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On-line Access: 2019-10-09

Received: 2019-04-21

Revision Accepted: 2019-07-09

Crosschecked: 2019-09-12

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Journal of Zhejiang University SCIENCE B 2019 Vol.20 No.11 P.868-876


Scavenging activity and mechanism study of ferulic acid against reactive carbonyl species acrolein

Author(s):  Zhi-Hao Tao, Chang Li, Xiao-Fei Xu, Yuan-Jiang Pan

Affiliation(s):  Department of Chemistry, Zhejiang University, Hangzhou 310027, China; more

Corresponding email(s):   lichang@zju.edu.cn, panyuanjiang@zju.edu.cn

Key Words:  Acrolein, Reactive carbonyl species, Ferulic acid, Cytotoxicity, Oxidative stress

Zhi-Hao Tao, Chang Li, Xiao-Fei Xu, Yuan-Jiang Pan. Scavenging activity and mechanism study of ferulic acid against reactive carbonyl species acrolein[J]. Journal of Zhejiang University Science B, 2019, 20(11): 868-876.

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author="Zhi-Hao Tao, Chang Li, Xiao-Fei Xu, Yuan-Jiang Pan",
journal="Journal of Zhejiang University Science B",
publisher="Zhejiang University Press & Springer",

%0 Journal Article
%T Scavenging activity and mechanism study of ferulic acid against reactive carbonyl species acrolein
%A Zhi-Hao Tao
%A Chang Li
%A Xiao-Fei Xu
%A Yuan-Jiang Pan
%J Journal of Zhejiang University SCIENCE B
%V 20
%N 11
%P 868-876
%@ 1673-1581
%D 2019
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.B1900211

T1 - Scavenging activity and mechanism study of ferulic acid against reactive carbonyl species acrolein
A1 - Zhi-Hao Tao
A1 - Chang Li
A1 - Xiao-Fei Xu
A1 - Yuan-Jiang Pan
J0 - Journal of Zhejiang University Science B
VL - 20
IS - 11
SP - 868
EP - 876
%@ 1673-1581
Y1 - 2019
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.B1900211

acrolein, known as one of the most common reactive carbonyl species, is a toxic small molecule affecting human health in daily life. This study is focused on the scavenging abilities and mechanism of ferulic acid and some other phenolic acids against acrolein. Among the 13 phenolic compounds investigated, ferulic acid was found to have the highest efficiency in scavenging acrolein under physiological conditions. ferulic acid remained at (3.04±1.89)% and acrolein remained at (29.51±4.44)% after being incubated with each other for 24 h. The molecular mechanism of the detoxifying process was also studied. Detoxifying products, namely 2-methoxy-4-vinylphenol (product 21) and 5-(4-hydroxy-3-methoxyphenyl)pent-4-enal (product 22), were identified though nuclear magnetic resonance (NMR) and gas chromatography-mass spectrometry (GC-MS), after the scavenging process. ferulic acid showed significant activity in scavenging acrolein under physiological conditions. This study indicates a new method for inhibiting damage from acrolein.




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[1]Ålin P, Danielson UH, Mannervik B, 1985. 4-Hydroxyalk-2-enals are substrates for glutathione transferase. FEBS Lett, 179(2):267-270.

[2]Amro B, Aburjai T, Al-Khalil S, 2002. Antioxidative and radical scavenging effects of olive cake extract. Fitoterapia, 73(6):456-461.

[3]Balasubashini MS, Rukkumani R, Menon VP, 2003. Protective effects of ferulic acid on hyperlipidemic diabetic rats. Acta Diabetol, 40(3):118-122.

[4]Barone E, Calabrese V, Mancuso C, 2009. Ferulic acid and its therapeutic potential as a hormetin for age-related diseases. Biogerontology, 10(2):97-108.

[5]Baskaran X, Vigila AVG, Zhang S, et al., 2018. A review of the use of pteridophytes for treating human ailments. J Zhejiang Univ-Sci B (Biomed & Biotechnol), 19(2):85-119.

[6]Calabrese V, Calafato S, Puleo E, et al., 2008. Redox regulation of cellular stress response by ferulic acid ethyl ester in human dermal fibroblasts: role of vitagenes. Clin Dermatol, 26(4):358-363.

