Delta-Tocopherol (BioDeep_00000002843)

 

Secondary id: BioDeep_00000405543, BioDeep_00000868463

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

化学式: C27H46O2 (402.3497616)
中文名称: Delta-生育酚, δ-生育酚
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.04%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Delta-Tocopherol. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/delta-tocopherol (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000002843). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=C(C)C2O[C@@](CCC[C@]([H])(C)CCC[C@]([H])(C)CCCC(C)C)(C)CCC=2C=C1O
InChI: InChI=1/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1

描述信息

Tocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. Vitamin E is often used in skin creams and lotions because it is believed to play a role in encouraging skin healing and reducing scarring after injuries such as burns. -- Wikipedia; Natural vitamin E exists in eight different forms or isomers, four tocopherols and four tocotrienols. All isomers have a chromanol ring, with a hydroxyl group which can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain which allows for penetration into biological membranes. There is an alpha, beta, gamma and delta form of both the tocopherols and tocotrienols, determined by the number of methyl groups on the chromanol ring. Each form has its own biological activity, the measure of potency or functional use in the body. -- Wikipedia; Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to alpha tocopherol. It increases naturally to about 150\\\\\% of normal in the maternal circulation during human pregnancies. 1 IU of vitamin E is defined as the biological equivalent of 0.667 milligrams of d-alpha-tocopherol, or of 1 milligram of dl-alpha-tocopherol acetate. The other isomers are slowly being recognized as research begins to elucidate their additional roles in the human body. Many naturopathic and orthomolecular medicine advocates suggest that vitamin E supplements contain at least 20\\\\\% by weight of the other natural vitamin E isomers. Commercially available blends of natural vitamin E include "mixed tocopherols" and "high gamma tocopherol" formulas. Also selenium, Coenzyme Q10, and ample vitamin C have been shown to be essential cofactors of natural tocopherols. -- Wikipedia; Synthetic vitamin E, usually marked as d,l-tocopherol or d,l tocopheryl acetate, with 50\\\\\% d-alpha tocopherol moiety and 50\\\\\% l-alpha-tocopherol moiety, as synthesized by an earlier process is now actually manufactured as all-racemic alpha tocopherol, with only about one alpha tocopherol molecule in 8 molecules as actual d-alpha tocpherol. The synthetic form is not as active as the natural alpha tocopherol form. The 1950s thalidomide disaster with numerous severe birth defects is a common example of d- vs l- epimer forms type problem with synthesized racemic mixtures. Information on any side effects of the synthetic vitamin E epimers is not readily available. Naturopathic and orthomolecular medicine advocates have long considered the synthetic vitamin E forms to be with little or no merit for cancer, circulatory and heart diseases. -- Wikipedia; Abetalipoproteinemia is a rare inherited disorder of fat metabolism that results in poor absorption of dietary fat and vitamin E. The vitamin E deficiency associated with this disease causes problems such as poor transmission of nerve impulses, muscle weakness, and degeneration of the retina that can cause blindness. Individuals with abetalipoproteinemia may be prescribed special vitamin E supplements by a physician to treat this disorder. -- Wikipedia; Recent studies also show that vitamin E acts as an effective free radical scavenger and can lower the incidence of lung cancer in smokers. The effects are opposite to that of the clinical trials based on administering carotenoid to male smokers, that resulted in increased risk of lung cancer. Hence vitamin E is an effective antagonist to the oxidative stress that is imposed by high carotenoids in certain patients. -- Wikipedia; A cataract is a condition of clouding of the tissue of the lens of the eye. They increase the risk of disability and blindness in aging adults. Antioxidants are being studied to determine whether they can help prevent or delay cataract growth. Observational studies have found that lens clarity, wh...
Delta-Tocopherol is an isomer of Vitamin E.
Delta-Tocopherol is an isomer of Vitamin E.

