Acrolein: Hazard Characterization and Exposure–response Analysis

Gomes, Ronaldo Barros; Liteplo, Robert G.; Meek, M.E.

doi:10.1081/gnc-100103579

Cited by 11 publications

(7 citation statements)

References 47 publications

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“…If this is correct, then it should be possible to prevent TS-induced lung and bladder cancer by neutralizing sufficient amount of TS aldehydes in vivo. It has long been recognized that the carbonyl group and the olefinic bond in Acr are the active moieties that can interact with DNA and proteins to form DNA and protein adducts ( 41 , 42 ). These reactions can be prevented by numerous antioxidants and reducing agents with molecules that have sulfhydryl groups ( 43 – 45 ).…”

Section: Resultsmentioning

confidence: 99%

Aldehydes are the predominant forces inducing DNA damage and inhibiting DNA repair in tobacco smoke carcinogenesis

Weng

Lee

Park

et al. 2018

Proc. Natl. Acad. Sci. U.S.A.

101

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SignificanceTobacco smoke (TS) contains numerous carcinogens. Intriguingly, while TS itself is a weak carcinogen in animal models, many of the TS components, such as 4-(methylnitrosamine)-1-(3-pyridyl)-1-butanone (NNK) and polycyclic aromatic hydrocarbons (PAHs), are strong carcinogens. We found that TS induces mainly aldehyde-DNA adducts in mice and humans. TS reduces DNA repair activity and repair proteins in mouse lung. All of these TS-induced effects can be reduced by diet polyphenols. Aldehydes prevent PAHs and NNK from inducing DNA damage in human cells. We propose that, because they act to damage DNA, reduce DNA repair activity, and inhibit NNK and PAHs from becoming DNA-damaging agents, aldehydes are the major TS carcinogens. These insights allow for better TS cancer risk assessment and the design of effective preventive measures.

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Section: Resultsmentioning

confidence: 99%

Aldehydes are the predominant forces inducing DNA damage and inhibiting DNA repair in tobacco smoke carcinogenesis

Weng

Lee

Park

et al. 2018

Proc. Natl. Acad. Sci. U.S.A.

101

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“…Ferreira found that ACR existed in all four stages of wine-making (grape, must, fermentation, and wine), and the advancement of the degree of ripeness and increasing the grape maceration time seemed to result in higher concentrations of ACR . Kächele reported that the average ACR content in fruit spirits (0.591 mg/L) and tequila (0.404 mg/L) in Germany was even higher than that in frying fats and oils (0.276 mg/L), while other literature showed that the level of ACR was up to 1.5 mg/L in brandy, 0.7–11.1 mg/L in Bourbon whiskey, and 3.8 mg/L in wine. , These reported ACR concentrations exceed a provisional tolerable oral ACR concentration of 1.5 mg/L, corresponding to 7.5 μg/kg body weight/day derived by the WHO. , If the ACR level in liquor or fruit wine reaches 1.5–3.8 mg/L, for a 60 kg person, the intake should not exceed 118–300 mL/day; unfortunately, according to statistics, the amount of alcohol consumption per day (200–300 mL) of China’s drinkers is often beyond this range. As reported in Brazil, the ACR contents in Merlot and Syrah wines were also sufficient to present risk to human health.…”

Section: Introductionmentioning

confidence: 99%

Inhibitory Effect on Acrolein by Cyanidin-3-O-glucoside and Its Acrolein Adducts from the Pigment of Mynica Red

