7-Hydroxycholesterol (BioDeep_00000175118)

   

human metabolite blood metabolite


代谢物信息卡片


2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

化学式: C27H46O2 (402.34976159999997)
中文名称:
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



数据库引用编号

2 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)

3 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Morten Blaabjerg, Dragan Marjanovic. [Cerebrotendinous xanthomatosis is a rare disorder, which requires a specific treatment]. Ugeskrift for laeger. 2013 Jan; 175(5):285-6. doi: ". [PMID: 23369332]
  • 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]
  • Wei Li, Moumita Ghosh, Sina Eftekhari, Xi-Ming Yuan. Lipid accumulation and lysosomal pathways contribute to dysfunction and apoptosis of human endothelial cells caused by 7-oxysterols. Biochemical and biophysical research communications. 2011 Jun; 409(4):711-6. doi: 10.1016/j.bbrc.2011.05.071. [PMID: 21621514]
  • Yongsheng Wang, Lili Wang, Yan Hu, Lantong Zhang, Zhihan Wang. Isolation and identification of two steroid compounds from Oviductus Ranae. Natural product research. 2010 Oct; 24(16):1518-22. doi: 10.1080/14786419.2010.484391. [PMID: 20835952]
  • Zhongmei Tang, F Peter Guengerich. Dansylation of unactivated alcohols for improved mass spectral sensitivity and application to analysis of cytochrome P450 oxidation products in tissue extracts. Analytical chemistry. 2010 Sep; 82(18):7706-12. doi: 10.1021/ac1015497. [PMID: 20795636]
  • Akira Honda, Kouwa Yamashita, Takashi Hara, Tadashi Ikegami, Teruo Miyazaki, Mutsumi Shirai, Guorong Xu, Mitsuteru Numazawa, Yasushi Matsuzaki. Highly sensitive quantification of key regulatory oxysterols in biological samples by LC-ESI-MS/MS. Journal of lipid research. 2009 Feb; 50(2):350-7. doi: 10.1194/jlr.d800040-jlr200. [PMID: 18815436]
  • Bianca Fuhrman, Ayelet Partoush, Nina Volkova, Michael Aviram. Ox-LDL induces monocyte-to-macrophage differentiation in vivo: Possible role for the macrophage colony stimulating factor receptor (M-CSF-R). Atherosclerosis. 2008 Feb; 196(2):598-607. doi: 10.1016/j.atherosclerosis.2007.06.026. [PMID: 17675037]
  • Danuta Zapolska-Downar, Grazyna Nowicka, Grazyna Sygitowicz, Mirosław Jarosz. Anthocyanin-rich Aronox extract from Aronia melanocarpa E protects against 7beta-hydroxycholesterol-induced apoptosis of endothelial cells. Annals of nutrition & metabolism. 2008; 53(3-4):283-94. doi: 10.1159/000191290. [PMID: 19142035]
  • Yasukazu Yoshida, Yoshiro Saito, Mieko Hayakawa, Yoko Habuchi, Yasuharu Imai, Yoshiyuki Sawai, Etsuo Niki. Levels of lipid peroxidation in human plasma and erythrocytes: comparison between fatty acids and cholesterol. Lipids. 2007 May; 42(5):439-49. doi: 10.1007/s11745-007-3037-5. [PMID: 17476548]
  • Marcello Arca, Silvia Natoli, Fausta Micheletta, Sara Riggi, Emanuele Di Angelantonio, Anna Montali, Teresa Maria Antonini, Roberto Antonini, Ulf Diczfalusy, Luigi Iuliano. Increased plasma levels of oxysterols, in vivo markers of oxidative stress, in patients with familial combined hyperlipidemia: reduction during atorvastatin and fenofibrate therapy. Free radical biology & medicine. 2007 Mar; 42(5):698-705. doi: 10.1016/j.freeradbiomed.2006.12.013. [PMID: 17291993]
