Mutagenicity of islandicin and chrysophanol in the Salmonella/microsome system

The mutagenicity of senna glycosides and extracts of senna folium and senna fructus was investigated in the Salmonella typhimurium reversion assay. Senna glycosides were inactive in all strains, except for a slight, but significant increase in mutant frequency in TA102 in the absence and presence of liver microsomes. Extracts of senna fructus and senna folium demonstrated weak activity in TA97a, TA100 and TA102 in the presence of liver microsomes, and in TA97a and TA102 in the absence of liver microsomes. A strong increase in mutant frequency (3- to 5-fold above background frequency) was observed with all extracts in TA98 in the presence of liver microsomes. This activity increased further following enzymatic hydrolysis with hesperidinase of extracts of senna fructus from one source, and could be correlated to the release of the flavonol aglycones kaempferol and quercetin. The weak or lacking activity of anthraquinone aglycones in the tested strains of Salmonella typhimurium indicates that mutagenicity can not be attributed solely to the anthraquinone content of these plant materials. The chemical nature of other mutagenic components has not been elucidated.

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“…5) was unexpected. In previous studies (Wehner et al 1979;Brown 1980;Liberman et al 1980;Tikkanen et al 1983;Westendorf et crl. 1990).…”

Section: Discussionmentioning

confidence: 93%

Mutagenicity of Crude Senna and Senna Glycosides in Salmonella typhimurium

Sandnes

Johansen

Teien

et al. 1992

Pharmacology & Toxicology

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“…(Mori et al, 1986;Wehner, Marasas, et al, 1978;Wehner, Thiel, et al, 1978;Wong et al, 1977;Xu, Whong, & Ong, 1984;Yourtee & Kirk-Yourtee, 1986) S. typhimurium SV50 ara + (Xu et al, 1984) E. coli PQ37 strains + (Auffray & Boutibonnes, 1987;Krivobok et al, 1987;Sakai et al, 1992) Rat and Mice Bone marrow + + (Corcuera et al, 2015;Madle et al, 1986) Rat and Mice Hepatocyte, Liver + + (Corcuera et al, 2015;Mirsalis, Tyson, & Butterworth, 1982;Mori et al, 1984) Mice Embrio - (Matthiaschk & Korte, 1986) Mice C3H,FM3A +? + (Umeda, Tsutsui, & Saito, 1977 (Fleck, Burkhardt, Pfeiffer, & Metzler, 2012;Fleck et al, 2016;Schrader et al, 2006) S. typhimurium LT2 strains + (Schrader et al, 2001(Schrader et al, , 2006 (Sakai et al, 1992) S. typhimurium LT2 strains + (Liberman et al, 1980;Tikkanen et al, 1983) S. typhimurium TM677,LT2 strains - (Stark et al, 1978) Human Lung A549 + (Ni et al, 2014) Rat and Mice Hepatocyte - (Mori et al, 1984) Mice Lymphoma L5178Y --- (Mueller et al, 1999 (Auffray & Boutibonnes, 1987;…”

Section: Resultsmentioning

confidence: 99%

Genotoxic and mutagenic effects of mycotoxins: a review

Aydın¹,

Rencüzoğulları²

2019

Commagene Journal of Biology

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In this article, genotoxic and mutagenic effects of mycotoxins that are produced by various fungus species have been reviewed. A total of 259 mycotoxins were found in the literature. Genotoxic effects of 109 of these were investigated. Among the studied mycotoxins, only actinomycin D, aflatoxin, alternariol, chrysazin (dantron), citrinin, fumonisin, mytomycin C, nivalenol, ochratoxin A, patulin, sterigmatocystin, versicolorin A and B, vomitoxin, and zearalenone have sufficient number of studies that present or prove their genotoxic effects. Additional studies are required in order to determine whether other mycotoxins have any genotoxic effects. The current study provides valuable information regarding studied mycotoxins. Therefore, it may lead researchers for designing future mycotoxin-related studies that have never been studied.

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“…Talaromyces islandicus , formerly designated as Penicillium islandicum (Samson et al ., ), is a commonly found grain decaying mold and an important foodborne species in tropical regions (Frisvad and Thrane, ). T. islandicus produces more than 20 mainly polyene‐like or quinoid pigments (Yilmaz et al ., ) including skyrin, erythroskyrin and islandicin, some of which show pronounced hepatotoxicity (Cole et al ., ; Liberman et al ., ; Kawai et al ., ). Furthermore, T. islandicus is known to produce the halogenated peptide cyclochlorotine which is toxic and carcinogenic to liver cells of mice (Uraguchi et al ., ).…”

Section: Introductionmentioning

confidence: 96%

The cyclochlorotine mycotoxin is produced by the nonribosomal peptide synthetase CctN in Talaromyces islandicus (‘Penicillium islandicum’)

Schafhauser

Kirchner

Kulik

et al. 2016

Environmental Microbiology

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Talaromyces islandicus ('Penicillium islandicum') is a widespread foodborne mold that produces numerous secondary metabolites, among them potent mycotoxins belonging to different chemical classes. A notable metabolite is the hepatotoxic and carcinogenic pentapeptide cyclochlorotine that contains the unusual amino acids β-phenylalanine, 2-aminobutyrate and 3,4-dichloroproline. Although the chemical structure has been known for over five decades, nothing is known about the biosynthetic pathway of cyclochlorotine. Bioinformatic analysis of the recently sequenced genome of T. islandicus identified a wealth of gene clusters potentially coding for the synthesis of secondary metabolites. Here, we show by RNA interference-mediated gene silencing that a nonribosomal peptide synthetase, CctN, is responsible for the synthesis of cyclochlorotine. Moreover, we identified novel cyclochlorotine chemical variants, whose production also depended on cctN expression. Surprisingly, the halogenase required for cyclochlorotine biosynthesis is not encoded in the cct cluster. Nonetheless, our findings enabled us to propose a detailed model for cyclochlorotine biosynthesis. In addition, comparative genomics revealed that cct-like clusters are present in all of the sequenced Talaromyces strains indicating a high prevalence of cyclochlorotine production ability.

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Mutagenicity of islandicin and chrysophanol in the Salmonella/microsome system

Abstract: Chrysophanol and islandicin, two anthraquinones which are structurally related to emodin, were found to be frame-shift mutagens for Salmonella typhimurium strain TA 1537 after metabolic activation.

Cited by 29 publications

References 11 publications

Mutagenicity of Crude Senna and Senna Glycosides in Salmonella typhimurium

Mutagenicity of Crude Senna and Senna Glycosides in Salmonella typhimurium

Genotoxic and mutagenic effects of mycotoxins: a review

The cyclochlorotine mycotoxin is produced by the nonribosomal peptide synthetase CctN in Talaromyces islandicus (‘Penicillium islandicum’)

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