alpha-Tocotrienol (BioDeep_00000014559)

 

Secondary id: BioDeep_00000400387

natural product human metabolite Endogenous blood metabolite


代谢物信息卡片


(2R)-2,5,7,8-Tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

化学式: C29H44O2 (424.3341124)
中文名称: D-ALPHA-(P)-生育三烯酚, D-a-生育三烯酚
谱图信息: 最多检出来源 Viridiplantae(plant) 0.01%

分子结构信息

SMILES: c1(c(c(c2c(c1C)O[C@](CC2)(C)CC/C=C(/C)\CC/C=C(\C)/CCC=C(C)C)C)O)C
InChI: InChI=1/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1

描述信息

alpha-Tocotrienol (CAS: 1721-51-3), also known as 5,7,8-trimethyltocotrienol, belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. They differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, alpha-tocotrienol is considered to be a quinone lipid molecule. alpha-Tocotrienol is found in the blood plasma and all lipoprotein subfractions. Compared to tocopherols, alpha-tocotrienols are poorly studied. Its presence in the blood plasma at nanomolar concentrations is thought to help to prevent stroke-related neurodegeneration (PMID: 16771695). alpha-Tocotrienol has been found to have vitamin E activity.
D020011 - Protective Agents > D000975 - Antioxidants > D024508 - Tocotrienols
Acquisition and generation of the data is financially supported in part by CREST/JST.

同义名列表

16 个代谢物同义名

(2R)-2,5,7,8-Tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol; 2R,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol; (2R,3e,7e)-alpha-Tocotrienol; (2R,3’E,7’e)-α-tocotrienol; 5,7,8-Trimethyltocotrienol; (2R,3e,7e)-Α-tocotrienol; (R)-alpha-Tocotrienol; Tocotrienol, alpha; alpha-Tocotrienol; (R)-Α-tocotrienol; zeta1-tocopherol; α tocotrienol; Ζ1-tocopherol; α-tocotrienol; a-Tocotrienol; α-Tocotrienol



数据库引用编号

25 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

73 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(71)

