Effects of antioxidants on metabolism of aromatic polycyclic hydrocarbons

Wattenberg, Lee W.; Speier, Jennine L.; Kotake, Alvin N.

doi:10.1016/0065-2571(76)90020-0

Cited by 15 publications

(4 citation statements)

References 20 publications

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“…A number of phenolic antioxidants, some of which are commonly used as food additives (e.g., 2(3)-tert-butyl-4-hydroxyanisole (BHA), 3,5-di-tert-butyl-4-hydroxytoluene (BHT)) have been shown to protect against carcinogenesis and mutagenesis. [35][36][37][38][39] The relationship between their antioxidant properties and their ability to serve as chemoprotective agents is probably not a coincidence, since free radical-mediated processes are believed to be associated with the occurrence of many human diseases, including cancer. 40 This prompted us to examine the free radical-scavenging capacity of several quinone reductase inducers obtained in the course of this study.…”

Section: Introductionmentioning

confidence: 99%

Chemoprotective Properties of Phenylpropenoids, Bis(benzylidene)cycloalkanones, and Related Michael Reaction Acceptors: Correlation of Potencies as Phase 2 Enzyme Inducers and Radical Scavengers

1998

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Induction of phase 2 enzymes (e.g., glutathione transferases, NAD(P)H:quinone reductase, glucuronosyltransferases, epoxide hydrolase) is a major strategy for reducing the susceptibility of animal cells to neoplasia and other forms of electrophile toxicity. In a search for new chemoprotective enzyme inducers, a structure-activity analysis was carried out on two types of naturally occurring and synthetic substituted phenylpropenoids: (a) Ar-CH=CH-CO-R, where R is OH, OCH3, CH3, or Ar, including cinnamic, coumaric, ferulic, and sinapic acid derivatives, their ketone analogues, and chalcones; and (b) bis(benzylidene)cycloalkanones, Ar-CH=C(CH2)n(CO)C=CH-Ar, where n = 5, 6, or 7. The potencies of these compounds in inducing NAD(P)H:quinone reductase activity in murine hepatoma cells paralleled their Michael reaction acceptor activity (Talalay, P.; De Long, M. J.; Prochaska, H. J. Proc. Natl. Acad. Sci. U.S.A. 85, 1988, 8261-8265). Unexpectedly, the bis(benzylidene)cycloalkanones also powerfully quenched the lucigenin-derived chemiluminescence evoked by superoxide radicals. Introduction of o-hydroxyl groups on the aromatic rings of these phenylpropenoids dramatically enhanced their potencies not only as inducers for quinone reductase but also as quenchers of superoxide. These potentiating o-hydroxyl groups are hydrogen-bonded, as shown by moderate downfield shift of their proton NMR resonances and their sensitivities to the solvent environment. The finding that the potencies of a series of bis(benzylidene)cycloalkanones in inducing quinone reductase appear to be correlated with their ability to quench superoxide radicals suggests that the regulation of phase 2 enzymes may involve both Michael reaction reactivity and radical quenching mechanisms.

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Section: Introductionmentioning

confidence: 99%

Chemoprotective Properties of Phenylpropenoids, Bis(benzylidene)cycloalkanones, and Related Michael Reaction Acceptors: Correlation of Potencies as Phase 2 Enzyme Inducers and Radical Scavengers

1998

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“…Indeed, novel anticarcinogens have been isolated and identified solely on the basis of their ability to induce phase II enzymes(50,51). (ii) Such anticarcinogens alter the metabolism of carcinogens and decrease the formation of mutagenic metabolites(52)(53)(54). [QR; NAD(P)H:(quinone-acceptor) oxidoreductase, EC 1.6.99.2], UDP-glucuronosyltransferases, protect against the toxicities of electrophiles such as ultimate carcinogens.…”

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confidence: 99%

Rapid Detection of Inducers of Enzymes That Protect Against Carcinogens

Prochaska

Santamaria

Talalay

2005

Food and Cancer Prevention

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“…On the other hand a number of phenolic antioxidants have been shown to protect against carcinogenesis and mutagenesis. 1 The relationship between their antioxidant properties and their ability to serve as chemoprotective agents have been linked because free radical-mediated processes are believed to be associated with the occurrence of many human diseases, including cancer. 2 The electrochemistry of chalcones was initiated in the early 70's (3).…”

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confidence: 99%