DNA Breakage by Phenyl Compounds

Yamaguchi, Koji; Shirahata, Sanetaka; Murakami, Hiroki; Nishiyama, Kazuo; Shinohara, Kazuki; Ômura, Hirohisa

doi:10.1080/00021369.1985.10866902

Cited by 16 publications

(16 citation statements)

References 3 publications

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“…In addition, it has been reported that o-diphenols such as epinephrine are incorporated into rat fetal lung cells and induce cellular DNA breakage through their binding to chromosomal DNA (25). On the other hand, a earboxylated o-diphenol compound, 3-(3,4-dihydroxyphenyl)-alanine, could not break cellular DNA, though it exerted prominent DNA breaking activity in vitro (26). The addition of the highly hydrophilic carboxyl group to phenolic compounds may decrease membrane permeability of the compounds.…”

Section: Discussionmentioning

confidence: 97%

Structure-activity relationship of polyphenols on inhibition of chemical mediator release from rat peritoneal exudate cells

Yamada

Shoji

Mori

et al. 1999

In Vitro Cell.Dev.Biol.-Animal

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The effect of phenolic compounds in foodstuffs on histamine and leukotriene B4 (LTB4) release from rat peritoneal exudate cells and their antioxidative activity were examined to assess their antiallergenic activities. Among them, triphenols such as pyrogallol and gallic acid inhibited histamine release from the cells, but diphenols did not. On the other hand, o- and p-diphenols such as catechol and hydroquinone with strong antioxidative activity inhibited LTB4 release as strongly as pyrogallol, but an m-derivative resorcinol with weak antioxidative activity did not. Though carboxylated compounds and their noncarboxylated counterparts were antioxidative, the former exerted a much weaker inhibitory effect on the LTB4 release than the latter. In flavonols, only myricetin with a triphenolic B ring strongly inhibited histamine release, but all flavonols strongly suppressed LTB4 release irrespective of the number of OH groups in the B ring. Among flavonoids with an o-diphenolic B ring, flavonol and flavone with a C4-carbonyl group strongly inhibited LTB4 release, whereas the activity of anthocyan without C4-carbonyl was much weaker than the above compounds. These results suggest that triphenolic structure is essential for the inhibition of histamine release. On the other hand, antioxidative activity and membrane permeability of phenolic compounds seemed to be essential for the inhibition of LTB4 release. In addition, the C4-carbonyl group seemed to be important for strongly inhibiting LTB4 release.

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Section: Discussionmentioning

confidence: 97%

Structure-activity relationship of polyphenols on inhibition of chemical mediator release from rat peritoneal exudate cells

Yamada

Shoji

Mori

et al. 1999

In Vitro Cell.Dev.Biol.-Animal

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“…DNA is a polyanion and its structure consists of two helical DNA chains coiled around the same axis to form a right-handed double helix. The interactions between DNA and small molecules, like dopamine (DA), often result from combinations of several kinds of binding forces and are important to understand the role of those molecules in important events like DNA breakage [1] and apoptosis in human neuronal cells [2,3]. In order to better understand the process of DNA binding in different surfaces, and the role of experimental parameters on the mechanism of DNA adsorption and release on surfaces, more information is needed.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of DNA films using oleylamine modified Au surfaces

Borges

Ribeiro

Pereira

et al. 2011

Journal of Colloid and Interface Science

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“…DNA-breakage by phenolic compounds, including trihydroxyphenols and flavonoids, is widely reported, although the literature emphasized in vitro studies of purified reaction components and the generation of reactive oxygen species (Kawanishi et al, 1989; Kim et al, 2008; Lee et al, 1995; Said Ahmad et al, 1992; Yamada et al, 1985). Pyrogallol is also reported to induce mutations in some strains of Salmonella (NTP, 2012), to induce chromosomal aberrations in CHO cells (Stich et al, 1981), cultured human lymphocytes (NIEHS, 1998), and bone marrow cells in vivo in mice (NIEHS, 1998), to induce micronuclei and sister chromatid exchanges in V79 cells (Glatt et al, 1989), to induce mutations in L5178Y mouse lymphoma cells (NIEHS, 1998), and to increase the frequency of micronucleated polychromatic erythrocytes in mice (Gocke et al, 1981).…”

Section: Discussionmentioning

confidence: 99%

Biological clues to potent DNA-damaging activities in food and flavoring

Hossain

Gilbert

Patel

et al. 2013

Food and Chemical Toxicology

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Population differences in age-related diseases and cancer could stem from differences in diet. To characterize DNA strand-breaking activities in selected foods/beverages, flavorings, and some of their constituent chemicals, we used p53R cells, a cellular assay sensitive to such breaks. Substances testing positive included reference chemicals: quinacrine (peak response, 51X) and etoposide (33X); flavonoids: EGCG (19X), curcumin (12X), apigenin (9X), and quercetin (7X); beverages: chamomile (11X), green (21X), and black tea (26X) and coffee (3 to 29X); and liquid smoke (4 to 28X). Damage occurred at dietary concentrations: etoposide near 5 μg/ml produced responses similar to a 1:1000 dilution of liquid smoke, a 1:20 dilution of coffee, and a 1:5 dilution of tea. Pyrogallol-related chemicals and tannins are present in dietary sources and individually produced strong activity: pyrogallol (30X), 3-methoxycatechol (25X), gallic acid (21X), and 1,2,4-benzenetriol (21X). From structure-activity relationships, high activities depended on specific orientations of hydroxyls on the benzene ring. Responses accompanied cellular signals characteristic of DNA breaks such as H2AX phosphorylation. Breaks were also directly detected by comet assay. Cellular toxicological effects of foods and flavorings could guide epidemiologic and experimental studies of potential disease risks from DNA strand-breaking chemicals in diets.

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DNA Breakage by Phenyl Compounds

Cited by 16 publications

References 3 publications

Structure-activity relationship of polyphenols on inhibition of chemical mediator release from rat peritoneal exudate cells

Structure-activity relationship of polyphenols on inhibition of chemical mediator release from rat peritoneal exudate cells

Preparation and characterization of DNA films using oleylamine modified Au surfaces

Biological clues to potent DNA-damaging activities in food and flavoring

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