Two New Dioxopiperazine Derivatives, Arestrictins A and B, Isolated from Aspergillus restrictus and Aspergillus penicilloides.

Itabashi, Takeshi; Matsuishi, Natsuna; Hosoe, Tomoo; Toyazaki, Norihiro; Udagawa, Shun‐ichi; Imai, Tomoaki; Adachi, Mitsuru; Kawai, Ken‐ichi

doi:10.1002/chin.200721187

Cited by 5 publications

(5 citation statements)

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“…A Japanese study has isolated asperglaucide, one of the most prevalent metabolites in our study, from the organic extract of the xerophilic fungi Aspergillus restrictus and Aspergillus penicillioides. 38 However, we only detected A. penicillioides from one sample with culturing and 13.6% of samples with DNA sequencing. Integracin B was more prevalent than A (93% vs 71%), and they are produced by the endophyte, Cytonaema species 39 and Cytospora species 40 which were not identified in our samples.…”

Section: Citreorosein Emodin Alternariol Mme Integracin a Integracin mentioning

confidence: 76%

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

et al. 2018

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Recent developments in molecular and chemical methods have enabled the analysis of fungal DNA and secondary metabolites, often produced during fungal growth, in environmental samples. We compared 3 fungal analytical methods by analysing floor dust samples collected from an office building for fungi using viable culture, internal transcribed spacer (ITS) sequencing and secondary metabolites using liquid chromatography-tandem mass spectrometry. Of the 32 metabolites identified, 29 had a potential link to fungi with levels ranging from 0.04 (minimum for alternariol monomethylether) to 5700 ng/g (maximum for neoechinulin A). The number of fungal metabolites quantified per sample ranged from 8 to 16 (average = 13/sample). We identified 216 fungal operational taxonomic units (OTUs) with the number per sample ranging from 6 to 29 (average = 18/sample). We identified 37 fungal species using culture, and the number per sample ranged from 2 to 13 (average = 8/sample). Agreement in identification between ITS sequencing and culturing was weak (kappa = -0.12 to 0.27). The number of cultured fungal species poorly correlated with OTUs, which did not correlate with the number of metabolites. These suggest that using multiple measurement methods may provide an improved understanding of fungal exposures in indoor environments and that secondary metabolites may be considered as an additional source of exposure.

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Section: Citreorosein Emodin Alternariol Mme Integracin a Integracin mentioning

confidence: 76%

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

et al. 2018

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“…Such changes in secondary metabolite clusters may have a specific ecological significance among xerophilic fungi, as these are in general quite poor producers of secondary metabolites. For example, members of Aspergillus section Restricti have only been reported to produce asperglaucide and arestrictin A and B and cristatin A (Itabashi et al, 2006). Other closely related xerophilic species, such as Aspergillus section Aspergillus, formerly called Eurotium, produce ascomata (sexual structures) with many more secondary metabolites (Slack et al, 2009), whereas strains with only an Aspergillus state (i.e.…”

Section: Minimal Production Of Secondary Metabolitesmentioning

confidence: 99%

Genome and physiology of the ascomycete filamentous fungus Xeromyces bisporus, the most xerophilic organism isolated to date

Leong

Lantz

Pettersson

et al. 2014

Environmental Microbiology

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SummaryXeromyces bisporus can grow on sugary substrates down to 0.61, an extremely low water activity. Its genome size is approximately 22 Mb. Gene clusters encoding for secondary metabolites were conspicuously absent; secondary metabolites were not detected experimentally. Thus, in its 'dry' but nutrientrich environment, X. bisporus appears to have relinquished abilities for combative interactions. Elements to sense/signal osmotic stress, e.g. HogA pathway, were present in X. bisporus. However, transcriptomes at optimal (∼ 0.89) versus low a w (0.68) revealed differential expression of only a few stress-related genes; among these, certain (not all) steps for glycerol synthesis were upregulated. Xeromyces bisporus increased glycerol production during hypoand hyper-osmotic stress, and much of its wet weight comprised water and rinsable solutes; leaked solutes may form a protective slime. Xeromyces bisporus and other food-borne moulds increased membrane fatty acid saturation as water activity decreased. Such modifications did not appear to be transcriptionally regulated in X. bisporus; however, genes modulating sterols, phospholipids and the cell wall were differentially expressed. Xeromyces bisporus was previously proposed to be a 'chaophile', preferring solutes that disorder biomolecular structures. Both X. bisporus and the closely related xerophile, Xerochrysium xerophilum, with low membrane unsaturation indices, could represent a phylogenetic cluster of 'chaophiles'.

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“…22) bearing a prenylated and reverse prenylated Z-DTrp residue was isolated from the Indian herb Lepidagathis cristata by Venkateswarlu and co-workers. 66 Its small optical rotation ([a] D þ1.2, CHCl 3 ), combined with the fact that S-30 subsequently isolated by Kawai and co-workers from the fungus Aspergillus restrictus has a large optical rotation ([a] D À26.3, CHCl 3 ), 67 has led to speculation that the original material was obtained as essentially a racemic mixture. Essentially racemic 30 was also found in the leaves of Acacia auriculiformis in 2012 by Hasan, Thurston, and co-workers.…”

Section: Trisubstituted Ab-dehydroamino Acidsmentioning

confidence: 98%

Bulky α,β-dehydroamino acids: their occurrence in nature, synthesis, and applications

Jiang

Castle

2015

Tetrahedron

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Two New Dioxopiperazine Derivatives, Arestrictins A and B, Isolated from Aspergillus restrictus and Aspergillus penicilloides.

Cited by 5 publications

References 1 publication

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

Genome and physiology of the ascomycete filamentous fungus Xeromyces bisporus, the most xerophilic organism isolated to date

Bulky α,β-dehydroamino acids: their occurrence in nature, synthesis, and applications

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