Cultures of the basidiomycete Mycena avenacea TA 8480 were shown to metabolize pentachlorophenol (PCP), 2,3,5,6-tetrachloro-p-hydroquinone (TeCHQ), and 2,3,5,6-tetrachloro-p-benzoquinone (TeCBQ). The first metabolite of the PCP degradation pathway was identified as TeCBQ which in a second reaction is reduced to the hydroquinone TeCHQ. Subsequently dechlorination of TeCHQ yielded 3,5,6-trichloro-2-hydroxy-p-benzoquinone (TCOHBQ). The specific degradation rate for PCP was 1.4 mg x g dry mycelia -1 x day-1. The initial dechlorination rate of TeCHQ was 5.9 mg x g dry mycelia-1 x hour-1. None of the compounds supported growth of the fungus.

Basidiomycota↗

PubMedDate not supplied

Xylaramide, a new antifungal compound, and other secondary metabolites from Xylaria longipes.

Xylaramide (1), possessing potent antifungal activity towards Nematospora coryli and Saccharomyces cerevisiae, was isolated from the culture fluids of the wood-inhabiting ascomycete Xylaria longipes together with tyrosol (2), 2,5-bis(hydroxymethyl)furan (3) and 2-hexyli-dene-3-methylsuccinic acid (4). The latter has been known as a Xylaria metabolite for many years. Compounds 2 and 3 have been previously reported from other fungi, whereas 1 is a new natural N-(2-phenylethenyl)-2-hydroxypropanamide. The isolation, structure determination and biological properties of xylaramide are described. The biological activities of the other compounds are included.

Amides↗

PubMedDate not supplied

New botrydial sesquiterpenoids from Hymenoscyphus epiphyllus.

Four new botrydial derivatives, hymendial (1), 7 alpha-hydroxydihydrobotrydial (2), 7 alpha-hydroxy-10-O-methyldihydrobotrydial (4), and 7 alpha-acetoxy-15 alpha-methoxy-10-O-methyl-dihydrobotrydial (5) were isolated together with dihydrobotrydial (3) from the culture fluid of the ascomycete Hymenoscyphus epiphyllus. In addition, cytochalasin H (6a), 18-deoxycytochalasin H (6b) and (+)-mellein (7) were produced by this fungus. Hymendial (1), possessing an alpha, beta-unsaturated dialdehyde functionality, exhibits antimicrobial and cytotoxic activities and is mutagenic in the Ames Salmonella assay.

Animals↗

PubMedDate not supplied

Flavipucine and brunnescin, two antibiotics from cultures of the mycophilic fungus Cladobotryum rubrobrunnescens.

Two antimicrobial metabolites were isolated from submerged cultures of Cladobotryum rubrobrunnescens, a mycophilic fungus growing on a Inocybe species. One of the compounds proved to be identical to flavipucine (2), an antibiotic previously isolated from Aspergillus flavipes (Casinovi et al., 1968) and from a Macrophoma species (Sassa T. and Onuma Y. (1983), Agric. Biol. Chem. 47, 1155-1157). The other metabolite, brunnescin (1), is a new tetrasubstituted furan derivative which exhibits antibacterial, antifungal and cytotoxic effects.

Animals↗

PubMedDate not supplied

Lachnellins A, B, C, D, and naphthalene-1,3,8-triol, biologically active compounds from a Lachnellula species (ascomycetes).

In the course of our search for new biologically active metabolites, lachnellin A (1), a metabolite with high cytotoxic and antimicrobial activities, the structurally related lachnellins B, C and D (3, 4, 7), and naphthalene-1,3,8-triol (8), an inhibitor of malate synthase (EC 4.1.3.2), were isolated from submerged cultures of the ascomycete Lachnellula sp. A 32-89. The antimicrobial, cytotoxic and phytotoxic activities of lachnellin A depended on its reactivity and could be abolished by the addition of cysteine. The enzyme inhibiting activity of (8) was due to reactive intermediates during melanization and was no longer observed in the presence of serum albumin. In addition, rac-scytalone (9), (+)-trans-3,4-dihydro-3,4,8-trihydroxy-1 (2H)-naphthalenone (10), 2,5-dihydroxytoluene (11), and (R)-(-)-5-methylmellein (12) were obtained from the same source and biologically characterized.

Animals↗