Patulin and secondary metabolite production by marine-derived Penicillium strains

Vansteelandt, Marieke; Kerzaon, Isabelle; Blanchet, Élodie; Tankoua, Olivia Fossi; Pont, Thibaut Robiou du; Joubert, Yolaine; Monteau, Fabrice; Bizec, Bruno Le; Frisvad, Jens Christian; Pouchus, Yves François; Grovel, Olivier

doi:10.1016/j.funbio.2012.06.005

Cited by 51 publications

(21 citation statements)

References 44 publications

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“…The pitfalls of scoring can be illustrated with patulin, a bioactive “nuisance” compound that is widely distributed in fungi that cause interference in many types of bioassays [45,46,47]. Patulin was identified in ESI − in marine-derived strains of Penicillium antarcticum (Figure 3).…”

Section: Resultsmentioning

confidence: 99%

Accurate Dereplication of Bioactive Secondary Metabolites from Marine-Derived Fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library

et al. 2014

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In drug discovery, reliable and fast dereplication of known compounds is essential for identification of novel bioactive compounds. Here, we show an integrated approach using ultra-high performance liquid chromatography-diode array detection-quadrupole time of flight mass spectrometry (UHPLC-DAD-QTOFMS) providing both accurate mass full-scan mass spectrometry (MS) and tandem high resolution MS (MS/HRMS) data. The methodology was demonstrated on compounds from bioactive marine-derived strains of Aspergillus, Penicillium, and Emericellopsis, including small polyketides, non-ribosomal peptides, terpenes, and meroterpenoids. The MS/HRMS data were then searched against an in-house MS/HRMS library of ~1300 compounds for unambiguous identification. The full scan MS data was used for dereplication of compounds not in the MS/HRMS library, combined with ultraviolet/visual (UV/Vis) and MS/HRMS data for faster exclusion of database search results. This led to the identification of four novel isomers of the known anticancer compound, asperphenamate. Except for very low intensity peaks, no false negatives were found using the MS/HRMS approach, which proved to be robust against poor data quality caused by system overload or loss of lock-mass. Only for small polyketides, like patulin, were both retention time and UV/Vis spectra necessary for unambiguous identification. For the ophiobolin family with many structurally similar analogues partly co-eluting, the peaks could be assigned correctly by combining MS/HRMS data and m/z of the [M + Na]+ ions.

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Section: Resultsmentioning

confidence: 99%

Accurate Dereplication of Bioactive Secondary Metabolites from Marine-Derived Fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library

et al. 2014

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“…As marine isolates of this species are known to produce patulin (Vansteelandt et al . ), a mycotoxin cytotoxic on various cell lines (Iwamoto et al . ; Heussner et al .…”

Section: Resultsmentioning

confidence: 99%

“…In previous studies, it has been shown that Penicillium strains sampled from shellfish‐farming areas produced roquefortine C and patulin (Vansteelandt et al . ) and that some toxic fungal metabolites like gliotoxin or peptaibols produced by marine‐derived fungi can be detected in marine sediments and can be accumulated in filter‐feeding molluscs under laboratory conditions (Sallenave et al . ; Grovel et al .…”

Section: Introductionmentioning

confidence: 99%

“…Marinederived fungi form a group of potential contaminants for marine bivalves such as mussels (Zvereva and Vysotskaya 2005;Zielinski et al 2009). In previous studies, it has been shown that Penicillium strains sampled from shellfish-farming areas produced roquefortine C and patulin (Vansteelandt et al 2012) and that some toxic fungal metabolites like gliotoxin or peptaibols produced by marine-derived fungi can be detected in marine sediments and can be accumulated in filter-feeding molluscs under laboratory conditions (Sallenave et al 1999;Grovel et al 2003). In situ contamination of bivalves by fungal compounds could be one of the origins of the unexplained toxicities of seafood observed along the French coast since the beginning of the 1990s (Belin et al 2009).…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity and mycotoxin production of shellfish-derived Penicillium spp., a risk for shellfish consumers

