11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from a streptomyces cyanogenus K62 mutant strain

Khaled A. Shaaban, Chris Stamatkin, Chendil Damodaran, Jürgen Rohr

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Four new angucyclin(on)es, 11-deoxylandomycinone (1) and landomycins X-Z (2-4) were isolated from the crude extract of Streptomyces cyanogenus K62 mutant strain, along with the recently reported landomycins S, T and V (5-7) and five other known compounds. The structures of the new compounds 1-4 were elucidated by 1D and 2D NMR studies along with HR-MS analyses. Unique about the structures is that the fourth sugar moiety (sugar D) in landomycins X-Z (2-4) was β-D-amicetose instead of β-D-olivose, usually found in this position. The new angucyclin(on)es were biologically evaluated in comparison with previously known congeners against a small panel of MCF-7 (estrogen responsive) and MDA 231 (estrogen refractory) breast cancer cell lines. 11- deoxylandomycinone (IC50 2.1±0.3 and 1.2±0.4 μM) and landomycin Y (IC50 1.0±0.1 and 2.0±0.1 μM) showed the highest cytotoxic potencies against both the cell lines.

Original languageEnglish
Pages (from-to)141-150
Number of pages10
JournalJournal of Antibiotics
Volume64
Issue number1
DOIs
StatePublished - Jan 2011

Bibliographical note

Funding Information:
The mass spectrometry department, University of Wisconsin Biotechnology Centre is acknowledged for the HR-MS data. This work was supported by grant CA 102102 from the US National Institutes of Health to JR.

Keywords

  • angucyclines
  • anticancer agents
  • cytotoxicity
  • landomycins
  • polyketides
  • structureactivity relationships

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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