Isolation, structure elucidation and biological activity of angucycline antibiotics from an epiphytic yew streptomycete.
In the course of study of epiphytic microorganisms occurring on the surface of roots of Taxus baccata L. a new strain Streptomyces sp. AC113 was isolated. According to 16S ribosomal DNA-based identification the new strain is 99% identical with Streptomyces flavidofuscus. This strain cultivated in an arginine glycerol medium produced three major metabolites identified as (-)-8-O -methyltetrangomycin (1), 8-O -methyltetrangulol (2) and 8-O -methyl-7-deoxo-7-hydroxytetrangomycin (3). The chemical structures of these angucyclines were elucidated by 1D and 2D NMR as well as by mass spectrometry. Isolated angucycline metabolites showed significant antimicrobial activity against Bacillus cereus and Listeria mocytogenes. Cytotoxic activities of compounds 1, 2 and 3 against four cell lines (B16, HT-29 and non - tumor V79, L929) were evaluated. Compound 3 was the most potent anticancer agents with IC(50) 0.054 microg/ml against cell line B16.
Maruna
Michal
M
Department of Biochemical Technology, Institute of Biotechnology and Food Science, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Slovak Republic. michal.maruna@stuba.sk
Sturdikova
Maria
M
Liptaj
Tibor
T
Godany
Andrej
A
Muckova
Marta
M
Certik
Milan
M
Pronayova
Nadezda
N
Proksa
Bohumil
B
D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D001409:Bacillus cereus / Q000187:drug effects; D002460:Cell Line; D003470:Culture Media / Q000737:chemistry; D004269:DNA, Bacterial / Q000737:chemistry / Q000235:genetics; D004275:DNA, Ribosomal / Q000737:chemistry / Q000235:genetics; D006801:Humans; D020128:Inhibitory Concentration 50; D008089:Listeria monocytogenes / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D018517:Plant Roots / Q000382:microbiology; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D017422:Sequence Analysis, DNA; D013302:Streptomyces / Q000302:isolation & purification* / Q000378:metabolism*; D020946:Taxus / Q000382:microbiology*
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D003470:Culture Media; D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D012336:RNA, Ribosomal, 16S; C510997:angucyclinone