New aromatic nitro compounds from Salegentibacter sp. T436, an arctic sea ice bacterium: Taxonomy, fermentation, isolation and biological activities

Journal of Antibiotics

Volumn 60, Issue 5, 2007, Pages 301-308

  Al Zereini, Wael ^a   Schuhmann, Imelda ^b   Laatsch, Hartmut ^b   Helmke, Elisabeth ^c   Anke, Heidrun ^a  

^a Institute for Biotechnology and Drug Research (IBWF)   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

^c ALFRED WEGENER INSTITUTE FOR POLAR AND MARINE RESEARCH   (Germany)

Author keywords

Antibacterial activity; Aromatic nitro compounds; Cytotoxic activity; Marine bacteria; Salegentibacter

Indexed keywords

(4 HYDROXY 3 NITROPHENYL)ACETIC ACID; (4 HYDROXY 3 NITROPHENYL)ACETIC ACID METHYL ESTER; (4 HYDROXY 3 NITROPHENYL)PROPIONIC ACID; (4 HYDROXY 3,5 DINITROPHENYL)ACETIC ACID; (4 HYDROXY 3,5 DINITROPHENYL)ACETIC ACID METHYL ESTER; (4 HYDROXY 3,5 DINITROPHENYL)PROPIONIC ACID; (4 HYDROXY 3,5 DINITROPHENYL)PROPIONIC ACID METHYL ESTER; 2 (4 HYDROXY 3 NITROPHENYL)ETHANOL; 2 (4 HYDROXY 3,5 DINITROPHENYL)ETHANOL; 2 (4 HYDROXY 3,5 DINITROPHENYL)ETHYLCHLORIDE; 2 CHLORO 3 (4 HYDROXY 3,5 DINITROPHENYL)PROPIONIC ACID METHYL ESTER; 2 HYDROXY 3 (4 HYDROXY 3 DINITROPHENYL)PROPIONIC ACID METHYL ESTER; 2 NITRO 4 (2' NITROETHYL)PHENOL; 3 NITRO 1H INDOLE; 3 NITROGENISTEIN; 3',5' DINITROGENISTEIN; 4 HYDROXY 3 NITROBENZOIC ACID; 4,5 DINITRO 3 METHOXYPHENOL; 4,6 DINITROGUIACOL; AROMATIC NITRO COMPOUND; RNA 16S; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; ANTINEOPLASTIC ANTIBIOTIC; BACTERIAL DNA; NITRO DERIVATIVE;

ANIMAL CELL; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIUM; BACTERIUM CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DILUTION; DRUG ISOLATION; DRUG POTENCY; DRUG PURIFICATION; DRUG SYNTHESIS; FERMENTATION; GENE SEQUENCE; HUMAN; HUMAN CELL; NONHUMAN; NUCLEOTIDE SEQUENCE; PLANT GROWTH; PRIORITY JOURNAL; SALEGENTIBACTER; SEA ICE; TAXONOMY; ARCTIC; CHEMISTRY; CLASSIFICATION; DNA SEQUENCE; DRUG EFFECT; DRUG SCREENING; FUNGUS; GENETICS; ISOLATION AND PURIFICATION; MICROBIOLOGICAL EXAMINATION; OXYGEN CONSUMPTION; TUMOR CELL LINE; ULTRASTRUCTURE;

BACTERIA (MICROORGANISMS); SALEGENTIBACTER;

ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; ARCTIC REGIONS; BACTERIA; CELL LINE, TUMOR; DNA, BACTERIAL; DRUG SCREENING ASSAYS, ANTITUMOR; FERMENTATION; FUNGI; HUMANS; MICROBIAL SENSITIVITY TESTS; NITRO COMPOUNDS; OXYGEN CONSUMPTION; SEQUENCE ANALYSIS, DNA;

EID: 34548385685     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2007.38     Document Type: Article

References (31)

