New mycotoxins from the scale insect fungus Aschersonia coffeae Henn. BCC 28712

Kornsakulkarn, Jittra; Saepua, Siriporn; Srichomthong, Kitlada; Supothina, Sumalee; Thongpanchang, Chawanee

doi:10.1016/j.tet.2012.07.059

Cited by 38 publications

(40 citation statements)

References 27 publications

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“…Within Aspergillus, there are some interesting differences between sections: Aflatoxins G 1 and G 2 has only been found in section Flavi, while species in other sections never produce aflatoxins G 1 and G 2 , but accumulate both sterigmatocystin and aflatoxin B 1 . Concomitant accumulation of aflatoxin B 1 and sterigmatocystins is also seen in Aschersonia coffeae and Aschersonia marginata (Kornsakulkarn et al 2012(Kornsakulkarn et al , 2013. Production of sterigmatocystin is restricted to the subgebera Circumdati section Flavi and Nidulantes sections Aenei, Ochraceorosei, Versicolores and Nidulantes, but has also been detected in the more distantly related A. inflatus in section Cremei Samson et al 2014).…”

Section: Unique Extrolites In Subgenus Fumigatimentioning

confidence: 92%

“…Since it appears improbable that a common ancestor of all ascomycetes could produce sterigmatocystin or its precursors, the ability to produce this secondary metabolite must have evolved independently a large number of times, or the gene cluster or a chromosome carrying, it must have been horizontally transferred as suggested by Slot and Rokas (2011) for Aspergillus and Podospora. Secondary metabolites derived from sterigmatocystin, aflatoxins, are present in only two genera: Aspergillus ) and Aschersonia (Kornsakulkarn et al 2012(Kornsakulkarn et al , 2013. Within Aspergillus, there are some interesting differences between sections: Aflatoxins G 1 and G 2 has only been found in section Flavi, while species in other sections never produce aflatoxins G 1 and G 2 , but accumulate both sterigmatocystin and aflatoxin B 1 .…”

Section: Unique Extrolites In Subgenus Fumigatimentioning

confidence: 99%

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Chemodiversity in the genus Aspergillus

Frisvad

Larsen

2015

Appl Microbiol Biotechnol

113

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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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Section: Unique Extrolites In Subgenus Fumigatimentioning

confidence: 92%

Section: Unique Extrolites In Subgenus Fumigatimentioning

confidence: 99%

Chemodiversity in the genus Aspergillus

Frisvad

Larsen

2015

Appl Microbiol Biotechnol

113

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“…In the course of a study on invertebrate-pathogenic fungi collected from the tropical rainforest in Thailand, a collection of spider-associated fungal specimens was encountered in order to generate their HPLC profiles. Compounds possessing a 4-methylglucose moiety have rarely been found in natural sources, except for some insect pathogenic fungi [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. In the current study, we report the isolation, structure elucidation, absolute configuration and biological activity of four new α-pyrone derivatives bearing a 4- O -methyl-β- d -glucopyranose, for which we propose the trivial names, akanthopyrones A–D ( 1 – 4 ; Figure 1 ), from the spider-associated fungus A. novoguineensis .…”

Section: Introductionmentioning

confidence: 99%

Akanthopyrones A–D, α-Pyrones Bearing a 4-O-Methyl-β-d-glucopyranose Moiety from the Spider-Associated Ascomycete Akanthomyces novoguineensis

et al. 2017

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Hypocrealean fungi have proved to be prolific bioactive metabolite producers; they have caught the attention of mycologists throughout the world. However, only a few studies on the insect and spider parasitic genus Akanthomyces have so far been carried out. In this study, we report the isolation, structural elucidation and biological activities of four unprecedented glycosylated α-pyrone derivatives, akanthopyrones A–D (1–4), from a culture of Akanthomyces novoguineensis collected in Thailand. The chemical structures of the akanthopyrones were determined by extensive 1D- and 2D-NMR, and HRMS spectroscopic analysis. Their absolute configurations were determined. Akanthopyrone A (1) exhibited weak antimicrobial activity against Bacillus subtilis DSM10 and cytotoxicity against the HeLa cell line KB-3-1, while akanthopyrone D (4) showed weak activity against Candida tenuis MUCL 29892.

