CHEBI:33277 (BioDeep_00000861638)

Main id: BioDeep_00000395484

 

PANOMIX_OTCML-2023


代谢物信息卡片


2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)

化学式: C28H42O2 (410.3184632)
中文名称: γ-生育三烯酚
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=C(C=C2CCC(OC2=C1C)(C)CCC=C(C)CCC=C(C)CCC=C(C)C)O
InChI: InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1

描述信息

γ-Tocotrienol is an active form of vitamin E. γ-tocotrienol reverses the multidrug resistance (MDR) of breast cancer cells through the signaling pathway of NF-κB and P-gp. γ-Tocotrienol is also a novel radioprotector agent, can mitigate bone marrow radiation damage during targeted radionuclide treatment[1][2][3].
γ-Tocotrienol is an active form of vitamin E. γ-tocotrienol reverses the multidrug resistance (MDR) of breast cancer cells through the signaling pathway of NF-κB and P-gp. γ-Tocotrienol is also a novel radioprotector agent, can mitigate bone marrow radiation damage during targeted radionuclide treatment[1][2][3].

同义名列表

17 个代谢物同义名

2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI); 2H-1-benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)-; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, [R-(E,E)]-; (2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol; (R-(E,E))-3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol; (2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-6-chromanol; (2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol; 6-Chromanol, 2,7,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)- (7CI,8CI); 7,8-Dimethyltocotrienol; (R)-gamma-Tocotrienol; D-gamma-Tocotrienol; gamma-Tocotrienol; Plastochromanol 3; γ-Tocotrienol; CHEBI:33277; 14101-61-2; C14155



数据库引用编号

5 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)

