Beta-tocopherol (BioDeep_00000004165)

 

Secondary id: BioDeep_00000395664, BioDeep_00000557285

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol

化学式: C28H48O2 (416.3654)
中文名称: β-生育酚
谱图信息: 最多检出来源 Homo sapiens(feces) 41.43%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Beta-tocopherol. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/beta-tocopherol (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000004165). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c1(c2c(c(cc1O)C)O[C@@](CC2)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)C
InChI: InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3

描述信息

beta-Tocopherol is an antioxidant which is synthesized by photosynthetic organisms and plays an important role in human and animal nutrition. beta-Tocopherols can be oxidized in dry CH2Cl2 or CH3CN by one electron to form cation radicals that deprotonate to form the neutral phenoxyl radicals, which are then immediately further oxidized by one electron to the phenoxonium cations (an ECE electrochemical mechanism, where E signifies an electron transfer and C represents a chemical step, with the electrochemical mechanism having been determined by in situ spectroscopic analysis). The phenoxonium cation of beta-tocopherol is stable for several minutes (PMID: 16771430). beta-Tocopherol has been identified in the human placenta (PMID: 32033212).


(rel)-β-Tocopherol is a relative configuration of β-Tocopherol.(±)-β-Tocopherol is a lipid-soluble form of vitamin E with antioxidant activity. β-Tocopherol can inhibit tyrosinase activity and melanin synthesis. β-Tocopherol also can prevent the inhibition of cell growth and of PKC activity caused by d-alpha-tocopherol[1].

同义名列表

29 个代谢物同义名

(2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol; (2R)-3,4-dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol; 3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12- trimethyltridecyl)-2H-1-benzopyran-6-ol; (2R)-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol; 2,5,8-Trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol; (2R,4r,8r)-beta-Tocopherol; (2R,4r,8r)-Β-tocopherol; (2R,4r,8r)-b-Tocopherol; (R,R,R)-beta-Tocopherol; b-Tocopherol skeleton; Β-tocopherol skeleton; (R,R,R)-b-Tocopherol; (R,R,R)-Β-tocopherol; RRR-beta-Tocopherol; DL-beta-Tocopherol; 5,8-Dimethyltocol; rac-B-tocopherol; p-Xylotocopherol; RRR-b-Tocopherol; RRR-Β-tocopherol; beta-Tocopherol; beta Tocopherol; DL-Β-tocopherol; Cumotocopherol; Neotocopherol; β-Tocopherol; b-Tocopherol; (rel)-β-Tocopherol; beta-Tocopherol



数据库引用编号

24 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

133 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(127)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

