Catechins in green tea powder (matcha) are heat-stable scavengers of acrolein, a lipid peroxide-derived reactive carbonyl species

Sugimoto, Koh‐ichi; Matsuoka, Yasumasa; Kyoko, Sakai; Fujiya, Norika; Fujii, Hiroyuki; Mano, Junichi

doi:10.1016/j.foodchem.2021.129403

Cited by 34 publications

(20 citation statements)

References 31 publications

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“…Here, it was reported for the first time that C-5′ in the B-ring was the active site to trap ACR, which was different from the previously reported active sites at C-6 and C-8 in the A-ring of flavonoids, such as hesperetin, EGCG, phloretin, quercetin, and genistein, or at C-2′ in the B-ring of flavonoids, such as myricetin …”

Section: Resultscontrasting

confidence: 96%

“…Flavonoids or polyphenols have aromatic carbons or hydroxyl groups that are highly nucleophilic in structure and can undergo nucleophilic addition reactions with the nucleophilic carbanion in ACR to form additional heterocycles, 21 thus directly eliminating ACR. For example, hesperetin, 21 quercetin, 22 epicatechin, 23 phloretin, 23 myricetin, 24 and catechins 25 are known to capture ACR in vitro or in vivo, but their application in the food industry is limited because they are not authorized as food additives.…”

Section: ■ Introductionmentioning

confidence: 99%

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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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Section: Resultscontrasting

confidence: 96%

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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“…Wang et al found that resveratrol and hesperetin can remove acrolein rapidly under a simulated physiological condition [72]. Koichi et al reported that the addition of matcha powder can suppress acrolein accumulation during cake baking and detected mono catechin-acrolein adducts in cakes with matcha powder added to them [73]. In recent years, Lv et al successively published their research on the control of acrolein by polyphenols, such as myricetin [74], epigallocatechin-3-gallate (EGCG), genistein [75] and cyanidin-3-O-glucoside (C3G) [76].…”

Section: Interactions Of Acrolein With Antioxidant and Natural Productsmentioning

confidence: 99%

Origin and Fate of Acrolein in Foods

Jiang

Huang

Liu

et al. 2022

Foods

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Acrolein is a highly toxic agent that may promote the occurrence and development of various diseases. Acrolein is pervasive in all kinds of foods, and dietary intake is one of the main routes of human exposure to acrolein. Considering that acrolein is substantially eliminated after its formation during food processing and re-exposed in the human body after ingestion and metabolism, the origin and fate of acrolein must be traced in food. Focusing on molecular mechanisms, this review introduces the formation of acrolein in food and summarises both in vitro and in vivo fates of acrolein based on its interactions with small molecules and biomacromolecules. Future investigation of acrolein from different perspectives is also discussed.

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“…Polyphenols (which are rich in plants) are also candidate RCS scavengers. Certain types of polyphenols such as phloretin in tea leaf and apple fruit (Zhu et al, 2009), pelargonidin in brown rice (Colzani et al, 2018), and catechins in tea leaf (Sugimoto et al, 2021) can trap acrolein and HNE in vitro, but their in planta function to scavenge RCS has not been verified.…”

Section: Reactive Carbonyl Species Scavenging Compounds and Enzymesmentioning

confidence: 99%

Lipid Peroxide-Derived Reactive Carbonyl Species as Mediators of Oxidative Stress and Signaling

Biswas

Mano

2021

Front. Plant Sci.

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Oxidation of membrane lipids by reactive oxygen species (ROS) or O2/lipoxygenase leads to the formation of various bioactive compounds collectively called oxylipins. Reactive carbonyl species (RCS) are a group of oxylipins that have the α,β-unsaturated carbonyl structure, including acrolein and 4-hydroxy-(E)-2-nonenal. RCS provides a missing link between ROS stimuli and cellular responses in plants via their electrophilic modification of proteins. The physiological significance of RCS in plants has been established based on the observations that the RCS-scavenging enzymes that are overexpressed in plants or the RCS-scavenging chemicals added to plants suppress the plants’ responses to ROS, i.e., photoinhibition, aluminum-induced root damage, programmed cell death (PCD), senescence, abscisic acid-induced stomata closure, and auxin-induced lateral root formation. The functions of RCS are thus a key to ROS- and redox-signaling in plants. The chemical species involved in distinct RCS signaling/damaging phenomena were recently revealed, based on comprehensive carbonyl determinations. This review presents an overview of the current status of research regarding RCS signaling functions in plants and discusses present challenges for gaining a more complete understanding of the signaling mechanisms.

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Catechins in green tea powder (matcha) are heat-stable scavengers of acrolein, a lipid peroxide-derived reactive carbonyl species

Cited by 34 publications

References 31 publications

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

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

Origin and Fate of Acrolein in Foods

Lipid Peroxide-Derived Reactive Carbonyl Species as Mediators of Oxidative Stress and Signaling

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