11 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

  • Hanqing Zhao, Xin Guo, Yunxuan Lei, Wenjie Xia, Feiyang Cai, Dehao Zhu, Yang An, Yebin Xi, Xiaoyin Niu, Zhaojun Wang, Tao Yue, Guangjie Chen. γ-Tocotrienol inhibits T helper 17 cell differentiation via the IL-6/JAK/STAT3 signaling pathway. Molecular immunology. 2022 11; 151(?):126-133. doi: 10.1016/j.molimm.2022.09.007. [PMID: 36126500]
  • Elliot Rosen, Oluseyi O Fatanmi, Stephen Y Wise, V Ashutosh Rao, Vijay K Singh. Gamma-tocotrienol, a radiation countermeasure, reverses proteomic changes in serum following total-body gamma irradiation in mice. Scientific reports. 2022 03; 12(1):3387. doi: 10.1038/s41598-022-07266-5. [PMID: 35233005]
  • Grazyna Nowak, Judit Megyesi. γ-Tocotrienol Protects against Mitochondrial Dysfunction, Energy Deficits, Morphological Damage, and Decreases in Renal Functions after Renal Ischemia. International journal of molecular sciences. 2021 Nov; 22(23):. doi: 10.3390/ijms222312674. [PMID: 34884479]
  • Jerzy Kruk, Renata Szymańska. Singlet oxygen oxidation products of carotenoids, fatty acids and phenolic prenyllipids. Journal of photochemistry and photobiology. B, Biology. 2021 Mar; 216(?):112148. doi: 10.1016/j.jphotobiol.2021.112148. [PMID: 33556703]
  • Mohd Saufi Harun, Tin Wui Wong, Chee Wai Fong. Advancing skin delivery of α-tocopherol and γ-tocotrienol for dermatitis treatment via nanotechnology and microwave technology. International journal of pharmaceutics. 2021 Jan; 593(?):120099. doi: 10.1016/j.ijpharm.2020.120099. [PMID: 33259902]
  • Aleksander Siger, Michał Michalak, Justyna Lembicz, Małgorzata Nogala-Kałucka, Teresa Cegielska-Taras, Laurencja Szała. Genotype × environment interaction on tocochromanol and plastochromanol-8 content in seeds of doubled haploids obtained from F1 hybrid black × yellow seeds of winter oilseed rape (Brassica napus L.). Journal of the science of food and agriculture. 2018 Jul; 98(9):3263-3270. doi: 10.1002/jsfa.8829. [PMID: 29230831]
  • Evan L Pannkuk, Evagelia C Laiakis, Albert J Fornace, Oluseyi O Fatanmi, Vijay K Singh. A Metabolomic Serum Signature from Nonhuman Primates Treated with a Radiation Countermeasure, Gamma-tocotrienol, and Exposed to Ionizing Radiation. Health physics. 2018 07; 115(1):3-11. doi: 10.1097/hp.0000000000000776. [PMID: 29787425]
  • Victoria E Palau, Kanishka Chakraborty, Daniel Wann, Janet Lightner, Keely Hilton, Marianne Brannon, William Stone, Koyamangalath Krishnan. γ-Tocotrienol induces apoptosis in pancreatic cancer cells by upregulation of ceramide synthesis and modulation of sphingolipid transport. BMC cancer. 2018 May; 18(1):564. doi: 10.1186/s12885-018-4462-y. [PMID: 29769046]
  • Fei Xu, Janam K Pandya, Cheryl Chung, David Julian McClements, Amanda J Kinchla. Emulsions as delivery systems for gamma and delta tocotrienols: Formation, properties and simulated gastrointestinal fate. Food research international (Ottawa, Ont.). 2018 03; 105(?):570-579. doi: 10.1016/j.foodres.2017.11.033. [PMID: 29433249]
  • Sébastien Pellaud, Alexandre Bory, Valentin Chabert, Joëlle Romanens, Laurie Chaisse-Leal, Anh Vu Doan, Lucas Frey, Andrea Gust, Katharina M Fromm, Laurent Mène-Saffrané. WRINKLED1 and ACYL-COA:DIACYLGLYCEROL ACYLTRANSFERASE1 regulate tocochromanol metabolism in Arabidopsis. The New phytologist. 2018 Jan; 217(1):245-260. doi: 10.1111/nph.14856. [PMID: 29105089]
  • Amrita K Cheema, Khyati Y Mehta, Oluseyi O Fatanmi, Stephen Y Wise, Charles P Hinzman, Josh Wolff, Vijay K Singh. A Metabolomic and Lipidomic Serum Signature from Nonhuman Primates Administered with a Promising Radiation Countermeasure, Gamma-Tocotrienol. International journal of molecular sciences. 2017 Dec; 19(1):. doi: 10.3390/ijms19010079. [PMID: 29283379]
  • Jo Aan Goon, Nor Helwa Ezzah Nor Azman, Siti Madiani Abdul Ghani, Zalina Hamid, Wan Zurinah Wan Ngah. Comparing palm oil tocotrienol rich fraction with α-tocopherol supplementation on oxidative stress in healthy older adults. Clinical nutrition ESPEN. 2017 10; 21(?):1-12. doi: 10.1016/j.clnesp.2017.07.004. [PMID: 30014863]