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

  • Daisuke Watase, Shuichi Setoguchi, Nami Nagata-Akaho, Shotaro Goto, Hirofumi Yamakawa, Ayano Yamada, Mitsuhisa Koga, Yoshiharu Karube, Kazuhisa Matsunaga, Jiro Takata. Cationic N,N-Dimethylglycine Ester Prodrug of 2R-α-Tocotrienol Promotes Intestinal Absorption via Efficient Self-Micellization with Intrinsic Bile Acid Anion. Molecules (Basel, Switzerland). 2022 Apr; 27(9):. doi: 10.3390/molecules27092727. [PMID: 35566078]
  • Ailar Tupal, Mehdi Sabzichi, Roya Bazzaz, Nazila Fathi Maroufi, Maryam Mohammadi, Seyed Mohammadbagher Pirouzpanah, Fatemeh Ramezani. Application of ɑ-Tocotrienol-Loaded Biocompatible Precirol in Attenuation of Doxorubicin Dose-Dependent Behavior in HUH-7 Hepatocarcinoma Cell Line. Nutrition and cancer. 2020; 72(4):653-661. doi: 10.1080/01635581.2019.1650191. [PMID: 31390910]
  • Thomas Nury, Randa Sghaier, Amira Zarrouk, Franck Ménétrier, Tugba Uzun, Valerio Leoni, Claudio Caccia, Wiem Meddeb, Amira Namsi, Khouloud Sassi, Wafa Mihoubi, Jean-Marc Riedinger, Mustapha Cherkaoui-Malki, Thibault Moreau, Anne Vejux, Gérard Lizard. Induction of peroxisomal changes in oligodendrocytes treated with 7-ketocholesterol: Attenuation by α-tocopherol. Biochimie. 2018 Oct; 153(?):181-202. doi: 10.1016/j.biochi.2018.07.009. [PMID: 30031877]
  • Imeddedine Arbi Nehdi, Hassen Mohamed Sbihi, Chin Ping Tan, Umer Rashid, Saud Ibrahim Al-Resayes. Chemical Composition of Date Palm (Phoenix dactylifera L.) Seed Oil from Six Saudi Arabian Cultivars. Journal of food science. 2018 Mar; 83(3):624-630. doi: 10.1111/1750-3841.14033. [PMID: 29377104]
  • Giuseppe Bombai, Federica Pasini, Vito Verardo, Onur Sevindik, Michele Di Foggia, Paola Tessarin, Anna Maria Bregoli, Maria F Caboni, Adamo D Rombolà. Monitoring of compositional changes during berry ripening in grape seed extracts of cv. Sangiovese (Vitis vinifera L.). Journal of the science of food and agriculture. 2017 Jul; 97(9):3058-3064. doi: 10.1002/jsfa.8151. [PMID: 27873332]
  • Takaya Nakazawa, Yuta Miyanoki, Yasuomi Urano, Madoka Uehara, Yoshiro Saito, Noriko Noguchi. Effect of vitamin E on 24(S)-hydroxycholesterol-induced necroptosis-like cell death and apoptosis. The Journal of steroid biochemistry and molecular biology. 2017 05; 169(?):69-76. doi: 10.1016/j.jsbmb.2016.03.003. [PMID: 26953980]
  • Weng-Yew Wong, Leigh C Ward, Chee Wai Fong, Wei Ney Yap, Lindsay Brown. Anti-inflammatory γ- and δ-tocotrienols improve cardiovascular, liver and metabolic function in diet-induced obese rats. European journal of nutrition. 2017 Feb; 56(1):133-150. doi: 10.1007/s00394-015-1064-1. [PMID: 26446095]
  • Ping Tou Gee, Chen Yee Liew, Meng Chil Thong, Melvin C L Gay. Vitamin E analysis by ultra-performance convergence chromatography and structural elucidation of novel α-tocodienol by high-resolution mass spectrometry. Food chemistry. 2016 Apr; 196(?):367-73. doi: 10.1016/j.foodchem.2015.09.073. [PMID: 26593503]
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  • Constanze M Walde, Astrid M Drotleff, Waldemar Ternes. Comparison of dietary tocotrienols from barley and palm oils in hen's egg yolk: transfer efficiency, influence of emulsification, and effect on egg cholesterol. Journal of the science of food and agriculture. 2014 Mar; 94(4):810-8. doi: 10.1002/jsfa.6484. [PMID: 24254057]
  • Kazuo Mukai, Eri Ishikawa, Aya Ouchi, Shin-Ichi Nagaoka, Tomomi Suzuki, Katsuhiro Izumisawa, Taisuke Koike. Kinetic study of the quenching reaction of singlet oxygen by α-, β-, γ-, δ-tocotrienols, and palm oil and soybean extracts in solution. Bioscience, biotechnology, and biochemistry. 2014; 78(12):2089-101. doi: 10.1080/09168451.2014.943653. [PMID: 25093256]
  • Stephanie Hagl, Alexa Kocher, Christina Schiborr, Schamim H Eckert, Ion Ciobanu, Marc Birringer, Hesham El-Askary, Amr Helal, Mohamed T Khayyal, Jan Frank, Walter E Muller, Gunter P Eckert. Rice bran extract protects from mitochondrial dysfunction in guinea pig brains. Pharmacological research. 2013 Oct; 76(?):17-27. doi: 10.1016/j.phrs.2013.06.008. [PMID: 23827162]
  • Na Young Jung, Kyung Hee Lee, Ran Won, Bae Hwan Lee. Neuroprotective effects of α-tocotrienol on kainic acid-induced neurotoxicity in organotypic hippocampal slice cultures. International journal of molecular sciences. 2013 Sep; 14(9):18256-68. doi: 10.3390/ijms140918256. [PMID: 24013375]
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  • Gui-Yun Zhang, Ru-Ru Liu, Geng Xu, Peng Zhang, Yin Li, Ke-Xuan Tang, Guo-Hua Liang, Qiao-Quan Liu. Increased α-tocotrienol content in seeds of transgenic rice overexpressing Arabidopsis γ-tocopherol methyltransferase. Transgenic research. 2013 Feb; 22(1):89-99. doi: 10.1007/s11248-012-9630-2. [PMID: 22763462]
  • Anne Büsing, Astrid M Drotleff, Waldemar Ternes. Identification of α-tocotrienolquinone epoxides and development of an efficient molecular distillation procedure for quantitation of α-tocotrienol oxidation products in food matrices by high-performance liquid chromatography with diode array and fluorescence detection. Journal of agricultural and food chemistry. 2012 Aug; 60(34):8302-13. doi: 10.1021/jf301137b. [PMID: 22747466]
