Synerazol, a new antifungal antibiotic.

Ando, Osamu; Satake, Hitomi; Nakajima, Mutsuo; Sato, Akira; Nakamura, Takemichi; Kinoshita, Takeshi; Furuya, Kouhei; Haneishi, Tatsuo

doi:10.7164/antibiotics.44.382

Cited by 68 publications

(36 citation statements)

References 14 publications

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“…[11] Together with 8-O-demethylpseurotin A (2) and synerazol (3), it was also isolated from A. fumigatus. [12,13,14] Azaspirene (4), with the same core structure, was obtained from A C H T U N G T R E N N U N G Neosartorya sp. [15] Pseurotin A is derived from l-phenylalanine, propionate, malonate and l-methionine, as proven by feeding experiments with 13 C-labelled precursors.…”

Section: Bioinformaticsmentioning

confidence: 99%

Identification of a Hybrid PKS/NRPS Required for Pseurotin A Biosynthesis in the Human Pathogen Aspergillus fumigatus

et al. 2007

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The genome sequence of Aspergillus fumigatus revealed the presence of a single hybrid polyketide synthase-non-ribosomal peptide synthetase (PKS/NRPS) gene that is present within a cluster of five genes suggestive of its involvement in secondary metabolism. Here, we present evidence that it is required for the biosynthesis of pseurotin A, a compound with an unusual heterospirocyclic gamma-lactam structure. We have confirmed that the genome reference strain A. fumigatus Af293 produces pseurotin A, a compound previously reported to be a competitive inhibitor of chitin synthase and an inducer of nerve-cell proliferation. Deletion or overexpression of the PKS/NRPS gene psoA in A. fumigatus leads to the absence or accumulation of pseurotin A, respectively; this indicates that this gene is essential for the biosynthesis of pseurotin A. It is likely that the first product of psoA is converted to pseurotin A by the products of other genes in this cluster.

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Section: Bioinformaticsmentioning

confidence: 99%

Identification of a Hybrid PKS/NRPS Required for Pseurotin A Biosynthesis in the Human Pathogen Aspergillus fumigatus

et al. 2007

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“…Fumifungin was produced by a strain isolated from a Himalayan soil sample 10 and synerazol was produced by a strain from Thailand soil sample. 11 The study of a Brazilian strain of A. fumigatus, aiming to isolate and identify antimicrobial compounds, was undertaken based on the wide variability encountered for this species.…”

Section: Introductionmentioning

confidence: 99%

Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain

Furtado¹,

Pupo²,

Carvalho³

et al. 2005

J. Braz. Chem. Soc.

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“…Although the structure frame of 1 and 2 is similar to that of pseurotin A, synerazol (Ando et al, 1991) and azaspirene (Asami et al, 2002), compounds 1 and 2 had unique characteristic such as the presence of an ethyl furan ring bearing to 1-oxa-7-azaspiro [4, 4] non-2-ene-4, 6-dione skeleton instead of a vicinal diol or several conjugated double bonds. To the best of our knowledge, they are new hetero-spirocyclic γ-lactams reported for the first time.…”

Section: Resultsmentioning

confidence: 99%