85 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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 ACE2, AKT1, ALB, CAT, MAPK8, PRKCA, PTGS2, STAT3, TTPA, TYR, VEGFA
Peripheral membrane protein 2 PRKCA, PTGS2
Endoplasmic reticulum membrane 1 PTGS2
Mitochondrion membrane 1 PRKCA
Nucleus 7 AKT1, ALB, JUND, MAPK8, PRKCA, STAT3, VEGFA
cytosol 9 AKT1, ALB, CAT, LIPE, MAPK8, PRKCA, PRKCQ, STAT3, TTPA
mitochondrial membrane 1 PRKCA
centrosome 1 ALB
nucleoplasm 6 AKT1, JUND, MAPK8, PRKCA, RRS1, STAT3
RNA polymerase II transcription regulator complex 2 JUND, STAT3
Cell membrane 5 ACE2, AKT1, ITGAM, LIPE, PRKCA
lamellipodium 1 AKT1
Synapse 1 MAPK8
cell cortex 1 AKT1
cell surface 3 ACE2, ITGAM, VEGFA
glutamatergic synapse 1 AKT1
Golgi apparatus 3 ALB, CCN2, VEGFA
Golgi membrane 1 INS
postsynapse 1 AKT1
Cytoplasm, cytosol 1 LIPE
Lysosome 1 TYR
plasma membrane 8 ACE2, AKT1, CCN2, F2, ITGAM, PRKCA, PRKCQ, STAT3
Membrane 7 ACE2, AKT1, CAT, ITGAM, LIPE, PRKCA, VEGFA
apical plasma membrane 1 ACE2
axon 1 MAPK8
caveola 2 LIPE, PTGS2
extracellular exosome 7 ACE2, ALB, CAT, F2, ITGAM, PRKCA, SHBG
endoplasmic reticulum 5 ALB, PRKCA, PTGS2, RRS1, VEGFA
extracellular space 7 ACE2, ALB, CCN2, F2, INS, ITGAM, VEGFA
perinuclear region of cytoplasm 2 PRKCA, TYR
adherens junction 1 VEGFA
mitochondrion 2 CAT, PRKCA
protein-containing complex 4 AKT1, ALB, CAT, PTGS2
intracellular membrane-bounded organelle 3 CAT, CCN2, TYR
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 3 ACE2, ITGAM, TYR
Secreted 7 ACE2, ALB, CCN2, F2, INS, SHBG, VEGFA
extracellular region 8 ACE2, ALB, CAT, CCN2, F2, INS, SHBG, VEGFA
mitochondrial matrix 1 CAT
anchoring junction 1 ALB
transcription regulator complex 2 JUND, STAT3
Cell projection, cilium 1 ACE2
centriolar satellite 1 PRKCQ
external side of plasma membrane 1 ITGAM
Secreted, extracellular space, extracellular matrix 2 CCN2, VEGFA
microtubule cytoskeleton 1 AKT1
nucleolus 1 RRS1
Melanosome membrane 1 TYR
cell-cell junction 1 AKT1
Golgi-associated vesicle 1 TYR
vesicle 1 AKT1
Apical cell membrane 1 ACE2
Membrane raft 2 ACE2, ITGAM
focal adhesion 1 CAT
spindle 1 AKT1
extracellular matrix 2 CCN2, VEGFA
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 F2
secretory granule 1 VEGFA
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 TTPA
neuron projection 1 PTGS2
ciliary basal body 3 AKT1, ALB, PRKCA
cilium 1 ACE2
chromatin 2 JUND, STAT3
centriole 1 ALB
brush border membrane 1 ACE2
spindle pole 1 ALB
blood microparticle 2 ALB, F2
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
Melanosome 1 TYR
plasma membrane raft 1 ITGAM
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 5 ACE2, ALB, F2, INS, PTGS2
transcription repressor complex 1 JUND
platelet alpha granule lumen 2 ALB, VEGFA
endocytic vesicle membrane 1 ACE2
transport vesicle 1 INS
preribosome, large subunit precursor 1 RRS1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
condensed nuclear chromosome 1 RRS1
basal dendrite 1 MAPK8
integrin complex 1 ITGAM
transcription factor AP-1 complex 1 JUND
catalase complex 1 CAT
alphav-beta3 integrin-PKCalpha complex 1 PRKCA
integrin alphaM-beta2 complex 1 ITGAM
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
ciliary transition fiber 1 ALB
[Processed angiotensin-converting enzyme 2]: Secreted 1 ACE2
[Isoform 2]: Apical cell membrane 1 ACE2


