Genotoxicity of naturally occurring hydroxyanthraquinones

Westendorf, Johannes; Marquardt, H; Poginsky, B.; Dominiak, Marion; Schmidt, J.; Marquardt, Hans

doi:10.1016/0165-1218(90)90002-j

Cited by 173 publications

(100 citation statements)

References 15 publications

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“…More recently, an additional two-year carcinogenicity study conducted on male and female F344 (27) which were fed a diet containing 0, 2.5 or 5.0% of colouring compounds extracted from madder roots clearly indicate that this dyestuff-rich in alizarin, lucidin-3-O-primeveroside and ruberythric acid, all classified in the 'group E 3 ' of HAQN and synthesized via the chorismate/-succinylbenzoic acid pathway as mentioned above-exerts a carcinogenic potential in both the kidney and the liver, even with the lower dose of the study 113 . These studies support data in other previous studies 114,115 and provide clear evidence that madder colour exerts unequivocal carcinogenicity against renal tubule cells and hepatocytes in rats. Therefore, the authors 113 concluded that further studies on these individual HAQN components should be performed to clarify which anthraquinone is responsible for carcinogenicity.…”

Section: Kerriasupporting

confidence: 81%

Natural hydroxyanthraquinoid pigments as potent food grade colorants: an overview

Caro

Anamale

Fouillaud

et al. 2012

Nat. Prod. Bioprospect.

146

109

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Natural pigments and colorants are widely used in the world in many industries such as textile dying, food processing or cosmetic manufacturing. Among the natural products of interest are various compounds belonging to carotenoids, anthocyanins, chlorophylls, melanins, betalains… The review emphasizes pigments with anthraquinoid skeleton and gives an overview on hydroxyanthraquinoids described in Nature, the first one ever published. Trends in consumption, production and regulation of natural food grade colorants are given, in the current global market. The second part focuses on the description of the chemical structures of the main anthraquinoid colouring compounds, their properties and their biosynthetic pathways. Main natural sources of such pigments are summarized, followed by discussion about toxicity and carcinogenicity observed in some cases. As a conclusion, current industrial applications of natural hydroxyanthraquinoids are described with two examples, carminic acid from an insect and Arpink red™ from a filamentous fungus.

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Section: Kerriasupporting

confidence: 81%

Natural hydroxyanthraquinoid pigments as potent food grade colorants: an overview

Caro

Anamale

Fouillaud

et al. 2012

Nat. Prod. Bioprospect.

146

109

View full text Add to dashboard Cite

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“…About 90% of these compounds occur as derivatives of 9, 10-anthracenedione with several hydroxy and other functional groups such as methyl, hydroxy methyl or carboxyl side chain. Hydroxy anthraquinones are the active principles of many phyto-therapeutic drugs (Westendorf et al 1990).…”

mentioning

confidence: 99%

Evaluation of anti-genotoxicity of the leaf extracts of Morinda citrifolia Linn.

Sreeranjini¹,

Siril²

2011

Plant Soil Environ.

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Morinda citrifolia Linn. (family Rubiaceae) is a small tree occurring in tropical areas of the world. The plant contains several medicinally active components that exhibit the therapeutic effects such as antibacterial, antiviral and anticancer activities. Anti-genotoxic effects of aqueous extracts prepared using dried leaves of M. citrifolia was studied. Allium cepa root tip meristem cells treated with 7% hydrogen peroxide were used for eliciting antigenotoxicity. For this purpose experiments were performed with A. cepa onion bulbs treated for 24 h with different concentrations (15 or 30 g/L) of aqueous extract with or without pre-treatment (1 h) with 7% hydrogen peroxide. A significant reduction in mitotic index was recorded in treatment groups over negative control. Chromosomal aberrations such as breaks, bridges, stickiness and polar deviations were observed in positive control and treatment groups. The highest (21.48) percentage of chromosomal aberrations was noticed in positive control. A significant reduction in chromosomal aberrations (9.39) was recorded in root tips treated with hydrogen peroxide followed by 15 g/L extract. H 2 O 2 induced chromosomal aberrations were reduced due to leaf extract treatment indicates antimutagenic potential of the M. citrifolia. The observations suggest that M. citrifolia aqueous leaf extracts have antimitotic and anti-genotoxic effects; consequently oxidative stress induced aberrations due to H 2 O 2 are efficiently restored in the extract treated A. cepa root meristem cells.

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“…Induction of carcinomas by anthranoid laxatives have been demonstrated in animal studies (Mori et al, 1985) and mutagenic and genotoxic effects were described in bacterial strains (Westendorf et al, 1990;Brown and Brown, 1976). Mutations occurred predominantly in those strains sensitive to frame-shifting mutagens (Brown and Dietrich, 1979), which suggest that anthranoids might achieve DNA-damage probably by intercalation.…”

Section: Discussionmentioning

confidence: 95%

“…In addition, a single high-dose of sennosides was shown to induce an increase in proliferative activity of colonic epithelial cells (Kleibeuker et al, 1995), which is generally considered to be one of the first steps in colorectal carcinogenesis (Preston-Martin et al, 1990). Furthermore, several in vitro and animal studies have demonstrated mutagenic (Westendorf et al, 1990), genotoxic (Westendorf et al, 1990;Brown, 1980) and carcinogenic (Mori et al, 1985) effects of different anthranoid laxatives.…”

mentioning

confidence: 99%

Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1

et al. 2002

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Anthranoid laxatives, belonging to the anthraquinones as do anthracyclines, possibly increase colorectal cancer risk. Anthracyclines interfere with topoisomerase II, intercalate DNA and are substrates for P-glycoprotein and multidrug resistanceassociated protein 1. P-glycoprotein and multidrug resistance-associated protein 1 protect colonic epithelial cells against xenobiotics. The aim of this study was to analyse the interference of anthranoids with these natural defence mechanisms and the direct cytotoxicity of anthranoids in cancer cell lines expressing these mechanisms in varying combinations. A cytotoxicity profile of rhein, aloe emodin and danthron was established in related cell lines exhibiting different levels of topoisomerases, multidrug resistance-associated protein 1 and P-glycoprotein. Interaction of rhein with multidrug resistance-associated protein 1 was studied by carboxy fluorescein efflux and direct cytotoxicity by apoptosis induction. Rhein was less cytotoxic in the multidrug resistance-associated protein 1 overexpressing GLC4/ADR cell line compared to GLC4. Multidrug resistanceassociated protein 1 inhibition with MK571 increased rhein cytotoxicity. Carboxy fluorescein efflux was blocked by rhein. No P-glycoprotein dependent rhein efflux was observed, nor was topoisomerase II responsible for reduced toxicity. Rhein induced apoptosis but did not intercalate DNA. Aloe emodin and danthron were no substrates for MDR mechanisms. Rhein is a substrate for multidrug resistance-associated protein 1 and induces apoptosis. It could therefore render the colonic epithelium sensitive to cytotoxic agents, apart from being toxic in itself.

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Genotoxicity of naturally occurring hydroxyanthraquinones

Cited by 173 publications

References 15 publications

Natural hydroxyanthraquinoid pigments as potent food grade colorants: an overview

Natural hydroxyanthraquinoid pigments as potent food grade colorants: an overview

Evaluation of anti-genotoxicity of the leaf extracts of Morinda citrifolia Linn.

Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1

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