Xanthone and anthraquinone-type mycotoxins from the scale insect fungus Aschersonia marginata BCC 28721

Kornsakulkarn, Jittra; Saepua, Siriporn; Laksanacharoen, Pattiyaa; Rachtawee, Pranee; Thongpanchang, Chawanee

doi:10.1016/j.tetlet.2013.05.036

Cited by 15 publications

(12 citation statements)

References 17 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

109

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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

109

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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%

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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“…Xanthones are naturally oxygenated heterocycles with γ-pyron moiety fused with two benzene rings (Figure 1). There has been strong interest of this class of compounds due to their unique chemical structures containing different types of substituent in different positions, which leads to a large variety of pharmacological activities [1,2]. They have remarkable biological and pharmacological properties such as antibacterial, antioxidant, antiviral, anticancer, anti-inflammatory and antifungal.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral Characterisation and Antimicrobial Properties of Cu(II) and Fe(II) Complexes with Xanthone

Ni¹,

Mohamadin²,

Jong³

2017

Sci. Res. J.

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The new complexes [CuL2(H2O)2] and [FeL2(CH3O)2] in which L = β-mangostin were synthesised and characterised. The structure of the ligand, β-mangostin was confirmed using NMR and the purity of ligand was determined using HPLC. Both Cu(II) and Fe(II) complexes were prepared by reaction between the ligand and the acetate of the metals in one-step reaction. The synthesised compounds have been characterisedusing UV-Visible, FTIR and CHNS analyser. Ligand and metal complexes were tested against bacteria to assess on their antimicrobial properties using Minimum Inhibitory Concentrations (MICs) and Minimum Bactericidal Concentrations (MBCs) method. The elemental analysis and spectra data suggested octahedral geometry for both Cu(II) and Fe(II) complexes. The IR spectroscopy revealed that the chelation of Cu2+ and Fe2+ ion occurred with hydroxyl and carbonyl group at C9 and C1 respectively of β-mangostin. Both Cu(II) and Fe(II) complexes showed stronger inhibition against Pseudomonas aeruginosa, Proteus vulgaris, Klebsiella pneumoniae and Salmonella pneumonia at concentration 900 mg/mL and Escherichia coli at 450 mg/mL compared to the ligand itself.

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Xanthone and anthraquinone-type mycotoxins from the scale insect fungus Aschersonia marginata BCC 28721

Cited by 15 publications

References 17 publications

Chemodiversity in the genus Aspergillus

Chemodiversity in the genus Aspergillus

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

Synthesis, Spectral Characterisation and Antimicrobial Properties of Cu(II) and Fe(II) Complexes with Xanthone

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