V. M. Adanin

Penicillium aurantiogriseum Dierckx 1901: Producer of Diketopiperazine Alkaloids (Roquefortine and 3,12-Dihydroroquefortine), Isolated from Permafrost

Secondary metabolites of three strains of Penicillium aurantiogriseumisolated from permafrost sediments were identified. It was found that these fungi synthesized the diketopiperazine alkaloids roquefortine and 3,12-dihydroroquefortine. The strain VKM FW-766 synthesized alkaloids in the course of certain growth-related processes. When the strain was grown on a mineral medium, the time courses of the roquefortine and 3,12-dihydroroquefortine concentrations were characterized by biphasic curves.

Rugulosuvines A and B, Diketopiperazine Alkaloids of Penicillium rugulosumand Penicillium piscariumFungi

Two diketopiperazine alkaloids, rugulosuvines A and B (tryptophan and phenylalanine are their precursors), were isolated and purified from a culture liquid of Penicillium rugulosumVKM F-352 and Penicillium piscariumVKM F-325 fungi. Physical and physicochemical studies showed the absolute structure of rugulosuvine A. The absolute structure of rugulosuvine B was demonstrated to be identical to that of rugulosuvine A.

The Biosynthesis of Low-Molecular-Weight Nitrogen-Containing Secondary Metabolites—Alkaloids—by the Resident Strains of Penicillium chrysogenum and Penicillium expansum Isolated on Board the Mir Space Station

The analysis of the absorption spectra of the low-molecular-weight nitrogen-containing secondary metabolites—alkaloids—of four Penicillium chrysogenum strains and six P. expansum strains isolated on board the Mir space station showed that all these strains synthesize metabolites of alkaloid origin (roquefortine, 3,12-dihydroroquefortine, meleagrin, viridicatin, viridicatol, isorugulosuvin, rugulosuvin B, N acetyltryptamine, and a “yellow metabolite” containing the benzoquinone chromophore).

Diketopiperazine Alkaloids from the fungusPenicillium piscarium westling

Fungi of the speciesPenicillium piscarium produced diketopiperazine alkaloids (isorugulosuvine, puberuline, verrucosine, prolyltryptophanyldiketopiperazine, 12,13-dehydroprolyltryptophanyldiketopiperazine, fellutanine A, phenylalanylphenylalanyldiketopiperazine, as well as roquefortine and 3,12-dihydroroquefortine, whose precursors are tryptophan, phenylalanine, leucine, proline, and histidine.

[The fungus Penicillium citrinum Thom 1910 VKM FW-800 isolated from ancient permafrost sediments as a producer of the ergot alkaloids agroclavine-1 and epoxyagroclavine-1].

The study of the secondary metabolites of the relict strain Penicillium citrinum VKM FW-800 isolated from ancient Arctic permafrost sediments showed that this fungus produces agroclavine-1 and epoxyagroclavine-1, which are rare ergot alkaloids with the 5R,10S configuration of the tetracyclic ergoline ring system. The production of the alkaloids by the fungus showed a biphasic behavior, being intense in the phase of active growth and slowing down in the adaptive lag phase and in the stationary growth phase. The addition of zinc ions to the incubation medium led to a fivefold increase in the yield of the alkaloids. The alkaloid-producing Penicillium fungi isolated from different regions exhibited the same tendencies of growth and alkaloid production.

Penicillium expansum, a Resident Fungal Strain of the Orbital Complex Mir, Producing Xanthocyllin X and Questiomycin A

It was demonstrated that the fungus Penicillium expansum 2-7, a resident strain of the orbital complex Mir, which became dominant at the end of a long-term space flight, formed biologically active secondary metabolites (antibiotics). Using physicochemical methods these metabolites were identified as xanthocyllin X and questiomycin A. The time courses of their biosyntheses during the growth and development of the producer culture were studied. The addition of zinc to the culture medium affected both the growth of the culture and the biosyntheses of the antibiotics. The concentrations of zinc in the medium, optimum for xanthocyllin X and questiomycin A production, were 0.3 and 3.0 mg/l, respectively.

A New 16N-Carboxyethyl Derivative of 3,12-Dihydroroquefortin

New 16N-carboxyethyl derivative (2) of 3,12-dihydroroquefortin (1) was isolated from the fermentation broth of Penicillium aureovirens VKM FW-766. Structure of 2 was settled on the basis of MS spectrometry, 1D and 2D NMR spectroscopy.

Taxonomic position and nitrogen-containing secondary metabolites of the fungusPenicillium vitale pidoplichko et bilai apud bilai

The type strainPenicillium vitale Pidoplichko et Bilai apud Bilai 1961 VKM F-3624 was found to considerably differ from a sibling speciesP. janthinellium (syn.P. simplicissimum) in some physiological and morphological features (growth rates at different temperatures, the size of philiades, and the shape of conidia), as well as in the pattern of the nitrogen-containing secondary metabolites produced (roquefortine, 3,12-dihydroroquefortine, meleagrin, aurantioclavine, indole-3-acetic acid, andN-acetyltryptamine). The data obtained suggest thatP. vitale represents an independent species.