7β-hydroxycholesterol (BioDeep_00001871409)

   


代谢物信息卡片


7beta-hydroxycholesterol

化学式: C27H46O2 (402.34976159999997)
中文名称: 7-羟基胆固醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C
InChI: InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1

描述信息

同义名列表

2 个代谢物同义名

7beta-hydroxycholesterol; 7β-hydroxycholesterol



数据库引用编号

6 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)

4 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

  • Imen Ghzaiel, Amira Zarrouk, Vivien Pires, Jean-Paul Pais de Barros, Sonia Hammami, Mohamed Ksila, Mohamed Hammami, Taoufik Ghrairi, Pierre Jouanny, Anne Vejux, Gérard Lizard. 7β-Hydroxycholesterol and 7-ketocholesterol: New oxidative stress biomarkers of sarcopenia inducing cytotoxic effects on myoblasts and myotubes. The Journal of steroid biochemistry and molecular biology. 2023 Jun; 232(?):106345. doi: 10.1016/j.jsbmb.2023.106345. [PMID: 37286110]
  • Leila Rezig, Imen Ghzaiel, Mohamed Ksila, Aline Yammine, Thomas Nury, Amira Zarrouk, Mohammad Samadi, Moncef Chouaibi, Anne Vejux, Gérard Lizard. Cytoprotective activities of representative nutrients from the Mediterranean diet and of Mediterranean oils against 7-ketocholesterol- and 7β-hydroxycholesterol-induced cytotoxicity: Application to age-related diseases and civilization diseases. Steroids. 2022 11; 187(?):109093. doi: 10.1016/j.steroids.2022.109093. [PMID: 36029811]
  • Imen Ghzaiel, Amira Zarrouk, Soukaina Essadek, Lucy Martine, Souha Hammouda, Aline Yammine, Mohamed Ksila, Thomas Nury, Wiem Meddeb, Mounia Tahri Joutey, Wafa Mihoubi, Claudio Caccia, Valerio Leoni, Mohammad Samadi, Niyazi Acar, Pierre Andreoletti, Sonia Hammami, Taoufik Ghrairi, Anne Vejux, Mohamed Hammami, Gérard Lizard. Protective effects of milk thistle (Sylibum marianum) seed oil and α-tocopherol against 7β-hydroxycholesterol-induced peroxisomal alterations in murine C2C12 myoblasts: Nutritional insights associated with the concept of pexotherapy. Steroids. 2022 07; 183(?):109032. doi: 10.1016/j.steroids.2022.109032. [PMID: 35381271]
  • T Nury, A Yammine, I Ghzaiel, K Sassi, A Zarrouk, F Brahmi, M Samadi, S Rup-Jacques, D Vervandier-Fasseur, J P Pais de Barros, V Bergas, S Ghosh, M Majeed, A Pande, A Atanasov, S Hammami, M Hammami, J Mackrill, B Nasser, P Andreoletti, M Cherkaoui-Malki, A Vejux, G Lizard. Attenuation of 7-ketocholesterol- and 7β-hydroxycholesterol-induced oxiapoptophagy by nutrients, synthetic molecules and oils: Potential for the prevention of age-related diseases. Ageing research reviews. 2021 07; 68(?):101324. doi: 10.1016/j.arr.2021.101324. [PMID: 33774195]
  • Souha Hammouda, Imen Ghzaiel, Pol Picón-Pagès, Wiem Meddeb, Wided Khamlaoui, Sonia Hammami, Francisco J Muñoz, Mohamed Hammami, Amira Zarrouk. Nigella and Milk Thistle Seed Oils: Potential Cytoprotective Effects against 7β-Hydroxycholesterol-Induced Toxicity on SH-SY5Y Cells. Biomolecules. 2021 05; 11(6):. doi: 10.3390/biom11060797. [PMID: 34071950]
  • Mason McComb, Richard W Browne, Sonia Bhattacharya, Mary Lou Bodziak, Dejan Jakimovski, Bianca Weinstock-Guttman, Jens Kuhle, Robert Zivadinov, Murali Ramanathan. The cholesterol autoxidation products, 7-ketocholesterol and 7β-hydroxycholesterol are associated with serum neurofilaments in multiple sclerosis. Multiple sclerosis and related disorders. 2021 May; 50(?):102864. doi: 10.1016/j.msard.2021.102864. [PMID: 33677412]
