Spectroscopic evidences of toxic trans‐crotonaldehyde trapped and transformed by resveratrol to prevent the damage of mitochondrial DNA

Su, Yun-Ai; Chen, Lei; Su, Yanwen; Li, Zhengqiang; Zhang, Chuang; Mu, Tongxing

doi:10.1002/iub.1631

Cited by 7 publications

(4 citation statements)

References 56 publications

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“…16 Increasing evidence shows that the abnormal accumulation of RCS favors carbonyl stress, promoting modification of tissue protein and DNA. 17 To date, several inhibitors have been well documented that capture RCS, such as polyphenols (e.g., (−)-epigallocatechin gallate (EGCG) for ACR, CRO, 18 MGO, and GO; 19 resveratrol for ACR, MGO, 20 and CRO; 21 myricetin for ACR 22 and MGO; 23 quercetin for ACR, CRO, 24 MGO, and GO 25 ), alkaloid (such as theophylline 26 and synephrine 27 for ACR), and amino acids (such as γ-aminobutyric acid 28 and lysine 29 for ACR; cysteine and glycine for ACR, MGO, and GO 30 ). most research focused on the inhibitory ability of a single inhibitor on a single RCS, with minimal attention to the impact of inhibitors on multiple RCS.…”

Section: ■ Introductionmentioning

confidence: 99%

Theanine in Tea: An Effective Scavenger of Single or Multiple Reactive Carbonyl Species at the Same Time

Zhong,

Lu,

2023

J. Agric. Food Chem.

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Reactive carbonyl species (RCS) are generated during thermal food processing, and their accumulation in the body increases the risk of various chronic diseases. Herein, the RCS-scavenging ability of theanine, a unique nonproteinogenic amino acid, was evaluated in terms of the scavenging rate, reaction kinetics, and reaction pathway using LC–MS/MS. Three major products of theanine conjugated with acrolein (ACR) and glyoxal (GO) were prepared and identified using nuclear magnetic resonance. Thereafter, the simultaneous reactions of four types of RCS (namely, ACR, crotonaldehyde, methylglyoxal, and GO) with theanine were discussed in RCS–theanine and RCS–tea models. Under different reaction ratios, theanine could nonspecifically scavenge the four coexisting RCS by forming adducts with them. The amount of theanine–RCS adducts in green and black tea was more than that of catechin (epigallocatechin gallate, epigallocatechin, epicatechin gallate, and epicatechin)–RCS adducts despite the lower content of theanine than catechins. Thus, theanine, as a food additive and dietary supplement, could demonstrate new bioactivity as a promising RCS scavenger in food processing.

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Section: ■ Introductionmentioning

confidence: 99%

Theanine in Tea: An Effective Scavenger of Single or Multiple Reactive Carbonyl Species at the Same Time

Zhong,

Lu,

2023

J. Agric. Food Chem.

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“…It should be noted that compared with report from Daria Mochly-Rosen 17 , when EtOH (0.5 g/kg, approximately equal to 163 mM) was injected into the abdominal cavity, the ischemia and reperfusion injury of the left anterior descending coronary artery was significantly reduced without causing any side effects in vivo . And then combined with the latest research results of this group, resveratrol (0.01 mM) has a significant regulatory effect on the structure of TCA-CH=O for preventing mtDNA damage 30 . Therefore, when the -OH of EtOH changed the structure of TCA-CH=O, its concentration was significantly lower than the safe concentration of ethanol.…”