同义名列表

26 个代谢物同义名

(2R)-3,4-Dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol; (2R)-2,8-Dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol; (2R,4r,8r)-delta-Tocopherol; (2R,4’R,8’r)-δ-tocopherol; (R,R,R)-delta-Tocopherol; (2R,4r,8r)-Δ-tocopherol; (+)-delta-Tocopherol; (R,R,R)-Δ-tocopherol; RRR-delta-Tocopherol; delta-D-Tocopherol; δ-Tocopherol; D-delta-Tocopherol; Delta-Tocopherol; delta tocopherol; RRR-Δ-tocopherol; (+)-Δ-tocopherol; delta-Vitamin e; UNII-ZL0RFA4E5N; Δ-D-tocopherol; D-Δ-tocopherol; 8-Methyltocol; Δ-tocopherol; Δ-vitamin e; Vitamine e; e309



数据库引用编号

22 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

236 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(230)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

132 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

  • Vassilis Athanasiadis, Theodoros Chatzimitakos, Dimitrios Kalompatsios, Dimitrios Palaiogiannis, Ioannis Makrygiannis, Eleni Bozinou, Stavros I Lalas. Evaluation of the Efficacy and Synergistic Effect of α- and δ-Tocopherol as Natural Antioxidants in the Stabilization of Sunflower Oil and Olive Pomace Oil during Storage Conditions. International journal of molecular sciences. 2023 Jan; 24(2):. doi: 10.3390/ijms24021113. [PMID: 36674630]
  • Truong Nhat Van Do, Tho Huu Le, Hai Xuan Nguyen, Trang Ngoc Tran Vo, Phu Hoang Dang, Nhan Trung Nguyen, Mai Thanh Thi Nguyen. δ-Tocopherol derivatives from the leaves of Muntingia calabura L. Natural product research. 2022 Nov; 36(21):5524-5529. doi: 10.1080/14786419.2021.2018589. [PMID: 34933616]
  • Junjie Hong, Yu-Shan Cheng, Shu Yang, Manju Swaroop, Miao Xu, Jeanette Beers, Jizhong Zou, Wenwei Huang, Juan J Marugan, Xiujun Cai, Wei Zheng. iPS-derived neural stem cells for disease modeling and evaluation of therapeutics for mucopolysaccharidosis type II. Experimental cell research. 2022 03; 412(1):113007. doi: 10.1016/j.yexcr.2021.113007. [PMID: 34990619]
  • Rieko Tanaka-Yachi, Rena Otsu, Chie Takahashi-Muto, Chikako Kiyose. Delta-Tocopherol Suppresses the Dysfunction of Thermogenesis due to Inflammatory Stimulation in Brown Adipocytes. Journal of oleo science. 2022; 71(11):1647-1653. doi: 10.5650/jos.ess22184. [PMID: 36310052]
  • Qilong Xie, Ming Xia, Dekui Sun, Jiangping Cao, Yong Xiao, Mingui Lin, Bo Hou, Litao Jia, Debao Li. Deep eutectic solvent-based liquid-phase microextraction coupled with reversed-phase high-performance liquid chromatography for determination of α-, β-, γ-, and δ-tocopherol in edible oils. Analytical and bioanalytical chemistry. 2021 Jan; 413(2):577-584. doi: 10.1007/s00216-020-03029-1. [PMID: 33205254]
  • Liangxiao Zhang, Sujun Wang, Ruinan Yang, Jin Mao, Jun Jiang, Xiupin Wang, Wen Zhang, Qi Zhang, Peiwu Li. Simultaneous determination of tocopherols, carotenoids and phytosterols in edible vegetable oil by ultrasound-assisted saponification, LLE and LC-MS/MS. Food chemistry. 2019 Aug; 289(?):313-319. doi: 10.1016/j.foodchem.2019.03.067. [PMID: 30955618]
  • Leqi Cui, Peiyi Shen, Zili Gao, Jianhua Yi, Bingcan Chen. New Insights into the Impact of Sodium Chloride on the Lipid Oxidation of Oil-in-Water Emulsions. Journal of agricultural and food chemistry. 2019 Apr; 67(15):4321-4327. doi: 10.1021/acs.jafc.9b00396. [PMID: 30883113]
  • Mylinh Vu, Rong Li, Amanda Baskfield, Billy Lu, Atena Farkhondeh, Kirill Gorshkov, Omid Motabar, Jeanette Beers, Guokai Chen, Jizhong Zou, Angela J Espejo-Mojica, Alexander Rodríguez-López, Carlos J Alméciga-Díaz, Luis A Barrera, Xuntian Jiang, Daniel S Ory, Juan J Marugan, Wei Zheng. Neural stem cells for disease modeling and evaluation of therapeutics for Tay-Sachs disease. Orphanet journal of rare diseases. 2018 09; 13(1):152. doi: 10.1186/s13023-018-0886-3. [PMID: 30220252]
