Metabolites of Aspergillus indicus: The structure and some aspects of the biosynthesis of dihydrocanadensolide

Birch, A. J.; Qureshi, A.A.; Rickards, RW

doi:10.1071/ch9682775

Cited by 8 publications

(9 citation statements)

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“…1976 ), (-)-canadensolide ( Berg et al . 1976 ), cyclopiazonic acid ( Dorner 1983 ), dihydrocanadensolide, fumaric acid, fumaryl- D,L -alanine ( Birch et al . 1968 ), fumigaclavine A ( Jahardhanan et al .…”

Section: Resultsmentioning

confidence: 99%

“…1968 ), fumigaclavine A ( Jahardhanan et al . 1984 ), kojic acid ( Birkinshaw et al., 1931 , Manabe et al., 1984 ), 3-nitropropionic acid ( Birch et al . 1968 ), speradine A ( Tsuda et al .…”

Section: Resultsmentioning

confidence: 99%

“…1968 ), speradine A ( Tsuda et al . 2003 ), succinic acid ( Birch et al . 1968 ) Aspirochlorin (8/15 strains), citreoisocoumarin (2/15 strains), cyclopiazonic acid (9/15 strains), kojic acid (13/15 strains), tenuazonic acid (4/15 strains) CBS 103.14 T , CBS 104.14, CBS 129.49, CBS 109.63, CBS 167.63, CBS 484.65, CBS 575.65, CBS 579.65, CBS 591.68, CBS 117626, CBS 126844, IBT 29248, IBT 29229, NRRL 4860, NRRL 8101 A. togoensis Aflatoxin B1 ( Rank et al .…”

Section: Resultsmentioning

confidence: 99%

“…indicus ). Isolation of dihydrocanadensolide, fumaric acid, fumaryl-D,L-alanine, indazonic acid = cyclopiazonic acid, kojic acid, succinic acid and 3-nitropropionic acid show that these metabolites can be produced by A. tamarii ( Birch et al, 1968 ) MG662407 MG517624 MG518001 MG517807 DTO 065-A4 Indoor environment, Germany MH279381 MG517648 MG517984 MG517835 DTO 066-A1 Corn kernels, Indonesia - MG517649 MG517988 MG517836 DTO 145-C3 Indoor environment, Germany MH279382 MG517655 MG517993 MG517843 DTO 266-D7 House dust, Mexico - MG517730 MG518100 MG517921 DTO 364-E3 Air in chocolate factory, the Netherlands MH279435 MG517781 MG518151 MG517971 NRRL 425 Unknown source, representative of Aspergillus lutescens nomen nudum EF661558 EF661475 EF661524 EU021648 NRRL 426 = DTO 010-H3 = CBS 579.65 = IBT 3681 = IBT 3826 = IBT 10827 Unknown substrate, USA, ex neotype of Aspergillus terricola EF661559 EF661472 EF661525 EU021649 NRRL 4911 = CBS 484.65 = IBT 3659 Air contaminant, Brazil, ex neotype of Aspergillus flavofurcatus EF661565 EF661473 EF661527 EU021651 Aspergillus togoensis CBS 205.75 T = LCP 67.3456 = NRRL 13551 = IBT 14899 = IBT 21943 Decaying fruit of Landolphia sp., Central African Republic, ex type of Aspergillus...…”

Section: Methodsmentioning

confidence: 99%

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Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Frisvad

Hubka

Ezekiel

et al. 2019

Studies in Mycology

420

387

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Aflatoxins and ochratoxins are among the most important mycotoxins of all and producers of both types of mycotoxins are present in Aspergillus section Flavi, albeit never in the same species. Some of the most efficient producers of aflatoxins and ochratoxins have not been described yet. Using a polyphasic approach combining phenotype, physiology, sequence and extrolite data, we describe here eight new species in section Flavi. Phylogenetically, section Flavi is split in eight clades and the section currently contains 33 species. Two species only produce aflatoxin B1 and B2 (A. pseudotamarii and A. togoensis), and 14 species are able to produce aflatoxin B1, B2, G1 and G2: three newly described species A. aflatoxiformans, A. austwickii and A. cerealis in addition to A. arachidicola, A. minisclerotigenes, A. mottae, A. luteovirescens (formerly A. bombycis), A. nomius, A. novoparasiticus, A. parasiticus, A. pseudocaelatus, A. pseudonomius, A. sergii and A. transmontanensis. It is generally accepted that A. flavus is unable to produce type G aflatoxins, but here we report on Korean strains that also produce aflatoxin G1 and G2. One strain of A. bertholletius can produce the immediate aflatoxin precursor 3-O-methylsterigmatocystin, and one strain of Aspergillus sojae and two strains of Aspergillus alliaceus produced versicolorins. Strains of the domesticated forms of A. flavus and A. parasiticus, A. oryzae and A. sojae, respectively, lost their ability to produce aflatoxins, and from the remaining phylogenetically closely related species (belonging to the A. flavus-, A. tamarii-, A. bertholletius- and A. nomius-clades), only A. caelatus, A. subflavus and A. tamarii are unable to produce aflatoxins. With exception of A. togoensis in the A. coremiiformis-clade, all species in the phylogenetically more distant clades (A. alliaceus-, A. coremiiformis-, A. leporis- and A. avenaceus-clade) are unable to produce aflatoxins. Three out of the four species in the A. alliaceus-clade can produce the mycotoxin ochratoxin A: A. alliaceus s. str. and two new species described here as A. neoalliaceus and A. vandermerwei. Eight species produced the mycotoxin tenuazonic acid: A. bertholletius, A. caelatus, A. luteovirescens, A. nomius, A. pseudocaelatus, A. pseudonomius, A. pseudotamarii and A. tamarii while the related mycotoxin cyclopiazonic acid was produced by 13 species: A. aflatoxiformans, A. austwickii, A. bertholletius, A. cerealis, A. flavus, A. minisclerotigenes, A. mottae, A. oryzae, A. pipericola, A. pseudocaelatus, A. pseudotamarii, A. sergii and A. tamarii. Furthermore, A. hancockii produced speradine A, a compound related to cyclopiazonic acid. Selected A. aflatoxiformans, A. austwickii, A. cerealis, A. flavus, A. minisclerotigenes, A. pipericola and A. sergii strains produced small sclerotia containing the mycotoxin aflatrem. Kojic acid has been found in all species in section Flavi, except A. avenaceus and A. coremiiformis. Only six species in the section did not produce any known mycotoxins: A. aspearensis, A. coremii...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Frisvad