Song

Yang

Bo³

et al. 2021

J. Agric. Food Chem.

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Acrolein (ACR), the simplest α,β-unsaturated aldehyde, possesses high reactivity and toxicity both in vitro and in vivo and results in various chronic diseases. This has attracted increasing interest from researchers to screen various bioactive compounds to control it. In this article, we attempted to discover a new attribute of cyanidin-3-O-glucoside (C3G), including its ACR-scavenging capacity, reaction pathway, and possible application. Our findings revealed that C3G could capture ACR to form mono- and diadducts at room temperature by using liquid chromatography–mass spectrometry, and we further synthesized and elucidated the structures of C3G–ACR and C3G–2ACR using HRMS and 2D NMR. The structural data validated that there were two active sites of C3G for trapping ACR: at C-6 in the A-ring and C-5′ in the B-ring. In addition, we found that C3G–ACR exhibited a more remarkable clearing ability than C3G within a short time. More than 65.9% of ACR was eliminated by C3G–ACR within 5 min via further formation of C3G–2ACR, but there was no obvious effect of C3G on ACR. When the incubation time was extended to 120 min, C3G could remove up to 83.2% of ACR. Subsequently, we also observed that mynica red (>5% C3G), as a pigmented food additive, could efficiently eliminate ACR generated in the Chinese liquor model and real red bayberry wine products to form C3G–ACR and C3G–2ACR. Both adducts increased significantly, by 10 times to a 100 times, after adding mynica red to red bayberry wine products for 24 h; they also increased rapidly with prolonged incubation time in the liquor–mynica red model system. Therefore, our findings suggest that C3G or mynica red may be developed as a promising novel ACR inhibitor in fruit wine and assembled alcoholic drinks or as a health food.

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“…Methyl vinyl ketone is a direct-acting irritant that targets the upper respiratory tract causing nasal lesions (Cunningham et al 2001). Acrolein is considered highly acutely toxic, is a known sensory and upper respiratory irritant, and causes changes in respiratory function such as decrease in respiratory rate, rhythm, and amplitude [Gomes and Meek 2002; World Health Organization (WHO) 1992]. Studies show that formaldehyde is a moderate sensory irritant with carcinogenic evidence from occupational exposures (Liteplo et al 2002; WHO 1989).…”

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confidence: 99%

Effects of 1,3-Butadiene, Isoprene, and Their Photochemical Degradation Products on Human Lung Cells

Doyle¹,

Sexton²,

Jeffries³

et al. 2004

Environ Health Perspect

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Because of potential exposure both in the workplace and from ambient air, the known carcinogen 1,3-butadiene (BD) is considered a priority hazardous air pollutant. BD and its 2-methyl analog, isoprene (ISO), are chemically similar but have very different toxicities, with ISO showing no significant carcinogenesis. Once released into the atmosphere, reactions with species induced by sunlight and nitrogen oxides convert BD and ISO into several photochemical reaction products. In this study, we determined the relative toxicity and inflammatory gene expression induced by exposure of A549 cells to BD, ISO, and their photochemical degradation products in the presence of nitric oxide. Gas chromatography and mass spectrometry analyses indicate the initial and major photochemical products produced during these experiments for BD are acrolein, acetaldehyde, and formaldehyde, and products for ISO are methacrolein, methyl vinyl ketone, and formaldehyde; both formed < 200 ppb of ozone. After exposure the cells were examined for cytotoxicity and interleukin-8 (IL-8) gene expression, as a marker for inflammation. These results indicate that although BD and ISO alone caused similar cytotoxicity and IL-8 responses compared with the air control, their photochemical products significantly enhanced cytotoxicity and IL-8 gene expression. This suggests that once ISO and BD are released into the environment, reactions occurring in the atmosphere transform these hydrocarbons into products that induce potentially greater adverse health effects than the emitted hydrocarbons by themselves. In addition, the data suggest that based on the carbon concentration or per carbon basis, biogenic ISO transforms into products with proinflammatory potential similar to that of BD products.

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Acrolein: Hazard Characterization and Exposure–response Analysis

Cited by 11 publications

References 47 publications

Aldehydes are the predominant forces inducing DNA damage and inhibiting DNA repair in tobacco smoke carcinogenesis

Aldehydes are the predominant forces inducing DNA damage and inhibiting DNA repair in tobacco smoke carcinogenesis

Inhibitory Effect on Acrolein by Cyanidin-3-O-glucoside and Its Acrolein Adducts from the Pigment of Mynica Red

Effects of 1,3-Butadiene, Isoprene, and Their Photochemical Degradation Products on Human Lung Cells

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