  • Anne Vejux, Dehbia Abed-Vieillard, Khadija Hajji, Amira Zarrouk, John J Mackrill, Shubhrima Ghosh, Thomas Nury, Aline Yammine, Mohamed Zaibi, Wafa Mihoubi, Habiba Bouchab, Boubker Nasser, Yaël Grosjean, Gérard Lizard. 7-Ketocholesterol and 7β-hydroxycholesterol: In vitro and animal models used to characterize their activities and to identify molecules preventing their toxicity. Biochemical pharmacology. 2020 03; 173(?):113648. doi: 10.1016/j.bcp.2019.113648. [PMID: 31586589]
  • Hiroshi Takahashi, Tatsuya Hoshino. A comparative study of the effects of 7β-hydroxycholesterol, 25-hydroxycholesterol, and cholesterol on the structural and thermal phase behavior of multilamellar dipalmitoylphosphatidylcholine bilayer vesicles. Chemistry and physics of lipids. 2020 03; 227(?):104872. doi: 10.1016/j.chemphyslip.2020.104872. [PMID: 31926857]
  • Thomas Nury, Aline Yammine, Franck Menetrier, Amira Zarrouk, Anne Vejux, Gérard Lizard. 7-Ketocholesterol- and 7β-Hydroxycholesterol-Induced Peroxisomal Disorders in Glial, Microglial and Neuronal Cells: Potential Role in Neurodegeneration : 7-ketocholesterol and 7β-hydroxycholesterol-Induced Peroxisomal Disorders and Neurodegeneration. Advances in experimental medicine and biology. 2020; 1299(?):31-41. doi: 10.1007/978-3-030-60204-8_3. [PMID: 33417205]
  • William J Griffiths, Eylan Yutuc, Jonas Abdel-Khalik, Peter J Crick, Thomas Hearn, Alison Dickson, Brian W Bigger, Teresa Hoi-Yee Wu, Anu Goenka, Arunabha Ghosh, Simon A Jones, Douglas F Covey, Daniel S Ory, Yuqin Wang. Metabolism of Non-Enzymatically Derived Oxysterols: Clues from sterol metabolic disorders. Free radical biology & medicine. 2019 11; 144(?):124-133. doi: 10.1016/j.freeradbiomed.2019.04.020. [PMID: 31009661]
  • Randa Sghaier, Thomas Nury, Valerio Leoni, Claudio Caccia, Jean-Paul Pais De Barros, Ameur Cherif, Anne Vejux, Thibault Moreau, Khalifa Limem, Mohammad Samadi, John J Mackrill, Ahmed Slaheddine Masmoudi, Gérard Lizard, Amira Zarrouk. Dimethyl fumarate and monomethyl fumarate attenuate oxidative stress and mitochondrial alterations leading to oxiapoptophagy in 158N murine oligodendrocytes treated with 7β-hydroxycholesterol. The Journal of steroid biochemistry and molecular biology. 2019 11; 194(?):105432. doi: 10.1016/j.jsbmb.2019.105432. [PMID: 31344443]
  • K Sassi, T Nury, A Zarrouk, R Sghaier, A Khalafi-Nezhad, A Vejux, M Samadi, F Ben Aissa-Fennira, G Lizard. Induction of a non-apoptotic mode of cell death associated with autophagic characteristics with steroidal maleic anhydrides and 7β-hydroxycholesterol on glioma cells. The Journal of steroid biochemistry and molecular biology. 2019 07; 191(?):105371. doi: 10.1016/j.jsbmb.2019.04.020. [PMID: 31034873]
  • B Šošić-Jurjević, D Lütjohann, K Renko, B Filipović, N Radulović, V Ajdžanović, S Trifunović, N Nestorović, J Živanović, M Manojlović Stojanoski, J Kӧhrle, V Milošević. The isoflavones genistein and daidzein increase hepatic concentration of thyroid hormones and affect cholesterol metabolism in middle-aged male rats. The Journal of steroid biochemistry and molecular biology. 2019 06; 190(?):1-10. doi: 10.1016/j.jsbmb.2019.03.009. [PMID: 30885834]