  • Clett Erridge, David J Webb, Corinne M Spickett. 25-Hydroxycholesterol, 7beta-hydroxycholesterol and 7-ketocholesterol upregulate interleukin-8 expression independently of Toll-like receptor 1, 2, 4 or 6 signalling in human macrophages. Free radical research. 2007 Mar; 41(3):260-6. doi: 10.1080/10715760601070091. [PMID: 17364953]
  • Soichi Kitano, Yasukazu Yoshida, Katsumi Kawano, Nozomu Hibi, Etsuo Niki. Oxidative status of human low density lipoprotein isolated by anion-exchange high-performance liquid chromatography--assessment by total hydroxyoctadecadienoic acid, 7-hydroxycholesterol, and 8-iso-prostaglandin F(2alpha). Analytica chimica acta. 2007 Feb; 585(1):86-93. doi: 10.1016/j.aca.2006.12.032. [PMID: 17386651]
  • S Ferderbar, E C Pereira, E Apolinário, M C Bertolami, A Faludi, O Monte, L E Calliari, J E Sales, A R Gagliardi, H T Xavier, D S P Abdalla. Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes/metabolism research and reviews. 2007 Jan; 23(1):35-42. doi: 10.1002/dmrr.645. [PMID: 16634125]
  • Stamatiki Roussi, Francine Gossé, Dalal Aoudé-Werner, Xin Zhang, Philippe Geoffroy, Michel Miesch, Eric Marchioni, Francis Raul. Perturbation of polyamine metabolism and its relation to cell death in human colon cancer cells treated by 7beta-hydroxycholesterol and 7beta-hydroxysitosterol. International journal of oncology. 2006 Dec; 29(6):1549-54. doi: . [PMID: 17088995]
  • Zhi-Hua Chen, Yasukazu Yoshida, Yoshiro Saito, Azusa Sekine, Noriko Noguchi, Etsuo Niki. Induction of adaptive response and enhancement of PC12 cell tolerance by 7-hydroxycholesterol and 15-deoxy-delta(12,14)-prostaglandin J2 through up-regulation of cellular glutathione via different mechanisms. The Journal of biological chemistry. 2006 May; 281(20):14440-5. doi: 10.1074/jbc.m600260200. [PMID: 16565077]
  • Y Guéguen, M Souidi, C Baudelin, N Dudoignon, S Grison, I Dublineau, C Marquette, P Voisin, P Gourmelon, J Aigueperse. Short-term hepatic effects of depleted uranium on xenobiotic and bile acid metabolizing cytochrome P450 enzymes in the rat. Archives of toxicology. 2006 Apr; 80(4):187-95. doi: 10.1007/s00204-005-0027-3. [PMID: 16231126]
  • C Prunet, J M Petit, A Ecarnot-Laubriet, A Athias, C Miguet-Alfonsi, J F Rohmer, E Steinmetz, D Néel, P Gambert, G Lizard. High circulating levels of 7beta- and 7alpha-hydroxycholesterol and presence of apoptotic and oxidative markers in arterial lesions of normocholesterolemic atherosclerotic patients undergoing endarterectomy. Pathologie-biologie. 2006 Feb; 54(1):22-32. doi: 10.1016/j.patbio.2004.11.002. [PMID: 16376175]
  • Wei Li, Anna Hellsten, Li-Hua Xu, Da-Ming Zhuang, Katarina Jansson, Ulf T Brunk, Xi-Ming Yuan. Foam cell death induced by 7beta-hydroxycholesterol is mediated by labile iron-driven oxidative injury: mechanisms underlying induction of ferritin in human atheroma. Free radical biology & medicine. 2005 Oct; 39(7):864-75. doi: 10.1016/j.freeradbiomed.2005.05.006. [PMID: 16140207]
  • M Napolitano, E Bravo. Lipid metabolism and TNF-alpha secretion in response to dietary sterols in human monocyte derived macrophages. European journal of clinical investigation. 2005 Aug; 35(8):482-90. doi: 10.1111/j.1365-2362.2005.01523.x. [PMID: 16101668]
