黄酮类化合物与α-羟乙基过氧自由基反应的脉冲辐解研究

doi:10.3866/PKU.WHXB201210232

Abstract

Abstract:

Lipid peroxidation (LPO) plays an important role in many pathological processes (such as hepatitis, hepatic sclerosis, atherosclerosis, cerebral hemorrhage and so on), and flavonoids are considered to be effective LPO-inhibitors. Thus we investigated the relationship between the chemical structure of flavonoids and the LPO activity and the antioxidant mechanism of flavonoids. In this work, α-hydroxyl ethyl peroxyl radicals were produced from radiolysis of aerated ethanol to model lipid peroxyl radicals. By detecting the decay of α-hydroxyl ethyl peroxyl radicals in the presence of different concentrations of flavonoids using pulse radiolysis, the reaction rate constants of α-hydroxyl ethyl peroxyl radicals with quercetin, rutin, catechin, and baicalin are determined for the first time. The antioxidant activity of these flavonoids decreases in the order: rutin > quercetin > baicalin > catechin. Flavone and pyrocatechol were used as model compounds for the different components in flavonoids and their reaction rate constants towards α-hydroxyl ethyl peroxyl radicals were (1.7±0.1)×10⁶ and (2.9±0.1)×10⁵ mol^-1·dm³· s^-1, respectively. The effect of chemical structure on the scavenging activity towards α-hydroxyl ethyl peroxyl radicals was investigated. The coexistence of the C₅-hydroxyl group in the A ring with the C₂＝C₃ in the C ring or the conjugated double bond of the B-C ring and the catechol group in the B ring provides the best antioxidant activity. In addition, the C₂＝C₃ in the C ring or the conjugated double bond of the B-C ring is more effective than the catechol group in the B ring, while the C₃-rutinose in the C ring has no obvious effect. Therefore, we conclude that the addition reaction between double bonds with peroxyl radicals plays an important role in the antioxidant activity of flavonoids in LPO.

Key words: Flavonoids, Anti-lipid peroxidation, Pulse radiolysis, Dynamics, Chemical structure

MSC2000:

O643.12

ZHANG Fu-Gen, ZHOU Han-Yang, PENG Jing, WU Ji-Lan. Reactions between Flavonoids and α-Hydroxyl Ethyl Peroxyl Radicals: a Pulse Radiolysis Study[J].Acta Phys. -Chim. Sin., 2013, 29(01): 199-204.