  • Ahmed Abu-Fayyad, Sami Nazzal. Gemcitabine-vitamin E conjugates: Synthesis, characterization, entrapment into nanoemulsions, and in-vitro deamination and antitumor activity. International journal of pharmaceutics. 2017 Aug; 528(1-2):463-470. doi: 10.1016/j.ijpharm.2017.06.031. [PMID: 28627455]
  • JuHee Song, Mi-Ja Kim, Young-Jun Kim, JaeHwan Lee. Monitoring changes in acid value, total polar material, and antioxidant capacity of oils used for frying chicken. Food chemistry. 2017 Apr; 220(?):306-312. doi: 10.1016/j.foodchem.2016.09.174. [PMID: 27855904]
  • Eva Fleta-Soriano, Sergi Munné-Bosch. Enhanced plastochromanol-8 accumulation during reiterated drought in maize (Zea mays L.). Plant physiology and biochemistry : PPB. 2017 Mar; 112(?):283-289. doi: 10.1016/j.plaphy.2017.01.016. [PMID: 28119116]
  • Yingyi Mao, Jigang Han, Fang Tian, Xue Tang, Yonghong Hu, Yan Guan. Chemical Composition Analysis, Sensory, and Feasibility Study of Tree Peony Seed. Journal of food science. 2017 Feb; 82(2):553-561. doi: 10.1111/1750-3841.13593. [PMID: 28135396]
  • Chiaki Sato, Saki Kaneko, Ayami Sato, Nantiga Virgona, Kozue Namiki, Tomohiro Yano. Combination Effect of δ-Tocotrienol and γ-Tocopherol on Prostate Cancer Cell Growth. Journal of nutritional science and vitaminology. 2017; 63(5):349-354. doi: 10.3177/jnsv.63.349. [PMID: 29225320]
  • Aleksander Siger, Marta Józefiak, Paweł Górnaś. Cold-pressed and hot-pressed rapeseed oil: The effects of roasting and seed moisture on the antioxi- dant activity, canolol, and tocopherol level. Acta scientiarum polonorum. Technologia alimentaria. 2017 Jan; 16(1):69-81. doi: 10.17306/j.afs.2017.0458. [PMID: 28362474]
  • Daniela Strenkert, Clariss Ann Limso, Abdelhak Fatihi, Stefan Schmollinger, Gilles J Basset, Sabeeha S Merchant. Genetically Programmed Changes in Photosynthetic Cofactor Metabolism in Copper-deficient Chlamydomonas. The Journal of biological chemistry. 2016 09; 291(36):19118-31. doi: 10.1074/jbc.m116.717413. [PMID: 27440043]
  • Teresa Cegielska-Taras, Małgorzata Nogala-Kałucka, Laurencja Szala, Aleksander Siger. Study of variation of tocochromanol and phytosterol contents in black and yellow seeds of Brassica napus L. doubled haploid populations. Acta scientiarum polonorum. Technologia alimentaria. 2016 Jul; 15(3):321-332. doi: 10.17306/j.afs.2016.3.31. [PMID: 28071031]
  • Shuya Yamashita, Kiwako Baba, Akiko Makio, Motofumi Kumazoe, Yuhui Huang, I-Chian Lin, Jaehoon Bae, Motoki Murata, Shuhei Yamada, Hirofumi Tachibana. γ-Tocotrienol upregulates aryl hydrocarbon receptor expression and enhances the anticancer effect of baicalein. Biochemical and biophysical research communications. 2016 05; 473(4):801-807. doi: 10.1016/j.bbrc.2016.03.111. [PMID: 27055589]
  • 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]
  • Lu Zhao, Xiefan Fang, Maurice R Marshall, Soonkyu Chung. Regulation of Obesity and Metabolic Complications by Gamma and Delta Tocotrienols. Molecules (Basel, Switzerland). 2016 Mar; 21(3):344. doi: 10.3390/molecules21030344. [PMID: 26978344]
  • Yongeun Kim, Wei Wang, Meshail Okla, Inhae Kang, Regis Moreau, Soonkyu Chung. Suppression of NLRP3 inflammasome by γ-tocotrienol ameliorates type 2 diabetes. Journal of lipid research. 2016 Jan; 57(1):66-76. doi: 10.1194/jlr.m062828. [PMID: 26628639]
  • Osama A Alawin, Rayan A Ahmed, Baher A Ibrahim, Karen P Briski, Paul W Sylvester. Antiproliferative effects of γ-tocotrienol are associated with lipid raft disruption in HER2-positive human breast cancer cells. The Journal of nutritional biochemistry. 2016 Jan; 27(?):266-77. doi: 10.1016/j.jnutbio.2015.09.018. [PMID: 26507543]
  • Jolanta Dłużewska, Renata Szymańska, Michal Gabruk, Peter B Kós, Beatrycze Nowicka, Jerzy Kruk. Tocopherol Cyclases-Substrate Specificity and Phylogenetic Relations. PloS one. 2016; 11(7):e0159629. doi: 10.1371/journal.pone.0159629. [PMID: 27462710]
  • Eun-Ha Kim, Yongjik Lee, Hyun Uk Kim. Fibrillin 5 Is Essential for Plastoquinone-9 Biosynthesis by Binding to Solanesyl Diphosphate Synthases in Arabidopsis. The Plant cell. 2015 Oct; 27(10):2956-71. doi: 10.1105/tpc.15.00707. [PMID: 26432861]
