Emmyguyacins A and B: Unusual glycolipids from a sterile fungus species that inhibit the low-pH conformational change of hemagglutinin A during replication of influenza virus

Two novel glycolipids, emmyguyacin A (1a) and emmyguyacin B (1b), were isolated at concentrations of 1-51 g/L from a potato dextrose agar fermentation of a sterile fungus species. The compounds inhibit replication of influenza A virus (A/X31) in MDCK cells by inhibiting the pH-dependent conformational change of hemagglutinin A IC50 9 muM). The structures were deduced using one- and two-dimensional NMR techniques and mass spectrometric analyses on both the parent compounds and a host of degradation products and derivatives. A novel and unusual oxalic acid ester of a monohydroxylated fatty acid (5, 17-oxalyloxydocosanoic acid) is reported. The first isolation and characterization of the fatty acid 17-hydroxydocosanoic acid (3) itself is also reported as a saponification product of 1.