alpha-Tocopherolquinone (BioDeep_00000021717)

 

Secondary id: BioDeep_00000265863, BioDeep_00000619033, BioDeep_00000837648

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

化学式: C29H50O3 (446.37597500000004)
中文名称: 托可醌
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.5%

分子结构信息

SMILES: C1(=C(C(=O)C(=C(C1=O)CC[C@@](O)(C)CCC[C@@H](CCC[C@H](CCCC(C)C)C)C)C)C)C
InChI: InChI=1S/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3

描述信息

Isolated from spinach (Spinacia oleracea) chloroplasts and many other plant sources. alpha-Tocopherolquinone is found in many foods, some of which are brassicas, spinach, barley, and anise.
alpha-Tocopherolquinone is found in anise. alpha-Tocopherolquinone is isolated from spinach (Spinacia oleracea) chloroplasts and many other plant source
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents
D006401 - Hematologic Agents > D000925 - Anticoagulants
D020011 - Protective Agents > D000975 - Antioxidants
D-α-Tocopherylquinone (α-Tocopherylquinone) is a quinone, can be isolated from Phaeodactylum tricornutum. D-α-Tocopherylquinone is a oxidation product of α-Tocopherol (vitamin E). D-α-Tocopherylquinone can act as an anticoagulant and as an antioxidant[1][2].

同义名列表

26 个代谢物同义名

2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione; 2 (3-Hydroxy-3,7,11,15-tetramethylhexadecyl)- 3,5,6-trimethyl-1,4-benzoquinone; Tocopherylquinone, ((3R*,7R*,11R*)-(+-))-isomer; alpha-tocopheryl quinone; alpha-Tocopherol quinone; delta-Tocopherylquinone; alpha-Tocopherolquinone; gamma-Tocopherylquinone; alpha-Tocopheroquinone; a-Tocopheryl quinone; Α-tocopherolquinone; a-Tocopherolquinone; alpha-Tocoquinone; Tocopherylquinone; Tocopherolquinone; Vitamin e quinone; a-Tocoquinone; Vitapressina; Tensiopress; Ipotensil; Eutrophyl; Metorena; Trimina; D 178; α-Tocopherylquinone; D-α-Tocopherylquinone



