Langkocyclines: Novel angucycline antibiotics from Streptomyces sp. Acta 3034

Journal of Antibiotics

Volumn 66, Issue 10, 2013, Pages 609-616

  Kalyon, Bahar ^a   Tan, Geok Yuan A ^b   Pinto, John M ^b   Foo, Cheau Yee ^b   Wiese, Jutta ^c   Imhoff, Johannes F ^c   Süssmuth, Roderich D ^a   Sabaratnam, Vikineswary ^b   Fiedler, Hans Peter ^d  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF MALAYA   (Malaysia)

^c GEOMAR HELMHOLTZ CENTRE FOR OCEAN RESEARCH KIEL   (Germany)

^d UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Angucyclines; Antitumor; Streptomyces; Structure elucidation; Taxonomy

Indexed keywords

ANTIBIOTIC AGENT; BENZ[A]ANTHRACENE DERIVATIVE; LANGKOCYCLINE A1; LANGKOCYCLINE A2; LANGKOCYCLINE A3; LANGKOCYCLINE B1; LANGKOCYCLINE B2; RNA 16S; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANTIBACTERIAL ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMOTAXONOMY; COLOR; CONTROLLED STUDY; DIODE ARRAY DETECTION; DRUG HYDROLYSIS; DRUG SCREENING; DRUG STRUCTURE; FUNGAL STRAIN; FUNGAL STRUCTURES; FUNGUS CULTURE; FUNGUS GROWTH; GENE SEQUENCE; GRAM POSITIVE BACTERIUM; HETERONUCLEAR MULTIPLE BOND CORRELATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; MALAYSIA; MASS SPECTROMETRY; NONHUMAN; NUCLEOTIDE SEQUENCE; PHENOTYPE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RNA GENE; SOIL; STREPTOMYCES; STREPTOMYCES LANATUS; STREPTOMYCES PSAMMOTICUS; TUMOR CELL LINE;

ANIMALS; ANTHRAQUINONES; ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; DNA, BACTERIAL; DNA, RIBOSOMAL; GRAM-POSITIVE BACTERIA; HEP G2 CELLS; HUMANS; MALAYSIA; MICE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; NIH 3T3 CELLS; OLIGOSACCHARIDES; PHYLOGENY; POLYCYCLIC HYDROCARBONS, AROMATIC; RHIZOSPHERE; RNA, RIBOSOMAL, 16S; SEQUENCE ANALYSIS, DNA; SOIL MICROBIOLOGY; STREPTOMYCES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84886784598     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2013.53     Document Type: Article

References (29)

