Mutagenicity of a furocoumarin epoxide, heraclenin, in Chlamydomonas reinhardii

Schimmer, Oskar; Abel, G.

doi:10.1016/0165-1218(86)90017-0

Cited by 8 publications

(1 citation statement)

References 9 publications

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“…5-MOP and 8-MOP were reported to form noncovalent DNA complexes in the dark , , which, upon UVA radiation, bind covalently − and can form interstrand cross-links . In bacterial or yeast mutagenicity tests, a number of furocoumarins were shown to be weakly or not mutagenic in the absence of light but exhibited strong mutagenicity when combined with UVA light ,− . In mammalian cells, some studies report on a weak mutagenicity of furocoumarins in the absence of light − .…”

Section: Discussionmentioning

confidence: 99%

Relative Photomutagenicity of Furocoumarins and Limettin in the Hypoxanthine Phosphoribosyl Transferase Assay in V79 Cells

Raquet

Schrenk

2009

Chem. Res. Toxicol.

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Furocoumarins are phototoxic and photomutagenic natural plant constituents found in many medicinal plants and food items. Because plants contain mixtures of several furocoumarins, there is a need for a comparative risk assessment of a large number of furocoumarins. Little is known about the photomutagenicity of the structurally related family of coumarins, which are also abundant in many plant species. In this study, we analyzed the photomutagenic potency of the linear furocoumarins 5-methoxypsoralen (5-MOP) and 8-methoxypsoralen (8-MOP), the angular furocoumarin angelicin, and the coumarin limettin. Above certain concentrations, all test compounds were more or less phototoxic in the presence of UVA doses between 50 and 200 mJ/cm(2), 5-MOP being the most phototoxic compound. At nonphototoxic concentrations, linear correlations were found between concentration and mutagenicity at a UVA dose of 125 mJ/cm(2) for all test compounds including limettin. For 5-MOP, strictly linear correlations were also found for the relationships of mutagenicity vs concentration at various UVA doses or vs UVA dose at given concentrations, respectively. These data indicate that the photomutagenicity of 5-MOP is proportional to the UVA dose x concentration product for noncytotoxic combinations of both factors. They also suggest that the slope of the concentration-photomutagenicity correlation at a given UVA dose may provide a basis for comparison between individual compounds. Applying this concept, in vitro photomutagenicity equivalency factors at 125 mJ/cm(2) were as follows: 1.0 (5-MOP, reference compound), 0.25 (8-MOP), and 0.02 (angelicin and limettin, respectively). These findings provide a new concept for the description of the relative photomutagenic potency of coumarins and furocoumarins and indicate that, in V79 cells, 8-MOP is less photomutagenic and limettin and angelicin are much less photomutagenic than 5-MOP.

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Section: Discussionmentioning

confidence: 99%

Relative Photomutagenicity of Furocoumarins and Limettin in the Hypoxanthine Phosphoribosyl Transferase Assay in V79 Cells

Raquet

Schrenk

2009

Chem. Res. Toxicol.

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Defense of parsnip webworm against phototoxic furanocoumarins: Role of antioxidant enzymes

Lee

Berenbaum

1990

J Chem Ecol

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The parsnip webworm,Depressaria pastinacella (Lepidoptera: Oecophoridae), feeds on plants rich in furanocoumarins, phototoxic allomones. Final-instar larvae possess high levels of activities of antioxidant enzymes (Superoxide dismutase, catalase, glutathione reductase), which detoxify oxygen radicals generated from the furanocoumarins of their host plants. When added to an artificial diet, three linear furanocoumarins (xanthotoxin, bergapten, imperatorin) do not increase levels of the antioxidant enzymes. However, on diets containing both xanthotoxin and piperonyl butoxide, a cytochrome P-450 inhibitor, food utilization indices of the insect are reduced and superoxide dismutase activity is enhanced. These data suggest that cytochrome P-450s act as a primary detoxification system of ingested furanocoumarin, and antioxidant enzymes as a backup system to detoxify oxygen radicals generated by unmetabolized furanocoumarins.

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Chromosome-damaging effects of heraclenin in human lymphocytes in vitro

Abel

Schimmer

1986

Mutation Research/Genetic Toxicology

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Mutagenicity of a furocoumarin epoxide, heraclenin, in Chlamydomonas reinhardii

Cited by 8 publications

References 9 publications

Relative Photomutagenicity of Furocoumarins and Limettin in the Hypoxanthine Phosphoribosyl Transferase Assay in V79 Cells

Relative Photomutagenicity of Furocoumarins and Limettin in the Hypoxanthine Phosphoribosyl Transferase Assay in V79 Cells

Defense of parsnip webworm against phototoxic furanocoumarins: Role of antioxidant enzymes

Chromosome-damaging effects of heraclenin in human lymphocytes in vitro

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