The structure of rubratoxin a, a toxic metabolite of penicillium rubrum

Moss, Maurice O.; Wood, A. B.; Robinson, Francis

doi:10.1016/s0040-4039(01)87693-0

Cited by 31 publications

(9 citation statements)

References 3 publications

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“…Rubratoxins are common mycotoxins of Penicillium sp. [52,53] with specific protein phosphatase A2 inhibitory and anticancer/antimetastasis activities [54]. Rubratoxins A ( 18 , m / z [M + H] + 521.1890) and B ( 17 , m / z [M + H] + 519.1832) were only annotated in the toxic PDM-L and Cza-L extracts of strain 50 ( Penicillium sp.)…”

Section: Discussionmentioning

confidence: 99%

Influence of OSMAC-Based Cultivation in Metabolome and Anticancer Activity of Fungi Associated with the Brown Alga Fucus vesiculosus

et al. 2019

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The fungi associated with marine algae are prolific sources of metabolites with high chemical diversity and bioactivity. In this study, we investigated culture-dependent fungal communities associated with the Baltic seaweed Fucus vesiculosus. Altogether, 55 epiphytic and endophytic fungi were isolated and identified. Twenty-six strains were selected for a small-scale One-Strain-Many-Compounds (OSMAC)-based fermentation in four media under solid and liquid culture regimes. In total, 208 fungal EtOAc extracts were tested for anticancer activity and general cytotoxicity. Ten most active strains (i.e., 80 extracts) were analyzed for their metabolome by molecular networking (MN), in-silico MS/MS fragmentation analysis (ISDB–UNPD), and manual dereplication. Thirty-six metabolites belonging to 25 chemical families were putatively annotated. The MN clearly distinguished the impact of culture conditions in chemical inventory and anticancer activity of the fungal extracts that was often associated with general toxicity. The bioactivity data were further mapped into MN to seek metabolites exclusively expressed in the active extracts. This is the first report of cultivable fungi associated with the Baltic F. vesiculosus that combined an OSMAC and an integrated MN-based untargeted metabolomics approaches for efficient assessment and visualization of the impact of the culture conditions on chemical space and anticancer potential of the fungi.

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Section: Discussionmentioning

confidence: 99%

Influence of OSMAC-Based Cultivation in Metabolome and Anticancer Activity of Fungi Associated with the Brown Alga Fucus vesiculosus

et al. 2019

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“…Factors such as age, race, gender, overall health and underlying liver problems may also influence a person's risk of developing liver problems and the severity of the symptoms. The hepatotoxic substance from the cultures of P. rubrum produced toxic hepatitis and body hemorrhages in white mice, guinea pigs, rabbits, and dogs [173,174]. Neubert and Merker [175] described several biochemical and histological observations in hepatic cells of rats injected with this material.…”

Section: Natural Productsmentioning

confidence: 99%

Clinical Biochemistry of Hepatotoxicity

Sharma¹

2014

J Clinic Toxicol

103

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Liver plays a central role in the metabolism and excretion of xenobiotics which makes it highly susceptible to their adverse and toxic effects. Liver injury caused by various toxic chemicals or their reactive metabolites [hepatotoxicants) is known as hepatotoxicity. The present review describes the biotransformation of hepatotoxicants and various models used to study hepatotoxicity. It provides an overview of pathological and biochemical mechanism involved during hepatotoxicity together with alteration of clinical biochemistry during liver injury. The review has been supported by a list of important hepatotoxicants as well as common hepatoprotective herbs.

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“…However, bioassays showed that the yellow pigments, mitorubrin and mitorubrinol, in P. rubrum did not cause any toxicity in mice [ 59 ], implying that they were non-toxic compounds. The toxicity agent in P. rubrum was later confirmed to be rubratoxin B in 1968 [ 60 , 61 ]. After the discovery of mitorubrin and its derivatives, these pigments were gradually found as the main yellow colorants in the ascomata of Talaromyces species, including T. austrocalifornicus , T. convolutes , T. emodensis , T. hachijoensis and T. wortmannii var.…”

Section: Pigments and Toxins In P Marneffeimentioning

confidence: 99%

Polyketides, Toxins and Pigments in Penicillium marneffei

Tam

Tsang

Lau

et al. 2015

Toxins

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Penicillium marneffei (synonym: Talaromyces marneffei) is the most important pathogenic thermally dimorphic fungus in China and Southeastern Asia. The HIV/AIDS pandemic, particularly in China and other Southeast Asian countries, has led to the emergence of P. marneffei infection as an important AIDS-defining condition. Recently, we published the genome sequence of P. marneffei. In the P. marneffei genome, 23 polyketide synthase genes and two polyketide synthase-non-ribosomal peptide synthase hybrid genes were identified. This number is much higher than those of Coccidioides immitis and Histoplasma capsulatum, important pathogenic thermally dimorphic fungi in the Western world. Phylogenetically, these polyketide synthase genes were distributed evenly with their counterparts found in Aspergillus species and other fungi, suggesting that polyketide synthases in P. marneffei did not diverge from lineage-specific gene duplication through a recent expansion. Gene knockdown experiments and ultra-high performance liquid chromatography-photodiode array detector/electrospray ionization-quadruple time of flight-mass spectrometry analysis confirmed that at least four of the polyketide synthase genes were involved in the biosynthesis of various pigments in P. marneffei, including melanin, mitorubrinic acid, mitorubrinol, monascorubrin, rubropunctatin, citrinin and ankaflavin, some of which were mycotoxins and virulence factors of the fungus.

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The structure of rubratoxin a, a toxic metabolite of penicillium rubrum

Cited by 31 publications

References 3 publications

Influence of OSMAC-Based Cultivation in Metabolome and Anticancer Activity of Fungi Associated with the Brown Alga Fucus vesiculosus

Influence of OSMAC-Based Cultivation in Metabolome and Anticancer Activity of Fungi Associated with the Brown Alga Fucus vesiculosus

Clinical Biochemistry of Hepatotoxicity

Polyketides, Toxins and Pigments in Penicillium marneffei

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