Section: Resultsmentioning

confidence: 93%

Influences of ethanol on the structure of toxic trans-crotonaldehyde in mitochondria coming from rat myocardium

et al. 2017

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Inappropriate use of ethanol (EtOH) had led to noticeable health problems, but a beneficial phenomenon was found that EtOH displayed unique influences for toxic trans-crotonaldehyde (TCA) derived from mitochondrial lipid peroxidation. The influences of EtOH on the structure of TCA were systematically probed by UV-vis & Raman spectroscopy in the absence and presence of mitochondria, respectively. The maximum UV-vis peak at 301 nm of TCA was red shifted by hydroxyl (-OH) and methyl (-CH3) of EtOH, respectively. Raman stretching band of aldehyde (-CH=O) of TCA (TCA-CH=O) was split by the -CH3 of EtOH. The -CH3 increased TCA-CH=O stretching frequency while the -OH induced it. The more exposed -OH, the less stretching frequency. The ectopic -CH3 red shifted the UV-vis peak at 301 nm and Raman band of TCA-CH=O. In mitochondria, EtOH red shifted Raman stretching band of TCA-CH=O. Raman stretching bands of C-H, C-O and C-C of EtOH were red shifted, while Raman stretching bands of -CH2 and C-C-O of EtOH disappeared. The paper unearths the influences of EtOH to trap and transform the structure of TCA-CH=O. This discovery has an important contribution to eliminate TCA in order to protect and repair mtDNA by means of the decrease of 8-oxoG.

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“…Mitochondria obtained from the heart of rats were prepared by a modified method of differential centrifugation . All animal experiments were performed in strict compliance with the ARRIVE guidelines and in accordance with the UK Animals (Scientific Procedures) Act 1986 and associated guidelines, EU Directive 2010/63/EU for animal experiments, and the National Institutes of Health guide for the care and use of laboratory animals (NIH Publications No.…”

Section: Methodsmentioning

confidence: 99%

Toxic trans‐crotonaldehyde in mitochondria intercepted by oxyresveratrol contributing to anticancer

Sun

Chen

et al. 2019

IUBMB Life

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The aim of this study was to explore how the toxic trans‐crotonaldehyde (TCA) in mitochondria or aldehyde dehydrogenase (ALDH) at different pHs was intercepted by oxyresveratrol (Oxy‐Res) contributing to anticancer. Ultraviolet–visible (UV–vis) spectroscopy and Raman spectroscopy were employed. UV–vis spectra showed that the Oxy‐Res red shifted the peak of the toxic TCA from 316 nm to 325 nm, while the peaks of the Oxy‐Res shifted from 329 nm with 290 nm and 300 nm to 325 nm with 303 nm. In the mitochondria, the Oxy‐Res blue shifted the peaks of the toxic TCA from 325 nm with 303 nm to 321 nm with 301 nm. Raman spectra revealed that the Oxy‐Res caused shifting of the CHO of the toxic TCA from 1,689 cm−1 to 1,671 cm−1 with band decline. The CC of the toxic TCA at 1641 cm−1 was split into 1,639 cm−1 and 1,642 cm−1 with band decline. The bands of the Oxy‐Res at 1634 cm−1, 1,617 cm−1, and 1,595 cm−1 disappeared. In the mitochondria, the CC of the toxic TCA at 1641 cm−1 splitting disappeared. In ALDH, with the decrease of pH from 7.8 to 6.5, the CHO of the toxic TCA did not red shift from 1,689 cm−1 to 1,674 cm−1 up to pH 6.5. There was no change in the CC of the toxic TCA at 1640 cm−1 in ALDH at different pHs. The conclusion of the study was that the CHO of the toxic TCA was intercepted by the Oxy‐Res under the action of ALDH in the mitochondria, particularly at pH 7.8. © 2019 IUBMB Life, 2019

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Spectroscopic evidences of toxic trans‐crotonaldehyde trapped and transformed by resveratrol to prevent the damage of mitochondrial DNA

Cited by 7 publications

References 56 publications

Theanine in Tea: An Effective Scavenger of Single or Multiple Reactive Carbonyl Species at the Same Time

Theanine in Tea: An Effective Scavenger of Single or Multiple Reactive Carbonyl Species at the Same Time

Influences of ethanol on the structure of toxic trans-crotonaldehyde in mitochondria coming from rat myocardium

Toxic trans‐crotonaldehyde in mitochondria intercepted by oxyresveratrol contributing to anticancer

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