New haliangicin isomers, potent antifungal metabolites produced by a marine myxobacterium

Haliangicin is a beta-methoxyacrylate-type polyene antibiotic isolated from the unique marine myxobacterium Haliangium ochraceum. A further investigation of the extract of this microorganism has resulted in the isolation of haliangicin as well as its geometrical isomers. The configuration of the epoxide in haliangicin, which was unknown previously, was determined in this study. The planar structures with partial stereochemistry of these isomers were elucidated by spectroscopic analyses. The major isomer, cis-haliangicin, is a cis isomer of the epoxide portion of haliangicin. Haliangicins Bsimilar toD are geometrical isomers of the polyene moiety, and present as an inseparable mixture of cis and trans epoxide isomers. Their antifungal activities were also evaluated in comparison with haliangicin.