Roquefortine and isofumigaclavine A, metabolites fromPenicillium roqueforti

Scott, P. M.; Merrien, Marie-Annick; Polonsky, Judith

doi:10.1007/bf01937728

Cited by 139 publications

(78 citation statements)

References 10 publications

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“…The meleagrin and roquefortine groups, mainly isolated from Penicillium species, are biogenetically interrelated alkaloids [1][2][3][4][5][6][7] with promising biological properties, such as neurotoxic, 1 antibacterial, 8 cytochrome P450 inhibitory 9 and tubulin polymerization inhibitory activity. 10 We have previously reported on meleagrin B (5), a novel complex compound composed of a meleagrin alkaloid moiety and a rare diterpene moiety, from a deep ocean sediment-derived fungus Penicillium sp.…”

Section: Introductionmentioning

confidence: 99%

Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities

Feng

Zhao

et al. 2010

J Antibiot

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Four new alkaloids, including two new meleagrin analogs, meleagrin D (1) and E (2), and two new diketopiperazines, roquefortine H (3) and I (4), were isolated from a deep ocean sediment-derived fungus Penicillium sp. Meleagrin D (1) and E (2) possess unprecedented acetate-mevalonate-derived side chains on the imidazole moiety. These new meleagrins showed weak cytotoxicity against the A-549 cell line, whereas meleagrin B (5) and meleagrin (6), which were isolated previously from the same strain, induced HL-60 cell apoptosis or arrested the cell cycle through G 2 /M phase, respectively. The results indicate that the distinct substitutions on the imidazole ring significantly influence the cytotoxicity of the meleagrin alkaloids.

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Section: Introductionmentioning

confidence: 99%

Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities

Feng

Zhao

et al. 2010

J Antibiot

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“…Next to penicillins, secondary metabolites such as roquefortines and glandicolines were isolated from liquid cultures of P. chrysogenum, which show pharmaceutically interesting properties, such as neurotoxic (2), antimicrobial (3,4), and antitumor (5) activities. They are structurally closely related and arise from the roquefortine/meleagrin pathway, which contains a dimodular nonribosomal peptide synthetase flanked by six associated genes (6,7).…”

mentioning

confidence: 99%

Novel Key Metabolites Reveal Further Branching of the Roquefortine/Meleagrin Biosynthetic Pathway

Ries

Ali

Lankhorst

et al. 2013

Journal of Biological Chemistry

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Background:The fungal roquefortine/meleagrin gene cluster is a source of diverse bioactive molecules. Results: Novel metabolites of the roquefortine/meleagrin biosynthetic pathway were discovered, and synthetase genes were assigned to biosynthetic reactions. Conclusion: Distinctive unspecificity of modifying enzymes leads to excessive branching in the pathway, resulting in various intermediates and products. Significance: Metabolites from the roquefortine/meleagrin gene cluster have potential antimicrobial and chemotherapeutic application.

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“…6,12 Several reports attribute neurotoxic properties to roquefortine based on the work of Frayssinet and Frayssinet (cited by Scott et al, 1975). 15 The brief citation reported that intraperitoneal (IP) administration of 10 mg/kg of roquefortine caused muscle contractions and ataxia in mice. At higher doses (50-100 mg/kg) of roquefortine, prostration with intermittent seizures was reported.…”

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confidence: 99%

Using Roquefortine C as a Biomarker for Penitrem A Intoxication

Tiwary¹,

Puschner²,

Poppenga³

2009

J VET Diagn Invest

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Abstract. Penitrem A is a well-recognized tremorgenic mycotoxin produced by several Penicillium spp. However, most natural cases of penitrem A intoxication have been associated with Penicillium crustosum. Another Penicillium sp., Penicillium roqueforti, is used for the production of blue cheese and is found in silage and feeds. Penicillium roqueforti produces a mycotoxin, roquefortine C, which is also produced by P. crustosum. In contrast to a tremorgenic syndrome produced by penitrem A, roquefortine C toxicosis is characterized by a paralytic syndrome. Two cases of penitrem A intoxication in dogs are presented to investigate the use of roquefortine C as a biomarker for penitrem A exposure. The vomitus, serum, and urine were analyzed for roquefortine C and penitrem A. Results suggest that roquefortine C can be a sensitive biomarker for penitrem A intoxication. However, the detection of roquefortine C in the absence of penitrem A could merely suggest ingestion of blue cheese or spoilt silage or feed. A review of the literature did not identify any case positive for penitrem A but negative for roquefortine C. In cases in which both mycotoxins were detected, roquefortine C concentration was always higher than penitrem A concentration. In contrast, several cases have been described where the clinical history suggested penitrem A intoxication, but only roquefortine C was detected. In conclusion, roquefortine C can serve as a sensitive biomarker for penitrem A intoxication, but the clinical presentation needs to be considered for proper interpretation of its detection in the absence of penitrem A.

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Roquefortine and isofumigaclavine A, metabolites fromPenicillium roqueforti

Cited by 139 publications

References 10 publications

Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities

Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities

Novel Key Metabolites Reveal Further Branching of the Roquefortine/Meleagrin Biosynthetic Pathway

Using Roquefortine C as a Biomarker for Penitrem A Intoxication

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