[7]Cassano R, Trombino S, Cilea A, et al., 2010. L-lysine pro-prodrug containing trans-ferulic acid for 5-amino salicylic acid colon delivery: synthesis, characterization and in vitro antioxidant activity evaluation. Chem Pharm Bull (Tokyo), 58(1):103-105.

[8]Catino S, Paciello F, Miceli F, et al., 2016. Ferulic acid regulates the Nrf2/heme oxygenase-1 system and counteracts trimethyltin-induced neuronal damage in the human neuroblastoma cell line SH-SY5Y. Front Pharmacol, 6:305.

[9]Cox PJ, 1979. Cyclophosphamide cystitis—Identification of acrolein as the causative agent. Biochem Pharmacol, 28(13):2045-2049.

[10]DeJarnett N, Conklin DJ, Riggs DW, et al., 2014. Acrolein exposure is associated with increased cardiovascular disease risk. J Am Heart Assoc, 3(4):e000934.

[11]Doggui S, Belkacemi A, Paka GD, et al., 2013. Curcumin protects neuronal-like cells against acrolein by restoring Akt and redox signaling pathways. Mol Nutr Food Res, 57(9):1660-1670.

[12]Esterbauer H, Schaur RJ, Zollner H, 1991. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic Biol Med, 11(1):81-128.

[13]Fetoni AR, Mancuso C, Eramo SLM, et al., 2010. In vivo protective effect of ferulic acid against noise-induced hearing loss in the guinea-pig. Neuroscience, 169(4): 1575-1588.

[14]He S, Jiang LY, Wu B, et al., 2009. Pallidol, a resveratrol dimer from red wine, is a selective singlet oxygen quencher. Biochem Biophys Res Commun, 379(2):283-287.

[15]Huang RT, Huang Q, Wu GL, et al., 2017. Evaluation of the antioxidant property and effects in Caenorhabditis elegans of Xiangxi flavor vinegar, a Hunan local traditional vinegar. J Zhejiang Univ-Sci B (Biomed & Biotechnol), 18(4):324-333.

[16]Joshi G, Perluigi M, Sultana R, et al., 2006. In vivo protection of synaptosomes by ferulic acid ethyl ester (FAEE) from oxidative stress mediated by 2,2-azobis(2-amidino-propane)dihydrochloride (AAPH) or Fe2+/H2O2: insight into mechanisms of neuroprotection and relevance to oxidative stress-related neurodegenerative disorders. Neurochem Int, 48(4):318-327.

[17]Jung SH, Kim JH, 2002. Efficient method for β-conjugate addition of α,β-unsaturated lactones and esters. Bull Korean Chem Soc, 23(3):365-366.

[18]Kovalev IP, Kolmogorov YN, Yinogradov MG, et al., 1990. The linear dimerization of vinyl ketones catalyzed by the [RhCl(C2H4)2]2-GeCl2 system. Russ Chem Bull, 39(5): 1070-1071.

[19]Kumar N, Pruthi V, 2014. Potential applications of ferulic acid from natural sources. Biotechnol Rep, 4:86-93.

[20]Li C, Xu XF, Tao ZH, et al., 2015. Resveratrol dimers, nutritional components in grape wine, are selective ROS scavengers and weak Nrf2 activators. Food Chem, 173: 218-223.

[21]Liu F, Li XL, Lin T, et al., 2012. The cyclophosphamide metabolite, acrolein, induces cytoskeletal changes and oxidative stress in Sertoli cells. Mol Biol Rep, 39(1):493-500.

[22]Lovell MA, Xie CS, Markesbery WR, 2001. Acrolein is increased in Alzheimer’s disease brain and is toxic to primary hippocampal cultures. Neurobiol Aging, 22(2):187-194.

[23]Luo J, Shi RY, 2005. Acrolein induces oxidative stress in brain mitochondria. Neurochem Int, 46(3):243-252.

[24]Mancuso C, Santangelo R, 2014. Ferulic acid: pharmacological and toxicological aspects. Food Chem Toxicol, 65: 185-195.