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

7 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Miroslav Dragoun, Kateřina Klausová, Petra Šimicová, Tereza Honzíková, Jiří Stejskal, Klára Navrátilová, Jana Hajšlová, Jan Bárta, Veronika Bártová, Markéta Jarošová, Marie Bjelková, Vladimír Filip, Jan Kyselka. Formation of Previously Undescribed Δ7-Phytosterol Oxidation Products and Tocopherylquinone Adducts in Pumpkin Seed Oil during Roasting, Screw-Pressing, and Simulated Culinary Processing at Elevated Temperatures. Journal of agricultural and food chemistry. 2022 Sep; 70(37):11689-11703. doi: 10.1021/acs.jafc.2c03292. [PMID: 36094395]
  • Tao Sun, Bing Zhang, Qing-Jing Ru, Xiao-Mei Chen, Bo-Dong Lv. Tocopheryl quinone improves non-alcoholic steatohepatitis (NASH) associated dysmetabolism of glucose and lipids by upregulating the expression of glucagon-like peptide 1 (GLP-1) via restoring the balance of intestinal flora in rats. Pharmaceutical biology. 2021 Dec; 59(1):723-731. doi: 10.1080/13880209.2021.1916542. [PMID: 34139927]
  • Etsuo Niki, Noriko Noguchi. Antioxidant action of vitamin E in vivo as assessed from its reaction products with multiple biological oxidants. Free radical research. 2021 Apr; 55(4):352-363. doi: 10.1080/10715762.2020.1866181. [PMID: 33327809]
  • Pierangelo Torquato, Desirée Bartolini, Danilo Giusepponi, Marta Piroddi, Bartolomeo Sebastiani, Giorgio Saluti, Roberta Galarini, Francesco Galli. Increased plasma levels of the lipoperoxyl radical-derived vitamin E metabolite α-tocopheryl quinone are an early indicator of lipotoxicity in fatty liver subjects. Free radical biology & medicine. 2019 02; 131(?):115-125. doi: 10.1016/j.freeradbiomed.2018.11.036. [PMID: 30508576]
  • Luke Taylor, Nick Krueger, Olga Malysheva, Jeffrey Atkinson, Robert S Parker. ω-Hydroxylation of α-tocopheryl quinone reveals a dual function for cytochrome P450-4F2 in vitamin E metabolism. Bioorganic & medicinal chemistry. 2018 11; 26(20):5555-5565. doi: 10.1016/j.bmc.2018.10.002. [PMID: 30316641]
  • Shao-Wei Wang, Shi-Gao Yang, Wen Liu, Yang-Xin Zhang, Peng-Xin Xu, Teng Wang, Tie-Jun Ling, Rui-Tian Liu. Alpha-tocopherol quinine ameliorates spatial memory deficits by reducing beta-amyloid oligomers, neuroinflammation and oxidative stress in transgenic mice with Alzheimer's disease. Behavioural brain research. 2016 Jan; 296(?):109-117. doi: 10.1016/j.bbr.2015.09.003. [PMID: 26358659]
  • Mototada Shichiri, Nobuyoshi Harada, Noriko Ishida, Lilian Kaede Komaba, Sunao Iwaki, Yoshihisa Hagihara, Etsuo Niki, Yasukazu Yoshida. Oxidative stress is involved in fatigue induced by overnight deskwork as assessed by increase in plasma tocopherylhydroqinone and hydroxycholesterol. Biological psychology. 2013 Dec; 94(3):527-33. doi: 10.1016/j.biopsycho.2013.10.002. [PMID: 24121154]
  • Penelope C McLernon, Lisa G Wood, Vanessa E Murphy, Nicolette A Hodyl, Vicki L Clifton. Circulating antioxidant profile of pregnant women with asthma. Clinical nutrition (Edinburgh, Scotland). 2012 Feb; 31(1):99-107. doi: 10.1016/j.clnu.2011.09.006. [PMID: 21962399]
  • Amale Hawi, Sarah Heald, Thomas Sciascia. Use of an adaptive study design in single ascending-dose pharmacokinetics of A0001 (α-tocopherylquinone) in healthy male subjects. Journal of clinical pharmacology. 2012 Jan; 52(1):65-77. doi: 10.1177/0091270010390807. [PMID: 21343342]
  • Tie-Jun Ling, Wei-Wei Ling, Yuan-Jun Chen, Xiao-Chun Wan, Tao Xia, Xian-Feng Du, Zheng-Zhu Zhang. Antiseptic activity and phenolic constituents of the aerial parts of Vitex negundo var. cannabifolia. Molecules (Basel, Switzerland). 2010 Nov; 15(11):8469-77. doi: 10.3390/molecules15118469. [PMID: 21088661]