  • H Hansen, T Wang, David Dolde, Hongwei Xin. Tocopherol and annatto tocotrienols distribution in laying-hen body. Poultry science. 2015 Oct; 94(10):2421-33. doi: 10.3382/ps/pev228. [PMID: 26286995]
  • Puvaneswari Meganathan, Rafid Salim Jabir, Ho Gwo Fuang, Nirmala Bhoo-Pathy, Roma Basu Choudhury, Nur Aishah Taib, Kalanithi Nesaretnam, Zamri Chik. A new formulation of Gamma Delta Tocotrienol has superior bioavailability compared to existing Tocotrienol-Rich Fraction in healthy human subjects. Scientific reports. 2015 Sep; 5(?):13550. doi: 10.1038/srep13550. [PMID: 26323969]
  • Nam Ho Kim, Jieun Kwak, Ji Yeon Baik, Mi-Ra Yoon, Jeom-Sig Lee, Sung Won Yoon, In-Hwan Kim. Changes in lipid substances in rice during grain development. Phytochemistry. 2015 Aug; 116(?):170-179. doi: 10.1016/j.phytochem.2015.05.004. [PMID: 26021733]
  • Hong Yong Peh, Wanxing Eugene Ho, Chang Cheng, Tze Khee Chan, Ann Ching Genevieve Seow, Albert Y H Lim, Chee Wai Fong, Kok Yong Seng, Choon Nam Ong, W S Fred Wong. Vitamin E Isoform γ-Tocotrienol Downregulates House Dust Mite-Induced Asthma. Journal of immunology (Baltimore, Md. : 1950). 2015 Jul; 195(2):437-44. doi: 10.4049/jimmunol.1500362. [PMID: 26041537]
  • L Zhao, I Kang, X Fang, W Wang, M A Lee, R R Hollins, M R Marshall, S Chung. Gamma-tocotrienol attenuates high-fat diet-induced obesity and insulin resistance by inhibiting adipose inflammation and M1 macrophage recruitment. International journal of obesity (2005). 2015 Mar; 39(3):438-46. doi: 10.1038/ijo.2014.124. [PMID: 25042861]
  • Emily J Watts, Yu Shen, Ephraim P Lansky, Eviatar Nevo, Gerd Bobe, Maret G Traber. High environmental stress yields greater tocotrienol content while changing vitamin e profiles of wild emmer wheat seeds. Journal of medicinal food. 2015 Feb; 18(2):216-23. doi: 10.1089/jmf.2014.0017. [PMID: 25105230]
  • Jerzy Kruk, Renata Szymańska, Jana Cela, Sergi Munne-Bosch. Plastochromanol-8: fifty years of research. Phytochemistry. 2014 Dec; 108(?):9-16. doi: 10.1016/j.phytochem.2014.09.011. [PMID: 25308762]
  • Suryatheja Ananthula, Parash Parajuli, Fathy A Behery, Alaadin Y Alayoubi, Khalid A El Sayed, Sami Nazzal, Paul W Sylvester. Oxazine derivatives of γ- and δ-tocotrienol display enhanced anticancer activity in vivo. Anticancer research. 2014 Jun; 34(6):2715-26. doi: . [PMID: 24922632]
  • Lu Zhao, Jung-Heun Ha, Meshail Okla, Soonkyu Chung. Activation of autophagy and AMPK by gamma-tocotrienol suppresses the adipogenesis in human adipose derived stem cells. Molecular nutrition & food research. 2014 Mar; 58(3):569-79. doi: 10.1002/mnfr.201300157. [PMID: 24668775]
  • 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]
  • Komsak Pintha, Supachai Yodkeeree, Pornsirit Pitchakarn, Pornngarm Limtrakul. Anti-invasive activity against cancer cells of phytochemicals in red jasmine rice (Oryza sativa L.). Asian Pacific journal of cancer prevention : APJCP. 2014; 15(11):4601-7. doi: 10.7314/apjcp.2014.15.11.4601. [PMID: 24969892]
  • Anna Block, Rikard Fristedt, Sara Rogers, Jyothi Kumar, Brian Barnes, Joshua Barnes, Christian G Elowsky, Yashitola Wamboldt, Sally A Mackenzie, Kevin Redding, Sabeeha S Merchant, Gilles J Basset. Functional modeling identifies paralogous solanesyl-diphosphate synthases that assemble the side chain of plastoquinone-9 in plastids. The Journal of biological chemistry. 2013 Sep; 288(38):27594-27606. doi: 10.1074/jbc.m113.492769. [PMID: 23913686]
  • Jacopo Martinis, Gaétan Glauser, Sergiu Valimareanu, Felix Kessler. A chloroplast ABC1-like kinase regulates vitamin E metabolism in Arabidopsis. Plant physiology. 2013 Jun; 162(2):652-62. doi: 10.1104/pp.113.218644. [PMID: 23632854]
  • F Mangialasche, E Westman, M Kivipelto, J-S Muehlboeck, R Cecchetti, M Baglioni, R Tarducci, G Gobbi, P Floridi, H Soininen, I Kłoszewska, M Tsolaki, B Vellas, C Spenger, S Lovestone, L-O Wahlund, A Simmons, P Mecocci. Classification and prediction of clinical diagnosis of Alzheimer's disease based on MRI and plasma measures of α-/γ-tocotrienols and γ-tocopherol. Journal of internal medicine. 2013 Jun; 273(6):602-21. doi: 10.1111/joim.12037. [PMID: 23343471]
