Marjorie Anchel

Frustulosinol, an antibiotic metabolite of Stereum frustulosum: Revised structure of frustulosin

Abstract On the basis of chemical reactions and spectroscopic data, frustulosinol, a new antibiotic metabolite of Stereum frustulosum , has been assigned an acetylenic structure. This has led to a revised structure for the related metabolite, frustulosin.

The biogenesis of illudins S and M in clitocybe illudens

Abstract Illudin S and illudin M were biologically labelled with C 14 by adding mevalonic acid 2-C 14 as precursor to cultures of Clitocybe illudens . The positions of the label, determined by degradation, are consistent with the origin of these sesquiterpenes from 3 molecules of mevalonic acid.

PRODUCTION OF OOSPOREIN AND ITS LEUCO FORM BY BASIDIOMYCETE SPECIES.

Oosporein, a dibenzoquinone pigment previously obtained from an Ascomycete and from several species of Fungi Imperfecti, has been isolated from two basidiomycete species of the genus Phlebia. The leuco form, not previously reported as a natural product, accompanied the quinone in culture liquids.

Metabolic products of Clitocybe diatreta. I. Diatretyne amide and diatretyne nitrile

Abstract The isolation of diatretyne amide and diatretyne nitrile from culture liquids of the basidiomycete, Clitocybe diatreta , is described. Proof is presented for the structure of the amide as 7-carbamidohepta-2-en-4, 6-diynoic acid (I) and of the nitrile as 7-cyanohepta-2-en-4, 6-diynoic acid. The microbiological activity and toxicity for mice of the two compounds is reported.

Atromentic acid from Clitocybe illudens

Abstract Atromentic acid was isolated from culture liquids of Clitocybe illudens . Identification, based on analyses and spectra of the compound and a number of new derivatives, was confirmed by direct comparison of its tetramethylated derivative with a synthetic sample. Products, giving a blueing reaction have been detected in the same culture liquids, and an as yet unidentified compound has been isolated in crystalline form as its methylation product, C 42 H 36 O 12 . The presence of pulvinic acid derivatives in Basidiomycetes other than the Boletaceae has been reported in only one other instance.

Characterization of drosophilin C as a polyacetylene

Abstract The antibiotic material “drosophilin C” has been further purified, using the reported ultraviolet absorption spectrum as a guide. The purified compound has been found not to be responsible for the high activity ascribed to the fraction previously referred to as “drosophilin C.” Drosophilin C, as defined by its spectrum, has been characterized as a polyacetylene. The spectra of both drosophilin C and D undergo changes, when the compounds are treated with alkali, which closely resemble the changes previously described for nemotin and for mycomycin. The conversion products have antibacterial activity of a somewhat lower order than, but distinct from, that of the parent compounds.

Isolation of dihydroilludin M from Clitocybe illudens

Abstract Dihydroilludin M (Ia) has been isolated from culture liquids of Clitocybe illudens . This metabolite differs from the dihydroilludin M obtained by borohydride reduction of illudin M, only in the configuration at C-7, one of three asymmetric centers in the molecule.

Metabolic products of Clitocybe diatreta. II. Biochemical variation of cultures; production of diatretyne 3.

Abstract Available cultures of the basidiomycete, Clitocybe diatreta, were found to contain biochemical variants, one of which produced the polyacetylene, diatretyne nitrile, the other a new polyacetylene with a more extensive chromophoric system, “diatretyne 3.” The variants have been isolated and maintained as separate cultures.

The structure of illudol

Abstract Detailed evidence is given for the structure and partial stereochemistry of illudol, a sesquiterpenoid triol obtained from the Basidiomycete Clitocybe illudens .

Origin of the methylenedioxy carbon in phlebiarubrone: Formate and methionine as precursors

Abstract The relative efficiency of methionine and formate as precursors of the methylenedioxy carbon of phlebiarubrone has been investigated using methionine-Me- 14 C and formate- 13 C. When the substrates are added separately, incorporation is similar for both. When methionine and formate are added together, the incorporation of formate is markedly reduced.