  • Beatrycze Nowicka, Jerzy Kruk. Occurrence, biosynthesis and function of isoprenoid quinones. Biochimica et biophysica acta. 2010 Sep; 1797(9):1587-605. doi: 10.1016/j.bbabio.2010.06.007. [PMID: 20599680]
  • Xue-Mei Gao, Ting Yu, Fanny Shuk Fan Lai, Yan Zhou, Xin Liu, Chun-Feng Qiao, Jing-Zheng Song, Shi-Lin Chen, Kathy Qian Luo, Hong-Xi Xu. Identification and evaluation of apoptotic compounds from Garcinia paucinervis. Bioorganic & medicinal chemistry. 2010 Jul; 18(14):4957-64. doi: 10.1016/j.bmc.2010.06.014. [PMID: 20594858]
  • Melissa E Reichelt, Anu Shanu, Laura Willems, Paul K Witting, Natasha A Ellis, Michael R Blackburn, John P Headrick. Endogenous adenosine selectively modulates oxidant stress via the A1 receptor in ischemic hearts. Antioxidants & redox signaling. 2009 Nov; 11(11):2641-50. doi: 10.1089/ars.2009.2644. [PMID: 19552606]
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  • Wolfgang Gregor, Katrin Staniek, Hans Nohl, Lars Gille. Distribution of tocopheryl quinone in mitochondrial membranes and interference with ubiquinone-mediated electron transfer. Biochemical pharmacology. 2006 May; 71(11):1589-601. doi: 10.1016/j.bcp.2006.02.012. [PMID: 16569397]
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  • Sergi Munné-Bosch, Toshiharu Shikanai, Kozi Asada. Enhanced ferredoxin-dependent cyclic electron flow around photosystem I and alpha-tocopherol quinone accumulation in water-stressed ndhB-inactivated tobacco mutants. Planta. 2005 Oct; 222(3):502-11. doi: 10.1007/s00425-005-1548-y. [PMID: 15912357]
  • Rakesh Sachdeva, Beena Thomas, Xinhe Wang, Jiyan Ma, Kenneth H Jones, Patrick G Hatcher, David G Cornwell. Tocopherol metabolism using thermochemolysis: chemical and biological properties of gamma-tocopherol, gamma-carboxyethyl-hydroxychroman, and their quinones. Chemical research in toxicology. 2005 Jun; 18(6):1018-25. doi: 10.1021/tx0496441. [PMID: 15962937]
  • Dagmar Pollok, Hans-Ulrich Melchert. Determination of alpha-tocopherolquinone in human serum samples by liquid chromatography with fluorescence detection and on-line post-column derivatization. Journal of chromatography. A. 2004 Nov; 1056(1-2):257-62. doi: 10.1016/s0021-9673(04)01079-9. [PMID: 15595560]
  • Lars Gille, Wolfgang Gregor, Katrin Staniek, Hans Nohl. Redox-interaction of alpha-tocopheryl quinone with isolated mitochondrial cytochrome bc1 complex. Biochemical pharmacology. 2004 Jul; 68(2):373-81. doi: 10.1016/j.bcp.2004.03.031. [PMID: 15194009]
  • Prabhudas R Palan, Angela L Woodall, Patrick S Anderson, Magdy S Mikhail. Alpha-tocopherol and alpha-tocopheryl quinone levels in cervical intraepithelial neoplasia and cervical cancer. American journal of obstetrics and gynecology. 2004 May; 190(5):1407-10. doi: 10.1016/j.ajog.2004.01.067. [PMID: 15167851]
  • Achim Stocker, Ulrich Baumann. Supernatant protein factor in complex with RRR-alpha-tocopherylquinone: a link between oxidized Vitamin E and cholesterol biosynthesis. Journal of molecular biology. 2003 Sep; 332(4):759-65. doi: 10.1016/s0022-2836(03)00924-0. [PMID: 12972248]
  • Kazushi Shinozaki, Hiroshi Takeda, Masato Inazu, Teruhiko Matsumiya, Masaru Takasaki. Abnormal incorporation and utilization of alpha-tocopherol in erythrocyte membranes of streptozotocin-induced diabetic rats. European journal of pharmacology. 2002 Dec; 456(1-3):133-9. doi: 10.1016/s0014-2999(02)02618-3. [PMID: 12450579]
  • Andrew C Terentis, Shane R Thomas, Jeanne A Burr, Daniel C Liebler, Roland Stocker. Vitamin E oxidation in human atherosclerotic lesions. Circulation research. 2002 Feb; 90(3):333-9. doi: 10.1161/hh0302.104454. [PMID: 11861423]