Geiger

Guitton

Vansteelandt

et al. 2013

Letters in Applied Microbiology

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Significance and Impact of the Study: Penicillium strains isolated from bivalve molluscs produce extracts exhibiting a higher cytotoxicity than extracts from Penicillium strains isolated from the surrounding marine environment. The use of a mussel-based medium for cultures of some shellfish-derived strains enhances the cytotoxicity of extracts when compared with classical media. The production of cytotoxic compounds and of the mycotoxin patulin on such a host-derived medium highlights a potential health risk for shellfish consumers. AbstractIn order to assess the putative toxigenic risk associated with the presence of fungal strains in shellfish-farming areas, Penicillium strains were isolated from bivalve molluscs and from the surrounding environment, and the influence of the sample origin on the cytotoxicity of the extracts was evaluated. Extracts obtained from shellfish-derived Penicillia exhibited higher cytotoxicity than the others. Ten of these strains were grown on various media including a medium based on mussel extract (Mytilus edulis), mussel flesh-based medium (MES), to study the influence of the mussel flesh on the production of cytotoxic compounds. The MES host-derived medium was created substituting the yeast extract of YES medium by an aqueous extract of mussel tissues, with other constituent identical to YES medium. When shellfish-derived strains of fungi were grown on MES medium, extracts were found to be more cytotoxic than on the YES medium for some of the strains. HPLC-UV/DAD-MS/MS dereplication of extracts from Penicillium marinum and P. restrictum strains grown on MES medium showed the enhancement of the production of some cytotoxic compounds. The mycotoxin patulin was detected in some P. antarcticum extracts, and its presence seemed to be related to their cytotoxicity. Thus, the enhancement of the toxicity of extracts obtained from shellfish-derived Penicillium strains grown on a host-derived medium, and the production of metabolites such as patulin suggests that a survey of mycotoxins in edible shellfish should be considered.

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“…Paecilomyces niveus and Penicillium paneum can grow in substrates with a high concentration of acetic acid and thus can also be found in silage, and may produce patulin there (Gallo et al, 2015;O'Brien et al, 2006;Scurti et al, 1973). P. antarcticum is a marine-derived Penicillium species and may produce patulin on seaweed or even in shellfish (Geiger et al, 2013;Vansteelandt et al, 2012). Penicillium marinum is also marine-derived and may produce patulin in the same seaborne organisms .…”

Section: Penicillium Miczynskiimentioning

confidence: 99%

A critical review of producers of small lactone mycotoxins: patulin, penicillic acid and moniliformin

Frisvad

2018

WMJ

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A very large number of filamentous fungi has been reported to produce the small lactone mycotoxins patulin, penicillic acid and moniliformin. Among the 167 reported fungal producers of patulin, only production by 29 species could be confirmed. Patulin is produced by 3 Aspergillus species, 3 Paecilomyces species, 22 Penicillium species from 7 sections of Penicillium, and one Xylaria species. Among 101 reported producers of penicillic acid, 48 species could produce this mycotoxin. Penicillic acid is produced by 23 species in section Aspergillus subgenus Circumdati section Circumdati, by Malbranchea aurantiaca and by 24 Penicillium species from 9 sections in Penicillium and one species that does not actually belong to Penicillium (P. megasporum). Among 40 reported producers of moniliformin, five species have been regarded as doubtful producers of this mycotoxin or are now regarded as taxonomic synonyms. Moniliformin is produced by 34 Fusarium species and one Penicillium species. All the accepted producers of patulin, penicillic acid and moniliformin were revised according to the new one fungus – one name nomenclatural system, and the most recently accepted taxonomy of the species.

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Patulin and secondary metabolite production by marine-derived Penicillium strains

Cited by 51 publications

References 44 publications

Accurate Dereplication of Bioactive Secondary Metabolites from Marine-Derived Fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library

Accurate Dereplication of Bioactive Secondary Metabolites from Marine-Derived Fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library

Cytotoxicity and mycotoxin production of shellfish-derived Penicillium spp., a risk for shellfish consumers

A critical review of producers of small lactone mycotoxins: patulin, penicillic acid and moniliformin

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