文献列表

  • Sahabjada Siddiqui, Shivbrat Upadhyay, Rumana Ahmad, Md Abul Barkat, Azfar Jamal, Abdulaziz S Alothaim, Mohd Zaheen Hassan, Mohammad Akhlaquer Rahman, Md Arshad, Tanveer Ahamad, Mohammad Faheem Khan, Hari Shankar, M Ali, Sarjeel Kaleem, Jalal Ahmad. Interaction of Bioactive Compounds of Moringa oleifera Leaves with SARS-CoV-2 Proteins to Combat COVID-19 Pathogenesis: a Phytochemical and In Silico Analysis. Applied biochemistry and biotechnology. 2022 Dec; 194(12):5918-5944. doi: 10.1007/s12010-022-04040-1. [PMID: 35838886]
  • 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]
  • Felix Aladedunye, Roman Przybylski, Bertrand Matthaus. Performance of antioxidative compounds under frying conditions: A review. Critical reviews in food science and nutrition. 2017 May; 57(8):1539-1561. doi: 10.1080/10408398.2013.777686. [PMID: 25607749]
  • S A Nusaibah, A Siti Nor Akmar, A S Idris, M Sariah, Z Mohamad Pauzi. Involvement of metabolites in early defense mechanism of oil palm (Elaeis guineensis Jacq.) against Ganoderma disease. Plant physiology and biochemistry : PPB. 2016 Dec; 109(?):156-165. doi: 10.1016/j.plaphy.2016.09.014. [PMID: 27694009]
  • Hong Xu, Zibo Xiong, Johan Ärnlöv, Abdul Rashid Qureshi, Tommy Cederholm, Per Sjögren, Bengt Lindholm, Ulf Risérus, Juan Jesús Carrero. Circulating Alpha-Tocopherol and Insulin Sensitivity Among Older Men With Chronic Kidney Disease. Journal of renal nutrition : the official journal of the Council on Renal Nutrition of the National Kidney Foundation. 2016 05; 26(3):177-82. doi: 10.1053/j.jrn.2015.11.005. [PMID: 26776598]
  • 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]
  • Vanessa Vieira, Lillian Barros, Anabela Martins, Isabel C F R Ferreira. Nutritional and Biochemical Profiling of Leucopaxillus candidus (Bres.) Singer Wild Mushroom. Molecules (Basel, Switzerland). 2016 Jan; 21(1):99. doi: 10.3390/molecules21010099. [PMID: 26784162]
  • Ana Beatriz Zanqui, Damila Rodrigues de Morais, Claudia Marques da Silva, Jandyson Machado Santos, Sandra Terezinha Marques Gomes, Jesuí Vergílio Visentainer, Marcos Nogueira Eberlin, Lúcio Cardozo-Filho, Makoto Matsushita. Subcritical extraction of flaxseed oil with n-propane: Composition and purity. Food chemistry. 2015 Dec; 188(?):452-8. doi: 10.1016/j.foodchem.2015.05.033. [PMID: 26041217]
  • 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]
  • Adewale Adewuyi, Rotimi A Oderinde, B V S K Rao, R B N Prasad. Chemical composition and molecular speciation of the triacylglycerol of the oils of Lonchocarpus sericeus and Lonchocarpus cyanescens. Natural product research. 2012; 26(20):1954-6. doi: 10.1080/14786419.2011.643311. [PMID: 22168240]
  • Shiro Imagama, Yukiharu Hasegawa, Taisuke Seki, Yukihiro Matsuyama, Yoshihito Sakai, Zenya Ito, Naoki Ishiguro, Yoshinori Ito, Nobuyuki Hamajima, Koji Suzuki. The effect of β-carotene on lumbar osteophyte formation. Spine. 2011 Dec; 36(26):2293-8. doi: 10.1097/brs.0b013e3182254a18. [PMID: 21673632]
  • Maria Inês Dias, Lillian Barros, Maria João Sousa, Isabel C F R Ferreira. Comparative study of lipophilic and hydrophilic antioxidants from in vivo and in vitro grown Coriandrum sativum. Plant foods for human nutrition (Dordrecht, Netherlands). 2011 Jun; 66(2):181-6. doi: 10.1007/s11130-011-0227-3. [PMID: 21523411]
  • Oliver Fiehn, W Timothy Garvey, John W Newman, Kerry H Lok, Charles L Hoppel, Sean H Adams. Plasma metabolomic profiles reflective of glucose homeostasis in non-diabetic and type 2 diabetic obese African-American women. PloS one. 2010 Dec; 5(12):e15234. doi: 10.1371/journal.pone.0015234. [PMID: 21170321]
  • Anja Peuthert, Stephan Pflugmacher. Influence of the cyanotoxin microcystin-LR on tocopherol in Alfalfa seedlings (Medicago sativa). Toxicon : official journal of the International Society on Toxinology. 2010 Sep; 56(3):411-7. doi: 10.1016/j.toxicon.2010.04.004. [PMID: 20398686]
  • 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]
  • Seonyeong Wang, Hyunsuk Hwang, Sukhoo Yoon, Eunok Choe. Temperature dependence of autoxidation of perilla oil and tocopherol degradation. Journal of food science. 2010 Aug; 75(6):C498-505. doi: 10.1111/j.1750-3841.2010.01681.x. [PMID: 20722903]
