Absolute stereochemistry of unusual biopolymers from Ascomycete culture LL-W1278: examples that derivatives of (S)-6-hydroxymellein are also natural fungal metabolites.

The new linear polyesters, W1278-A, B, and C, were isolated from culture extracts of a freshwater Ascomycete fungus. Their structures were elucidated on the basis of spectroscopic analyses and chemical transformations, with the absolute configuration established by the circular dichroism (CD) method using (R)-(-)-6-hydroxymellein as reference. Unexpectedly, W1278-A, B, and C contain (S)-6-hydroxymellein residues as concluded from the display of the opposite ellipticity than that of known (3R)-(-)-3,4-dihydro-6,8-dihydroxy-3-methylisocoumarin as revealed by CD. 2004 Wiley-Liss, Inc.