The beneficial and hazardous effects of simple phenolic compounds

doi:10.1016/0165-1218(91)90125-6

Mutation Research/Genetic Toxicology

Volume 259, Issues 3–4, March–April 1991, Pages 307-324

https://doi.org/10.1016/0165-1218(91)90125-6 Get rights and content

Abstract

The current emphasis on screening the environment for man-made genotoxic and carcinogenic compounds detracts from studies on the possible health hazard or beneficial effects of naturally occurring agents to which humans are exposed daily. The simple phenolics, which are ubiquitous among plants, used as food additives, and ingested daily in milligram quantities, belong to this category of compounds. They induce double-strand DNA breaks, DNA adducts, mutations and chromosome aberrations in a great variety of test systems. However, they can suppress the genotoxic activity of numerous carcinogenic compounds in both in vitro and in vivo assays. This dual function of dietary phenolics also becomes evident when their carcinogenic or anticarcinogenic potential is examined. Some, but not all, phenolics induce precancerous lesions, papillomas and cancers, act as cocarcinogens, and exert a promoting effect in various rodent assays. On the other hand, phenolics have proved to be potent inhibitors of carcinogenesis at the initiation and promotion stages induced by carcinogens and promoters of different molecular structures. The extent to which a health hazard or protective activity of complex dietary mixtures is due to their phenolic content remains an unresolved issue. In addition, these multiple, occasionally contradictory functions of simple phenolics make it difficult to propose their use as chemopreventive agents.

References (174)

K. Alexandrov et al.
Comparison of metabolism of benzo[a]pyrene and binding to DNA caused by rat liver nuclei and chromosomes
Chem.-Biol. Interact.
(1976)
H.-J. Altmann et al.
Effects of BHA and related phenols on the forestomach of rats
Food Chem. Toxicol.
(1986)
S. Banic
Vitamin C acts as a carcinogen to methylcholanthrene in guinea-pigs
Cancer Lett.
(1981)
H. Bartsch et al.
Inhibitors of endogenous nitrosation
R. Ben-Gurion
Mutagenic and colicine-inducing activity of two antioxidants: pyrogallol and purpurogallin
Mutation Res.
(1979)
M.H. Bilimoria
The detection of mutagenic activity of chemicals and tobacco smoke in a bacterial system (Abstr.)
Mutation Res.
(1975)
S.G. Carmella et al.
Quantitative analysis of catechol and 4-methylcatechol in human urine
Food Chem. Toxicol.
(1982)
R.I.M. Chan et al.
Mechanism of inhibition of N-methyl-N′-nitro-N-nitrosoguanidine-induced mutagenesis by phenolic compounds
Cancer Lett.
(1986)
A.J. Collings et al.
The BHT content of human adipose tissues
Food Cosmet. Toxicol.
(1970)
M. Das et al.
Plant phenols as in vitro inhibitors of glutathione S-transferase(s)
Biochem. Biophys. Res. Commun.
(1984)

B.J. Del Tito et al.

Inhibition of epidermal metabolism and DNA binding of benzo[a]pyrene by ellagic acid

Biochem. Biophys. Res. Commun.

(1983)

A.R. Francis et al.

Modification of the mutagenicity of aflatoxin B1 and N-methyl-N′-nitro-N-nitrosoguanidine by certain phenolic compounds

Cancer Lett.

(1989)

A.F. Hanham et al.

Clastogenic activity of caffeic acid and its relationship to hydrogen peroxide generated during autooxidation

Mutation Res.

(1983)

S. Heim et al.

Constitutional chromosome instability and cancer risk

Mutation Res.

(1989)

F. Iverson et al.

A 12-week study of BHA in the cynomolgus monkey

Food Chem. Toxicol.

(1986)

T. Kada et al.

Detection and chemical identification of natural bio-antimutagens

W.A. Khan et al.

inhibition of the skin tumorigenicity of (∼)-7b,8a-dihydroxy-9a,10a-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene by tannic acid, green tea polyphenols and quercetin in Sencar mice

Cancer Lett.

(1988)

K. Kikugawa et al.

Formation of a mutagenic diazoquinone by interaction of phenol with nitrite

Food Chem. Toxicol.

(1988)

D.C. Kirkpatrick et al.

Intake of phenolic antioxidants from foods in Canada

Food Chem. Toxicol.

(1986)

J.T. MacGregor et al.

Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typhimurium

Mutation Res.