  • Kenan Gumustekin, Seyithan Taysi, Hamit Hakan Alp, Omer Aktas, Nuray Oztasan, Fatih Akcay, Halis Suleyman, Sedat Akar, Senol Dane, Mustafa Gul. Vitamin E and Hippophea rhamnoides L. extract reduce nicotine-induced oxidative stress in rat heart. Cell biochemistry and function. 2010 Jun; 28(4):329-33. doi: 10.1002/cbf.1663. [PMID: 20517898]
  • Shingo Kaida, Yoshiji Ohta, Yoichiro Imai, Koji Ohashi, Minoru Kawanishi. Compound 48/80 causes oxidative stress in the adrenal gland of rats through mast cell degranulation. Free radical research. 2010 Feb; 44(2):171-80. doi: 10.3109/10715760903380466. [PMID: 19886753]
  • Francesca Mangialasche, Miia Kivipelto, Patrizia Mecocci, Debora Rizzuto, Katie Palmer, Bengt Winblad, Laura Fratiglioni. High plasma levels of vitamin E forms and reduced Alzheimer's disease risk in advanced age. Journal of Alzheimer's disease : JAD. 2010; 20(4):1029-37. doi: 10.3233/jad-2010-091450. [PMID: 20413888]
  • 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]
  • Anchalee Sirikhachornkit, Jai W Shin, Irene Baroli, Krishna K Niyogi. Replacement of alpha-tocopherol by beta-tocopherol enhances resistance to photooxidative stress in a xanthophyll-deficient strain of Chlamydomonas reinhardtii. Eukaryotic cell. 2009 Nov; 8(11):1648-57. doi: 10.1128/ec.00124-09. [PMID: 19717743]
  • Ching Kuang Chow. Dietary beta-tocopherol and serum concentrations of sex hormone-binding globulin. The Journal of nutrition. 2009 Oct; 139(10):2007; author reply 2008. doi: 10.3945/jn.109.113571. [PMID: 19710160]
  • Gerard J Linden, Kathy M McClean, Jayne V Woodside, Chris C Patterson, Alun Evans, Ian S Young, Frank Kee. Antioxidants and periodontitis in 60-70-year-old men. Journal of clinical periodontology. 2009 Oct; 36(10):843-9. doi: 10.1111/j.1600-051x.2009.01468.x. [PMID: 19703237]
  • Fatima Nayeem, Manubai Nagamani, Karl E Anderson, Yafei Huang, James J Grady, Lee-Jane W Lu. Dietary beta-tocopherol and linoleic acid, serum insulin, and waist circumference predict circulating sex hormone-binding globulin in premenopausal women. The Journal of nutrition. 2009 Jun; 139(6):1135-42. doi: 10.3945/jn.108.103291. [PMID: 19339706]
  • Nurten Ozsoy, Eda Candoken, Nuriye Akev. Implications for degenerative disorders: antioxidative activity, total phenols, flavonoids, ascorbic acid, beta-carotene and beta-tocopherol in Aloe vera. Oxidative medicine and cellular longevity. 2009 Apr; 2(2):99-106. doi: 10.4161/oxim.2.2.8493. [PMID: 20357932]
  • Mohammed Hassan El-Mallah, Safinaz Mohammed El-Shami. Investigation of liquid wax components of Egyptian jojoba seeds. Journal of oleo science. 2009; 58(11):543-8. doi: 10.5650/jos.58.543. [PMID: 19844068]
  • E Mourvaki, G Collodel, E Moretti, I Cosci, C Castellini. Distribution of alpha-, gamma (+beta)- and delta-tocopherol in the seminal plasma, spermatozoa and seminal vesicles of rabbit. Andrologia. 2008 Oct; 40(5):282-5. doi: 10.1111/j.1439-0272.2008.00854.x. [PMID: 18811917]
  • Naoko Kobayashi, Dean DellaPenna. Tocopherol metabolism, oxidation and recycling under high light stress in Arabidopsis. The Plant journal : for cell and molecular biology. 2008 Aug; 55(4):607-18. doi: 10.1111/j.1365-313x.2008.03539.x. [PMID: 18452591]
  • Dragan Skorić, Sinisa Jocić, Zvonimir Sakac, Nada Lecić. Genetic possibilities for altering sunflower oil quality to obtain novel oils. Canadian journal of physiology and pharmacology. 2008 Apr; 86(4):215-21. doi: 10.1139/y08-008. [PMID: 18418432]
  • Kornél Nagy, Marie-Claude Courtet-Compondu, Birgit Holst, Martin Kussmann. Comprehensive analysis of vitamin E constituents in human plasma by liquid chromatography-mass spectrometry. Analytical chemistry. 2007 Sep; 79(18):7087-96. doi: 10.1021/ac0708689. [PMID: 17696496]
  • Julian Stüven, Stephan Pflugmacher. Antioxidative stress response of Lepidium sativum due to exposure to cyanobacterial secondary metabolites. Toxicon : official journal of the International Society on Toxinology. 2007 Jul; 50(1):85-93. doi: 10.1016/j.toxicon.2007.02.019. [PMID: 17434197]
