Jadomycins derived from the assimilation and incorporation of norvaline and norleucine

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DOIResolve DOI: http://doi.org/10.1021/np200689w
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TypeArticle
Journal titleJournal of Natural Products
ISSN0163-3864
Volume74
Issue11
Pages24202424; # of pages: 5
Subjectangucycline derivative; antineoplastic agent; Jadomycin dextro norleucine; Jadomycin dextro norvaline; natural product; norleucine; norvaline; unclassified drug; amino acid substitution; animal cell; antibacterial activity; article; bacterium culture; cancer cell culture; cancer inhibition; cell density; concentration response; cytotoxicity; DNA cleavage; drug isolation; Gram negative bacterium; Gram positive bacterium; human; human cell; in vitro study; LC 50; minimum inhibitory concentration; nonhuman; Staphylococcus epidermidis; Streptomyces venezuelae; Amino Acid Sequence; Amino Acids; Chloramphenicol; DNA; Drug Screening Assays, Antitumor; Gram-Negative Bacteria; Gram-Positive Bacteria; Isoquinolines; Microbial Sensitivity Tests; Molecular Structure; Norleucine; Oxazolone; Streptomyces; Valine
AbstractStreptomyces venezuelae ISP5230 is recognized for the production of chloramphenicol and the jadomycin family of natural products. The jadomycins are angucycline natural products containing a unique oxazolone ring incorporating an amino acid present in the minimal culture media. Substitution of different amino acids results in products of varying biological activity. Analysis of cultures of S. venezuelae ISP5230 incubated with l- and d-norvaline and l- and d-norleucine indicated that only the d-configured amino acids were incorporated into the natural products. Subsequently, jadomycin DNV and jadomycin DNL were isolated and characterized (titers 4 and 9 mg L -1, respectively). The compounds were evaluated in the National Cancer Institute cell line cancer growth inhibition and cytotoxicity screens, for antimicrobial activity against selected Gram-positive and Gram-negative bacteria, and as DNA-cleavage agents in vitro. © Published 2011 by the American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Institute for Marine Biosciences (IMB-IBM)
Peer reviewedYes
NPARC number21271103
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Record identifier01fa4f36-30fd-4c00-a917-cfaba38d9ec8
Record created2014-03-24
Record modified2016-05-09
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