(1978)

H. Mori et al.

Inhibitory effect of chlorogenic acid on methylazoxymethanol acetate induced carcinogenesis in large intestine and liver of hamsters

Cancer Lett.

(1986)

K. Morimoto et al.

Induction of sister-chromatid exchanges in human lymphocytes by microsomal activation of benzene metabolites

Mutation Res.

(1983)

H. Mukhtar et al.

Protection against 3-methylcholanthrene-induced skin tumorigenesis in BALB/C mice by ellagic acid

Biochem. Biophys. Res. Commun.

(1984)

M. Nagabhushan et al.

In vitro antimutagenicity of curcumin against environmental mutagens

Food Chem. Toxicol.

(1987)

E.A. Nera et al.

Short-term pathological and proliferative effects of butylated hydroxyanisole and other phenolic antioxidants in the forestomach of Fischer 344 rats

Toxicology

(1984)

E.R. Nestmann et al.

Mutagenicity of constituents identified in pulp and paper mill effluents using the Salmonella/mammalian-microsome assay

Mutation Res.

(1980)

H.-J. Altmann et al.

Induction of forestomach lesions by butylhydroxyanisole and structurally related substances

B.N. Ames

What are the major carcinogens in the etiology of human cancer?

B.N. Ames

Mutagenesis and carcinogenesis: endogenous and exogenous factors

Environ. Mol. Mutagen.

(1989)

M.W. Anderson et al.

Inhibition in vivo of the formation of adducts between metabolites of benzo[a]pyrene and DNA by butylated hydroxyanisole

Cancer Res.

(1981)

M.J. Arnaud

The metabolism of coffee constituents

M. Atchison et al.

Chemical cocarcinogenesis with the use of a subclone derived from Balb/3T3 cells with catechol as cocarcinogen

J. Natl. Cancer Inst.

(1982)

R.K. Bhattacharya et al.

Factors modulating the formation of DNA adducts by aflatoxin B1 in vitro

Carcinogenesis

(1984)

E. Cameron et al.

Ascorbic acid and cancer: a review

Cancer Res.

(1979)

B.C. Challis et al.

Possible cocarcinogenic effects of coffee constituents

Nature (London)

(1975)

R.L. Chang et al.

Effect of ellagic acid and hydroxylated flavonoids on the tumorigenicity of benzo[a]pyrene, and (∼)-7b,8a-dihydroxy-9a,10a-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene on mouse skin and in the newborn mouse

Carcinogenesis

(1985)

C.P. Crum et al.

Human papillomavirus type 16 and early cervical neoplasia

New Engl. J. Med.

(1984)

M. Das et al.

Effect of ellagic acid on hepatic and pulmonary xenobiotic metabolism in mice: studies on the mechanism of its anticarcinogenic action

Carcinogenesis

(1985)

M. Das et al.

Inhibition of epidermal xenobiotic metabolism in SENCAR mice by naturally occurring plant phenols

Cancer Res.

(1987)

M. Das et al.

inhibition of polycyclic aromatic hydrocarbon-DNA adduct formation in epidermis and lungs of SENCAR mice by naturally occurring plant phenols

Cancer Res.

(1987)

R. Dixit et al.

Inhibition of N-methyl-N-nitrosourea-induced mutagenicity and DNA methylation by ellagic acid

R. Dixit et al.

Inhibition of benzo[a]pyrene and benzo[a]pyrene-trans-7,8-diol metabolism and DNA binding in mouse lung explants by ellagic acid

Cancer Res.

(1985)

G.L. Erexson et al.

Sister chromatid exchange induction in human lymphocytes exposed to benzene and its metabolites in vitro

Cancer Res.

(1985)

FAO/WHO

Joint FAO/WHO Expert Committee on Food Additives

Y. Fukuhara et al.

Reduction of mutagenic products in the presence of polyphenols using pyrolysis of proteins

Agric. Biol. Chem.

(1981)

S. Fukushima et al.

Promoting effects of sodium l-ascorbate on two-stage urinary bladder carcinogenesis in rats

Cancer Res.

(1983)

S.S. Hecht et al.

