Abstract
To research the antioxidant chemical mechanism of theaflavin, the antioxidant activities of theaflavin were measured in vitro using several chemical models, including DPPH· (1,1-diphenyl-2-picryl-hydrazyl) scavenging, ABTS+· \[2,2’-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid)\] scavenging, and Cu2+-reducing power assays, which was compared with the positive control Trolox. In these assays, theaflavin along with positive control Trolox exhibited dose-dependently antioxidant abilities. The relative antioxidant levels of theaflavin vs Trolox (i.e. IC50,Trolox/IC50,theaflavin value) were calculated as 2.57, 3.13 and 3.74, respectively for DPPH·-scavenging assay, ABTS+·-scavenging assay, and Cu2+-reducing power assay. In conclusion, theaflavin possessed higher antioxidant levels than Trolox. Its antioxidant mechanisms may include hydrogen atom transfer (HAT) and electron transfer (ET). Through HAT mechanism, theaflavin may be transferred into stable ortho-quinone form.
Publication Date
3-28-2018
First Page
23
Last Page
26
DOI
10.13652/j.issn.1003-5788.2018.03.005
Recommended Citation
Hong, XIE; Zhicong, LUO; and Xican, LI
(2018)
"Chemical mechanism of antioxidation of theaflavin,"
Food and Machinery: Vol. 34:
Iss.
3, Article 5.
DOI: 10.13652/j.issn.1003-5788.2018.03.005
Available at:
https://www.ifoodmm.cn/journal/vol34/iss3/5
References
[1] KUSANO R, MATSUO Y, SAITO Y, et al. Oxidation mechanism of black tea pigment theaflavin by peroxidase[J]. Tetrahedron Letters, 2015, 56: 5 099-5 102.
[2] GAO Ying, RANKIN G O, TU You-ying, et al. Inhibitory effects of the four main theaflavin derivatives found in black tea on ovarian cancer cells[J]. Anticancer Research, 2016, 36(2): 643-651.
[3] CAI Fei, LI Cai-rong, WU Ji-liang, et al. Theaflavin ameliorates cerebral ischemia-reperfusion injury in rats through its anti-inflammatory effect and modulation of STAT-1[J]. Mediators of Inflammation, 2006, 5: 30 490.
[4] MANGERICH A, KNUTSON C G, PARRY N M, et al. Infection-induced colitis in mice causes dynamic and tissue-specific changes in stress response and DNA damage leading to colon cancer[J]. Proceedings of the National Academy of Sciences of the United states of America, 2012, 109(27): E1 820-E1 829.
[5] 沈丽萍. 茶黄素研究进展[J]. 中国农学通报, 2010, 26(1): 134-139.
[6] 陈虎, 胡英, 周睿, 等. 茶黄素的抗氧化机理的研究进展[J]. 茶叶科学, 2005, 25(4): 237-241.
[7] SUR S, PAL D, MANDAL S, et al. Tea polyphenols epigallocatechin gallete and theaflavin restrict mouse liver carcinogenesis through modulation of self-renewal Wnt and hedgehog pathways[J]. Journal of Nutritional Biochemistry, 2016, 27: 32-42.
[8] LI Xi-can, WEI Gang, WANG Xiao-zhen, et al. Targeting of the shh pathway by atractylenolides promotes chondrogenic differentiation of mesenchymal stem Cells[J]. Biological & Pharmaceutical Bulletin, 2012, 35: 1 328-1 335.
[9] WANG Ting-ting, ZENG Gong-chang, LI Xi-can, et al. In vitro studies on the antioxidant and protective effect of 2-substituted-8-hydroxyquinoline derivatives against H2O2-Induced oxidative stress in BMSCs[J]. Chemical Biological Drug Design, 2010, 75(2): 214-222.
[10] LI Xi-can, CHEN Dong-feng, MAI Ying, et al. Concordance between antioxidant activities in vitro and chemical components of Radix Astragali (Huangqi)[J]. Natural Product Research, 2012, 26: 1 050-1 053.
[11] LI Xi-can, LIU Jing-jing, LIN Jian, et al. Protective effects of dihydromyricetin against ·OH-induced mesenchymal stem cells damage and mechanistic chemistry[J]. Molecules, 2016, 21: 604.
[12] LI Xi-can, JIANG Qian, WANG Ting-ting, et al. Comparison of the antioxidant effects of quercitrin and isoquercitrin: Understand-ing the role of the 6″-OH group[J]. Molecules, 2016, 21: 1 246.
[13] LI Xi-can, HAN Lu, LI Yung-rong, et al. Protective effect of sinapine against hydroxyl radical-induced damage to mesenchymal stem cells and possible mechanisms[J]. Chemical & Pharmaceutical Bulletin, 2016, 64: 319-325.
[14] LI Xi-can, HAN Wei-juan, MAI Wen-qiong, et al. Antioxidant Activity and Mechanism of Tetrahydroamentoflavone in vitro[J]. Natural Product Communications, 2013, 8: 787-789.
[15] WANG Guang-rong, LI Xi-can, ZENG He-ping. Synthesis, antioxidation activity of (E)-9-p-Tolyl-3-[2-(8-hydroxy-quinol-2-yl)vinyl]-carbazole and (E)-9-(p-Anisyl)-3-[2-(8-hydroxy-quinol-2-yl)vinyl]-carbazole and their induction proliferation of mesenchymal stem cells[J]. Acta Chimica Sinica, 2009, 67(9): 974-982.
[16] CHEN Dong-feng, LI Xi-can, XU Zhi-wei, et al. Hexadecanoic acid from buzhong yiqi decoction induces proliferation of bone marrow mesenchymal stem cells[J]. Journal of Medicinal Food, 2010, 13: 967-970.
[17] LI Xi-can, HU Qiu-ping, JIANG Shu-xia, et al. Flos Chrysanthemi Indici protects against hydroxyl-induced damages to DNA and MSCs via antioxidant mechanism: A chemistry study[J]. Journal of Saudi Chemical Society, 2015, 19: 454-460.
[18] TAN Dun-xian, HARDELAND R, MANCHESTER L, et al. Mechanistic and comparative studies of melatonin and classic antioxidants in terms of their interactions with the ABTS cation radical[J]. Journal of Pineal Research, 2003, 34: 249-259.
[19] LIN Jian, LI Xi-can, CHEN Li, et al. Protective effect against hydroxyl radical-induced DNA damage and antioxidant mechanism of [6]-gingerol: A chemical study[J]. Bulletin of the Korean Chemical Society, 2014, 6: 1 633-1 638.
[20] LI Xi-can, MAI Wen-qiong, CHEN Dong-feng, et al. Chemical study on protective effect against hydroxyl-induced DNA damage and antioxidant mechanism of myricitrin[J]. Journal of the Chinese Chemical Society, 2014, 61: 383-390.
[21] LIU Jing-jing, LI Xi-can, LIN Jian, et al. Sarcandra glabra (Caoshanhu) protects mesenchymal stem cells from oxidative stress: A bioevaluation and mechanistic chemistry[J]. BMC Complementary and Alternative Medicine, 2016, 16: 423.
[22] VALENT I, TOPOLSK D, VALACHOV K, et al. Kine-tics of ABTS derived radical cation scavenging by bucillamine, cysteine, and glutathione: Catalytic effect of Cu2+ ions[J]. Biophysical Chemistry, 2016, 212: 9-16.