2. Academic Validation
  3. High Plasticity of the Amicetin Biosynthetic Pathway in Streptomyces sp. SHP 22-7 Led to the Discovery of Streptcytosine P and Cytosaminomycins F and G and Facilitated the Production of 12F-Plicacetin

High Plasticity of the Amicetin Biosynthetic Pathway in Streptomyces sp. SHP 22-7 Led to the Discovery of Streptcytosine P and Cytosaminomycins F and G and Facilitated the Production of 12F-Plicacetin

  • J Nat Prod. 2022 Mar 25;85(3):530-539. doi: 10.1021/acs.jnatprod.1c01051.
Niraj Aryal 1,  Junhong Chen 1,  Keshab Bhattarai 1,  Oliver Hennrich 2,  Ira Handayani 3,  Markus Kramer 4,  Jan Straetener 2,  Tatjana Wommer 2,  Anne Berscheid 2,  Silke Peter 5 6,  Norbert Reiling 7 8,  Heike Brötz-Oesterhelt 2 6,  Christian Geibel 9,  Michael Lämmerhofer 9,  Yvonne Mast 6 10,  Harald Gross 1 6
Affiliations

Affiliations

  • 1 Pharmaceutical Institute, Department of Pharmaceutical Biology, University of Tübingen, 72076 Tübingen, Germany.
  • 2 Department of Microbial Bioactive Compounds, Interfaculty Institute of Microbiology and Infection Medicine, Tübingen (IMIT), Cluster of Excellence 'Controlling Microbes to Fight Infections', University of Tübingen, 72076 Tübingen, Germany.
  • 3 Research Center for Biotechnology, National Research and Innovation Agency of Indonesia (RC Biotechnology BRIN), Jl.Raya Bogor Km.46, Cibinong, 16911, Bogor, West Java, Indonesia.
  • 4 Institute of Organic Chemistry, University of Tübingen, 72076 Tübingen, Germany.
  • 5 Institute of Medical Microbiology and Hygiene, University of Tübingen, 72076 Tübingen, Germany.
  • 6 German Center for Infection Research (DZIF), partner site Tübingen, 72076 Tübingen, Germany.
  • 7 Microbial Interface Biology, Research Center Borstel, Leibniz Lung Center, Parkallee 22, 23845 Borstel, Germany.
  • 8 German Center for Infection Research (DZIF), partner site Hamburg-Lübeck-Borstel-Riems, 20095 Hamburg, Germany.
  • 9 Pharmaceutical Institute, Department of Pharmaceutical Analysis and Bioanalysis, University of Tübingen, 72076 Tübingen, Germany.
  • 10 Department of Bioresources for Bioeconomy and Health Research, Leibniz Institute DSMZ-German Collection of Microorganisms and Cell Cultures, 38124 Braunschweig, Germany.
PMID: 35263115 DOI: 10.1021/acs.jnatprod.1c01051
Abstract

A chemical reinvestigation of the Indonesian strain Streptomyces sp. SHP 22-7 led to the isolation of three new pyrimidine nucleosides, along with six known analogues and zincphyrin. The structures of the new compounds (6, 7, 10) were elucidated by employing spectroscopic techniques (NMR, MS, CD, and IR) as well as enantioselective analyses of methyl branched side chain configurations. Application of the precursor-directed feeding approach led to the production and partial isolation of nine further pyrimidine analogues. The new compounds 6, 7, and 11 and three of the known compounds (2-4) were found to possess antimycobacterial and cytotoxic properties.

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