A study of tobacco carcinogenesis

K. Herrmann

Review on nonessential constituents of vegetables

M.J. Hill

Microbes and Human Carcinogenesis

(1986)

T. Hirayama

Epidemiological evaluation of the role of naturally occurring carcinogens and modulators of carcinogenesis

Cited by (173)

A Z-scheme photocatalysis for phenol eradication from water using peroxymonosulfate activation Ag/AgBr/SCN nanocomposite
2023, Journal of the Taiwan Institute of Chemical Engineers
The present work was mainly focused on construction of direct Z-scheme Ag/AgBr/SCN heterostructure and their photocatalytic ability to removal of phenol using synthesized photocatalysts. Ag/AgBr/SCN photocatalyst was prepared via facile deposition-precipitation method while bare g-C₃N₄ (GCN) and SCN (sulphur doped g-C₃N₄) were prepared via simple thermal-polycondensation method.
The Ag/AgBr/SCN Z-scheme heterostructure was fabricated by integration of 2D SCN with AgBr. Doping of sulphur in GCN structure has incremented the light absorption ability of GCN via reducing the energy gap to 2.64 eV from 2.7 eV. Different spectroscopic and analytical techniques have confirmed the successful formation of photocatalysts.
The addition of PMS during the photocatalytic experiment has enhanced the removal efficiency of photocatalysts due to more ^•OH and ^•SO₄⁻radicals generation. It was observed from the results that PMS assisted Ag/AgBr/SCN photocatalytic material exhibited highest removal efficiency i.e. 99% compared to other bare photocatalysts within 80 min of visible-light exposure. Proposed mechanism validated the Z-scheme charge transfer route in Ag/AgBr/SCN in accord to apt band alignment in SCN and AgBr. However, Ag metal acted as an electron mediator to just transfer the electron from CB of SCN to CB of AgBr. The transference of electron from sulphur doped g-C3N4 to AgBr through Ag improved electron transportation. This ultimately enhanced charge separation rate and reduced the charge recombination rate in Ag/AgBr/SCN nanocomposite. The proposed mechanism also presented that ^•OH, SO₄^•− and ^•O₂⁻ radicals were the primary reactive species during Ag/AgBr/SCN/PMS assisted photocatalytic phenol degradation process (verified through scavenging tests). Finally, the recyclability experiment confirmed the stability and reusability of the prepared photocatalyst to 5 consecutive cycles. Consequently, this work presents a new perspective to fabricate greener, cheaper and proficient visible driven photocatalytic material for wastewater detoxification and environmental remediation.
Effect of temperature on equilibria for physical and reactive extraction of protocatechuic acid
2020, Heliyon
Owing to its biological and chemical applications, the separation of protocatechuic acid, a polyphenol compound, is of interest to researchers. Extraction studies with initial acid concentration (0.001–0.01 kmol m⁻³) using aminic extractant tri-n-octyl amine (TOA) (0.2287 kmol m⁻³ -1.1436 kmol m⁻³) in diluent octanol at diverse temperature ranges from 288 K - 313 K was done. Parameters like loading ratio, distribution coefficient, equilibrium complexation constant, diffusion coefficient, number of stages necessary for protocatechuic acid counter-current extraction were obtained; this information is useful in designing a process for the in situ separation of the acid from the fermentation broth as well as from the waste streams. The increase in temperature distribution coefficient was found to increase up to the temperature of 303 K and was found to decrease with a further rise in temperature. The entropy and enthalpy values for the reaction at different temperatures were obtained. The highest extraction of 91.1 % and distribution coefficient of 1.14 were obtained at 313 K for an acid concentration of 0.01 kmol m^−3, and TOA concentration of 1.1436 kmol m⁻³ and 4 stages are required for counter-current extraction process for acquiring the required separation efficiency. Development of 1:1 complex of protocatechuic acid and TOA take place as concluded from the values of the loading ratio.
Performance of heterogeneous catalytic wet oxidation for the removal of phenolic compounds: Catalyst characterization and effect of pH, temperature, metal leaching and non-oxidative hydrothermal reaction
2017, Journal of Environmental Chemical Engineering
The present study investigated the efficiency of catalytic wet oxidation (CWO) for the destruction of three phenolic compounds (phenol, o-cresol and 2,5-dimethylphenol) individually as well as in mixture (phenolics concentration = 10 g/L, NaOH concentration = 10 g/L, chemical oxygen demand (COD) = 24000 mg/L, total organic carbon (TOC) = ∼7800 mg/L and pH ∼13). The oxidative hydrothermal reaction was carried out in a laboratory scale high pressure batch reactor (capacity = 0.7 L) at moderate temperature (120–160 °C) and pressure (oxygen partial pressure = 0.8 MPa) conditions in the presence of a heterogeneous catalyst (i.e., 5% Cu/activated carbon). After 4 h CWO reaction on the mixture of phenolics at a reaction temperature of 160 °C and initial reaction pH of 9.0, TOC and COD were reduced by ∼90% and 82%, respectively. The phenolics removal was mainly due to the oxidation reaction and the contribution of other reactions such as adsorption and/or hydrolysis was lower. The copper leaching in the solution was found to be 15–26 ppm. The characterization of recovered catalyst showed increase in carbon content thus confirming the deposition of carbonaceous deposit.