References

(1) Poli, G.; Albano, E.; Dianzani, M. U. Free Radicals: From Basic Science to Medicine; Birkhauser Verlag Basel:Switzerland, 1993; pp 65-79.
(2) Farkas, L.; Gabor, M.; Kalley, F. Flavonoids and Bioflavonoids;Szeged: Hungary, 1985; pp 423-436.
(3) Ratty, A. K.; Das, N. P. Biochemical Medicine and Metabolic Biology 1988, 39, 69. doi: 10.1016/0885-4505(88)90060-6
(4) Butkovic, V.; Klasinc, L.; Bors,W. Journal of Agricultural and Food Chemistry 2004, 52, 2816. doi: 10.1021/jf049880h
(5) Lu, X. X. Food Research and Development 2012, 33, 220.[鲁晓翔. 食品研究与开发, 2012, 33, 220.]
(6) Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.;Simic, M. G. J. Am. Chem. Soc. 1994, 116, 4846. doi: 10.1021/ja00090a032
(7) Jovanovic, S. V.; Hara, Y.; Steenken, S.; Simic, M. G. J. Am. Chem. Soc. 1995, 117, 9881. doi: 10.1021/ja00144a014
(8) Jovanovic, S. V.; Steenken, S.; Hara, Y.; Simic, M. G. Journal of the Chemical Society-Perkin Transactions 2 1996, 2497.
(9) Lundberg,W. O. Autoxidation and Antioxidants; Interscience:London, 1961; pp 133-169.
(10) Shieh, D. E.; Liu, L. T.; Lin, C. C. Anticancer Research 2000,20, 2861.
(11) Waisundara, V. Y.; Hsu, A. N.; Tan, B. K. H.; Huang, D. J.Journal of Agricultural and Food Chemistry 2009, 57, 4096.doi: 10.1021/jf8028539
(12) Min,W.; Lin, X. F.; Miao, X.;Wang, B. T.; Yang, Z. L.; Luo, D.American Journal of Chinese Medicine 2008, 36, 745. doi: 10.1142/S0192415X0800620X
(13) Liu, L. Y.;Wei, E. Q.; Zhao, Y. M.; Chen, F. X.;Wang, M. L.;Zhang,W. P.; Chen, Z. Journal of Pharmacy and Pharmacology2005, 57, 1019. doi: 10.1211/0022357056622
(14) Jin, F. M.; Leitich, J.; von Sonntag, C. Journal of the Chemical Society-Perkin Transactions 2 1993, 1583.
(15) Zhang, X. J.;Wu, J. L.; Cai, Z. L.; Yao, S. D.; Zuo, Z. H.; Lin,N. Y. Radiation Research 1995, 142, 227. doi: 10.2307/3579033
(16) Cai, Z. L.; He, Y. K.;Wu, J. L. Radiat. Phys. Chem. 1996, 47,213. doi: 10.1016/0969-806X(94)00182-J
(17) Cai, Z. L.; He, Y. K.;Wu, J. L. Radiat. Phys. Chem. 1996, 47,869. doi: 10.1016/0969-806X(95)00179-2
(18) Deng,W. G.; He, Y. K.; Fang, X.W.;Wu, J. L. Radiat. Phys. Chem. 1998, 53, 629. doi: 10.1016/S0969-806X(97)00276-4
(19) Bothe, E.; Schuchmann, M. N.; Schultefrohlinde, D.;Vonsonntag, C. Zeitschrift für Naturforschung Section B-a Journal of Chemical Sciences 1983, 38, 212.
(20) Vonsonntag, C.; Dowideit, P.; Fang, X.W.; Mertens, R.; Pan, X.M.; Schuchmann, M. N.; Schuchmann, H. P. Water Science and Technology 1997, 35, 9.
(21) Bothe, E.; Schuchmann, M. N.; Schultefrohlinde, D.;Vonsonntag, C. Photochemistry and Photobiology 1978, 28,639. doi: 10.1111/php.1978.28.issue-4-5
(22) Taub, I. A.; Dorfman, L. M. J. Am. Chem. Soc. 1962, 84, 4053.doi: 10.1021/ja00880a016
(23) Dorfman, L. M.; Taub, I. A. J. Am. Chem. Soc. 1963, 85, 2370.doi: 10.1021/ja00899a006
(24) MacLachlan, A. J. Am. Chem. Soc. 1965, 87, 960. doi: 10.1021/ja01083a004
(25) Emerit, I.; Packer, L.; Auclair, C. Antioxidants in Therapy and Preventive Medicine, Advances in Experimental Medicine and Biology; Plenum Press: New York, 1990; Vol. 264, pp 165-170.
(26) Zhu, D. Z.; Sun, D. M.; Jiang, Z. L.;Wang, S. L.; Sun, X. Y.; Ni,Y. M. Acta Phys. -Chim. Sin. 2008, 24, 2321. [朱大章, 孙冬梅, 蒋忠良, 汪世龙, 孙晓宇, 倪亚明. 物理化学学报, 2008, 24,2321.] doi: 10.3866/PKU.WHXB20081229
(27) Tang, R. Z.; Zhang, P.; Li, H. X.; Liu, Y. C.;Wang,W. F. Acta Phys. -Chim. Sin. 2011, 27, 1975. [唐睿智, 张鹏, 李海霞,刘艳成, 王文锋. 物理化学学报, 2011, 27, 1975.] doi: 10.3866/PKU.WHXB20110825
(28) Zhang, F. G.;Wu, J. L.; Li, F. M.; Liu, A. D. Chem. J. Chin. Univ. 2002, 23, 461. [张福根, 吴季兰, 李凤梅, 刘安东. 高等学校化学学报, 2002, 23, 461.]
(29) Liu, A. D.; Zhao, Z.W.; Tong, Z. L.; Sun, Y. X.; Gu, H. C.;Shun,W. H.; Hu, H. D.; Hao, Z. H.; Zhou, R. Y. Radiat. Phys. Chem. 1989, 34, 461.
(30) Adams, G. E.;Willson, R. L. Transactions of the Faraday Society 1969, 65, 2981. doi: 10.1039/tf9696502981
(31) Lee, J. H.; Kim, G. H. Journal of Food Science 2010, 75, H212.
(32) Roginsky, V. Archives of Biochemistry and Biophysics 2003,414, 261. doi: 10.1016/S0003-9861(03)00143-7
(33) Lu, N.; Zhang, Y.; Gao, Z. H. Toxicology in Vitro 2009, 23, 627.doi: 10.1016/j.tiv.2009.02.013
(34) Xiao, J. B.; Kai, G. Y.; Ni, X. L.; Yang, F.; Chen, X. Q.Molecular Biosystems 2011, 7, 1883. doi: 10.1039/c1mb05008g