Hubka

Ezekiel

et al. 2019

Studies in Mycology

420

387

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“…Intriguingly, fumaryl-L-alanine (FA, Fig. 4), a natural product composed of the preferred SidE substrates, has previously been isolated from Aspergillus indicus (35) and, as a racemic compound, from Penicillium resticulosum (36). Consequently, we heterologously produced hexahistidine-tagged full-length enzyme (237.0 kDa, 2,142 aa; see Fig.…”

Section: Biochemical Characterization Of Side Substrate Specificitiesmentioning

confidence: 99%

Bimodular Peptide Synthetase SidE Produces Fumarylalanine in the Human Pathogen Aspergillus fumigatus

Steinchen

Lackner

Schrettl

et al. 2013

Appl Environ Microbiol

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The filamentous mold Aspergillus fumigatus causes invasive aspergillosis, a potentially life-threatening infectious disease, in humans. The sidE gene encodes a bimodular peptide synthetase and was shown previously to be strongly upregulated during initiation of murine lung infection. In this study, we characterized the two adenylation domains of SidE with the ATP-[ 32 P]pyrophosphate exchange assay in vitro, which identified fumarate and L-alanine, respectively, as the preferred substrates. Using fulllength holo-SidE, fumarylalanine (FA) formation was observed in vitro. Furthermore, FA was identified in A. fumigatus culture supernatants under inducing conditions, unless sidE was genetically inactivated. As FA is structurally related to established pharmaceutical products exerting immunomodulatory activity, this work may contribute to our understanding of the virulence of A. fumigatus. T he fungusAspergillus fumigatus is an opportunistic pathogen, particularly with immunocompromised patients. It represents the most common etiological agent of invasive aspergillosis, which is associated with mortality rates as high as 30% to 90% (1). A. fumigatus small molecules, such as gliotoxin, are thought of as contributing to virulence (2). Consequently, the secondary metabolome of this fungus has been object of intensive research, with an emphasis on nonribosomal peptide synthetases (NRPSs). These are multidomain enzymes, which include all catalytic functions to assemble complex metabolites from amino acids or other building blocks (3). Adenylation (A) domains are integral components of NRPSs, which select and activate the monomeric substrates. The function of 8 of 14 nonribosomal peptide synthetases (NRPSs) (FtmA, GliP, HasD, PesL, PesM, Pes1, SidC, SidD) in A. fumigatus was previously clarified (4-10). The metabolite of a ninth NRPS (Pes3) has not yet been identified but is predicted to play a structural role (11). The A. fumigatus peptide synthetase gene sidE, which encodes a bimodular NRPS, is located in the vicinity of the genetic locus that is essential for biosynthesis of the siderophore fusarinine C. Therefore, SidE was expected to serve in siderophore production, too (12). However, unlike that of siderophore-related genes, its expression depends on the presence of LaeA, a positive regulator of virulence factors and secondary metabolism of A. fumigatus (13,14). Intriguingly, sidE is upregulated 16-fold in Aspergillus germlings growing in the neutropenic murine lung and is therefore believed to play a role in virulence (15). Here, we present genetic and biochemical evidence that SidE is unrelated to siderophore biosynthesis but has fumarylalanine (FA) synthetase activity. MATERIALS AND METHODS General. Tetrasodium [32 P]pyrophosphate (59.9 Ci/mmol) was from PerkinElmer. Plasmid propagation was done in Escherichia coli XL1 blue. Transformation of A. fumigatus was carried out as described previously for A. nidulans (16). A. fumigatus strains (see Table S1 in the supplemental material) were routinely cultured at 37°C on...

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Secondary Metabolites of Penicillium and Acremonium

Mantle¹

1987

Penicillium and Acremonium

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Metabolites of Aspergillus indicus: The structure and some aspects of the biosynthesis of dihydrocanadensolide

Cited by 8 publications

References 0 publications

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Taxonomy ofAspergillussectionFlaviand their production of aflatoxins, ochratoxins and other mycotoxins

Bimodular Peptide Synthetase SidE Produces Fumarylalanine in the Human Pathogen Aspergillus fumigatus

Secondary Metabolites of Penicillium and Acremonium

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