  • Mohd Nor Syidiq Rodzian, Ibrahim Abdel Aziz Ibrahim, Mohd Fahami Nur Azlina, Mohd Ismail Nafeeza. Pure tocotrienol concentrate protected rat gastric mucosa from acute stress-induced injury by a non-antioxidant mechanism. Polish journal of pathology : official journal of the Polish Society of Pathologists. 2013 Apr; 64(1):52-8. doi: 10.5114/pjp.2013.34604. [PMID: 23625601]
  • R Loganathan, K R Selvaduray, K Nesaretnam, A K Radhakrishnan. Tocotrienols promote apoptosis in human breast cancer cells by inducing poly(ADP-ribose) polymerase cleavage and inhibiting nuclear factor kappa-B activity. Cell proliferation. 2013 Apr; 46(2):203-13. doi: 10.1111/cpr.12014. [PMID: 23510475]
  • Yuhaniza Shafinie Kamsani, Mohd Hamim Rajikin, Nor-Ashikin Mohamed Nor Khan, Nuraliza Abdul Satar, Amar Chatterjee. Nicotine-induced cessation of embryonic development is reversed by γ-tocotrienol in mice. Medical science monitor basic research. 2013 Mar; 19(?):87-92. doi: 10.12659/msmbr.883822. [PMID: 23462735]
  • Rebecca M Kaup, Mohamed T Khayyal, Eugen J Verspohl. Antidiabetic effects of a standardized Egyptian rice bran extract. Phytotherapy research : PTR. 2013 Feb; 27(2):264-71. doi: 10.1002/ptr.4705. [PMID: 22566008]
  • Beatrycze Nowicka, Jolanta Gruszka, Jerzy Kruk. Function of plastochromanol and other biological prenyllipids in the inhibition of lipid peroxidation-A comparative study in model systems. Biochimica et biophysica acta. 2013 Feb; 1828(2):233-40. doi: 10.1016/j.bbamem.2012.08.018. [PMID: 22959712]
  • Fathy A Behery, Mohamed R Akl, Suryatheja Ananthula, Parash Parajuli, Paul W Sylvester, Khalid A El Sayed. Optimization of tocotrienols as antiproliferative and antimigratory leads. European journal of medicinal chemistry. 2013 Jan; 59(?):329-41. doi: 10.1016/j.ejmech.2012.11.012. [PMID: 23274571]
  • Gregor Carpentero Burdeos, Kiyotaka Nakagawa, Akio Watanabe, Fumiko Kimura, Teruo Miyazawa. γ-Tocotrienol attenuates triglyceride through effect on lipogenic gene expressions in mouse hepatocellular carcinoma Hepa 1-6. Journal of nutritional science and vitaminology. 2013; 59(2):148-51. doi: 10.3177/jnsv.59.148. [PMID: 23727646]
  • Su Liang, Xiaomei Bian, Jing Ma, Motolani Arogunjo, Amit A Deorukhkar, Sunil Krishnan, Huan Xie. Development and validation of a sensitive LC/MS/MS method for the determination of γ-tocotrienol in rat plasma: application to pharmacokinetic studies. Biomedical chromatography : BMC. 2013 Jan; 27(1):58-66. doi: 10.1002/bmc.2748. [PMID: 22522964]
  • Weili Xu, Ming Du, Yonghuan Zhao, Qi Wang, Wenguang Sun, Bingqing Chen. γ-Tocotrienol inhibits cell viability through suppression of β-catenin/Tcf signaling in human colon carcinoma HT-29 cells. The Journal of nutritional biochemistry. 2012 Jul; 23(7):800-7. doi: 10.1016/j.jnutbio.2011.04.003. [PMID: 21852086]
  • Bilal S Abuasal, Courtney Lucas, Breanne Peyton, Alaadin Alayoubi, Sami Nazzal, Paul W Sylvester, Amal Kaddoumi. Enhancement of intestinal permeability utilizing solid lipid nanoparticles increases γ-tocotrienol oral bioavailability. Lipids. 2012 May; 47(5):461-9. doi: 10.1007/s11745-012-3655-4. [PMID: 22271424]
  • Grazyna Nowak, Diana Bakajsova, Corey Hayes, Martin Hauer-Jensen, Cesar M Compadre. γ-Tocotrienol protects against mitochondrial dysfunction and renal cell death. The Journal of pharmacology and experimental therapeutics. 2012 Feb; 340(2):330-8. doi: 10.1124/jpet.111.186882. [PMID: 22040679]
  • 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]
  • Somak Das, Subhendu Mukherjee, Istvan Lekli, Narasimman Gurusamy, Jayeeta Bardhan, Utpal Raychoudhury, Runu Chakravarty, Sandip Banerji, Anne A Knowlton, Dipak K Das. Tocotrienols confer resistance to ischemia in hypercholesterolemic hearts: insight with genomics. Molecular and cellular biochemistry. 2012 Jan; 360(1-2):35-45. doi: 10.1007/s11010-011-1041-9. [PMID: 21918828]
