Isolation and Characterization of Tirandamycins from a Marine-Derived Streptomyces sp.

Jacob C. Carlson†, Shengying Li†, Douglas A. Burr and David H. Sherman*
Life Sciences Institute and Departments of Medicinal Chemistry, Microbiology & Immunology, and Chemistry, University of Michigan, Ann Arbor, Michigan 48109
J. Nat. Prod., 2009, 72 (11), pp 2076–2079
DOI: 10.1021/np9005597
Publication Date (Web): November 2, 2009
Copyright © 2009 The American Chemical Society and American Society of Pharmacognosy
* To whom correspondence should be addressed. Tel: 734-615-9907. Fax: 734-615-3641. E-mail: davidhs@umich.edu., †

These authors contributed equally to this work.

Abstract

Abstract Image

The novel dienoyl tetramic acids tirandamycin C (1) and tirandamycin D (2) with activity against vancomycin-resistant Enterococcus faecalis were isolated from the marine environmental isolate Streptomyces sp. 307-9, which also produces the previously identified compounds tirandamycins A (3) and B (4). Spectroscopic analysis of 1 and 2 indicated structural similarity to 3 and 4, with differences only in the pattern of pendant oxygenation on the bicyclic ketal system. The isolation of these putative biosynthetic intermediates was enabled by their sequestration on an adsorbent resin during early stationary-phase fermentation.

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History

  • Published In Issue November 30, 2009
  • Article ASAPNovember 02, 2009
  • Received: September 9, 2009

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