Pyrrocidines A and B, new antibiotics produced by a filamentous fungus

He, Haiyin; Yang, Hui; Bigelis, Ramunas; Solum, Eric H.; Greenstein, Michael; Carter, Guy T.

doi:10.1016/s0040-4039(02)00099-0

Cited by 128 publications

(104 citation statements)

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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%

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%

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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“…An antimicrobial activity against Staphylococcus and Enterococcus strains was also detected for pyrrocidine A and pyrrocidine B (2), 3,6-bisepi-3-desmethyl analogs of 1, whereas pyrrocidine A shows higher activities. 16 An antifungal activity of these compounds was found as well, including Aspergillus and Fusarium strains. 17 In our study, GKK1032A 2 (1) failed to inhibit vegetative growth of bacteria and fungi, whereas Jurkat cells were sensitive in presence of the compound.…”

Section: Biological Assaysmentioning

confidence: 93%

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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“…He et al [116] found that filamentous fungi species could produce pyrrocidines A and B, which are effective antibiotics against gram-positive bacteria including resistant strains. Echinocandins produced by Aspergillus species have been reported by Goswami et al [117] to inhibit an enzyme that facilitates fungal cell wall formation in fungal species.…”

Section: Pharmaceutical/medicalmentioning

confidence: 99%

A Review of the Ubiquity of Ascomycetes Filamentous Fungi in Relation to Their Economic and Medical Importance

Egbuta¹,

Mwanza²,

Babalola³

2016

AiM

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Filamentous fungi are found in different habitats in the environment including, air, water and soil. This group of fungi contains organisms from different classes under the sub-phylum Pezizomycotina. They occur in mixtures such that you find many genera of filamentous fungi dominating a particular habitat or substrate. The wide distribution of filamentous fungi has resulted in it being used for different purposes. This review aims to analyse the different genera of fungi species referred to as filamentous fungi and their relevance economically and medically.

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Pyrrocidines A and B, new antibiotics produced by a filamentous fungus

Cited by 128 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

A Review of the Ubiquity of Ascomycetes Filamentous Fungi in Relation to Their Economic and Medical Importance

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