<i>Penicillium digitatum</i> Metabolites on Synthetic Media and Citrus Fruits

Quesada, Antonio; Larsen, Thomas Ostenfeld; Peterson, Bent O; Duus, Jens Øllgaard; Barrero, A. F.

doi:10.1021/jf020398d

Cited by 50 publications

(37 citation statements)

References 22 publications

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“…The R configuration at position C12 is consistent with incorporation of a d -tryptophan moiety that likely arises through epimerization of l -tryptophan during NRPS assembly. The crystal structure is also consistent with the absolute configurations of 1 determined by NOE and of that of 4 from X-ray crystallography 17,27…”

Section: Resultssupporting

confidence: 78%

Fungal Indole Alkaloid Biosynthesis: Genetic and Biochemical Investigation of the Tryptoquialanine Pathway in Penicillium aethiopicum

Gao¹,

Chooi²,

et al. 2011

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Tremorgenic mycotoxins are a group of indole alkaloids which include the quinazoline-containing tryptoquivaline 2 that are capable of eliciting intermittent or sustained tremors in vertebrate animals. The biosynthesis of this group of bioactive compounds, which are characterized by an acetylated quinazoline ring connected to a 6-5-5 imidazoindolone ring system via a 5-membered spirolactone, has remained uncharacterized. Here, we report the identification of a gene cluster (tqa) from P. aethiopicum that is involved in the biosynthesis of tryptoquialanine 1, which is structurally similar to 2. The pathway has been confirmed to go through an intermediate common to the fumiquinazoline pathway, fumiquinazoline F, which originates from a fungal trimodular nonribosomal peptide synthetase (NRPS). By systematically inactivating every biosynthetic gene in the cluster, followed by isolation and characterization of the intermediates, we were able to establish the biosynthetic sequence of the pathway. An unusual oxidative opening of the pyrazinone ring by an FAD-dependent berberine bridge enzyme-like oxidoreductase has been proposed based on genetic knockout studies. Notably, a 2-aminoisobutyric acid (AIB)-utilizing NRPS module has been identified and reconstituted in vitro, along with two putative enzymes of unknown functions that are involved in the synthesis of the unnatural amino acid by genetic analysis. This work provides new genetic and biochemical insights into the biosynthesis of this group of fungal alkaloids, including the tremorgens related to 2.

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Section: Resultssupporting

confidence: 78%

Fungal Indole Alkaloid Biosynthesis: Genetic and Biochemical Investigation of the Tryptoquialanine Pathway in Penicillium aethiopicum

Gao¹,

Chooi²,

et al. 2011

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“…Tryptoquialanine is a tetrapeptide structurally similar to tryptoquivaline, which is a known tremorgen (Ariza et al, 2002; Clardy et al, 1975). Viridicatumtoxin is a hybrid polyketide-isoprenoid compound and is a rare example of tetracycline-like compounds produced by fungi.…”

Section: Introductionmentioning

confidence: 99%

Identification of the Viridicatumtoxin and Griseofulvin Gene Clusters from Penicillium aethiopicum

Chooi

Cacho

Tang

2010

Chemistry & Biology

160

201

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SUMMARY Penicillium aethiopicum produces two structurally interesting and biologically active polyketides: the tetracycline-like viridicatumtoxin 1 and the classic antifungal agent griseofulvin 2. Here, we report the concurrent discovery of the two corresponding biosynthetic gene clusters (vrt and gsf) by 454 shotgun sequencing. Gene deletions confirmed two nonreducing PKSs (NRPKS), vrtA and gsfA, are required for the biosynthesis of 1 and 2, respectively. Both PKSs share similar domain architectures and lack a C-terminal thioesterase domain. We identified gsfI as the chlorinase involved in the biosynthesis of 2, as deletion of gsfI resulted in the accumulation of decholorogriseofulvin 3. Comparative analysis with the P. chrysogenum genome revealed that both clusters are embedded within conserved syntenic regions of P. aethiopicum chromosomes. Discovery of the vrt and gsf clusters provided the basis for genetic and biochemical studies of the pathways.

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“…In addition, Ariza and coworkers reported an unknown volatile compound for oranges infected with P. digitatum with a molecular weight of 114 and causing the characteristic mouldy odour. [9] It is very likely that both research groups came across PEE, but were not able to identify the compound because its mass spectrum was only published in 2010. [3] This demonstrates that the relation of PEE and P. digitatum is not an exotic phenomenon, which is only present in our laboratories, but is likely a typical combination that has been detected but not identified by other, independent groups 19 and 12 years ago.…”

Section: Methodsmentioning

confidence: 99%

Prenyl Ethers: Novel Fungal Volatiles Formed by Penicillium digitatum

Amrein¹,

Frey²,

Meier³

et al. 2014

Chimia

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Prenyl ethyl ether (PEE) was previously described as the cause for a solvent-like off-note in ground hazelnuts, but its origin remained unclear. Investigations were carried out by analytical groups of Coop and Givaudan over four years to elucidate this phenomenon. From mouldy citrus fruits a strain of Penicillium digitatum was isolated and found to form PEE. Formation on citrus and other fruits was prominent and contributed to the particular smell of decayed fruits. Several strains of P. digitatum formed PEE, while other fungal species did not. In contrast to citrus fruit, prenyl methyl ether (PME) was formed as dominant prenyl ether on hazelnuts while only small amounts of PEE were found. PME has not been previously described as volatile metabolite of fungi or as a food-taint. Spiking experiments with deuterated ethanol showed that the ethyl group is likely incorporated into PEE via the aldehyde form. On hazelnuts strongly decayed by P. digitatum yet another prenyl ether was tentatively identified: Prenyl isopropyl ether. Prenyl ethers present a novel group of volatile metabolites of P. digitatum. They are likely typical for this species and have not been described before. Prenyl ethers seem to play a significant role in the smell of food decayed by P. digitatum and should be considered in cases of off-notes and taints.

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Penicillium digitatum Metabolites on Synthetic Media and Citrus Fruits

Cited by 50 publications

References 22 publications

Fungal Indole Alkaloid Biosynthesis: Genetic and Biochemical Investigation of the Tryptoquialanine Pathway in Penicillium aethiopicum

Fungal Indole Alkaloid Biosynthesis: Genetic and Biochemical Investigation of the Tryptoquialanine Pathway in Penicillium aethiopicum

Identification of the Viridicatumtoxin and Griseofulvin Gene Clusters from Penicillium aethiopicum

Prenyl Ethers: Novel Fungal Volatiles Formed by Penicillium digitatum

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