ISSN:
1434-193X
Keywords:
Myxobacteria
;
Antibiotics
;
Cytotoxic
;
Structure elucidation
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
---A novel highly cytotoxic metabolite, apicularen A (1), was isolated in a screening of the myxobacterial genus Chondromyces. The structure of 1 is characterized by a salicylic acid residue as part of a 10-membered lactone, which bears an acylenamine side chain. Compound 1 is an inhibitor of the proliferation of human cancer cell lines and induces apoptosis. Apicularen A (1) is present in nearly every strain of C. apiculatus, C. pediculatus, C. lanuginosus and C. robustus. Habitually 1 is accompanied by different amounts of a more polar variant, apicularen B (2), which was identified as 11-O-(2-N-acetamido-2-deoxy-β-D-glucopyranosyl)apicularen. According to feeding experiments with 13C-labeled acetates, glycine, and methionine, apicularen A (1) is an acetate-derived polyketide containing a glycine residue as precursor of the enamine. Uncommonly, the C3 starter unit is not assembled from propionate but from acetate and methionine.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