1. Fenical W. Chemical studies of marine bacteria: developing a new resource. Chem Rev 93: 1673-1683 (1993)
2. Laatsch H. Marine bacterial metabolites. In Frontiers in MarineBiotechnology. Ed. P. Proksch et al., pp. 225-288, Horizon Bioscience, Norfolk (2006)
3. Schuhmann I. Aufbau einer HPLC-UV-ESI-MS/MS-Datenbank und ihre Anwendung im Screening arktischer und antarktischer Meeresbakterien. PhD Thesis University of Göttingen 2005 and Schuhmann I, Al-Zereini W, Anke H, Laatsch H. New aromatic nitro compounds from Salegentibacter sp. T436. II. Physico-chemical properties and structure determination. In preparation
4. Brinkmeyer R, Knittel K, Jürgens J, Weyland H, Amann R, Helmke E. Diversity and structure of bacterial communities in Arctic versus Antarctic pack ice. Appl Environ Microbiol 69: 6610-6619 (2003)
5. Baumann L, Baumann P, Mandel M, Allen RD. Taxonomy of aerobic marine eubacteria. J Bacteriol 110: 402-429 (1972)
6. Süßmuth R, Eberspächer J, Haag R, Springer W. Mikrobiologisch-biochemisches Praktikum. Georg Thieme Verlag, Stuttgart (1999)
7. Helmke E, Weyland H. Rhodococcus marinonascens sp. nov., an actinomycete from the sea. Int J Syst Bacteriol 34: 127-138 (1984)
8. Sambrook J, Fritsch EF, Maniatis T. Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory Press. 3rd edition (2001)
9. Anke H, Bergendorff O, Sterner O. Assay of the biological activities of guaiane sesquiterpenoids isolated from the fruit bodies of edible Lactarius species. Food Chem Toxicol 27: 393-398 (1989)
10. Kettering M, Valdivia C, Sterner O, Anke H, Thines E. Heptemerones A-G, seven novel diterpenoids from Coprinus heptemerus: Producing organism, fermentation, isolation and biological activities. J Antibiot 58: 390-396 (2005)
11. Anke H, Stadler M, Mayer A, Sterner O. Secondary metabolites with nematicidal and antimicrobial activity from nematophagous fungi and Ascomycetes. Can J Bot 73: 932-939 (1995)
12. Zapf S, Hossfeld M, Anke H, Velten R, Steglich W. Darlucin A and B, new isocyanide antibiotics from Sphaerellopsis filum (Darluca filum). J Antibiot 48: 36-41 (1995)
13. Mierau V, Anke T, Sterner O. Dacrymenone and VM 3298-2-new antibiotics with antibacterial and antifungal activity. Z Naturforsch 58c: 541-546 (2003)
14. McCammon SA, Bowman JP. Taxonomy of the Antarctic Flavobacterium species: description of Flavobacterium gillisiae sp. nov., Flavobacterium tegetincola sp. nov., and Flavobacterium xanthum sp. nov., nom. rev. and reclassification of [Flavobacterium] salegens as Salegentibacter salegens gen. nov., comb. nov. Int J Syst Evol Microbiol 50: 1055-1063 (2000)
15. Bose AK, Urbanczyk-Lipkowska Z, Subbaraju GV, Manhas MS, Ganguly SN. An unusual secondary metabolite from an Indian mangrove plant, Sonneratia acida Linn. F. pp. 402-411, Oceanography of the Indian Ocean. Desai, B.N. (ed.). A.A. Balkema, Rotterdam, Netherlands (1992)
16. Mikami Y, Takahashi K, Fukushima K, Yazawa K, Arai T. A new pigment from Streptomyces lavendulae. J Antibiot 40: 385-387 (1987)
17. Mikami Y, Yazawa K, Maeda A, Uno J. Antifungal activity of SL-1, a β-nitrostyrene type pigment and its synthetic congeners. J Antibiot 44: 1454-1456 (1991)
18. Price DN, Wain RL. Studies on plant growth-regulating substances. XLI. Structure-activity relationships and metabolism of a group of nitrophenols capable of inhibiting chloroplast development. Ann Appl Biol 83: 115-124 (1976)
19. Rebstock MC, Crooks HM, Controulis J, Bartz QR. Chloramphenicol (Chloromycetin). IV. Chemical studies. J Am Chem Soc 71: 2458-2462 (1949)
20. Arima K, Imanaka H, Kousaka M, Fukuta A, Tamura J. Pyrrolnitrin, a new antibiotic substance produced by Pseudomonas. J Agric Biol Chem 24: 575-576 (1964)
21. Winkler R, Hertweck C. Sequential enzymatic oxidation of aminoarenes to nitroarenes via hydroxylamines. Angew Chem Int Ed 44: 4083-4087 (2005)
22. Carter GT, Nietsche JA, Goodman JJ, Torrey MJ, Dunne TS, Siegel MM, Borders DB. Direct biochemical nitration in the biosynthesis of dioxapyrrolomycin. A unique mechanism for the introduction of nitro groups in microbial products. J Chem Soc, Chem Commun: 1271-1273 (1989)
23. Kirner S, van Pée K-H. Biosynthese von Nitroverbindungen: Die enzymatische Oxidation einer Vorstufe mit Aminogruppe zu Pyrrolnitrin. Angew Chem 106: 346-347 (1994)
24. Kono Y, Yamasaki T, Ueda A, Shibata H. Catalase catalyses of peroxynitrite-mediated phenolic nitration. Biosci Biotechnol Biochem 62: 448-452 (1998)
25. Sakihama Y, Tamaki R, Shimoji H, Ichiba T, Fukush Y, Tahara S, Yamasaki H. Enzymatic nitration of phytophenolics: evidence for peroxynitrite-independent nitration of plant secondary metabolites. FEBS Lett 553: 377-380 (2003)
26. Shangguan D, Rong J, Baoyi L, Chunling X, Jianbo W. Production, isolation and structure elucidation of novel isoflavonoid compound K3-D4, K3-D5, K3-D6. Zhongguo Kangshengsu Zazhi 24: 254-257 (1999)
27. Sviridov SI, Ermolinskii BS. Secondary metabolites of Pyricularia oryzae. I. O-nitrophenol derivatives. Khimiya Prirodnykh Soedinenii 6: 811-818 (1990)
28. Ohta K. Chemical studies on biologically active substances in seaweeds. Proceedings-International Seaweed Symposium 9: 401-411 (1979)
29. 2. Zhongguo Kangshengsu Zazhi 15: 321-324 (1990)
30. Bose AK, Ganguly SN, Mannas MS, Rao S, Speck J, Pekelny U, Pombo-Villars E. Microwave promoted rapid nitration of phenolic compounds with calcium nitrate. Tetrahedron Lett 47: 1885-1888 (2006)
31. Berti G, Da Settimo A, Nannipieri E. The reactions of some indole derivatives with benzoyl nitrate. Novel oxidative coupling reactions of 2-methylindoles. J Chem Soc C: 2145-3151 (1968)