  • Koji Fukui, Keisuke Ushiki, Hirokatsu Takatsu, Tatsuro Koike, Shiro Urano. Tocotrienols prevent hydrogen peroxide-induced axon and dendrite degeneration in cerebellar granule cells. Free radical research. 2012 Feb; 46(2):184-93. doi: 10.3109/10715762.2011.647689. [PMID: 22149330]
  • Syed Fairus, Rosnah M Nor, Hwee M Cheng, Kalyana Sundram. Alpha-tocotrienol is the most abundant tocotrienol isomer circulated in plasma and lipoproteins after postprandial tocotrienol-rich vitamin E supplementation. Nutrition journal. 2012 Jan; 11(?):5. doi: 10.1186/1475-2891-11-5. [PMID: 22252050]
  • Shi Wei Tan, Rajesh Ramasamy, Maha Abdullah, Sharmili Vidyadaran. Inhibitory effects of palm α-, γ- and δ-tocotrienol on lipopolysaccharide-induced nitric oxide production in BV2 microglia. Cellular immunology. 2011; 271(2):205-9. doi: 10.1016/j.cellimm.2011.07.012. [PMID: 21839427]
  • Tomono Uchida, Saki Nomura, Tomio Ichikawa, Chisato Abe, Saiko Ikeda. Tissue distribution of vitamin E metabolites in rats after oral administration of tocopherol or tocotrienol. Journal of nutritional science and vitaminology. 2011; 57(5):326-32. doi: 10.3177/jnsv.57.326. [PMID: 22293209]
  • Yoshiro Saito, Keiko Nishio, Yoko Ogawa Akazawa, Kazunori Yamanaka, Akiko Miyama, Yasukazu Yoshida, Noriko Noguchi, Etsuo Niki. Cytoprotective effects of vitamin E homologues against glutamate-induced cell death in immature primary cortical neuron cultures: Tocopherols and tocotrienols exert similar effects by antioxidant function. Free radical biology & medicine. 2010 Nov; 49(10):1542-9. doi: 10.1016/j.freeradbiomed.2010.08.016. [PMID: 20736061]
  • Fengjuan Li, Wenjuan Tan, Zhanfang Kang, Chi-Wai Wong. Tocotrienol enriched palm oil prevents atherosclerosis through modulating the activities of peroxisome proliferators-activated receptors. Atherosclerosis. 2010 Jul; 211(1):278-82. doi: 10.1016/j.atherosclerosis.2010.01.015. [PMID: 20138624]
  • Mariarosaria Napolitano, Luca Avanzi, Stefano Manfredini, Elena Bravo. Effects of new combinative antioxidant FeAOX-6 and alpha-tocotrienol on macrophage atherogenesis-related functions. Vascular pharmacology. 2007 Jun; 46(6):394-405. doi: 10.1016/j.vph.2006.01.019. [PMID: 17331802]
  • Chisato Abe, Saiko Ikeda, Tomono Uchida, Kanae Yamashita, Tomio Ichikawa. Triton WR1339, an inhibitor of lipoprotein lipase, decreases vitamin E concentration in some tissues of rats by inhibiting its transport to liver. The Journal of nutrition. 2007 Feb; 137(2):345-50. doi: 10.1093/jn/137.2.345. [PMID: 17237309]
  • Savita Khanna, Sashwati Roy, Narasimham L Parinandi, Mariah Maurer, Chandan K Sen. Characterization of the potent neuroprotective properties of the natural vitamin E alpha-tocotrienol. Journal of neurochemistry. 2006 Sep; 98(5):1474-86. doi: 10.1111/j.1471-4159.2006.04000.x. [PMID: 16923160]
  • Suzanne G Yu, Ann M Thomas, Abdul Gapor, Barrie Tan, Nilofer Qureshi, Asaf A Qureshi. Dose-response impact of various tocotrienols on serum lipid parameters in 5-week-old female chickens. Lipids. 2006 May; 41(5):453-61. doi: 10.1007/s11745-006-5119-1. [PMID: 16933790]
  • Savita Khanna, Viren Patel, Cameron Rink, Sashwati Roy, Chandan K Sen. Delivery of orally supplemented alpha-tocotrienol to vital organs of rats and tocopherol-transport protein deficient mice. Free radical biology & medicine. 2005 Nov; 39(10):1310-9. doi: 10.1016/j.freeradbiomed.2005.06.013. [PMID: 16257640]
  • Laverne A Mooney, Ann M Madsen, Deliang Tang, Manuela A Orjuela, Wei-Yann Tsai, Elizabeth R Garduno, Frederica P Perera. Antioxidant vitamin supplementation reduces benzo(a)pyrene-DNA adducts and potential cancer risk in female smokers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2005 Jan; 14(1):237-42. doi: . [PMID: 15668500]
  • M Norazlina, C W Chua, S Ima-Nirwana. Vitamin E deficiency reduced lumbar bone calcium content in female rats. The Medical journal of Malaysia. 2004 Dec; 59(5):623-30. doi: NULL. [PMID: 15889565]
  • Yoshiro Saito, Yasukazu Yoshida, Keiko Nishio, Mieko Hayakawa, Etsuo Niki. Characterization of cellular uptake and distribution of vitamin E. Annals of the New York Academy of Sciences. 2004 Dec; 1031(?):368-75. doi: 10.1196/annals.1331.047. [PMID: 15753172]
  • Siew Ping Yap, Kah Hay Yuen. Influence of lipolysis and droplet size on tocotrienol absorption from self-emulsifying formulations. International journal of pharmaceutics. 2004 Aug; 281(1-2):67-78. doi: 10.1016/j.ijpharm.2004.05.015. [PMID: 15288344]
  • Noriko Noguchi, Ryuhei Hanyu, Aya Nonaka, Yuko Okimoto, Tatsuhiko Kodama. Inhibition of THP-1 cell adhesion to endothelial cells by alpha-tocopherol and alpha-tocotrienol is dependent on intracellular concentration of the antioxidants. Free radical biology & medicine. 2003 Jun; 34(12):1614-20. doi: 10.1016/s0891-5849(03)00216-8. [PMID: 12788481]
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  • Jürgen Fuchs, Stefan Weber, Maurizio Podda, Norbert Groth, Thomas Herrling, Lester Packer, Roland Kaufmann. HPLC analysis of vitamin E isoforms in human epidermis: correlation with minimal erythema dose and free radical scavenging activity. Free radical biology & medicine. 2003 Feb; 34(3):330-6. doi: 10.1016/s0891-5849(02)01293-5. [PMID: 12543248]
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