  • Renata Szymańska. [Chloroplast prenylated lipids in response to stress in plants]. Postepy biochemii. 2012; 58(4):372-6. doi: ". [PMID: 23662431]
  • Noriyuki Miyoshi, Yohei Wakao, Susumu Tomono, Masayuki Tatemichi, Tomohiro Yano, Hiroshi Ohshima. The enhancement of the oral bioavailability of γ-tocotrienol in mice by γ-cyclodextrin inclusion. The Journal of nutritional biochemistry. 2011 Dec; 22(12):1121-6. doi: 10.1016/j.jnutbio.2010.09.011. [PMID: 21292469]
  • Alaa H Abuznait, Hisham Qosa, Nicholas D O'Connell, Jessica Akbarian-Tefaghi, Paul W Sylvester, Khalid A El Sayed, Amal Kaddoumi. Induction of expression and functional activity of P-glycoprotein efflux transporter by bioactive plant natural products. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Nov; 49(11):2765-72. doi: 10.1016/j.fct.2011.08.004. [PMID: 21851848]
  • Lucia Eugeni Piller, Céline Besagni, Brigitte Ksas, Dominique Rumeau, Claire Bréhélin, Gaétan Glauser, Felix Kessler, Michel Havaux. Chloroplast lipid droplet type II NAD(P)H quinone oxidoreductase is essential for prenylquinone metabolism and vitamin K1 accumulation. Proceedings of the National Academy of Sciences of the United States of America. 2011 Aug; 108(34):14354-9. doi: 10.1073/pnas.1104790108. [PMID: 21844348]
  • Bilal Abuasal, Shawn Thomas, Paul W Sylvester, Amal Kaddoumi. Development and validation of a reversed-phase HPLC method for the determination of γ-tocotrienol in rat and human plasma. Biomedical chromatography : BMC. 2011 May; 25(5):621-7. doi: 10.1002/bmc.1493. [PMID: 20734323]
  • Maaike Berbée, Qiang Fu, Sarita Garg, Shilpa Kulkarni, K Sree Kumar, Martin Hauer-Jensen. Pentoxifylline enhances the radioprotective properties of γ-tocotrienol: differential effects on the hematopoietic, gastrointestinal and vascular systems. Radiation research. 2011 Mar; 175(3):297-306. doi: 10.1667/rr2399.1. [PMID: 21388273]
  • 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]
  • 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]
  • N Zaiden, W N Yap, S Ong, C H Xu, V H Teo, C P Chang, X W Zhang, K Nesaretnam, S Shiba, Y L Yap. Gamma delta tocotrienols reduce hepatic triglyceride synthesis and VLDL secretion. Journal of atherosclerosis and thrombosis. 2010 Oct; 17(10):1019-32. doi: 10.5551/jat.4911. [PMID: 20702976]
  • Laurent Mène-Saffrané, A Daniel Jones, Dean DellaPenna. Plastochromanol-8 and tocopherols are essential lipid-soluble antioxidants during seed desiccation and quiescence in Arabidopsis. Proceedings of the National Academy of Sciences of the United States of America. 2010 Oct; 107(41):17815-20. doi: 10.1073/pnas.1006971107. [PMID: 20837525]
  • Keisuke Nakashima, Nantiga Virgona, Mio Miyazawa, Takashi Watanabe, Tomohiro Yano. The tocotrienol-rich fraction from rice bran enhances cisplatin-induced cytotoxicity in human mesothelioma H28 cells. Phytotherapy research : PTR. 2010 Sep; 24(9):1317-21. doi: 10.1002/ptr.3107. [PMID: 20127663]
  • Ramaswamy Kannappan, Jayaraj Ravindran, Sahdeo Prasad, Bokyung Sung, Vivek R Yadav, Simone Reuter, Madan M Chaturvedi, Bharat B Aggarwal. Gamma-tocotrienol promotes TRAIL-induced apoptosis through reactive oxygen species/extracellular signal-regulated kinase/p53-mediated upregulation of death receptors. Molecular cancer therapeutics. 2010 Aug; 9(8):2196-207. doi: 10.1158/1535-7163.mct-10-0277. [PMID: 20682650]
  • 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]
  • Bilal Abuasal, Paul W Sylvester, Amal Kaddoumi. Intestinal absorption of gamma-tocotrienol is mediated by Niemann-Pick C1-like 1: in situ rat intestinal perfusion studies. Drug metabolism and disposition: the biological fate of chemicals. 2010 Jun; 38(6):939-45. doi: 10.1124/dmd.109.031567. [PMID: 20207946]
  • Amit B Shirode, Paul W Sylvester. Synergistic anticancer effects of combined gamma-tocotrienol and celecoxib treatment are associated with suppression in Akt and NFkappaB signaling. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2010 May; 64(5):327-32. doi: 10.1016/j.biopha.2009.09.018. [PMID: 19954924]