  • Randa Sghaier, Amira Zarrouk, Thomas Nury, Ilham Badreddine, Nora O'Brien, John J Mackrill, Anne Vejux, Mohammad Samadi, Boubker Nasser, Claudio Caccia, Valerio Leoni, Thibault Moreau, Mustapha Cherkaoui-Malki, Ahmed Salhedine Masmoudi, Gérard Lizard. Biotin attenuation of oxidative stress, mitochondrial dysfunction, lipid metabolism alteration and 7β-hydroxycholesterol-induced cell death in 158N murine oligodendrocytes. Free radical research. 2019 05; 53(5):535-561. doi: 10.1080/10715762.2019.1612891. [PMID: 31039616]
  • Amira Zarrouk, Mohammed Ali Smach, Jawhar Hafsa, Randa Sghaier, Hatem Majdoub, Mohammed Hammami, Bassem Charfeddine. Effects of Carpobrotus edulis Extract on Oxidative Stress and 158N Oligodendrocyte Death. Biomedical and environmental sciences : BES. 2019 Apr; 32(4):291-299. doi: 10.3967/bes2019.039. [PMID: 31217065]
  • Amira Zarrouk, Yosra Ben Salem, Jawhar Hafsa, Randa Sghaier, Bassem Charfeddine, Khalifa Limem, Mohamed Hammami, Hatem Majdoub. 7β-hydroxycholesterol-induced cell death, oxidative stress, and fatty acid metabolism dysfunctions attenuated with sea urchin egg oil. Biochimie. 2018 Oct; 153(?):210-219. doi: 10.1016/j.biochi.2018.06.027. [PMID: 30003930]
  • Yidan Sun, Susanne Kopp, Jasmin Strutz, Chaitanya Chakravarthi Gali, Martina Zandl-Lang, Elham Fanaee-Danesh, Andrijana Kirsch, Silvija Cvitic, Saša Frank, Richard Saffery, Ingemar Björkhem, Gernot Desoye, Christian Wadsack, Ute Panzenboeck. Gestational diabetes mellitus modulates cholesterol homeostasis in human fetoplacental endothelium. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2018 09; 1863(9):968-979. doi: 10.1016/j.bbalip.2018.05.005. [PMID: 29778664]
  • Monica Deiana, Simone Calfapietra, Alessandra Incani, Angela Atzeri, Daniela Rossin, Roberto Loi, Barbara Sottero, Noemi Iaia, Giuseppe Poli, Fiorella Biasi. Derangement of intestinal epithelial cell monolayer by dietary cholesterol oxidation products. Free radical biology & medicine. 2017 12; 113(?):539-550. doi: 10.1016/j.freeradbiomed.2017.10.390. [PMID: 29102636]
  • Frans Stellaard, Klaus von Bergmann, Thomas Sudhop, Dieter Lütjohann. The value of surrogate markers to monitor cholesterol absorption, synthesis and bioconversion to bile acids under lipid lowering therapies. The Journal of steroid biochemistry and molecular biology. 2017 05; 169(?):111-122. doi: 10.1016/j.jsbmb.2016.03.030. [PMID: 27060336]
  • Willem-Jan Keune, Jens Hausmann, Ruth Bolier, Dagmar Tolenaars, Andreas Kremer, Tatjana Heidebrecht, Robbie P Joosten, Manjula Sunkara, Andrew J Morris, Elisa Matas-Rico, Wouter H Moolenaar, Ronald P Oude Elferink, Anastassis Perrakis. Steroid binding to Autotaxin links bile salts and lysophosphatidic acid signalling. Nature communications. 2016 Apr; 7(?):11248. doi: 10.1038/ncomms11248. [PMID: 27075612]
  • Zoltán Pataj, Gerhard Liebisch, Gerd Schmitz, Silke Matysik. Quantification of oxysterols in human plasma and red blood cells by liquid chromatography high-resolution tandem mass spectrometry. Journal of chromatography. A. 2016 Mar; 1439(?):82-88. doi: 10.1016/j.chroma.2015.11.015. [PMID: 26607314]