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  • Bertrand Matthaus, Mehmet Musa Özcan, Fahad Al Juhaimi. Some rape/canola seed oils: fatty acid composition and tocopherols. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2016 Mar; 71(3-4):73-7. doi: 10.1515/znc-2016-0003. [PMID: 27023318]
  • Corrine Hanson, Elizabeth Lyden, Jeremy Furtado, Hannia Campos, David Sparrow, Pantel Vokonas, Augusto A Litonjua. Serum tocopherol levels and vitamin E intake are associated with lung function in the normative aging study. Clinical nutrition (Edinburgh, Scotland). 2016 Feb; 35(1):169-174. doi: 10.1016/j.clnu.2015.01.020. [PMID: 25715694]
  • M O W Grimm, C P Stahlmann, J Mett, V J Haupenthal, V C Zimmer, J Lehmann, B Hundsdörfer, K Endres, H S Grimm, T Hartmann. Vitamin E: Curse or Benefit in Alzheimer's Disease? A Systematic Investigation of the Impact of α-, γ- and δ-Tocopherol on Aß Generation and Degradation in Neuroblastoma Cells. The journal of nutrition, health & aging. 2015 Jun; 19(6):646-56. doi: 10.1007/s12603-015-0506-z. [PMID: 26054501]
  • Rosana Chirinos, Romina Pedreschi, Gilberto Domínguez, David Campos. Comparison of the physico-chemical and phytochemical characteristics of the oil of two Plukenetia species. Food chemistry. 2015 Apr; 173(?):1203-6. doi: 10.1016/j.foodchem.2014.10.120. [PMID: 25466144]
  • Yu Young Lee, Hyang Mi Park, Tae Young Hwang, Sun Lim Kim, Mi Jung Kim, Seuk Ki Lee, Min Jung Seo, Kee Jong Kim, Young-Up Kwon, Sang Chul Lee, Yul Ho Kim. A correlation between tocopherol content and antioxidant activity in seeds and germinating seeds of soybean cultivars. Journal of the science of food and agriculture. 2015 Mar; 95(4):819-27. doi: 10.1002/jsfa.6963. [PMID: 25475360]
  • Filipa S Reis, Lillian Barros, Ricardo C Calhelha, Ana Cirić, Leo J L D van Griensven, Marina Soković, Isabel C F R Ferreira. The methanolic extract of Cordyceps militaris (L.) Link fruiting body shows antioxidant, antibacterial, antifungal and antihuman tumor cell lines properties. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Dec; 62(?):91-8. doi: 10.1016/j.fct.2013.08.033. [PMID: 23994083]
  • Amanda K Smolarek, Jae Young So, Paul E Thomas, Hong Jin Lee, Shiby Paul, Anne Dombrowski, Chung-Xiou Wang, Constance Lay-Lay Saw, Tin Oo Khor, Ah-Ng Tony Kong, Kenneth Reuhl, Mao-Jung Lee, Chung S Yang, Nanjoo Suh. Dietary tocopherols inhibit cell proliferation, regulate expression of ERα, PPARγ, and Nrf2, and decrease serum inflammatory markers during the development of mammary hyperplasia. Molecular carcinogenesis. 2013 Jul; 52(7):514-25. doi: 10.1002/mc.21886. [PMID: 22389237]
  • Miao Xu, Ke Liu, Manju Swaroop, Forbes D Porter, Rohini Sidhu, Sally Firnkes, Sally Finkes, Daniel S Ory, Juan J Marugan, Jingbo Xiao, Noel Southall, William J Pavan, Cristin Davidson, Steven U Walkley, Alan T Remaley, Ulrich Baxa, Wei Sun, John C McKew, Christopher P Austin, Wei Zheng. δ-Tocopherol reduces lipid accumulation in Niemann-Pick type C1 and Wolman cholesterol storage disorders. The Journal of biological chemistry. 2012 Nov; 287(47):39349-60. doi: 10.1074/jbc.m112.357707. [PMID: 23035117]
  • Muhammad Zia-Ul-Haq, Shakeel Ahmad, Luca Calani, Teresa Mazzeo, Daniele Del Rio, Nicoletta Pellegrini, Vincenzo De Feo. Compositional study and antioxidant potential of Ipomoea hederacea Jacq. and Lepidium sativum L. seeds. Molecules (Basel, Switzerland). 2012 Aug; 17(9):10306-21. doi: 10.3390/molecules170910306. [PMID: 22932212]