1. Manderscheid, N. et al. Elaiomycins K and L, new azoxy antibiotics from Streptomyces sp. Tü 6399. J. Antibiot. 66, 85-88 (2013).
2. Fiedler, H. -P. Biosynthetic capacities of actinomycetes. 1. Screening for novel secondary metabolites by HPLC and UV-visible absorbance libraries. Nat. Prod. Lett. 2, 119-128 (1993).
3. Helaly, S. et al. Gombapyrones, new α-pyrone metabolites produced by Streptomyces griseoruber Acta 3662. J. Antibiot. 62, 445-452 (2009).
4. Helaly, S. E. et al. Langkolide, a 32-membered macrolactone antibiotic produced by Streptomyces sp. Acta 3062. J. Nat. Prod. 75, 1018-1024 (2012).
5. Schneider, K. et al. Nocardichelins A and B, siderophores from Nocardia strain Acta 3026. J. Nat. Prod. 70, 932-935 (2007). (Pubitemid 47056105)
6. Brötz, E. et al. Phenelfamycins G and H, new elfamycin-type antibiotics produced by Streptomyces albospinus Acta 3619. J. Antibiot. 64, 257-266 (2011).
7. Drautz, H., Zähner, H., Rohr, J. & Zeeck, A. Metabolic products of microorganisms. 234. Urdamycins, new angucycline antibiotics from Streptomyces fradiae. I. Isolation, characterization and biological properties. J. Antibiot. 39, 1657-1669 (1986). (Pubitemid 17210467)
8. Shirling, E. B. & Gottlieb, D. Methods for characterization of Streptomyces species. Int. J. Syst. Bacteriol. 16, 313-340 (1966).
9. Goodfellow, M. & Fiedler, H.-P. A guide to successful bioprospecting: informed by actinobacterial systematics. Antonie van Leeuwenhoek 98, 119-142 (2010).
10. 13C-NMR-Spektren und Biogenese von Resistomycin und Resistoflavin aus Streptomyces griseoflavus B 71 (Actinomycetales). Liebigs Ann. Chem. 1983, 835-843 (1983). (Pubitemid 13029952)
11. Dann, M. et al. Tetrangomycin, a new quinone antibiotic. Antimicrob. Agents Chemother. 1965, 832-835 (1965).
12. Künzel, E. et al. Inactivation of the urdGT2 gene, which encodes a glycosyltransferase responsible for the C-glycosyltransfer of activated D-olivose, leads to formation of the novel urdamycin I, J and K. J. Am. Chem. Soc. 121, 11058-11062 (1999). (Pubitemid 129541237)
13. Shaaban, K. A., Stamatkin, C., Damodaran, C. & Rohr, J. 11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from Streptomyces cyanogenus K62 mutant strain. J. Antibiot. 64, 141-150 (2011).
14. Klyne, W. The configuration of the anomeric carbon atoms in some cardiac glycosides. J Proc. Biochem. Soc. 47, XLI-XLII (1950).
15. Rix, U., Fischer, C., Remsing, L. L. & Rohr, J. Modification of post-PKS tailoring steps through combinatorial biosynthesis. Nat. Prod. Rep. 19, 542-580 (2002). (Pubitemid 35259018)
16. Rohr, J. & Zeeck, A. Urdamycins new angucycline antibiotics from Streptomyces fradiae III. The structures of urdamycins C and D. J. Antibiot. 41, 126-129 (1988). (Pubitemid 18057628)
17. Rohr, J. & Thiericke, R. Angucycline group antibiotics. Nat. Prod. Rep. 9, 103-137 (1992).
18. Nagasawa, T., Fukao, H., Irie, H. & Yamada, H. Sakyomicins A, B, C and D: new quinone-type antibiotics produced by a strain of Nocardia. Taxonomy, production, isolation and biological properties. J. Antibiot. 37, 693-699 (1984). (Pubitemid 14092033)
19. Hayakawa, Y., Iwakiri, T., Imamura, I., Seto, H. & Otake, N. Studies on the isotetracenone antibiotics II. Kerriamycins A, B and C, new antitumor antibiotics. J. Antibiot. 38, 960-963 (1985). (Pubitemid 15236253)
20. Sezaki, M., Kondo, S., Maeda, K., Umezawa, H. & Ohno, M. The structure of aquayamycin. Tetrahedron 26, 5171-5190 (1970).
21. Kharel, M. K. et al. Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis. Nat. Prod. Rep. 29, 264-325 (2012).
22. Nachtigall, J. et al. Benzoxacystol, a benzoxazine-type enzyme inhibitor from the deepsea strain Streptomyces sp. NTK 935. J. Antibiot. 64, 453-457 (2011).
23. Kornerup, A. & Wanscher, J. H. Meuthen Handbook of Colors (1961)-Color Codes. 2nd ed. (Meuthen, London, UK, 1967).
24. Tan, G. Y. A., Robinson, S., Lacey, E. & Goodfellow, M. Amycolatopsis australiensis sp nov., an actinomycete isolated from arid soils. Int. J. Syst. Evol. Microbiol. 56, 2297-2301 (2006). (Pubitemid 44566795)
25. Kim, O.-S. et al. Introducing EzTaxon-e: a prokaryotic 16S rRNA gene sequence database with phylotypes that represent uncultured species. Int. J. Syst. Evol. Microbiol. 62, 716-721 (2012).
26. Chun, J. PHYDIT version 3.1 (2001)http://plaza.snu.ac.kr/B~chun/phydit/
27. Jukes, T. H. & Cantor, C. R. Evolution of protein molecules. in Mammalian Protein Metabolism. Munro, N. (ed.) 21-132 (Academic Press, New York, NY, USA, 1969).
28. Van de Peer, Y. & De Wachter, R. TREECON for Windows: a software package for the construction and drawing of evolutionary trees for the Microsoft Windows environment. Comput. Applic. Biosci. 10, 569-570 (1994).
29. Schulz, D. et al. Abenquines A-D: aminoquinone derivatives produced by Streptomyces sp. strain DB634. J. Antibiot. 64, 763-768 (2011).