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:10.1248/cpb.54.1639

Cited by 30 publications

(23 citation statements)

References 8 publications

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“…The other metabolites could be attributed to more than one genus of indoor fungi (Laatsch, 2005). The results have emphasized the presence of the metabolite asperglaucide (2270 -14600 µg/kg), potentially indicative of xerophilic fungi as A. penicillioides and A. restrictus, but also plant's metabolite (Itabashi et al, 2006;Wu et al, 2011). Anyway, the particular structural characteristics of the repository do not permit a significant air exchange with the outside and the source of asperglaucide is more likely to have fungal origin.…”

Section: Discussionmentioning

confidence: 98%

“…known to produce sterigmatocystin, as A. versicolor and Emericella nidulans. However, very few studies have addressed methoxysterigmatocystin, and those studies were mostly concerned with contamination by A. versicolor (Klich, 2009;Nielsen et al, 1999 (Frisvad, 2015;Itabashi et al, 2006;Peterson, 2008;Tamura et al, 1999). For A. vitricola, in fact, no records were detected.…”

Section: Discussionmentioning

confidence: 99%

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Fungal secondary metabolite analysis applied to Cultural Heritage: the case of a contaminated library in Venice

Micheluz

Sulyok²,

Manente

et al. 2016

WMJ

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The secondary metabolite production of several fungal strains of Aspergillus creber, Aspergillus jensenii, Aspergillus penicillioides, Aspergillus protuberus, Aspergillus vitricola, Cladosporium cladosporioides, Eurotium chevalieri, Eurotium halophilicum, Penicillium brevicompactum and Penicillium chrysogenum were characterised by liquid chromatography tamdem mass spectometry. All fungi were isolated from both air and book covers as well as from settled dust from a contaminated library in Venice (Italy). For A. creber and A. jensenii, we identified sterigmatocystin, methoxysterigmatocystin, versicolorin A and related precursors/side metabolites from the biosynthetic pathways. Deoxybrevianamid E, neoechinulin A, pseurotin A and D, and rugulusovin were principally detected from the strains of E. halophilicum, an emerging fungal species implicated in book contaminations in specific indoor niches. The analysis of settled dust showed a wide range of toxic or bioactive fungal metabolites. Forty-five different metabolites were identified in different concentrations; in particular, high amounts of asperglaucide, alamethicin, andrastin A, terrecyclic acid and neoechinulin A were detected. Also one bacterial metabolite, chloramphenicole was detected. This study increases the knowledge about metabolite production of several fungal species, as well as on the indoor presence of fungi that are not detected by aerobiological sampling. These results emphasise how routine dusting operations are necessary and essential in order to prevent further microbiological developments in library environments.

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Section: Discussionmentioning

confidence: 98%

Section: Discussionmentioning

confidence: 99%

Fungal secondary metabolite analysis applied to Cultural Heritage: the case of a contaminated library in Venice

Micheluz

Sulyok²,

Manente

et al. 2016

WMJ

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“…5) (Verchère et al 1969;Turner 1971;Assante et al 1979;Dorner et al 1980;Selva et al 1980;Turner and Aldridge 1983;Scheweikert 2003, Cole et al 2003;Sun et al 2012). Asperglaucide from Aspergillus restrictus and Aspergillus penicillioides (Itabashi et al 2006) has a clear resemblance to asperphenamate found in Aspergillus flavipes in subgenus Circumdati section Flavipedes (Clark et al 1977).…”

Section: Unique Extrolites In Subgenus Fumigatimentioning

confidence: 99%

Chemodiversity in the genus Aspergillus

Frisvad

Larsen

2015

Appl Microbiol Biotechnol

115

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Isolates of Aspergillus species are able to produce a large number of secondary metabolites. The profiles of biosynthetic families of secondary metabolites are species specific, whereas individual secondary metabolite families can occur in other species, even those phylogenetically and ecologically unrelated to Aspergillus. Furthermore, there is a high degree of chemo-consistency from isolate to isolate in a species even though certain metabolite gene clusters are silenced in some isolates. Genome sequencing projects have shown that the diversity of secondary metabolites is much larger in each species than previously thought. The potential of finding even further new bioactive drug candidates in Aspergillus is evident, despite the fact that many secondary metabolites have already been structure elucidated and chemotaxonomic studies have shown that many new secondary metabolites have yet to be characterized. The genus Aspergillus is cladistically holophyletic but phenotypically polythetic and very diverse and is associated to quite different sexual states. Following the one fungus one name system, the genus Aspergillus is restricted to a holophyletic clade that include the morphologically different genera Aspergillus, Dichotomomyces, Phialosimplex, Polypaecilum and Cristaspora. Secondary metabolites common between the subgenera and sections of Aspergillus are surprisingly few, but many metabolites are common to a majority of species within the sections. We call small molecule extrolites in the same biosynthetic family isoextrolites. However, it appears that secondary metabolites from one Aspergillus section have analogous metabolites in other sections (here also called heteroisoextrolites). In this review, we give a genus-wide overview of secondary metabolite production in Aspergillus species. Extrolites appear to have evolved because of ecological challenges rather than being inherited from ancestral species, at least when comparing the species in the different sections of Aspergillus. Within the Aspergillus sections, secondary metabolite pathways seem to inherit from ancestral species, but the profiles of these secondary metabolites are shaped by the biotic and abiotic environment. We hypothesize that many new and unique section-specific small molecule extrolites in each of the Aspergillus will be discovered.

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“…Signals for the four protons at positions 4, 5, 6 and 7 of the indole ring were clearly observed (Table S1), and revealed that the prenyl moiety is connected to N-1 or C-2 of the indole ring. The signals of the methyl groups in the reverse prenyl moieties attached to C-2 of the indole rings of some diketopiperazine derivatives, for example, in echnulin-and isoechinulin-type alkaloids, [2][3][4] in deoxybrevianamide E [5] or okaramines, [6,7] were usually found in the range of 1.40 to 1.55 ppm. In comparison, the signals of the methyl groups in the prenyl moieties of the enzymatic products of CdpNPT are significantly up-field shifted to 0.9 to 1.1 ppm.…”

mentioning

confidence: 99%

Reinvestigation of a Cyclic Dipeptide N‐Prenyltransferase Reveals Rearrangement of N‐1 Prenylated Indole Derivatives

Ruan

Yin

et al. 2008

ChemBioChem

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

Cited by 30 publications

References 8 publications

Fungal secondary metabolite analysis applied to Cultural Heritage: the case of a contaminated library in Venice

Fungal secondary metabolite analysis applied to Cultural Heritage: the case of a contaminated library in Venice

Chemodiversity in the genus Aspergillus

Reinvestigation of a Cyclic Dipeptide N‐Prenyltransferase Reveals Rearrangement of N‐1 Prenylated Indole Derivatives

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