Multiwalled carbonnanotubes enhance the response and sensitivity of the ammonium biosensor based on alanine dehydrogenase
2017, Journal of Electroanalytical Chemistry
An amperometric ammonium biosensor based on alanine dehydrogenase of Bacillus subtilis and functionalized multiwalled carbonnanotubes was developed by using screen printed electrodes. The output current of the biosensor was increased around 2.4 times at 100 mM NH₄⁺ after the addition of functionalized multiwalled carbonnanotubes at the concentration of 0.1 μg/ml along with the enzyme. The biosensor showed much broader linearity range (0.05–500 mM NH₄⁺), better detection limit (0.001 mM NH₄⁺) and response time (30 s) due to the incorporation of the functionalized multiwalled carbonnanotubes. The cyclic voltammogram of enzyme-carbonnanotubes/carbon working electrode showed the output current at the oxidation peak, which was > 2 times higher compared to that of enzyme/carbon working electrode. This suggests the promotion of electron transfer from the enzyme to the working electrode by carbonnanotubes, which may act as electron transducers and rapidly transfer the electrons from the redox centre of the enzyme to the electrode, thereby improving the signal, response time and sensitivity. The sensor retained 89.93% of its initial output current after 119 days. The concentrations of NH₄⁺ detected by the biosensor were in close agreement with that of standard Nessler's reagent method suggesting the suitability of the present biosensor for the testing of water samples.
Behavior of phenol adsorption on thermal modified activated carbon
2016, Chinese Journal of Chemical Engineering
Adsorption process is acknowledged as an effective option for phenolic wastewater treatment. In this work, the activated carbon (AC) samples after thermal modification were prepared by using muffle furnace. The phenol adsorption kinetics and equilibrium measurements were carried out under static conditions at temperature ranging from 25 to 55 °C. The test results show that the thermal modification can enhance phenol adsorption on AC samples. The porous structure and surface chemistry analyses indicate that the decay in pore morphology and decrease of total oxygen-containing functional groups are found for the thermal modified AC samples. Thus, it can be further inferred that the decrease of total oxygen-containing functional groups on the modified AC samples is the main reason for the enhanced phenol adsorption capacity. For both the raw sample and the optimum modified AC sample at 900 °C, the pseudo-second order kinetics and Langmuir models are found to fit the experimental data very well. The maximum phenol adsorption capacity of the optimum modified AC sample can reach 144.93 mg·g^− 1 which is higher than that of the raw sample, i.e. 119.53 mg·g^− 1. Adsorption thermodynamics analysis confirms that the phenol adsorption on the optimum modified AC sample is an exothermic process and mainly via physical adsorption.
Isolation and characterization of flavanols from Anthocephalus cadamba and evaluation of their antioxidant, antigenotoxic, cytotoxic and COX-2 inhibitory activities
2016, Revista Brasileira de Farmacognosia
In search of lead molecules for use in disease prevention and as food additive from natural sources, two flavanols were isolated from leaves of Anthocephalus cadamba (Roxb.) Miq., Rubiaceae. Their structures were established as 6-hydroxycoumarin-(4⿳⿿8)-(⿿)-epicatechin and 6-hydroxycoumarin-(4⿳⿿8)-(⿿)-epicatechin-(4⿿6⿴)-(⿿)-epicatechin on the basis of spectroscopic data. Both the compounds exhibited potent antioxidant and antigenotoxic activity. 6-Hydroxycoumarin-(4⿳⿿8)-(⿿)-epicatechin scavenged DPPH, ABTS^+.and superoxide anion radicals with IC₅₀ values of 6.09 μg/ml, 5.95 μg/ml and 42.70 μg/ml respectively whereas the IC₅₀ values for 6-hydroxycoumarin-(4⿳⿿8)-(⿿)-epicatechin-(4⿿6⿴)-(⿿)-epicatechin were 6.62 μg/ml for DPPH free radicals, 6.93 μg/ml for ABTS radical cations and 49.08 μg/ml for superoxide anion radicals. Both the compounds also exhibited potent reducing potential in reducing power assay and protected the plasmid DNA (pBR322) against the attack of hydroxyl radicals generated by Fenton's reagent in DNA protection assay. In SOS chromotest, 6-hydroxycoumarin-(4⿳⿿8)-(⿿)-epicatechin decreased the induction factor induced by 4NQO (20 μg/ml) and aflatoxin B1 (20 μg/ml) by 31.78% and 65.04% respectively at a concentration of 1000 μg/ml. On the other hand, 6-hydroxycoumarin-(4⿳⿿8)-(⿿)-epicatechin-(4⿿6⿴)-(⿿)-epicatechin decreased the genotoxicity of these mutagens by 37.11% and 47.05% respectively. It also showed cytotoxicity in COLO-205 cancer cell line with GI₅₀ of 435.71 μg/ml. Both the compounds showed moderate cyclooxygenase-2 inhibitory activity.

