Phycomysterols and other sterols from the fungus Phycomyces blakesleeanus.

In the search for novel bioactive products from filamentous fungi, sterols and triterpenoids found in Phycomyces blakesleeanus were analyzed using semipreparative HPLC, GC-MS, and NMR techniques. Structures proposed for the three new compounds identified, phycomysterol A (1), phycomysterol B (2), and neoergosterol (3), were confirmed by chemical synthesis. Phycomysterols possess a new natural 19-norergostane skeleton with an aromatic B ring. Phycomysterol A showed anti-HIV activity.

Mutants of phycomyces with decreased gallic acid content.

Most plants and some fungi accumulate phenols. Two hydroxybenzoic acids, gallic and protocatechuic acids, are abundant in the giant sporangiophores of the zygomycete Phycomyces blakesleeanus, much more so than in the basal mycelium or the culture medium. The actual concentrations vary with illumination, age of the culture, and composition of the medium. We devised a simple screening procedure to isolate hba mutants whose sporangiophores contained less gallic acid than the wild type. The most useful mutant had very low concentrations of hydroxybenzoic acids in the sporangiophores, but about the same as the wild type in the basal mycelium and the medium. The mutant was only slightly different from the wild type in growth and morphology. Mutant and wild-type sporangiophores grew away from ultraviolet C sources (260 nm) equally well. Contrary to previous conjectures, ultraviolet tropism does not depend on the ultraviolet absorption of gallic acid or other free hydroxybenzoic acids in the sporangiophore. Against expectations, phenols did not impair DNA extraction: sporangiophores produced better DNA preparations than basal mycelia and the hba mutant only slightly better than the wild type.