[1]	Cheng Ma, Xiangyu Dou, Zeyu Liu, Peilong Liao, Zhiyang Zhu, Kaerdun Liu, Jianbin Huang. Application and Mechanism of a Novel CO₂-Oil Miscible Flooding Agent, CAA8-X [J]. Acta Phys. -Chim. Sin., 2022, 38(8): 2012019-.
[2]	Hongwei Yu, Shi Li, Jinlong Li, Shaohua Zhu, Chengzhen Sun. Interfacial Mass Transfer Characteristics and Molecular Mechanism of the Gas-Oil Miscibility Process in Gas Flooding [J]. Acta Phys. -Chim. Sin., 2022, 38(5): 2006061-.
[3]	Haoran Lu, Yaqing Wei, Run Long. Charge Localization Induced by Nanopore Defects in Monolayer Black Phosphorus for Suppressing Nonradiative Electron-Hole Recombination through Time-Domain Simulation [J]. Acta Phys. -Chim. Sin., 2022, 38(5): 2006064-.
[4]	Chong Cao, Pei Zhang, Lidong Cao, Mingxin Liu, Yuying Song, Peng Chen, Qiliang Huang, Buxing Han. Experimental and Molecular Dynamic Simulation of Droplet Deposition on Superhydrophobic Plant Leaf Surfaces [J]. Acta Phys. -Chim. Sin., 2022, 38(12): 2207006-.
[5]	Mengting Li, Xingqun Zheng, Li Li, Zidong Wei. Research Progress of Hydrogen Oxidation and Hydrogen Evolution Reaction Mechanism in Alkaline Media [J]. Acta Phys. -Chim. Sin., 2021, 37(9): 2007054-.
[6]	Wenqiong Chen, Yongji Guan, Jiao Zhang, Junjie Pei, Xiaoping Zhang, Youquan Deng. Atomistic Insight into Changes in the Vibrational Spectrum of Ionic Liquids under External Electric Field [J]. Acta Phys. -Chim. Sin., 2021, 37(10): 2001004-.
[7]	Fanghong Qin, Ting Wan, Jiangyuan Qiu, Yihui Wang, Biyuan Xiao, Zaiyin Huang. Temperature Effects on Photocatalytic Heat Changes and Kinetics via In Situ Photocalorimetry-Fluorescence Spectroscopy [J]. Acta Physico-Chimica Sinica, 2020, 36(6): 1905087-.
[8]	Zhenfeng Pang,Hanxi Guan,Lina Gao,Weicheng Cao,Jinglin Yin,Xueqian Kong. Fundamentals and Applications of NMR Hyperpolarization Techniques [J]. Acta Physico-Chimica Sinica, 2020, 36(4): 1906018-.
[9]	Chengzhen Sun, Runfeng Zhou, Bofeng Bai. Electrostatic Effect-based Selective Permeation Characteristics of Graphene Nanopores [J]. Acta Phys. -Chim. Sin., 2020, 36(11): 1911044-.
[10]	Mingliang Li, Shuo Li, Guozhi Wang, Xuefeng Guo. Effects of Alkyl-Chain Engineering on the Thermodynamic Properties of Amphiphilic Organic Semiconductors [J]. Acta Physico-Chimica Sinica, 2020, 36(11): 1908036-.
[11]	Tao ZHANG,Yunguang QIU,Qichao LUO,Xi CHENG,Lifen ZHAO,Xin YAN,Bo PENG,Hualiang JIANG,Huaiyu YANG. Concentration Dependent Effects of Ca²⁺ and Mg²⁺ on the Phosphatidylethanolamine-Phosphatidylglycerol Bilayer [J]. Acta Physico-Chimica Sinica, 2019, 35(8): 840-849.
[12]	Hai LIU,Yi LI,Zhaoxia MA,Zhixuan ZHOU,Junling LI,Yuanhang HE. Study on the Initial Decomposition Mechanism of Energetic Co-Crystal 2, 4, 6, 8, 10, 12-Hexanitro-2, 4, 6, 8, 10, 12-Hexaazaiso-Wurtzitane (CL-20)/1, 3, 5, 7-Tetranitro-1, 3, 5, 7-Tetrazacy-Clooctane (HMX) under a Steady Shock Wave [J]. Acta Physico-Chimica Sinica, 2019, 35(8): 858-867.
[13]	Wen XIE,Huan HE,Jiaxin DONG,Qinglian GUO,Yi LIU. Thermodynamics of the Interaction of Morin with Bovine Serum Albumin [J]. Acta Phys. -Chim. Sin., 2019, 35(7): 725-733.
[14]	Xiejun XU,Xingqing XIAO,Shouhong XU,Honglai LIU. Computational Study of Thermosensitivity of Liposomes Modulated by Leucine Zipper-Structured Lipopeptides [J]. Acta Physico-Chimica Sinica, 2019, 35(6): 598-606.
[15]	Kangjie LYU,Yanqiu PENG,Li XIAO,Juntao LU,Lin ZHUANG. Atomistic Understanding of the Peculiar Dissolution Behavior of Alkaline Polymer Electrolytes in Alcohol/Water Mixed Solvents [J]. Acta Phys. -Chim. Sin., 2019, 35(4): 378-384.

Reactions between Flavonoids and α-Hydroxyl Ethyl Peroxyl Radicals: a Pulse Radiolysis Study

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0