View all citing articles on Scopus

View full text

The beneficial and hazardous effects of simple phenolic compounds

Abstract

Chem.-Biol. Interact.

Food Chem. Toxicol.

Cancer Lett.

Mutation Res.

Mutation Res.

Food Chem. Toxicol.

Cancer Lett.

Food Cosmet. Toxicol.

Biochem. Biophys. Res. Commun.

Biochem. Biophys. Res. Commun.

Cancer Lett.

Mutation Res.

Mutation Res.

Food Chem. Toxicol.

Cancer Lett.

Food Chem. Toxicol.

Food Chem. Toxicol.

Mutation Res.

Cancer Lett.

Mutation Res.

Biochem. Biophys. Res. Commun.

Food Chem. Toxicol.

Toxicology

Mutation Res.

Induction of forestomach lesions by butylhydroxyanisole and structurally related substances

What are the major carcinogens in the etiology of human cancer?

Mutagenesis and carcinogenesis: endogenous and exogenous factors

Environ. Mol. Mutagen.

Inhibition in vivo of the formation of adducts between metabolites of benzo[a]pyrene and DNA by butylated hydroxyanisole

Cancer Res.

The metabolism of coffee constituents

Chemical cocarcinogenesis with the use of a subclone derived from Balb/3T3 cells with catechol as cocarcinogen

J. Natl. Cancer Inst.

Factors modulating the formation of DNA adducts by aflatoxin B1 in vitro

Carcinogenesis

Ascorbic acid and cancer: a review

Cancer Res.

Possible cocarcinogenic effects of coffee constituents

Nature (London)

Effect of ellagic acid and hydroxylated flavonoids on the tumorigenicity of benzo[a]pyrene, and (∼)-7b,8a-dihydroxy-9a,10a-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene on mouse skin and in the newborn mouse

Carcinogenesis

Human papillomavirus type 16 and early cervical neoplasia

New Engl. J. Med.

Effect of ellagic acid on hepatic and pulmonary xenobiotic metabolism in mice: studies on the mechanism of its anticarcinogenic action

Carcinogenesis

Inhibition of epidermal xenobiotic metabolism in SENCAR mice by naturally occurring plant phenols

Cancer Res.

inhibition of polycyclic aromatic hydrocarbon-DNA adduct formation in epidermis and lungs of SENCAR mice by naturally occurring plant phenols

Cancer Res.

Inhibition of N-methyl-N-nitrosourea-induced mutagenicity and DNA methylation by ellagic acid

Inhibition of benzo[a]pyrene and benzo[a]pyrene-trans-7,8-diol metabolism and DNA binding in mouse lung explants by ellagic acid

Cancer Res.

Sister chromatid exchange induction in human lymphocytes exposed to benzene and its metabolites in vitro

Cancer Res.

Joint FAO/WHO Expert Committee on Food Additives

Reduction of mutagenic products in the presence of polyphenols using pyrolysis of proteins

Agric. Biol. Chem.

Promoting effects of sodium l-ascorbate on two-stage urinary bladder carcinogenesis in rats

Cancer Res.

A study of tobacco carcinogenesis

Review on nonessential constituents of vegetables

Microbes and Human Carcinogenesis

Epidemiological evaluation of the role of naturally occurring carcinogens and modulators of carcinogenesis