  • Sunitha V Bachawal, Vikram B Wali, Paul W Sylvester. Enhanced antiproliferative and apoptotic response to combined treatment of gamma-tocotrienol with erlotinib or gefitinib in mammary tumor cells. BMC cancer. 2010 Mar; 10(?):84. doi: 10.1186/1471-2407-10-84. [PMID: 20211018]
  • W N Yap, N Zaiden, S Y Luk, D T W Lee, M T Ling, Y C Wong, Y L Yap. In vivo evidence of gamma-tocotrienol as a chemosensitizer in the treatment of hormone-refractory prostate cancer. Pharmacology. 2010; 85(4):248-58. doi: 10.1159/000278205. [PMID: 20375535]
  • A M Zahara, C C Lee, I Siti Fatimah, B K Poh, O Khairul, S Das, J Mohamad. Plasma vitamin C and tocotrienols changes in response to dietary supplementation among young male adults. La Clinica terapeutica. 2010; 161(2):121-4. doi: NULL. [PMID: 20499024]
  • Anna Maria Zbierzak, Marion Kanwischer, Christina Wille, Pierre-Alexandre Vidi, Patrick Giavalisco, Antje Lohmann, Isabel Briesen, Svetlana Porfirova, Claire Bréhélin, Felix Kessler, Peter Dörmann. Intersection of the tocopherol and plastoquinol metabolic pathways at the plastoglobule. The Biochemical journal. 2009 Dec; 425(2):389-99. doi: 10.1042/bj20090704. [PMID: 19843012]
  • Mohd Hamim Rajikin, Elda Surhaida Latif, Megat Radzi Mar, A Gapor Mat Top, Norfilza M Mokhtar. Deleterious effects of nicotine on the ultrastructure of oocytes: role of gamma-tocotrienol. Medical science monitor : international medical journal of experimental and clinical research. 2009 Dec; 15(12):BR378-83. doi: ". [PMID: 19946227]
  • Helene Freiser, Qing Jiang. Gamma-tocotrienol and gamma-tocopherol are primarily metabolized to conjugated 2-(beta-carboxyethyl)-6-hydroxy-2,7,8-trimethylchroman and sulfated long-chain carboxychromanols in rats. The Journal of nutrition. 2009 May; 139(5):884-9. doi: 10.3945/jn.108.103309. [PMID: 19297424]
  • Nami Akaho, Jiro Takata, Takeshi Fukushima, Kazuhisa Matsunaga, Akihiro Hattori, Ryoji Hidaka, Kosuke Fukui, Miyako Yoshida, Toshihiro Fujioka, Yoshiharu Karube, Kazuhiro Imai. Preparation and in vivo evaluation of a water-soluble prodrug for 2R-gamma-tocotrienol and as a two-step prodrug for 2,7,8-trimethyl-2S-(beta-carboxyethyl)-6-hydroxychroman (S-gamma-CEHC) in rat. Drug metabolism and disposition: the biological fate of chemicals. 2007 Sep; 35(9):1502-10. doi: 10.1124/dmd.106.014365. [PMID: 17537874]
  • Wakako Tsuzuki, Ritsuko Yunoki, Hiroyuki Yoshimura. Intestinal epithelial cells absorb gamma-tocotrienol faster than alpha-tocopherol. Lipids. 2007 Mar; 42(2):163-70. doi: 10.1007/s11745-007-3021-0. [PMID: 17393222]
  • 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]
  • Yuki Kawakami, Tsuyoshi Tsuzuki, Kiyotaka Nakagawa, Teruo Miyazawa. Distribution of tocotrienols in rats fed a rice bran tocotrienol concentrate. Bioscience, biotechnology, and biochemistry. 2007 Feb; 71(2):464-71. doi: 10.1271/bbb.60524. [PMID: 17284857]
  • G V Samant, P W Sylvester. gamma-Tocotrienol inhibits ErbB3-dependent PI3K/Akt mitogenic signalling in neoplastic mammary epithelial cells. Cell proliferation. 2006 Dec; 39(6):563-74. doi: 10.1111/j.1365-2184.2006.00412.x. [PMID: 17109639]
  • K Sree Kumar, Mythili Raghavan, Kevin Hieber, Christine Ege, Steven Mog, Nannette Parra, Annette Hildabrand, Vijay Singh, V Srinivasan, Raymond Toles, Patience Karikari, Gyorgy Petrovics, Thomas Seed, Shiv Srivastava, Andreas Papas. Preferential radiation sensitization of prostate cancer in nude mice by nutraceutical antioxidant gamma-tocotrienol. Life sciences. 2006 Mar; 78(18):2099-104. doi: 10.1016/j.lfs.2005.12.005. [PMID: 16413038]
  • Paul W Sylvester, Sumit J Shah, Ganesh V Samant. Intracellular signaling mechanisms mediating the antiproliferative and apoptotic effects of gamma-tocotrienol in neoplastic mammary epithelial cells. Journal of plant physiology. 2005 Jul; 162(7):803-10. doi: 10.1016/j.jplph.2005.04.014. [PMID: 16008108]
  • 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]
