LLU-alpha (BioDeep_00000639400)
代谢物信息卡片
(2S)-2,7,8-Trimethyl-6-hydroxychroman-2-propanoic acid
化学式: C15H20O4 (264.13615200000004)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1(C)=C(C)C2O[C@@](CCC(=O)O)(C)CCC=2C=C1O
InChI: InChI=1S/C15H20O4/c1-9-10(2)14-11(8-12(9)16)4-6-15(3,19-14)7-5-13(17)18/h8,16H,4-7H2,1-3H3,(H,17,18)/t15-/m0/s1
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)
0 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
- Tomono Uchida, Saki Nomura, Hiroaki Oda, Saiko Ikeda. γ-Tocopherol Is Metabolized Faster than α-Tocopherol in Young Japanese Women.
Journal of nutritional science and vitaminology.
2018; 64(6):399-403. doi:
10.3177/jnsv.64.399. [PMID: 30606962] - Antonella Fais, Enrico Cacace, Luigi Atzori, Benedetta Era, Valeria Ruggiero. Plasma phospholipase, γ-CEHC and antioxidant capacity in fibromyalgia.
International journal of rheumatic diseases.
2017 May; 20(5):550-554. doi:
10.1111/1756-185x.12787. [PMID: 26585319] - 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] - Michael W Clarke, John R Burnett, Jason H Y Wu, Jonathan M Hodgson, Thomas Ledowski, Ian B Puddey, Kevin D Croft. Vitamin E supplementation and hepatic drug metabolism in humans.
Journal of cardiovascular pharmacology.
2009 Dec; 54(6):491-6. doi:
10.1097/fjc.0b013e3181bfae18. [PMID: 19755916] - Joo-Youn Cho, Dong Wook Kang, Xiaochao Ma, Sung-Hoon Ahn, Kristopher W Krausz, Hans Luecke, Jeffrey R Idle, Frank J Gonzalez. Metabolomics reveals a novel vitamin E metabolite and attenuated vitamin E metabolism upon PXR activation.
Journal of lipid research.
2009 May; 50(5):924-37. doi:
10.1194/jlr.m800647-jlr200. [PMID: 19141872] - Jan Frank, Trevor W George, John K Lodge, Ana M Rodriguez-Mateos, Jeremy P E Spencer, Anne Marie Minihane, Gerald Rimbach. Daily consumption of an aqueous green tea extract supplement does not impair liver function or alter cardiovascular disease risk biomarkers in healthy men.
The Journal of nutrition.
2009 Jan; 139(1):58-62. doi:
10.3945/jn.108.096412. [PMID: 19056646] - 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] - Tomono Uchida, Tomio Ichikawa, Chisato Abe, Kanae Yamashita, Saiko Ikeda. Dietary sesame seed decreases urinary excretion of alpha- and gamma-tocopherol metabolites in rats.
Journal of nutritional science and vitaminology.
2007 Aug; 53(4):372-6. doi:
10.3177/jnsv.53.372. [PMID: 17934245] - José P Werba, Viviana Cavalca, Fabrizio Veglia, Paola Massironi, Michela De Franceschi, Lorenzo Zingaro, Elena Tremoli. A new compound-specific pleiotropic effect of statins: modification of plasma gamma-tocopherol levels.
Atherosclerosis.
2007 Jul; 193(1):229-33. doi:
10.1016/j.atherosclerosis.2006.06.020. [PMID: 16860808] - Jason H Y Wu, Jonathan M Hodgson, Natalie C Ward, Michael W Clarke, Ian B Puddey, Kevin D Croft. Nitration of gamma-tocopherol prevents its oxidative metabolism by HepG2 cells.
Free radical biology & medicine.
2005 Aug; 39(4):483-94. doi:
10.1016/j.freeradbiomed.2005.04.001. [PMID: 16043020] - S Yoshikawa, T Morinobu, K Hamamura, F Hirahara, T Iwamoto, H Tamai. The effect of gamma-tocopherol administration on alpha-tocopherol levels and metabolism in humans.
European journal of clinical nutrition.