  • Tong Zhang, Ya-Zhong Zhang, Jian-Sheng Tao. Antibacterial constituents from Stemona sessilifolia. Journal of Asian natural products research. 2007 Apr; 9(3-5):479-85. doi: 10.1080/10286020701189286. [PMID: 17701569]
  • Venkata S Tavva, Yul-Ho Kim, Isabelle A Kagan, Randy D Dinkins, Kyung-Hwan Kim, Glenn B Collins. Increased alpha-tocopherol content in soybean seed overexpressing the Perilla frutescens gamma-tocopherol methyltransferase gene. Plant cell reports. 2007 Jan; 26(1):61-70. doi: 10.1007/s00299-006-0218-2. [PMID: 16909228]
  • Shunxue Tang, Catherine G Hass, Steven J Knapp. Ty3/gypsy-like retrotransposon knockout of a 2-methyl-6-phytyl-1,4-benzoquinone methyltransferase is non-lethal, uncovers a cryptic paralogous mutation, and produces novel tocopherol (vitamin E) profiles in sunflower. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2006 Sep; 113(5):783-99. doi: 10.1007/s00122-006-0321-3. [PMID: 16902787]
  • Pera R Jambazian, Ella Haddad, Sujatha Rajaram, Jay Tanzman, Joan Sabaté. Almonds in the diet simultaneously improve plasma alpha-tocopherol concentrations and reduce plasma lipids. Journal of the American Dietetic Association. 2005 Mar; 105(3):449-54. doi: 10.1016/j.jada.2004.12.002. [PMID: 15746835]
  • Charles C McCormick, Robert S Parker. The cytotoxicity of vitamin E is both vitamer- and cell-specific and involves a selectable trait. The Journal of nutrition. 2004 Dec; 134(12):3335-42. doi: 10.1093/jn/134.12.3335. [PMID: 15570034]
  • Beatriz Nespereira, Maitane Pérez-Ilzarbe, Patricia Fernández, Angela M Fuentes, José A Páramo, José A Rodríguez. Vitamins C and E downregulate vascular VEGF and VEGFR-2 expression in apolipoprotein-E-deficient mice. Atherosclerosis. 2003 Nov; 171(1):67-73. doi: 10.1016/j.atherosclerosis.2003.08.009. [PMID: 14642407]
  • Abraham M Y Nomura, James Lee, Grant N Stemmermann, Adrian A Franke. Serum vitamins and the subsequent risk of bladder cancer. The Journal of urology. 2003 Oct; 170(4 Pt 1):1146-50. doi: 10.1097/01.ju.0000086040.24795.ad. [PMID: 14501712]
  • Daniel Hofius, Uwe Sonnewald. Vitamin E biosynthesis: biochemistry meets cell biology. Trends in plant science. 2003 Jan; 8(1):6-8. doi: 10.1016/s1360-1385(02)00002-x. [PMID: 12523993]
  • Maria Koch, Rainer Lemke, Klaus-Peter Heise, Hans-Peter Mock. Characterization of gamma-tocopherol methyltransferases from Capsicum annuum L and Arabidopsis thaliana. European journal of biochemistry. 2003 Jan; 270(1):84-92. doi: 10.1046/j.1432-1033.2003.03364.x. [PMID: 12492478]
  • Liv Førli, Jan I Pedersen, Oystein Bjørtuft, Rune Blomhoff, Johan Kofstad, Jacob Boe. Vitamins A and E in serum in relation to weight and lung function in patients with advanced pulmonary disease. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2002 Dec; 72(6):360-8. doi: 10.1024/0300-9831.72.6.360. [PMID: 12596500]
  • Beth Savidge, James D Weiss, Yun-Hua H Wong, Michael W Lassner, Timothy A Mitsky, Christine K Shewmaker, Dusty Post-Beittenmiller, Henry E Valentin. Isolation and characterization of homogentisate phytyltransferase genes from Synechocystis sp. PCC 6803 and Arabidopsis. Plant physiology. 2002 May; 129(1):321-32. doi: 10.1104/pp.010747. [PMID: 12011362]
  • F D Goffman, T Böhme. Relationship between fatty acid profile and vitamin E content in maize hybrids (Zea mays L.). Journal of agricultural and food chemistry. 2001 Oct; 49(10):4990-4. doi: 10.1021/jf010156y. [PMID: 11600056]
  • R V Cooney, L J Custer, L Okinaka, A A Franke. Effects of dietary sesame seeds on plasma tocopherol levels. Nutrition and cancer. 2001; 39(1):66-71. doi: 10.1207/s15327914nc391_9. [PMID: 11588904]
  • L A Poirier, P H Grantham, A E Rogers. The effects of a marginally lipotrope-deficient diet on the hepatic levels of S-adenosylmethionine and on the urinary metabolites of 2-acetylaminofluorene in rats. Cancer research. 1977 Mar; 37(3):744-8. doi: . [PMID: 65217]
  • F F Becker, D Stillman, S Sell. Serum alpha-fetoprotein in a mouse strain (C3H-Avy fB) with spontaneous hepatocellular carcinomas. Cancer research. 1977 Mar; 37(3):870-2. doi: NULL. [PMID: 65218]