  • Aliki A Rasmiena, Christopher K Barlow, Theodore W Ng, Dedreia Tull, Peter J Meikle. High density lipoprotein efficiently accepts surface but not internal oxidised lipids from oxidised low density lipoprotein. Biochimica et biophysica acta. 2016 Feb; 1861(2):69-77. doi: 10.1016/j.bbalip.2015.11.002. [PMID: 26569052]
  • Thomas Nury, Amira Zarrouk, John J Mackrill, Mohammad Samadi, Philippe Durand, Jean-Marc Riedinger, Margaux Doria, Anne Vejux, Emeric Limagne, Dominique Delmas, Michel Prost, Thibault Moreau, Mohamed Hammami, Régis Delage-Mourroux, Nora M O'Brien, Gérard Lizard. Induction of oxiapoptophagy on 158N murine oligodendrocytes treated by 7-ketocholesterol-, 7β-hydroxycholesterol-, or 24(S)-hydroxycholesterol: Protective effects of α-tocopherol and docosahexaenoic acid (DHA; C22:6 n-3). Steroids. 2015 Jul; 99(Pt B):194-203. doi: 10.1016/j.steroids.2015.02.003. [PMID: 25683890]
  • Oliver Weingärtner, Constanze Husche, Hans F Schött, Timo Speer, Michael Böhm, Charlotte M Miller, Florence McCarthy, Jogchum Plat, Dieter Lütjohann, Ulrich Laufs. Vascular effects of oxysterols and oxyphytosterols in apoE -/- mice. Atherosclerosis. 2015 May; 240(1):73-9. doi: 10.1016/j.atherosclerosis.2015.02.032. [PMID: 25765595]
  • Yalong Wang, Han Jiang, Huizhi Huang, Yanqi Xie, Yunshi Zhao, Xiuhua You, Lipeng Tang, Youqiong Wang, Wei Yin, Pengxin Qiu, Guangmei Yan, Haiyan Hu. Determination of neuroprotective oxysterols in Calculus bovis, human gallstones, and traditional Chinese medicine preparations by liquid chromatography with mass spectrometry. Journal of separation science. 2015 Mar; 38(5):796-803. doi: 10.1002/jssc.201400850. [PMID: 25545614]
  • C Helmschrodt, S Becker, J Thiery, U Ceglarek. Preanalytical standardization for reactive oxygen species derived oxysterol analysis in human plasma by liquid chromatography-tandem mass spectrometry. Biochemical and biophysical research communications. 2014 Apr; 446(3):726-30. doi: 10.1016/j.bbrc.2013.12.087. [PMID: 24370823]
  • Tadashi Ikegami, Akira Honda, Teruo Miyazaki, Motoyuki Kohjima, Makoto Nakamuta, Yasushi Matsuzaki. Increased serum oxysterol concentrations in patients with chronic hepatitis C virus infection. Biochemical and biophysical research communications. 2014 Apr; 446(3):736-40. doi: 10.1016/j.bbrc.2014.01.176. [PMID: 24525121]
  • Yoshiro Saito, Noriko Noguchi. 7-Hydroxycholestrol as a possible biomarker of cellular lipid peroxidation: difference between cellular and plasma lipid peroxidation. Biochemical and biophysical research communications. 2014 Apr; 446(3):741-4. doi: 10.1016/j.bbrc.2013.12.083. [PMID: 24380859]
  • Soliman Khatib, Jacob Vaya. Oxysterols and symptomatic versus asymptomatic human atherosclerotic plaque. Biochemical and biophysical research communications. 2014 Apr; 446(3):709-13. doi: 10.1016/j.bbrc.2013.12.116. [PMID: 24393847]
  • Christin Helmschrodt, Susen Becker, Jenny Schröter, Max Hecht, Gabriela Aust, Joachim Thiery, Uta Ceglarek. Fast LC-MS/MS analysis of free oxysterols derived from reactive oxygen species in human plasma and carotid plaque. Clinica chimica acta; international journal of clinical chemistry. 2013 Oct; 425(?):3-8. doi: 10.1016/j.cca.2013.06.022. [PMID: 23827692]