2005 Aug; 59(8):900-5. doi:
10.1038/sj.ejcn.1602154. [PMID: 15928686] - Maret G Traber, Lisbeth K Siddens, Scott W Leonard, Bettina Schock, Kishorchandra Gohil, Sharon K Krueger, Carroll E Cross, David E Williams. Alpha-tocopherol modulates Cyp3a expression, increases gamma-CEHC production, and limits tissue gamma-tocopherol accumulation in mice fed high gamma-tocopherol diets.
Free radical biology & medicine.
2005 Mar; 38(6):773-85. doi:
10.1016/j.freeradbiomed.2004.11.027. [PMID: 15721988] - Regina Brigelius-Flohé, Johannes M Roob, Beate Tiran, Sandra Wuga, Josep Ribalta, Edmond Rock, Brigitte M Winklhofer-Roob. The effect of age on vitamin E status, metabolism, and function: metabolism as assessed by labeled tocopherols.
Annals of the New York Academy of Sciences.
2004 Dec; 1031(?):40-3. doi:
10.1196/annals.1331.004. [PMID: 15753132] - Maiko Tanabe, Takeshi Fukushima, Noriko Usui, Nozomi Aoyama, Makoto Tsunoda, Kazuhiro Imai. Intravenous administration of 2,7,8-trimethyl-2-(beta-carboxyethyl)-6-hydroxy chroman (gamma-CEHC) to rats and determination of its plasma concentration and urinary sodium excretion.
Biomedical chromatography : BMC.
2004 Nov; 18(9):727-34. doi:
10.1002/bmc.385. [PMID: 15386582] - Francesco Galli, Marta Piroddi, Anna Lannone, Silvia Pagliarani, Aldo Tomasi, Ardesio Floridi. A comparison between the antioxidant and peroxynitrite-scavenging functions of the vitamin E metabolites alpha- and gamma-carboxyethyl-6-hydroxychromans.
International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition.
2004 Sep; 74(5):362-73. doi:
10.1024/0300-9831.74.5.362. [PMID: 15628675] - Yvonne M Jeanes, Wendy L Hall, Anna R Proteggente, John K Lodge. Cigarette smokers have decreased lymphocyte and platelet alpha-tocopherol levels and increased excretion of the gamma-tocopherol metabolite gamma-carboxyethyl-hydroxychroman (gamma-CEHC).
Free radical research.
2004 Aug; 38(8):861-8. doi:
10.1080/10715760410001715149. [PMID: 15493460] - Harumi Uto, Chikako Kiyose, Hisako Saito, Tadahiko Ueda, Takaharu Nakamijra, Osamu Igarashi, Kazuo Kondo. Gamma-tocopherol enhances sodium excretion as a natriuretic hormone precursor.
Journal of nutritional science and vitaminology.
2004 Aug; 50(4):277-82. doi:
10.3177/jnsv.50.277. [PMID: 15527070] - Karl-Heinz Wagner, Afaf Kamal-Eldin, Ibrahim Elmadfa. Gamma-tocopherol--an underestimated vitamin?.
Annals of nutrition & metabolism.
2004; 48(3):169-88. doi:
10.1159/000079555. [PMID: 15256801] - Francesco Galli, Rosalind Lee, Jeffrey Atkinson, Ardesio Floridi, Frank J Kelly. gamma-Tocopherol biokinetics and transformation in humans.
Free radical research.
2003 Nov; 37(11):1225-33. doi:
10.1080/10715760310001604125. [PMID: 14703735] - 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] - Qing Jiang, Bruce N Ames. Gamma-tocopherol, but not alpha-tocopherol, decreases proinflammatory eicosanoids and inflammation damage in rats.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2003 May; 17(8):816-22. doi:
10.1096/fj.02-0877com. [PMID: 12724340] - T Morinobu, S Yoshikawa, K Hamamura, H Tamai. Measurement of vitamin E metabolites by high-performance liquid chromatography during high-dose administration of alpha-tocopherol.
European journal of clinical nutrition.
2003 Mar; 57(3):410-4. doi:
10.1038/sj.ejcn.1601570. [PMID: 12627176] - Jiro Takata, Ryoji Hidaka, Akihiko Yamasaki, Akihiro Hattori, Takeshi Fukushima, Maiko Tanabe, Kazuhisa Matsunaga, Yoshiharu Karube, Kazuhiro Imai. Novel d-gamma-tocopherol derivative as a prodrug for d-gamma-tocopherol and a two-step prodrug for S-gamma-CEHC.
