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 (IC(50) 9 microM). 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.
Boros
Christie
C
MYCOsearch, Inc., a subsidiary of OSI Pharmaceuticals, Durham, North Carolina 27709, USA.
Katz
Barry
B
Mitchell
Scott
S
Pearce
Cedric
C
Swinbank
Karra
K
Taylor
Debra
D
D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002460:Cell Line / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D004187:Disaccharides / Q000032:analysis / Q000737:chemistry; D004847:Epithelial Cells / Q000187:drug effects; D005227:Fatty Acids / Q000032:analysis / Q000737:chemistry; D005658:Fungi / Q000737:chemistry*; D006017:Glycolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006389:Hemagglutinins, Viral / Q000276:immunology*; D009980:Influenza A virus; D020128:Inhibitory Concentration 50; D007668:Kidney; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D013714:Tennessee
D000998:Antiviral Agents; D004187:Disaccharides; D005227:Fatty Acids; D006017:Glycolipids; D006389:Hemagglutinins, Viral; C451127:emmyguyacin A; C451128:emmyguyacin B