  • Satoshi Hirayama, Saori Nakagawa, Satoshi Soda, Yumiko Kamimura, Emiko Nishioka, Tsuyoshi Ueno, Yoshifumi Fukushima, Ken-ichi Higuchi, Masanori Inoue, Utako Seino, Hirotoshi Ohmura, Susumu Yamato, Takashi Miida. Ezetimibe decreases serum oxidized cholesterol without impairing bile acid synthesis in Japanese hypercholesterolemic patients. Atherosclerosis. 2013 Sep; 230(1):48-51. doi: 10.1016/j.atherosclerosis.2013.06.016. [PMID: 23958251]
  • Tijana Mitić, Steven Shave, Nina Semjonous, Iain McNae, Diego F Cobice, Gareth G Lavery, Scott P Webster, Patrick W F Hadoke, Brian R Walker, Ruth Andrew. 11β-Hydroxysteroid dehydrogenase type 1 contributes to the balance between 7-keto- and 7-hydroxy-oxysterols in vivo. Biochemical pharmacology. 2013 Jul; 86(1):146-53. doi: 10.1016/j.bcp.2013.02.002. [PMID: 23415904]
  • Kévin Ragot, John J Mackrill, Amira Zarrouk, Thomas Nury, Virginie Aires, Agnès Jacquin, Anne Athias, Jean-Paul Pais de Barros, Anne Véjux, Jean-Marc Riedinger, Dominique Delmas, Gérard Lizard. Absence of correlation between oxysterol accumulation in lipid raft microdomains, calcium increase, and apoptosis induction on 158N murine oligodendrocytes. Biochemical pharmacology. 2013 Jul; 86(1):67-79. doi: 10.1016/j.bcp.2013.02.028. [PMID: 23473804]
  • Jan de Weille, Christine Fabre, Camille Gaven, Norbert Bakalara. Similar pyruvate kinase modifications in glioblastoma cells by 7β-hydroxycholesterol and glutamine withdrawal. Biochemical pharmacology. 2013 Jul; 86(1):161-7. doi: 10.1016/j.bcp.2013.03.012. [PMID: 23537700]
  • Raymond C S Seet, Amy M L Quek, Erle C H Lim, Barry Halliwell. Biomarkers of oxidative damage are elevated among individuals with high cardiovascular risk: refining subject selection strategies for antioxidant trials. Free radical research. 2013 Apr; 47(4):283-90. doi: 10.3109/10715762.2013.769215. [PMID: 23343456]
  • Ming Long Sirius Chung, Kai Yan Eric Lee, Chung-Yung Jetty Lee. Profiling of oxidized lipid products of marine fish under acute oxidative stress. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Mar; 53(?):205-13. doi: 10.1016/j.fct.2012.11.047. [PMID: 23220612]
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  • Mario Arciello, Salvatore Petta, Valerio Leoni, Gino Iannucci, Giancarlo Labbadia, Carlo Cammà, Antonio Craxì, Clara Balsano. Inverse correlation between plasma oxysterol and LDL-cholesterol levels in hepatitis C virus-infected patients. Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver. 2012 Mar; 44(3):245-50. doi: 10.1016/j.dld.2011.10.022. [PMID: 22154950]
  • Ludovic Clarion, Mathilde Schindler, Jan de Weille, Karine Lolmède, Audrey Laroche-Clary, Emmanuelle Uro-Coste, Jacques Robert, Marcel Mersel, Norbert Bakalara. 7β-Hydroxycholesterol-induced energy stress leads to sequential opposing signaling responses and to death of C6 glioblastoma cells. Biochemical pharmacology. 2012 Jan; 83(1):37-46. doi: 10.1016/j.bcp.2011.09.022. [PMID: 21983033]
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