Isolation and characterization of tirandamycins from a marine-derived Streptomyces sp.
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.
Carlson
Jacob C
JC
Life Sciences Institute and Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Li
Shengying
S
Burr
Douglas A
DA
Sherman
David H
DH
D000617:Aminoglycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013293:Enterococcus faecalis / Q000187:drug effects*; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013302:Streptomyces / Q000737:chemistry*; D020713:Vancomycin Resistance / Q000187:drug effects
D000617:Aminoglycosides; C545292:tirandamycin C; C545293:tirandamycin D