Premium
Secondary Metabolites by Chemical Screening, 24. Oasomycins, New Macrolactones of the Desertomycin Family
Author(s) -
Grabley Susanne,
Kretzschmar Gerhard,
Mayer Marion,
Philipps Siegrid,
Thiericke Ralf,
Wink Joachim,
Zeeck Axel
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930193
Subject(s) - moiety , chemistry , stereochemistry , biosynthesis , lactone , mannose , in vitro , strain (injury) , chemical structure , biochemistry , organic chemistry , biology , enzyme , anatomy
New macrolactones, named oasomycin A to D ( 1 to 4 ), were discovered by a chemical screening in the culture broth of Streptoverticillium baldacii subsp. netropse (strain FH‐S 1625). The structures were established by detailed spectroscopic analysis. The fundamental 42‐membered lactone moiety of oasomycin A and B ( 1 and 2 ) is analogous to that of desertomycin A ( 5 ), while the oasomycins C and D ( 3 and 4 ) are the first representatives of macrolactones bearing a 44‐membered skeleton. These metabolites can be distinguished by side chain modifications at C‐41 or C‐43 as well as the presence of an α‐linked D ‐mannose moiety attached to 22‐OH. Due to the structural similarities the oasomycins are integrated into the desertomycin family. In vitro testing by using the HEP‐G2 cell assay showed oasomycin A ( 1 ) to be an inhibitor of de novo cholesterol biosynthesis.