Disease-associated acrolein: A possible diagnostic and therapeutic substrate for in vivo synthetic chemistry

Muguruma, Kyohei; Pradipta, Ambara R.; Ode, Yudai; Terashima, Kazuki; Michiba, Hiroyuki; Fujii, Morimitsu; Tanaka, Katsunori

doi:10.1016/j.bmc.2020.115831

Cited by 17 publications

(17 citation statements)

References 65 publications

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“…The glycerol degradation in these and other apple-derived products can, by the action of lactic bacteria, lead to the formation of 3-hydroxypropanal, which is unstable and can spontaneously be transformed in acrolein [197,206]. Acrolein is an unsaturated aldehyde, with a high reactivity, which can frequently cause several diseases in humans [207][208][209][210].…”

Section: Health Effects Of Fermented Apple Productsmentioning

confidence: 99%

Apple Fermented Products: An Overview of Technology, Properties and Health Effects

et al. 2021

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As an easily adapted culture, with overloaded production in some parts of the globe, apples and their by-products are being redirected to pharmaceutical, canning and beverages industries, both alcoholic and non-alcoholic. Fermentation is generally considered to increase the bioavailability of bioactive compounds found in apple, by impacting, through a high degree of changes, the product’s properties, including composition and health-promoting attributes, as well as their sensory profile. Probiotic apple beverages and apple vinegar are generally considered as safe and healthy products by the consumers. Recently, contributions to human health, both in vivo and in vitro studies, of non-alcoholic fermented apple-based products have been described. This review highlighted the advances in the process optimization of apple-based products considering vinegar, cider, pomace, probiotic beverages and spirits’ technologies. The different processing impacts on physical-chemical, nutritional and sensory profiles of these products are also presented. Additionally, the harmful effects of toxic compounds and strategies to limit their content in cider and apple spirits are illustrated. New trends of fermented apple-based products applicability in tangential industries are summarized.

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Section: Health Effects Of Fermented Apple Productsmentioning

confidence: 99%

Apple Fermented Products: An Overview of Technology, Properties and Health Effects

et al. 2021

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“…The endogenously generated acrolein can subsequently react with nearby thiol, hydroxyl, or amino functional groups on DNA, proteins, or phosphatidyl ethanolamines, which subsequently could accelerate oxidative stress processes [8] . Consequently, a better understanding of acrolein conjugates should deepen our knowledge regarding acrolein and its effects on various diseases [9] …”

Section: Exploring the Reactivity Of Acrolein Imines And Functional Smentioning

confidence: 99%

Application of Acrolein Imines to Organic Synthesis, Biofunctional Studies, and Clinical Practice

Pradipta

Tanaka

2021

The Chemical Record

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N‐alkyl unsaturated imines derived from acrolein, a toxin produced during oxidative stress, and biogenic alkyl amines occur naturally and are considered biologically relevant compounds. However, despite the recent conceptual and technological advances in organic synthesis, research on the new reactivity of these compounds is lacking. This personal account discusses research on the reactivity that has been overlooked in acrolein imines, including the discovery of new methods to synthesize biologically active compounds, the determination of new functions of relevant imines and their precursors, i. e., aldehydes and amines, and the application of these methods for clinical diagnosis.

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“…Among these contaminants, propen‐2‐al (acrolein), a highly reactive α,β‐unsaturated aldehyde, is a compound that humans are exposed to in many situations and might be responsible for triggering different neurodegenerative diseases, such as cardiovascular diseases, diabetes, cancer, atherosclerosis, and Alzheimer's (Chang et al., 2022; Crowley et al., 2022; Igarashi et al., 2018; Jiang et al., 2022; Liu et al., 2019; X. Zhang et al., 2022; Zirak et al., 2019). Acrolein can be found mainly in foods and beverages that are rich in lipids, carbohydrates, and certain amino acids that are heated during processing, or in fermented products produced by the metabolism of lactic acid bacteria (Drakula et al., 2019; Lago & Welke, 2019; Muguruma et al., 2020; D. Zhang et al., 2020).…”

Section: Introductionmentioning

confidence: 99%

“…Zhang et al, 2022;Zirak et al, 2019). Acrolein can be found mainly in foods and beverages that are rich in lipids, carbohydrates, and certain amino acids that are heated during processing, or in fermented products produced by the metabolism of lactic acid bacteria (Drakula et al, 2019;Lago & Welke, 2019;Muguruma et al, 2020;D. Zhang et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

Correlation of the presence of acrolein with higher alcohols, glycerol, and acidity in cachaças

Alvarenga

Machado

Barbosa

et al. 2023

Journal of Food Science

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Acrolein is a toxic aldehyde that can be present in various beverages, such as cachaça and other distilled spirits from sugarcane. The objective of this work was to detect and quantify acrolein in samples of cachaça produced by different processes in all regions of Brazil and to evaluate the possible routes of formation of this contaminant from the correlation with other secondary compounds present in the beverage using principal component analysis. Approximately 27.0% of the samples analyzed were outside the limit established by Brazilian legislation for this contaminant, with an average acrolein concentration of 14.01 mg 100 mL −1 anhydrous alcohol (aa). In the other samples, the average concentration was 0.97 mg 100 mL −1 aa. After selecting the variables that most closely correlated with the presence of acrolein in beverages, a positive correlation was found with the presence of butan-2-ol, propan-1-ol and volatile acids, and a slight correlation with the presence of phenolic compounds. Therefore, the presence of acrolein in cachaça can be associated with contamination of the fermentation must by bacteria of the genus Lactobacillus, as a result of the chemical degradation and enzymatic conversion of the glycerol produced during fermentation.

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Disease-associated acrolein: A possible diagnostic and therapeutic substrate for in vivo synthetic chemistry

Cited by 17 publications

References 65 publications

Apple Fermented Products: An Overview of Technology, Properties and Health Effects

Apple Fermented Products: An Overview of Technology, Properties and Health Effects

Application of Acrolein Imines to Organic Synthesis, Biofunctional Studies, and Clinical Practice

Correlation of the presence of acrolein with higher alcohols, glycerol, and acidity in cachaças

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