The mutagenicities of safrole, estragole, eugenol, trans-anethole, and some of their known or possible metabolites for Salmonella typhimurium mutants

Swanson, Anne; Chambliss, Diane D.; Blomquist, Judith C.; Miller, Elizabeth C.; Miller, James A.

doi:10.1016/0027-5107(79)90178-7

Cited by 115 publications

(41 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Eugenol also induces UDS in SHE cells in the presence of exogenous metabolic activation (5). Although eugenol is negative in the Salmonella mutagenicity tests with or without exogenous metabolic activation (13), its metabolite, eugenol-2',3'-oxide is positive in the tests (15). In the present study, eugenol exhibited clastogenic activity in SHE cells that was enhanced in the presence of exogenous metabolic activation.…”

Section: Discussionmentioning

confidence: 41%

Ability of Fourteen Chemical Agents Used in Dental Practice to Induce Chromosome Aberrations in Syrian Hamster Embryo Cells

et al. 2005

View full text Add to dashboard Cite

Abstract. To assess the genotoxicity of 14 chemical agents used in dental practice, the ability of these agents to induce chromosome aberrations was examined using Syrian hamster embryo (SHE) cells. Statistically significant increases in the frequencies of chromosome aberrations were induced in SHE cells treated with 7 of 10 chemical agents used as endodontic medicaments, that is, carbol camphor, m-cresol, eugenol, guaiacol, zinc oxide, hydrogen peroxide, and formaldehyde. The other 3 chemical agents, that is, thymol, glutaraldehyde, and iodoform, did not increase the levels of chromosome aberrations. Of the 4 chemical agents that are used as an antiseptic on the oral mucosa, chromosome aberrations were induced by iodine, but not by the other 3 antiseptics, benzalkonium chloride, benzethonium chloride, and chlorhexidine. Among the 6 chemical agents exhibiting a negative response in the assay, only thymol induced chromosome aberrations in the presence of exogenous metabolic activation. Our results indicate that chemical agents having a positive response in the present study are potentially genotoxic to mammalian cells and need to be studied further in detail.

show abstract

Section: Discussionmentioning

confidence: 41%

Ability of Fourteen Chemical Agents Used in Dental Practice to Induce Chromosome Aberrations in Syrian Hamster Embryo Cells

et al. 2005

View full text Add to dashboard Cite

show abstract

“…EUG was not mutagenic to Salmonella typhimuri- um TA1964, TA1535, TA1532, TA1531, TA1530, TA100 and TA98 with or without metabolic activation Dorange et al, 1977;Green and Savage, 1978;Swanson et al, 1979;Eder et al, 1980), and not mutagenic to Escherichia coli WP2 uvrA with or without metabolic activation (Sekizawa and Shibamoto, 1982). However, EUG induced chromosomal aberrations in Chinese hamster ovary cells with or without metabolic activation (Stich et al, 1981;NTP, 1983).…”

Section: Discussionmentioning

confidence: 99%

Lack of modifying effects of eugenol on development of lung proliferative lesions induced by urethane in transgenic mice carrying the human prototype c-Ha-ras gene.

et al. 2001

View full text Add to dashboard Cite

To investigate the modifying effects of eugenol (EUG), a component of cigarette smoke, on lung carcinogenesis, male and female transgenic mice carrying the human prototype c-Ha-ras gene (rasH2 mice) were given a single intraperitoneal injection of 250 mg/kg urethane (UR) or saline, followed by a diet containing 6,000 ppm EUG or basal diet for 26 weeks. Their non-transgenic CB6F1 littermates (non-Tg mice) were also treated in the same manner. In both male and female rasH2 mice, alveolar/bronchiolar hyperplasias, adenomas and carcinomas were observed in all UR-treated groups. However, there were no significant intergroup differences in the incidences and multiplicities of these lesions between the UR alone and UR EUG groups. In non-Tg mice, alveolar/bronchiolar hyperplasias, adenomas or carcinomas were sporadically observed in UR-treated groups of both sexes, with no significant differences in the incidences and multiplicities between the UR alone and UR EUG groups. There were no intergroup differences between them in the PCNA-positive ratios of adenomas or carcinomas and the areas of adenomas or carcinomas to the whole lung area examined. The present results suggest that the EUG treatment does not exert modifying effects on lung carcinogenesis induced by UR in both male and female rasH2 mice and non-Tg mice.

show abstract

“…Many of these essential oil components play a role in the plant defense system and, despite their poor solubility, are extremely toxic for microorganisms (2)(3)(4)(5). Phenylpropenoides can potentially serve as a good source of starting material for the production of aromatic aldehydes for flavorings and aromas.…”

mentioning

confidence: 99%

The trans-Anethole Degradation Pathway in an Arthrobacter sp.

Shimoni

Baasov

Ravid

et al. 2002

Journal of Biological Chemistry

View full text Add to dashboard Cite

A bacterial strain (TA13) capable of utilizing t-anethole as the sole carbon source was isolated from soil. The strain was identified as Arthrobacter aurescens based on its 16 S rRNA gene sequence. Key steps of the degradation pathway of t-anethole were identified by the use of t-anethole-blocked mutants and specific inducible enzymatic activities. In addition to t-anethole, strain TA13 is capable of utilizing anisic acid, anisaldehyde, and anisic alcohol as the sole carbon source. t-Anethole-blocked mutants were obtained following mutagenesis and penicillin enrichment. Some of these blocked mutants, accumulated in the presence of t-anethole quantitative amounts of tanethole-diol, anisic acid, and 4,6-dicarboxy-2-pyrone and traces of anisic alcohol and anisaldehyde. Enzymatic activities induced by t-anethole included: 4-methoxybenzoate O-demethylase, p-hydroxybenzoate 3-hydroxylase, and protocatechuate-4,5-dioxygenase. These findings indicate that t-anethole is metabolized to protocatechuic acid through t-anethole-diol, anisaldehyde, anisic acid, and p-hydroxybenzoic acid. The protocatechuic acid is then cleaved by protocatechuate-4,5-dioxygenase to yield 2-hydroxy-4-carboxy muconate-semialdehyde. Results from inducible uptake ability and enzymatic assays indicate that at least three regulatory units are involved in the t-anethole degradation pathway. These findings provide new routes for environmental friendly production processes of valuable aromatic chemicals via bioconversion of phenylpropenoids.

show abstract

The mutagenicities of safrole, estragole, eugenol, trans-anethole, and some of their known or possible metabolites for Salmonella typhimurium mutants

Cited by 115 publications

References 10 publications

Ability of Fourteen Chemical Agents Used in Dental Practice to Induce Chromosome Aberrations in Syrian Hamster Embryo Cells

Ability of Fourteen Chemical Agents Used in Dental Practice to Induce Chromosome Aberrations in Syrian Hamster Embryo Cells

Lack of modifying effects of eugenol on development of lung proliferative lesions induced by urethane in transgenic mice carrying the human prototype c-Ha-ras gene.

The trans-Anethole Degradation Pathway in an Arthrobacter sp.

Contact Info

Product

Resources

About