Journal of lipid research.
2002 Dec; 43(12):2196-204. doi:
10.1194/jlr.d200027-jlr200. [PMID: 12454283] - Dragan Radosavac, Peter Graf, M Cristina Polidori, Helmut Sies, Wilhelm Stahl. Tocopherol metabolites 2, 5, 7, 8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman (alpha-CEHC) and 2, 7, 8-trimethyl-2-(2'-carboxyethyl)-6-hydroxychroman (gamma-CEHC) in human serum after a single dose of natural vitamin E.
European journal of nutrition.
2002 Jun; 41(3):119-24. doi:
10.1007/s00394-002-0365-3. [PMID: 12111049] - Q Jiang, S Christen, M K Shigenaga, B N Ames. gamma-tocopherol, the major form of vitamin E in the US diet, deserves more attention.
The American journal of clinical nutrition.
2001 Dec; 74(6):714-22. doi:
10.1093/ajcn/74.6.714. [PMID: 11722951] - D Appenroth, E Karge, G Kiessling, W J Wechter, K Winnefeld, C Fleck. LLU-alpha, an endogenous metabolite of gamma-tocopherol, is more effective against metal nephrotoxicity in rats than gamma-tocopherol.
Toxicology letters.
2001 Jul; 122(3):255-65. doi:
10.1016/s0378-4274(01)00368-x. [PMID: 11489360] - C Kiyose, H Saito, K Kaneko, K Hamamura, M Tomioka, T Ueda, O Igarashi. Alpha-tocopherol affects the urinary and biliary excretion of 2,7,8-trimethyl-2 (2'-carboxyethyl)-6-hydroxychroman, gamma-tocopherol metabolite, in rats.
Lipids.
2001 May; 36(5):467-72. doi:
10.1007/s11745-001-0744-2. [PMID: 11432458] - A Hattori, T Fukushima, K Hamamura, M Kato, K Imai. A fluorimetric, column-switching HPLC and its application to an elimination study of LLU-alpha enantiomers in rat plasma.
Biomedical chromatography : BMC.
2001 Apr; 15(2):95-9. doi:
10.1002/bmc.42. [PMID: 11268049] - 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] - A Hattori, T Fukushima, K Imai. Occurrence and determination of a natriuretic hormone, 2,7,8-trimethyl-2-(beta-carboxyethyl)-6-hydroxy chroman, in rat plasma, urine, and bile.
Analytical biochemistry.
2000 Jun; 281(2):209-15. doi:
10.1006/abio.2000.4566. [PMID: 10870837] - W Stahl, P Graf, R Brigelius-Flohé, W Wechter, H Sies. Quantification of the alpha- and gamma-tocopherol metabolites 2,5,7, 8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman and 2,7, 8-trimethyl-2-(2'-carboxyethyl)-6-hydroxychroman in human serum.
Analytical biochemistry.
1999 Nov; 275(2):254-9. doi:
10.1006/abio.1999.4312. [PMID: 10552913] - J E Swanson, R N Ben, G W Burton, R S Parker. Urinary excretion of 2,7, 8-trimethyl-2-(beta-carboxyethyl)-6-hydroxychroman is a major route of elimination of gamma-tocopherol in humans.
Journal of lipid research.
1999 Apr; 40(4):665-71. doi:
10.1016/s0022-2275(20)32145-3. [PMID: 10191290] - W J Wechter, E D Murray. Has the elusive 'natriuretic factor' been discovered, and if so, is it a hormone?.
Experimental nephrology.
1998 Nov; 6(6):488-90. doi:
10.1159/000020561. [PMID: 9807018] - D Kantoci, W J Wechter, E D Murray, S A Dewind, D Borchardt, S I Khan. Endogenous natriuretic factors 6: the stereochemistry of a natriuretic gamma-tocopherol metabolite LLU-alpha.
The Journal of pharmacology and experimental therapeutics.
1997 Aug; 282(2):648-56. doi:
. [PMID: 9262326] - . .
.
. doi:
. [PMID: 11983822]