CLC number: O69
On-line Access: 2024-08-27
Received: 2023-10-17
Revision Accepted: 2024-05-08
Crosschecked: 2019-09-12
Cited: 0
Clicked: 4167
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,in press.Frontiers of Information Technology & Electronic Engineering,in press.https://doi.org/10.1631/jzus.B1900211 @article{title="Scavenging activity and mechanism study of ferulic acid against reactive carbonyl species acrolein", %0 Journal Article TY - JOUR
阿魏酸对活性羰基化合物丙烯醛清除活性及机理研究创新点:发现了常见的天然酚酸阿魏酸具有有效清除丙烯醛的活性,且其反应位点与其他具有丙烯醛清除活性的酚酸类化合物不同.研究了该反应的过程,推测了其反应机理,并考察了该反应的构效关系. 方法:(1)通过相同时间内阿魏酸对丙烯醛、谷胱甘肽的影响考察其清除活性;(2)运用气相色谱-质谱联用技术(GC-MS)、核磁共振技术(NMR)等技术鉴定产物结构;(3)通过研究阿魏酸、丙烯醛和反应产物之间的互相转化关系,推断该反应的过程. 结论:(1)阿魏酸可以有效抑制丙烯醛对细胞抗氧化系统的破坏;(2)该反应的过程是由阿魏酸在丙烯醛作用下脱羧,得到脱羧产物,再与丙烯醛进行迈克尔加成,得到最终加合产物;(3)苯环4号位的羟基对于脱羧过程是必需的;(4)苯环3号位的甲氧基可以大幅度提高加合产物的产率;(5)阿魏酸及其类似物的酯与丙烯醛不发生反应. 关键词组: Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article
Reference[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. ![]() [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 ![]() [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 23–25 ![]() [47]Table S1 Diseases proved to be related to acrolein ![]() Journal of Zhejiang University-SCIENCE, 38 Zheda Road, Hangzhou
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