Vermicillin, a new metabolite from Penicillium vermiculatum inhibiting tumor cells in vitro.

Fuska, J.; Němec, Pavel; Fusková, A

doi:10.7164/antibiotics.32.667

Cited by 20 publications

(8 citation statements)

References 7 publications

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“…So far, dilactones vermiculine [ 11, vermiculinol and vermiculidiol [2], phtslidopyranone derivative vermistatin [3] and vermicillin [4] have been isolated from the strain Talaromyces flavus". Vermiculine, vermistatin and vermicillin inhibited proliferation and biochemical functions of cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of dehydroaltenusin by talaromyces flavus

Fuska

Proksa

Uhrían

et al. 1991

Acta Biotechnologica

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Section: Introductionmentioning

confidence: 99%

Biosynthesis of dehydroaltenusin by talaromyces flavus

Fuska

Proksa

Uhrían

et al. 1991

Acta Biotechnologica

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“…Desmethyldehydroaltenusin (14)4 is the second metabolite isolated in the form of its acetate (15). The sequential loss of three molecules of ketene from the parent ion (CZ0Hl6o9) in the mass spectrum affords an ion corresponding to a molecular formula C14H1006, which differs from that of dehydroaltenusin (12) (11) and dehydroaltenusin (12), and the previously unreported desmethyldehydroaltenusin (14), may be envisaged as proceeding by cyclization of a heptaketide precursor to give the biphenyl derivative shown in Scheme 2. An oxidation and reduction sequence, and methylation of the phenol indicated, afford the biphenyl metabolite altenusin (11).…”

Section: Discussionmentioning

confidence: 99%

“…This afforded the crude diacetate (13), which was purified by passage through a small silica gel pipette column, eluting with Skellysolve B -acetone (2:l). Dehydroaltenusin diacetate (13) crystallized from the eluent as white flakes (0. …”

Section: Isolation Of the Metabolitesmentioning

confidence: 99%

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The metabolites of Talaromycesflavus: Part 1. Metabolites of the organic extracts

Ayer¹,

Racok²

1990

Can. J. Chem.

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The soil fungus Talaromycesjavus (Klocker) Stolk and Samson is an effective biological control for Verticillium wilt of eggplant (Solanum melongena L.), a disease caused by the fungus Verticillium dahliae Kleb. The organic soluble metabolites produced when the fungus is grown in liquid still culture include D-glucono-1 ,4-lactone (I), 5-hydroxymethylfurfural (S), the previously unreported tetraketides, 4,6-dihydroxy-5-methylphthalide (3) and methyl 4-carboxy-5-hydroxyphthalaldehydate (8), a hexaketide, 7-hydroxy-2,5-dimethylchromone (6), and a metabolite believed to be 3-hydroxymethyl-6,8-dimethoxycoumarin (10). A number of higher order polyketides have been isolated including altenusin (ll), dehydroaltenusin (12), and the previously unreported desmethyldehydroaltenusin (14). A structurally and biosynthetically interesting spirocyclic metabolite, which we have named talaroflavone (16), as well as a related compound, deoxytalaroflavone (18), have also been obtained. Chem. 68, 2085Chem. 68, (1990.Le champignon du sol Talaromycesjavus (Klocker) Stolk et Samson contr6le biologiquement et d'une f a~o n efficace la flktrissure par le Verticillium de l'aubergine (Solanum melongena L.), une maladie causCe par le champignon Verticillium dahliae Kleb. Les metabolites organiques solubles qui sont produits lorsqu'on fait croitre le champignon dans un milieu de culture comprennent : la ~-g l~~0 n 0 -1 , 4 -l a~t 0 n e (I), le 5-hydroxyrnCthylfurfura1 (S), les tCtrakCtides 4,6-dihydroxy-5-mCthylphtalide (3) et 4-carboxy-5-hydroxyphtalaldChydate de mCthyle (8) qui n'avaient pas Ct C rapportts anterieurement, un hexakktide, la 7-hydroxy-2,5-dimCthylchromone (6), ainsi qu'un mCtabolite que l'on croit Ctre la 3-hydroxymCthy1-6,8-dimCthoxycoumarine (10). On a aussi isole un certain nombre de polykCtides d'ordre plus ClevC, dont I'altCnusine (11), la dChydroaltCnusine (12) ainsi que la desmCthyldChydroaltCnusine (14) qui n'avait pas Ct C rapportCe antkrieurement. On a aussi obtenu un mCtabolite spirocyclique, intCressant d'un point de vue structural et biosynthetique, que l'on a appelC talaroflavone (16) ainsi qu'un composC apparentC, la dCsoxytalaroflavone (18).Mots clks : Talaromycesjavus, metabolites de champignon, talaroflavone, 4,6-dihydroxy-5-mkthylphtalide.[Traduit par la revue]

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“…Duclauxin was also reported from Penicillium herquei and P. manginii (Bryant et al 1993;Cao et al 2015), but the strains used had been misidentified, and the producers were Talaromyces species as well. Vermicillin is the third anticancer agent from T. amazonensis (Fuska et al 1979). Mitorubrinic acid is a common azaphilone metabolite in the genus Talaromyces (Frisvad et al 1990).…”

Section: Taxonomymentioning

confidence: 99%

Four novel Talaromyces species isolated from leaf litter from Colombian Amazon rain forests

et al. 2016

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Various Talaromyces strains were isolated during a survey of fungi involved in leaf litter decomposition in tropical lowland forests in the Caquetá and Amacayacu areas of the Colombian Amazon. Four new Talaromyces species are described using a polyphasic approach, which includes phenotypic characters, extrolite profiles and phylogenetic analysis of the internal transcribed spacer region (ITS) barcode, and betatubulin (BenA) and calmodulin (CaM) gene regions. Talaromyces amazonensis sp. nov., T. francoae sp. nov. and T. purgamentorum sp. nov. belong to Talaromyces section Talaromyces, and T. columbiensis sp. nov. is located in section Bacillispori. The new species produce several bioactive compounds: T. amazonensis produces the potential anticancer agents duclauxin, berkelic acid and vermicillin, and T. columbiensis produces the effective anticancer agent wortmannin (together with duclauxin). In addition to the new species, T. aculeatus and T. macrosporus were isolated during this study on leaf litter decomposition.

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Vermicillin, a new metabolite from Penicillium vermiculatum inhibiting tumor cells in vitro.

Cited by 20 publications

References 7 publications

Biosynthesis of dehydroaltenusin by talaromyces flavus

Biosynthesis of dehydroaltenusin by talaromyces flavus

The metabolites of Talaromycesflavus: Part 1. Metabolites of the organic extracts

Four novel Talaromyces species isolated from leaf litter from Colombian Amazon rain forests

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