The structure of vermistatin, a new metabolite from Penicillium vermiculatum.

Fuska, J.; Uhrı́n, Dušan; Proksa, B.; Votický, Z.; Ruppeldt, J.

doi:10.7164/antibiotics.39.1605

Cited by 57 publications

(47 citation statements)

References 12 publications

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“…By establishing a convenient assay system using C. albicans and miconazole, four funicone-related compounds including new actofunicone were isolated from the culture broth of T. flavus FKI-0076. As we expected, the funicones did not inhibit the growth of C. albicans even at was reported that they showed very weak antifungal activity7, 8,11). However, the funicones showed dosedependent anti-C. albicans activity in combination with although miconazole alone gave no effect on the fungal growth at the concentration.…”

Section: Discussionmentioning

confidence: 58%

Funicone-related Compounds, Potentiators of Antifungal Miconazole Activity, Produced by Talaromyces flavus FKI-0076.

et al. 2002

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Talaromyces flavus FKI-0076, a soil isolate, was found to produce compounds which reinforce the anti-Candida albicans activity of miconazole. Four structurally related compounds, a novel one, designated actofunicone, and the knowns deoxyfunicone, vermistatin and NG-012, were isolated from the culture broth by solvent extraction, ODS column chromatography and HPLC. The structure of actofunicone was elucidated as benzoic acid, 3,5-dimethoxy-2-[[4-oxo-6-(2-acetyloxy propyl)-4H-pyran-3-yl]carbonyl]-, methyl ester by various spectroscopic analyses including NMR experiments. These compounds potentiated the anti-C. albicans activity of miconazole, decreasing the IC50

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Section: Discussionmentioning

confidence: 58%

Funicone-related Compounds, Potentiators of Antifungal Miconazole Activity, Produced by Talaromyces flavus FKI-0076.

et al. 2002

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“…chiana (40). 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.…”

Section: Discussionmentioning

confidence: 99%

“…'of Talaromyces (4-10) other than T. jlavus. The imperfect (conidial) state of T. jlavus, Penicillium dangeardii Pitt, produces three metabolites that are reported to show antibiotic activity (11)(12)(13)(14)(15). The isolation of a water soluble compound possessing antibiotic activity from T. jlavus has recently been reported (16).…”

Section: Introductionmentioning

confidence: 99%

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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“…IR spectra were recorded on a Shimadzu 435-U-04 spectrophotometer (KBr pellets). 1 H and 13 C NMR spectra were obtained using Bruker DRX-300 Advance spectrometer in DMSO-d 6 or CDCl 3 using TMS as an internal reference. Melting points were determined in open capillary tubes in a Stuart BI Branstead Electrothermal Cat No: IA9200 apparatus and uncorrected.…”

Section: Methodsmentioning

confidence: 99%

“…Typical examples are are fuscinarin (1) 1 , typhaphthalide (2) 2 , catalpalactone (3) 3 , alcyopterosin E (4) 4 , (+)-spirolaxine (5) 5 , vermistatin (6) 6 , rubiginone-H (7) 7 , (-)-hydrastine (8) 8 , isopestacin (9) 9 , and cryphonectricacid (10) 10 .…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Isobenzofuran-1(3h)-Ones Using Sulfuric Acid Immobilized on Silica Under Solvent-Free Conditions and Survey of Third-Order Nonlinear Optical Properties

Maleki

Koushki

Baghayeri

et al. 2015

J. Chil. Chem. Soc.

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Solvent-free synthesis of isobenzofuran-1(3H)-ones have been described via reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl or cyclic ketones using sulfuric acid immobilized on silica (H 2 SO 4 -SiO 2 ) in excellent yields (70-88%). The catalyst can be recovered by simple filtration and reused. Also, some of these compounds has been studied the third-order nonlinear optical properties by laser Gaussian z-scan techniques.

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The structure of vermistatin, a new metabolite from Penicillium vermiculatum.

Cited by 57 publications

References 12 publications

Funicone-related Compounds, Potentiators of Antifungal Miconazole Activity, Produced by Talaromyces flavus FKI-0076.

Funicone-related Compounds, Potentiators of Antifungal Miconazole Activity, Produced by Talaromyces flavus FKI-0076.

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

One-Pot Synthesis of Isobenzofuran-1(3h)-Ones Using Sulfuric Acid Immobilized on Silica Under Solvent-Free Conditions and Survey of Third-Order Nonlinear Optical Properties

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