, 0.3, 0.02, and 0.01 μM, respectively, and 3–5 were more potent than the positive control, ascorbic acid (IC50, 20.0 μM).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Feling RH, Buchanan GO, Mincer TJ, Kaufman CA, Jensen PR, Fenical W (2003) Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora. Angew Chem Int Ed 42:355–357
Huang HB, Xiao ZE, Feng XJ, Huang CH, Zhu X, Ju JH, Li MF, Lin YC, Liu L, She ZG (2011) Cytotoxic naphtha-γ-pyrones from the mangrove endophytic fungus Aspergillus tubingensis (GX1-5E). Helv Chim Acta 94:1732–1740
Lam KS, Tsueng G, McArthur KA, Mitchell SS, Potts BCM, Xu J (2007) Effects of halogens on the production of salinosporamides by the obligate marine actinomycete Salinispora tropica. J Antibiot 60:13–19
Leutou AS, Yun K, Kang JS, Son BW (2013) Induced production of methyl bromodihydroxyphenyl acetates by the marine-derived fungus Aspergillus sp. Chem Pharm Bull 61:483–485
Leutou AS, Yun K, Son BW (2014) Microbial transformation of dihydroxyphenylacetic acid by the marine-derived bacterium Stappia sp. Bull Korean Chem Soc 35:2870–2872
Sakai K, Ohte S, Ohshiro T, Matsuda D, Masuma R, Rudel LL, Tomoda H (2008) Selective inhibition of Acyl-CoA: cholesterol acyltransferase 2 isozyme by flavasperone and sterigmatocystin from Aspergillus species. J Antibiot 61:568–572
Sakurai M, Kohno J, Yamamoto K, Okuda T, Nishio M, Kawano K, Ohnuki T (2002) TMC-256A1 and C1, new inhibitors of IL-4 signal transduction produced by Aspergillus niger var niger TC 1629. J Antibiot 55:685–692
Scott AI (1964) Interpretation of the ultraviolet spectra of natural products. Pergamon, Oxford, p 140
Siriwardane AMDA, Kumar NS, Jayasinghe L, Fujimoto Y (2015) Chemical investigation of metabolites produced by an endophytic Aspergillus sp. isolated from Limonia acidissima. Nat Prod Res 29:1384–1387
Stadler M, Anke H, Sterner O (1995a) Metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum. V. Production, isolation and biological activities of bromine-containing mycorrhizin and lachnumon derivatives and four additional new bioactive metabolites. J Antibiot 48:149–153
Stadler M, Anke H, Sterner O (1995b) Metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. III. Production of novel isocoumarin derivatives, isolation and biological activities. J Antibiot 48:261–266
Acknowledgments
This work was supported by a Research Grant of Pukyong National University (2015 year).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
All the authors have no conflict of interest to declare.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Leutou, A.S., Yun, K. & Son, B.W. Induced production of 6,9-dibromoflavasperone, a new radical scavenging naphthopyranone in the marine-mudflat-derived fungus Aspergillus niger . Arch. Pharm. Res. 39, 806–810 (2016). https://doi.org/10.1007/s12272-016-0764-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-016-0764-2