Premium
Antibiotics from Gliding Bacteria, LXXVI. Vioprolides: New Antifungal and Cytotoxic Peptolides from Cystobacter violaceus
Author(s) -
Schummer Dietmar,
Höfle Gerhard,
Forche Edgar,
Reichenbach Hans,
Wray Victor,
Domke Tobias
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960617
Subject(s) - chemistry , glyceric acid , antifungal , hydrolysis , amide , stereochemistry , fermentation , acid hydrolysis , absolute configuration , strain (injury) , cytotoxic t cell , organic chemistry , biochemistry , microbiology and biotechnology , in vitro , medicine , biology , catalysis
The antifungal and cytotoxic metabolites vioprolides A‐D ( 1 – 4 ) were obtained from the myxobacterium Cystobacter violaceus strain Cb vi35 by fermentation in the presence of the adsorber resin XAD‐1180. Peptolide structures 1–4 composed of eight amino acids and a glyceric acid were determined by spectroscopic methods and total hydrolysis. The absolute configurations of the building blocks were established by GC analysis on chiral stationary phases. Common building blocks of 1–4 are l ‐Ala, l ‐Cys, D ‐Leu, l ‐Thr, l ‐MeVal, ( E )‐dehydrobutyrine ( E ‐Dhb), and l ‐glyceric acid ( l ‐Gla). Two variable positions are occupied by l ‐Pro or l ‐Homopro and l ‐Pro or trans ‐(2 S ,4 R )‐4‐methylazetidinecarboxylic acid [(2 S ,4 R )‐Maz]. Two defined isomers of 1 were detected in CDCl 3 in a ratio of 3 : 2 (2D‐ 1 H NOESY) and assigned to rotational isomers at the amide bond of ThrMeVal.