Nigerasperones A∼C, new monomeric and dimeric naphtho-γ-pyrones from a marine alga-derived endophytic fungus Aspergillus niger EN-13

Journal of Antibiotics

Volumn 60, Issue 3, 2007, Pages 204-210

  Zhang, Yi ^a,b   Li, Xiao Ming ^a   Wang, Bin Gui ^a  

^a INSTITUTE OF OCEANOLOGY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Algous endophytic fungus; Aspergillus niger; Colpomenia sinuosa; Naphtho pyrone

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; AMPHOTERICIN B; ASPERPYRONE A; ASPERPYRONE C; AURASPERONE A; AURASPERONE B; CHLORAMPHENICOL; DIANHYDROAURASPERONE C; FONSECINONE A; FONSECINONE B; FONSECINONE C; FONSECINONE D; NIGERASPERONE A; NIGERASPERONE B; NIGERASPERONE C; PYRONE DERIVATIVE; UNCLASSIFIED DRUG; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; NAPHTHALENE DERIVATIVE;

ALGA; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; COLPOMENIA SINUOSA; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; FUNGAL STRAIN; FUNGUS ISOLATION; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; TUMOR CELL LINE; BIOLOGY; BROWN ALGA; CELL LINE; CHEMISTRY; CYTOLOGY; DIMERIZATION; DRUG EFFECT; EPITHELIUM CELL; ISOLATION AND PURIFICATION; LUNG; METABOLISM; MICROBIOLOGICAL EXAMINATION; MICROBIOLOGY;

ALGAE; ASPERGILLUS NIGER; CANDIDA ALBICANS; COLPOMENIA SINUOSA; FUNGI; PHAEOPHYCEAE;

ALGAE, BROWN; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ASPERGILLUS NIGER; CANDIDA ALBICANS; CELL LINE; CELL LINE, TUMOR; DIMERIZATION; EPITHELIAL CELLS; HUMANS; LUNG; MARINE BIOLOGY; MICROBIAL SENSITIVITY TESTS; NAPHTHALENES; PYRONES;

EID: 34347398921     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2007.24     Document Type: Article

References (21)

1. Varoglu M, Corbett TH, Valeriote FA, Crews P. Asperazine, a selective cytotoxic alkaloid from a sponge-derived culture of Aspergillus niger. J Org Chem 62: 7078-7079 (1997)
2. Hiort J, Maksimenka K, Reichert M, Perovic-Ottstadt S, Lin WH, Wray V, Steube K, Schaumann K, Weber H, Proksch P, Ebel R, Muller WEG, Bringmann G. New natural products from the sponge-derived fungus Aspergillus niger. J Nat Prod 67: 1532-1543 (2004)
3. Bugni TS, Abbanat D, Bernan VS, Maiese WM, Greenstein M, Wagoner RMV, Ireland CM. Yanuthones: novel metabolites from a marine isolate of Aspergillus niger. J Org Chem 65: 7195-7200 (2000)
4. Ui H, Shiomi K, Yamaguchi Y, Masuma R, Nagamitsu T, Takano D, Sunazuka T, Namikoshi M, Ōmura S. Nafuredin, a novel inhibitor of NADH-fumarate reductase, produced by Aspergillus niger FT-0554. J Antibiot 54: 234-238 (2001)
5. Priestap HA. New naphthopyrones from Aspergillus fonsecaeus. Tetrahedron 40: 3617-3624 (1984)
6. Ehrlich KC, Delucca II AJ, Ciegler A. Naphtho-γ-pyrone production by Aspergillus niger isolated from stored cottonseed. Appl Environ Microbiol 48: 1-4 (1984)
7. Akiyama K, Teraguchi Y, Hamasaki Y, Mori M, Tatsumi K, Ohnishi K, Hayashi H. New dimeric naphthopyrones from Aspergillus niger. J Nat Prod 66: 136-139 (2003)
8. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82: 1107-1112 (1990)
9. Al-Burtamani SKS, Fatope MO, Marwah RG, Onifade AK, Al-Saidi SH. Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman. J Ethnopharmacol 96: 107-112 (2005)
10. Duan XJ, Zhang WW, Li XM, Wang BG. Evaluation of antioxidant property of extract and fractions obtained from a red alga, Polysiphonia urceolata. Food Chem 95: 37-43 (2006)
11. 13C NMR spectroscopy of naphtho-γ-pyrones. Magn Reson Chem 24: 875-878 (1986)
12. Galmarini OL, Stodola FH. Fonsecin, a pigment from an Aspergillus fonsecaeus Mutant. J Org Chem 30: 112-115 (1965)
13. Tanaka H, Wang PL, Yamada O, Tamura T. Yellow pigments of Aspergillus niger and A. awamori. Part I. Isolation of aurasperone A and related pigments. Agric Biol Chem 30: 107-113 (1966)
14. Galmarini OL, Mastronardi IO, Priestap HA. Two novel metabolites of Aspergillus fonsecaeus. Experientia 30: 586 (1974)
15. Ghosal S, Biswas K, Chakrabarti DK. Toxic naphtho-γ-pyrones from Aspergillus niger. J Agric Food. Chem 27: 1347-1351 (1979)
16. Bouras N, Mathieu F, Coppel Y, Lebrihi A. Aurasperone F-a new member of the naphtho-gamma-pyrone class isolated from a cultured micro fungus, Aspergillus niger C-433. Nat Prod Res 19: 653-659 (2005)
17. Ernst-Russell MA, Chai CLL, Wardlaw JH, Elix JA. Euplectin and coneuplectin, new naphthopyrones from the lichen Flavoparmelia euplecta. J Nat Prod 63: 129-131 (2000)
18. Coelho RG, Vilegas W, Devienne KF, Raddi MSG. A new cytotoxic naphthopyrone dimer from Paepalanthus bromelioides. Fitoterapia 71: 497-500 (2000)
19. Barbosa FG, Oliveira MCF, Braz-Filho R, Silveira ER. Anthraquinones and naphthopyrones from Senna rugosa. Biochem Syst Ecol 32: 363-365 (2004)
20. Song YC, Li H, Ye YH, Shan CY, Yang YM, Tan RX. Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116 cell and some microbial growths. FEMS Microbiol Lett 241: 67-72 (2004)
21. Sakurai M, Kohno J, Yamamoto K, Okuda T, Nishio M, Kawano K, Ohnuki T. TMC-256A1 and C1, new inhibitors of IL-4 signal transduction produced by Aspergillus niger var. niger TC 1629. J Antibiot 55: 685-692 (2002)