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“…), and Aschersonia (2 spp. ; Frisvad and Samson, 2004a ; Frisvad et al, 2005 ; Zalar et al, 2008 ; Varga et al, 2009 , 2011 ; Kornsakulkarn et al, 2012 , 2013 ; Massi et al, 2014 ). Three species in Aspergillus section Flavi and all the seven species outside section Flavi listed above only produce aflatoxins of the B type.…”

Section: Chemodiversitymentioning

confidence: 99%

“…Three species in Aspergillus section Flavi and all the seven species outside section Flavi listed above only produce aflatoxins of the B type. It is surprising that aflatoxins have never been found in Penicillium , but they have been found in the unrelated scale insect fungi Aschersonia coffea and Aschersonia marginata ( Kornsakulkarn et al, 2012 , 2013 ). However, the precursor sterigmatocystin, although end-product for some species, has been found in a large number of unrelated genera ( Rank et al, 2011 ), suggesting that this complicated gene cluster has been horizontally transfered between species in widely different genera, as shown by Slot and Rokas (2011) for Podospora anserina and A. nidulans .…”

Section: Chemodiversitymentioning

confidence: 99%

Taxonomy, chemodiversity, and chemoconsistency of Aspergillus, Penicillium, and Talaromyces species

Frisvad

2015

Front. Microbiol.

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Aspergillus, Penicillium, and Talaromyces are among the most chemically inventive of all fungi, producing a wide array of secondary metabolites (exometabolites). The three genera are holophyletic in a cladistic sense and polythetic classes in an anagenetic or functional sense, and contain 344, 354, and 88 species, respectively. New developments in classification, cladification, and nomenclature have meant that the species, series, and sections suggested are natural groups that share many extrolites, including exometabolites, exoproteins, exocarbohydrates, and exolipids in addition to morphological features. The number of exometabolites reported from these species is very large, and genome sequencing projects have shown that a large number of additional exometabolites may be expressed, given the right conditions (“cryptic” gene clusters for exometabolites). The exometabolites are biosynthesized via shikimic acid, tricarboxylic acid cycle members, nucleotides, carbohydrates or as polyketides, non-ribosomal peptides, terpenes, or mixtures of those. The gene clusters coding for these compounds contain genes for the biosynthetic building blocks, the linking of these building blocks, tailoring enzymes, resistance for own products, and exporters. Species within a series or section in Aspergillus, Penicillium, and Talaromyces have many exometabolites in common, seemingly acquired by cladogenesis, but some the gene clusters for autapomorphic exometabolites may have been acquired by horizontal gene transfer. Despite genome sequencing efforts, and the many breakthroughs these will give, it is obvious that epigenetic factors play a large role in evolution and function of chemodiversity, and better methods for characterizing the epigenome are needed. Most of the individual species of the three genera produce a consistent and characteristic profile of exometabolites, but growth medium variations, stimulation by exometabolites from other species, and variations in abiotic intrinsic and extrinsic environmental factors such as pH, temperature, redox potential, and water activity will add significantly to the number of biosynthetic families expressed in anyone species. An example of the shared exometabolites in a natural group such as Aspergillus section Circumdati series Circumdati is that most, but not all species produce penicillic acids, aspyrones, neoaspergillic acids, xanthomegnins, melleins, aspergamides, circumdatins, and ochratoxins, in different combinations.

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New mycotoxins from the scale insect fungus Aschersonia coffeae Henn. BCC 28712

Cited by 38 publications

References 27 publications

Chemodiversity in the genus Aspergillus

Chemodiversity in the genus Aspergillus

Akanthopyrones A–D, α-Pyrones Bearing a 4-O-Methyl-β-d-glucopyranose Moiety from the Spider-Associated Ascomycete Akanthomyces novoguineensis

Taxonomy, chemodiversity, and chemoconsistency of Aspergillus, Penicillium, and Talaromyces species

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