  • Kenneth H Jones, Jennifer J Liu, Jennifer S Roehm, Jason J Eckel, Tobin T Eckel, Chad R Stickrath, Craig A Triola, Zongcheng Jiang, Gianna M Bartoli, David G Cornwell. Gamma-tocopheryl quinone stimulates apoptosis in drug-sensitive and multidrug-resistant cancer cells. Lipids. 2002 Feb; 37(2):173-84. doi: 10.1007/s11745-002-0878-2. [PMID: 11908909]
  • Pascal Mottier, Eric Gremaud, Philippe A Guy, Robert J Turesky. Comparison of gas chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry methods to quantify alpha-tocopherol and alpha-tocopherolquinone levels in human plasma. Analytical biochemistry. 2002 Feb; 301(1):128-35. doi: 10.1006/abio.2001.5486. [PMID: 11811977]
  • R I van Haaften, C T Evelo, G R Haenen, A Bast. No reduction of alpha-tocopherol quinone by glutathione in rat liver microsomes. Biochemical pharmacology. 2001 Mar; 61(6):715-9. doi: 10.1016/s0006-2952(01)00545-7. [PMID: 11266656]
  • C Leray, M L Wiesel, M Freund, J P Cazenave, C Gachet. Long-chain n-3 fatty acids specifically affect rat coagulation factors dependent on vitamin K: relation to peroxidative stress. Arteriosclerosis, thrombosis, and vascular biology. 2001 Mar; 21(3):459-65. doi: 10.1161/01.atv.21.3.459. [PMID: 11231929]
  • T P Twaroski, M L O'Brien, N Larmonier, H P Glauert, L W Robertson. Polychlorinated biphenyl-induced effects on metabolic enzymes, AP-1 binding, vitamin E, and oxidative stress in the rat liver. Toxicology and applied pharmacology. 2001 Mar; 171(2):85-93. doi: 10.1006/taap.2000.9114. [PMID: 11222084]
  • J Kruk, K Strzalka. Redox changes of cytochrome b(559) in the presence of plastoquinones. The Journal of biological chemistry. 2001 Jan; 276(1):86-91. doi: 10.1074/jbc.m003602200. [PMID: 11022032]
  • H Kanazawa, C Miyata, Y Nagata, S Urano, Y Matsushima. Determination of alpha-tocopherol and alpha-tocopherylquinone in rat tissues and plasma by high-performance liquid chromatography with electrochemical detection. Chemical & pharmaceutical bulletin. 2000 Oct; 48(10):1462-6. doi: 10.1248/cpb.48.1462. [PMID: 11045451]
  • K Yanagawa, H Takeda, T Egashira, K Sakai, M Takasaki, T Matsumiya. Age-related changes in alpha-tocopherol dynamics with relation to lipid hydroperoxide content and fluidity of rat erythrocyte membrane. The journals of gerontology. Series A, Biological sciences and medical sciences. 1999 Sep; 54(9):B379-83. doi: 10.1093/gerona/54.9.b379. [PMID: 10536642]
  • K Yanagawa, H Takeda, T Matsumiya, M Takasaki. [Age-related change in the alpha-tocopherolquinone/alpha-tocopherol ratio in the rat erythrocyte membrane]. Nihon Ronen Igakkai zasshi. Japanese journal of geriatrics. 1999 May; 36(5):335-41. doi: 10.3143/geriatrics.36.335. [PMID: 10466351]
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  • D Siegel, E M Bolton, J A Burr, D C Liebler, D Ross. The reduction of alpha-tocopherolquinone by human NAD(P)H: quinone oxidoreductase: the role of alpha-tocopherolhydroquinone as a cellular antioxidant. Molecular pharmacology. 1997 Aug; 52(2):300-5. doi: 10.1124/mol.52.2.300. [PMID: 9271353]
  • A N Moore, K U Ingold. alpha-Tocopheryl quinone is converted into vitamin E in man. Free radical biology & medicine. 1997; 22(5):931-4. doi: 10.1016/s0891-5849(96)00276-6. [PMID: 9119264]
  • H Tohgi, T Abe, M Saheki, K Yamazaki, S Takahashi. alpha-Tocopherol quinone level is remarkably low in the cerebrospinal fluid of patients with sporadic amyotrophic lateral sclerosis. Neuroscience letters. 1996 Mar; 207(1):5-8. doi: 10.1016/0304-3940(96)12475-7. [PMID: 8710208]
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