Antifungal Substances Against Pathogenic Fungi, Talaroconvolutins, from <i>Talaromyces convolutus</i>

Suzuki, Shingo; Hosoe, Tomoo; Nozawa, Koohei; Kawai, Ken‐ichi; Yaguchi, Takashi; Udagawa, Shun‐ichi

doi:10.1021/np990371x

Cited by 78 publications

(61 citation statements)

References 4 publications

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“…Some secondary metabolites that contain the deoxy-tetramic acid ring system have been reported, such as oteromycin, [6] ZG-1494a, USC1025A and B, [8,9] pyrrocidines A and B, [10] ascosalipyrrolidinones A and B, [11] and talaroconvolutins A-D. [12] Although the biogenetic pathways of 1-5 and the deoxy-tetramic acid related compounds mentioned above remain unclear, a plausible pathway can be proposed. This pathway is based on the biosynthetic route of the tetramic acid analogue, trichosetin, and involves a polyketide reacting with one amino acid.…”

Section: Resultsmentioning

confidence: 99%

“…The methoxyl groups in 3 and 4 may be introduced during the extraction or isolation procedures, similar to the cases reported for ascosalipyrrolidinones [11] and talaroconvolutins. [12] Compound 5, the 5-(2-methylpropyldiene)-1H-pyrrol-2(5H)-one derivative, may be produced from 1 or 2 by dehydration.…”

Section: Resultsmentioning

confidence: 99%

“…For instance, some natural products, such as lipstatin, lactacystin, and some l-trans-(S,S)-epoxysuccinic acids actively react with target enzymes to form covalent complexes. [16] Some reports of deoxy-tetramic acids [12,15] suggest that an intramolecular OH group or extraction and isolation solvent molecules can attack the b position of an a,b-unsaturated ketone by way of a Michael reaction during the biogenetic route or in the processes of isolation and purification to form artificial products. The mechanism of action of 1-5 is currently under investigation.…”

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confidence: 99%

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Cytotoxic Polyketides Containing Tetramic Acid Moieties Isolated from the Fungus Myceliophthora Thermophila: Elucidation of the Relationship between Cytotoxicity and Stereoconfiguration

Yang

Chen

et al. 2007

Chemistry A European J

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Five new polyketides that contain tetramic acids, myceliothermophins A-E, were isolated from the thermophilic fungus Myceliophthora thermophila. Two sets of 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one diastereomers, myceliothermophins A/B and C/D, were separated as pure compounds by using silica-gel column chromatography and recycling reverse-phase high-performance liquid chromatography (RP-HPLC). The relative configurations of the chiral centers in 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one moieties were deduced from NOESY correlations. In the cytotoxic assay, the 5-(2-methylpropyldiene)-1H-pyrrol-2(5H)-one analogue (myceliothermophin E) exhibited inhibition against four cancer cell lines. In addition, the significant inhibitory effect of myceliothermophins A and C and the inactivity of myceliothermophins B and D revealed the importance of the relative configurations of 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one moieties on their cytotoxicity potency against cancer cells.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Cytotoxic Polyketides Containing Tetramic Acid Moieties Isolated from the Fungus Myceliophthora Thermophila: Elucidation of the Relationship between Cytotoxicity and Stereoconfiguration

Yang

Chen

et al. 2007

Chemistry A European J

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“…Refering to the chemical structures, the pyrrolidinone function of GKK1032A 2 (1) and the pyrrocidines has already been found in other antifungal compounds such as talaroconvolutin A. 19 But the macrocycle containing ether, phenyl, pyrrolidinone and ketone functions seems to be very rare in natural compounds. However, there exist some studies about this tricarbocyclic systems.…”