  • Laura L Baxter, Juan J Marugan, Jingbo Xiao, Art Incao, John C McKew, Wei Zheng, William J Pavan. Plasma and tissue concentrations of α-tocopherol and δ-tocopherol following high dose dietary supplementation in mice. Nutrients. 2012 06; 4(6):467-90. doi: 10.3390/nu4060467. [PMID: 22822447]
  • Fei Guan, Guangxun Li, Anna B Liu, Mao-Jung Lee, Zhihong Yang, Yu-Kuo Chen, Yong Lin, Weichung Shih, Chung S Yang. δ- and γ-tocopherols, but not α-tocopherol, inhibit colon carcinogenesis in azoxymethane-treated F344 rats. Cancer prevention research (Philadelphia, Pa.). 2012 Apr; 5(4):644-54. doi: 10.1158/1940-6207.capr-11-0521. [PMID: 22366914]
  • Lidia Del Moral, José M Fernández-Martínez, Begoña Pérez-Vich, Leonardo Velasco. Expression of modified tocopherol content and profile in sunflower tissues. Journal of the science of food and agriculture. 2012 Jan; 92(2):351-7. doi: 10.1002/jsfa.4585. [PMID: 21815166]
  • Russell L Blaylock, Joseph Maroon. Natural plant products and extracts that reduce immunoexcitotoxicity-associated neurodegeneration and promote repair within the central nervous system. Surgical neurology international. 2012; 3(?):19. doi: 10.4103/2152-7806.92935. [PMID: 22439110]
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  • Elena Moretti, Cesare Castellini, Evangelia Mourvaki, Serena Capitani, Michela Geminiani, Tommaso Renieri, Giulia Collodel. Distribution of α- and δ-tocopherols in seminal plasma and sperm fractions of men with normal and abnormal semen parameters. Journal of andrology. 2011 May; 32(3):232-9. doi: 10.2164/jandrol.109.009936. [PMID: 20930194]
  • Guang-Xun Li, Mao-Jung Lee, Anna B Liu, Zhihong Yang, Yong Lin, Weichung J Shih, Chung S Yang. δ-tocopherol is more active than α - or γ -tocopherol in inhibiting lung tumorigenesis in vivo. Cancer prevention research (Philadelphia, Pa.). 2011 Mar; 4(3):404-13. doi: 10.1158/1940-6207.capr-10-0130. [PMID: 21372040]
  • Jörg Hofmann, Frederik Börnke, Alfred Schmiedl, Tatjana Kleine, Uwe Sonnewald. Detecting functional groups of Arabidopsis mutants by metabolic profiling and evaluation of pleiotropic responses. Frontiers in plant science. 2011; 2(?):82. doi: 10.3389/fpls.2011.00082. [PMID: 22639613]
  • Shengbao Feng, Lixia Song, Yuan Kun Lee, Dejian Huang. The effects of fungal stress on the antioxidant contents of black soybeans under germination. Journal of agricultural and food chemistry. 2010 Dec; 58(23):12491-6. doi: 10.1021/jf102926r. [PMID: 21058652]
  • Augusta Caligiani, Francesca Bonzanini, Gerardo Palla, Martina Cirlini, Renato Bruni. Characterization of a potential nutraceutical ingredient: pomegranate (Punica granatum L.) seed oil unsaponifiable fraction. Plant foods for human nutrition (Dordrecht, Netherlands). 2010 Sep; 65(3):277-83. doi: 10.1007/s11130-010-0173-5. [PMID: 20607413]
  • Philippe Seguin, Gilles Tremblay, Denis Pageau, Wucheng Liu. Soybean tocopherol concentrations are affected by crop management. Journal of agricultural and food chemistry. 2010 May; 58(9):5495-501. doi: 10.1021/jf100455f. [PMID: 20402508]
  • Evangelia Mourvaki, Raffaella Cardinali, Alessandro Dal Bosco, Cesare Castellini. In vitro antioxidant activity of the prostatic secretory granules in rabbit semen after exposure to organic peroxides. Reproductive biology and endocrinology : RB&E. 2010 Feb; 8(?):16. doi: 10.1186/1477-7827-8-16. [PMID: 20178592]
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  • Janez Salobir, Tanja Pajk Zontar, Alenka Levart, Vida Rezar. The comparison of black currant juice and vitamin E for the prevention of oxidative stress. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2010 Jan; 80(1):5-11. doi: 10.1024/0300-9831/a000001. [PMID: 20533240]
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