Formation of di-cysteine acrolein adduct decreases cytotoxicity of acrolein by ROS alleviation and apoptosis intervention

Yin, Zhang; Jiang, Kaiyu; Shi, Lei; Fei, Jia; Zheng, Jie; Ou, Shiyi; Ou, Juanying

doi:10.1016/j.jhazmat.2019.121686

Cited by 28 publications

(37 citation statements)

References 36 publications

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“…In particular, cysteine and lysine eliminated more than 80% of acrolein . The adducts formed between acrolein with cysteine and lysine were identified by Furuhata et al, Jiang et al, Maeshima et al, and Yin et al as shown in Figure B.…”

Section: Acroleinmentioning

confidence: 87%

“…Based on the studies of Watzek et al and Yin et al, we derive the following two conclusions: (1) some acrolein adducts release acrolein after intake and absorption, and (2) some acrolein adducts with low toxicity are converted to adducts with high toxicity during absorption and metabolism. These works highlight the urgency of conducting an in-depth investigation on acrolein adducts formed in foods, including the kinds of adducts, their formation level, and their changes during absorption and metabolism.…”

Section: Acroleinmentioning

confidence: 99%

“…Acrolein is a toxic aldehyde with subcutaneous LD 50 = 30 mg/kg in mice and 50 mg/kg in rats. Acrolein toxicity is associated with various pathological conditions, including Alzheimer’s disease, cardiovascular diseases, atherosclerosis, lung cancer, and spinal cord injury …”

Section: Acroleinmentioning

confidence: 99%

“…Acrolein exists ubiquitously in the environment, as a result of endogenous formation, and in dietary foods . Anthropogenic activities lead to its emission in the environment, including industrial activities, biocide use, indoor fuel combustion, charcoal barbecue, and cigarette smoke. , More than 500 million pounds of acrolein are produced annually in the US . In humans and animals, acrolein is generated endogenously via the fragmentation of polyunsaturated fatty acids during lipid peroxidation and via the oxidation of spermine catalyzed by amine or polyamine oxidases .…”

Section: Acroleinmentioning

confidence: 99%

“…It is actually an adduct with low cytotoxicity that can be catalyzed by phosphate in cells to form a monocysteine–acrolein adduct (the second adduct in Figure B) via β-elimination and hence exhibit similar toxicity to acrolein. Excessive cysteine is necessary to prevent the conversion of dicysteine–acrolein to monocysteine–acrolein …”

Section: Acroleinmentioning

confidence: 99%

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Interaction of Acrylamide, Acrolein, and 5-Hydroxymethylfurfural with Amino Acids and DNA

Zheng

Huang

et al. 2020

J. Agric. Food Chem.

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Acrylamide, acrolein, and 5-hydroxymethylfurfural (HMF) are food-borne toxicants produced during the thermal processing of food. The α,β-unsaturated carbonyl group or aldehyde group in their structure can react easily with the amino, imino, and thiol groups in amino acids, proteins, and DNA via Michael addition and nucleophilic reactions in food and in vivo. This work reviews the interaction pathways of three toxins with amino acids and the cytotoxicity and changes after the digestion and absorption of the resulting adducts. Their interaction with DNA is also discussed. Amino acids ubiquitously exist in foods and are added as nutrients or used to control these food-borne toxicants. Hence, the interaction widely occurring in foods would greatly increase the internal exposure of these toxins and their derived compounds after food intake. This review aims to encourage further investigation on toxin-derived compounds, including their types, exposure levels, toxicities, and pharmacokinetics.

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Section: Acroleinmentioning

confidence: 87%

Section: Acroleinmentioning

confidence: 99%

Section: Acroleinmentioning

confidence: 99%

Section: Acroleinmentioning

confidence: 99%

Section: Acroleinmentioning

confidence: 99%

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Interaction of Acrylamide, Acrolein, and 5-Hydroxymethylfurfural with Amino Acids and DNA

Zheng

Huang

et al. 2020

J. Agric. Food Chem.

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Removal of C9‐aldehydes and ‐alcohols from melon juice via cysteine addition

et al. 2022

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Background The aroma of a melon fruit is among the most crucial qualities that influence consumer preferences. However, strong grassy and cucumber‐like aromas can prevent consumer acceptance. These grassy and cucumber‐like aromas are produced by aldehydes containing nine‐carbon chains. Several studies have revealed that aldehydes exhibit a high affinity toward cysteine. Thus, the effect of adding cysteine to volatile compounds to melon juice was investigated. Results The volatile compounds released from the melon juice were analyzed via solid‐phase microextraction coupled with gas chromatography–mass spectrometry (SPME–GC–MS) after 0.5, 5, and 24 h of adding cysteine. The results indicated that the concentrations of aldehydes, such as (E,Z)‐2,6‐nonadienal and (E)‐2‐nonenal, in the melon juice decreased after the addition of cysteine at all the analyzed times. Additionally, (E)‐2‐nonenol and (E,Z)‐2,6‐nonadien‐1‐ol, which were formed by the enzymatic reduction of the aldehydes, also decreased by cysteine addition. To confirm the binding of cysteine with the aldehydes, two cysteine adducts were analyzed via liquid chromatography–mass spectrometry (LC–MS) employing (E)‐2‐nonenal in the melon juice after the addition of cysteine. Conclusion This study demonstrates that cysteine addition could be potentially used to reduce the grassy and cucumber‐like aromas of melon juice. © 2022 Society of Chemical Industry.

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Exploring the molecular mechanisms of the inhibition of acrolein-induced BEAS-2B cytotoxicity by luteolin using network pharmacology and cell biology technology

Liú

Cheng

Chen

et al. 2022

Food and Chemical Toxicology

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Formation of di-cysteine acrolein adduct decreases cytotoxicity of acrolein by ROS alleviation and apoptosis intervention

Cited by 28 publications

References 36 publications

Interaction of Acrylamide, Acrolein, and 5-Hydroxymethylfurfural with Amino Acids and DNA

Interaction of Acrylamide, Acrolein, and 5-Hydroxymethylfurfural with Amino Acids and DNA

Removal of C9‐aldehydes and ‐alcohols from melon juice via cysteine addition

Exploring the molecular mechanisms of the inhibition of acrolein-induced BEAS-2B cytotoxicity by luteolin using network pharmacology and cell biology technology

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