[25]Mano J, 2012. Reactive carbonyl species: their production from lipid peroxides, action in environmental stress, and the detoxification mechanism. Plant Physiol Biochem, 59:90-97.

[26]Mano J, Miyatake F, Hiraoka E, et al., 2009. Evaluation of the toxicity of stress-related aldehydes to photosynthesis in chloroplasts. Planta, 230(4):639-648.

[27]Martirosyan A, Leonard S, Shi XL, et al., 2006. Actions of a histone deacetylase inhibitor NSC3852 (5-nitroso-8-quinolinol) link reactive oxygen species to cell differentiation and apoptosis in MCF-7 human mammary tumor cells. J Pharmacol Exp Ther, 317(2):546-552.

[28]Mhillaj E, Catino S, Miceli FM, et al., 2018. Ferulic acid improves cognitive skills through the activation of the heme oxygenase system in the rat. Mol Neurobiol, 55(2): 905-916.

[29]Picone P, Bondi ML, Montana G, et al., 2009. Ferulic acid inhibits oxidative stress and cell death induced by Ab oligomers: improved delivery by solid lipid nanoparticles. Free Radic Res, 43(11):1133-1145.

[30]Rom O, Korach-Rechtman H, Hayek T, et al., 2017. Acrolein increases macrophage atherogenicity in association with gut microbiota remodeling in atherosclerotic mice: protective role for the polyphenol-rich pomegranate juice. Arch Toxicol, 91(4):1709-1725.

[31]Shamoto-Nagai M, Maruyama W, Hashizume Y, et al., 2007. In parkinsonian substantia nigra, α-synuclein is modified by acrolein, a lipid-peroxidation product, and accumulates in the dopamine neurons with inhibition of proteasome activity. J Neural Transm (Vienna), 114(12): 1559-1567.

[32]Sheu SJ, Ho YS, Chen YP, et al., 1987. Analysis and processing of Chinese herbal drugs; VI. The study of Angelicae radix. Planta Med, 53(4):377-378.

[33]Srinivasan M, Sudheer AR, Menon VP, 2007. Ferulic acid: therapeutic potential through its antioxidant property. J Clin Biochem Nutr, 40(2):92-100.

[34]Stevens JF, Maier CS, 2008. Acrolein: sources, metabolism, and biomolecular interactions relevant to human health and disease. Mol Nutr Food Res, 52(1):7-25.

[35]Suzuki D, Miyata T, 1999. Carbonyl stress in the pathogenesis of diabetic nephropathy. Intern Med, 38(4):309-314.

[36]Trombino S, Cassano R, Ferrarelli T, et al., 2013. Trans-ferulic acid-based solid lipid nanoparticles and their antioxidant effect in rat brain microsomes. Colloids Surf B Biointerfaces, 109:273-279.

[37]Vandeputte C, Guizon I, Genestie-Denis I, et al., 1994. A microtiter plate assay for total glutathione and glutathione disulfide contents in cultured/isolated cells: performance study of a new miniaturized protocol. Cell Biol Toxicol, 10(5-6):415-421.

[38]Wang WX, Qi YJ, Rocca JR, et al., 2015. Scavenging of toxic acrolein by resveratrol and hesperetin and identification of adducts. J Agric Food Chem, 63(43):9488-9495.

[39]Wang Y, Cui P, 2015. Reactive carbonyl species derived from omega-3 and omega-6 fatty acids. J Agric Food Chem, 63(28):6293-6296.

[40]Yaylayan VA, Keyhani A, 2000. Origin of carbohydrate degradation products in L-alanine/D-[13C]glucose model systems. J Agric Food Chem, 48(6):2415-2419.

[41]Zamora R, Aguilar I, Granvogl M, et al., 2016. Toxicologically relevant aldehydes produced during the frying process are trapped by food phenolics. J Agric Food Chem, 64(27): 5583-5589.

[42]List of electronic supplementary materials

[43]Fig. S1 GC-MS of product 21

[44]Fig. S2 1H-NMR results of product 21

[45]Fig. S3 NMR results of product 22

[46]Fig. S4 Structures of compounds 2325

[47]Table S1 Diseases proved to be related to acrolein

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