  • M A Newaz, Z Yousefipour, N Nawal, N Adeeb. Nitric oxide synthase activity in blood vessels of spontaneously hypertensive rats: antioxidant protection by gamma-tocotrienol. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2003 Sep; 54(3):319-27. doi: . [PMID: 14566071]
  • Hisako Saito, Chikako Kiyose, Hiroyuki Yoshimura, Tadahiko Ueda, Kazuo Kondo, Osamu Igarashi. Gamma-tocotrienol, a vitamin E homolog, is a natriuretic hormone precursor. Journal of lipid research. 2003 Aug; 44(8):1530-5. doi: 10.1194/jlr.m300061-jlr200. [PMID: 12730299]
  • Saiko Ikeda, Tomoko Tohyama, Hiroyuki Yoshimura, Kimio Hamamura, Kouichi Abe, Kanae Yamashita. Dietary alpha-tocopherol decreases alpha-tocotrienol but not gamma-tocotrienol concentration in rats. The Journal of nutrition. 2003 Feb; 133(2):428-34. doi: 10.1093/jn/133.2.428. [PMID: 12566479]
  • 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]
  • Vikkie A Mustad, Carla A Smith, Peter P Ruey, Neile K Edens, Stephen J DeMichele. Supplementation with 3 compositionally different tocotrienol supplements does not improve cardiovascular disease risk factors in men and women with hypercholesterolemia. The American journal of clinical nutrition. 2002 Dec; 76(6):1237-43. doi: 10.1093/ajcn/76.6.1237. [PMID: 12450888]
  • D Raederstorff, V Elste, C Aebischer, P Weber. Effect of either gamma-tocotrienol or a tocotrienol mixture on the plasma lipid profile in hamsters. Annals of nutrition & metabolism. 2002; 46(1):17-23. doi: 10.1159/000046748. [PMID: 11914511]
  • P W Sylvester, B S McIntyre, A Gapor, K P Briski. Vitamin E inhibition of normal mammary epithelial cell growth is associated with a reduction in protein kinase C(alpha) activation. Cell proliferation. 2001 Dec; 34(6):347-57. doi: 10.1046/j.1365-2184.2001.00221.x. [PMID: 11736999]
  • S Ikeda, K Toyoshima, K Yamashita. Dietary sesame seeds elevate alpha- and gamma-tocotrienol concentrations in skin and adipose tissue of rats fed the tocotrienol-rich fraction extracted from palm oil. The Journal of nutrition. 2001 Nov; 131(11):2892-7. doi: 10.1093/jn/131.11.2892. [PMID: 11694614]
  • H Nakamura, F Furukawa, A Nishikawa, M Miyauchi, H Y Son, T Imazawa, M Hirose. Oral toxicity of a tocotrienol preparation in rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2001 Aug; 39(8):799-805. doi: 10.1016/s0278-6915(01)00025-4. [PMID: 11434987]
  • A A Qureshi, D M Peterson, J O Hasler-Rapacz, J Rapacz. Novel tocotrienols of rice bran suppress cholesterogenesis in hereditary hypercholesterolemic swine. The Journal of nutrition. 2001 Feb; 131(2):223-30. doi: 10.1093/jn/131.2.223. [PMID: 11160537]
  • J K Lodge, J Ridlington, S Leonard, H Vaule, M G Traber. Alpha- and gamma-tocotrienols are metabolized to carboxyethyl-hydroxychroman derivatives and excreted in human urine. Lipids. 2001 Jan; 36(1):43-8. doi: 10.1007/s11745-001-0666-z. [PMID: 11214728]
  • S P Yap, K H Yuen, J W Wong. Pharmacokinetics and bioavailability of alpha-, gamma- and delta-tocotrienols under different food status. The Journal of pharmacy and pharmacology. 2001 Jan; 53(1):67-71. doi: 10.1211/0022357011775208. [PMID: 11206194]
  • A Hattori, T Fukushima, H Yoshimura, K Abe, K Imai. Production of LLU-alpha following an oral administration of gamma-tocotrienol or gamma-tocopherol to rats. Biological & pharmaceutical bulletin. 2000 Nov; 23(11):1395-7. doi: 10.1248/bpb.23.1395. [PMID: 11085376]
  • T M Black, P Wang, N Maeda, R A Coleman. Palm tocotrienols protect ApoE +/- mice from diet-induced atheroma formation. The Journal of nutrition. 2000 Oct; 130(10):2420-6. doi: 10.1093/jn/130.10.2420. [PMID: 11015467]
  • S Ikeda, T Niwa, K Yamashita. Selective uptake of dietary tocotrienols into rat skin. Journal of nutritional science and vitaminology. 2000 Jun; 46(3):141-3. doi: 10.3177/jnsv.46.141. [PMID: 10955281]
  • F D Goffman, C Möllers. Changes in tocopherol and plastochromanol-8 contents in seeds and oil of oilseed rape (Brassica napus L.) during storage as influenced by temperature and air oxygen. Journal of agricultural and food chemistry. 2000 May; 48(5):1605-9. doi: 10.1021/jf9912755. [PMID: 10820066]