Section: Biological Assaysmentioning

confidence: 99%

GKK1032A2, a secondary metabolite from Penicillium sp. IBWF-029-96, inhibits conidial germination in the rice blast fungus Magnaporthe oryzae

et al. 2011

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The rice blast fungus Magnaporthe oryzae is the most important pathogen on cultivated rice because of its economic relevance and destructiveness. 1 Blast disease caused by this heterothallic ascomycete destroys about 10-30% rice yield every year. 2 In order to infect and colonize the host plant Oryza sativa, conidia of the fungus attach to the leaf surface and germinate by sending out a germ tube. Induced by the hard hydrophobic surface, appressoria required for penetration differentiate. Within the specialized infection structure compatible solutes, for example, glycerol, accumulate. 3 The solutes are retained within the cell by a melanin layer. As a consequence, water flows into the infection structure to generate turgor required for a mechanically penetration of the plant cuticle. As the functionality of the appressorium is an essential prerequisite for a successful infection of the host plant, the melanin layer is a pathogenicity factor in M. oryzae. Agrochemicals interfering with the biosynthesis of the biopolymer, for example, tricyclazole, have been successfully used in the past as protective agents. 4 After penetration, the hyphae disperse within the plant to form conidiophores and conidia. The spores are spread in the field via wind and water. 2 Due to the resistance development against commercially available fungicides, there is a demand for lead structures for the development of novel fungicides. 4 Secondary metabolites from nature have in the past been used as lead structures for successful pesticides. The widely used class of QoI (quinone outside inhibitor)-fungicides is based on the structure of strobilurin A, a secondary metabolite found in cultures of the basidiomycete Strobilurus tenacellus. 5 As fungi represent an almost inexhaustible reservoir for natural compounds, screening approaches are conducted for the identification of new secondary metabolites interfering either with pathogenic differentiation or fungal vegetative growth. In this course, compound GKK1032A 2 (1) was identified from cultures of the fungus Penicillium sp. IBWF-029-96. The compound has been described as a metabolite from fungal cultures. In this note, we describe a biological activity of this compound, which has not been reported before. 6,7 M. oryzae strain 70-15 was obtained from the Fungal Genetics Stock Centre, Kansas City, KS, USA. The strain was cultured on complete medium (CM) medium as described previously. 8 Botrytis cinerea, Fusarium graminearum and Phytophthora infestans were provided by BASF SE. EXPERIMENTAL PROCEDURE Organisms Fermentation and isolationThe strain Penicillium sp. IBWF-029-96 was fermented in yeast malt glucose medium in a 20-l fermenter (Biostat A-20, Braun Melsungen, Melsungen, Germany) at room temperature with aeration (4.5 l min À1 ) and agitation (120 r.p.m.). A well-grown culture (200 ml) in the same medium was used as inoculum. Daily samples were withdrawn to measure pH, glucose and maltose content as well as mycelial dry weight and in order to quantify the bioactive secondary metabolite ...

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“…The application of MCRs for the synthesis of dihydro-oxopyrrole derivatives has become a significant and attractive subject in organic syntheses since these compounds possess herbicidal [17], antitumor [18], pesticidal [19], anti-HIV [20], and antibiotic properties [21] and serve as nootropic agents [22]. Natural compounds were found to contain dihydro-2-oxopyrrole motifs, such as oteromycin [23], pyrrocidine A with potent antibiotic activity [24], talaroconvolutin A [25], quinolactacin C [26], and ypaoamide [27] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Nano-TiCl4/SiO2: an efficient catalyst for the one-pot synthesis of highly substituted dihydro-2-oxopyrroles

2015

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Nano-TiCl 4 /SiO 2 was used as a readily available, inexpensive, efficient, and environmentally benign heterogeneous solid acid catalyst for the one-pot cascade synthesis of highly functionalized dihydro-2-oxopyrroles. Four-component reaction (4CR) of dialkyl acetylenedicarboxylates, aniline derivatives, and formaldehyde was employed for the synthesis of these compounds under thermal conditions. Graphical abstract

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Antifungal Substances Against Pathogenic Fungi, Talaroconvolutins, from Talaromyces convolutus

Cited by 78 publications

References 4 publications

Cytotoxic Polyketides Containing Tetramic Acid Moieties Isolated from the Fungus Myceliophthora Thermophila: Elucidation of the Relationship between Cytotoxicity and Stereoconfiguration

Cytotoxic Polyketides Containing Tetramic Acid Moieties Isolated from the Fungus Myceliophthora Thermophila: Elucidation of the Relationship between Cytotoxicity and Stereoconfiguration

GKK1032A2, a secondary metabolite from Penicillium sp. IBWF-029-96, inhibits conidial germination in the rice blast fungus Magnaporthe oryzae

Nano-TiCl4/SiO2: an efficient catalyst for the one-pot synthesis of highly substituted dihydro-2-oxopyrroles

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