  • Robert Ringseis, Klaus Eder. Effects of dietary fat and oxidized cholesterol on gene expression in rat liver as assessed by cDNA expression array analysis. European journal of nutrition. 2005 Jun; 44(4):231-41. doi: 10.1007/s00394-004-0515-x. [PMID: 15309417]
  • S Roussi, A Winter, F Gosse, D Werner, X Zhang, E Marchioni, P Geoffroy, M Miesch, F Raul. Different apoptotic mechanisms are involved in the antiproliferative effects of 7beta-hydroxysitosterol and 7beta-hydroxycholesterol in human colon cancer cells. Cell death and differentiation. 2005 Feb; 12(2):128-35. doi: 10.1038/sj.cdd.4401530. [PMID: 15550935]
  • Wei Li, Anna Hellsten, Jerome Dinga Nyhalah, Xi-Ming Yuan. Enhanced expression of natural resistance-associated macrophage protein 1 in atherosclerotic lesions may be associated with oxidized lipid-induced apoptosis. Annals of the New York Academy of Sciences. 2004 Dec; 1030(?):202-7. doi: 10.1196/annals.1329.026. [PMID: 15659799]
  • Yasukazu Yoshida, Etsuo Niki. Detection of lipid peroxidation in vivo: total hydroxyoctadecadienoic acid and 7-hydroxycholesterol as oxidative stress marker. Free radical research. 2004 Aug; 38(8):787-94. doi: 10.1080/10715760410001700460. [PMID: 15493451]
  • Yasukazu Yoshida, Nanako Itoh, Yoshiro Saito, Mieko Hayakawa, Etsuo Niki. Application of water-soluble radical initiator, 2,2'-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride, to a study of oxidative stress. Free radical research. 2004 Apr; 38(4):375-84. doi: 10.1080/1071576042000191763. [PMID: 15190934]
  • Keri L H Carpenter, Peter J Kirkpatrick, Peter L Weissberg, Iain R Challis, Ian F Dennis, Mark A Freeman, Malcolm J Mitchinson. Oral alpha-tocopherol supplementation inhibits lipid oxidation in established human atherosclerotic lesions. Free radical research. 2003 Nov; 37(11):1235-44. doi: 10.1080/10715760310001604143. [PMID: 14703736]
  • Mary Y Chang, Christina Tsoi, Thomas N Wight, Alan Chait. Lysophosphatidylcholine regulates synthesis of biglycan and the proteoglycan form of macrophage colony stimulating factor. Arteriosclerosis, thrombosis, and vascular biology. 2003 May; 23(5):809-15. doi: 10.1161/01.atv.0000069208.20268.d0. [PMID: 12663372]
  • Serge Monier, Mohammad Samadi, Céline Prunet, Mikeäl Denance, Aline Laubriet, Anne Athias, Arnaud Berthier, Eric Steinmetz, Günter Jürgens, Anne Nègre-Salvayre, Ginette Bessède, Stéphanie Lemaire-Ewing, Dominique Néel, Philippe Gambert, Gérard Lizard. Impairment of the cytotoxic and oxidative activities of 7 beta-hydroxycholesterol and 7-ketocholesterol by esterification with oleate. Biochemical and biophysical research communications. 2003 Apr; 303(3):814-24. doi: 10.1016/s0006-291x(03)00412-1. [PMID: 12670484]
  • Sueli Regina Baggio, Eduardo Vicente, Neura Bragagnolo. Cholesterol oxides, cholesterol, total lipid, and fatty acid composition in turkey meat. Journal of agricultural and food chemistry. 2002 Oct; 50(21):5981-6. doi: 10.1021/jf020025c. [PMID: 12358469]
  • Carole Miguet-Alfonsi, Céline Prunet, Serge Monier, Ginette Bessède, Stéphanie Lemaire-Ewing, Arnaud Berthier, Franck Ménétrier, Dominique Néel, Philippe Gambert, Gérard Lizard. Analysis of oxidative processes and of myelin figures formation before and after the loss of mitochondrial transmembrane potential during 7beta-hydroxycholesterol and 7-ketocholesterol-induced apoptosis: comparison with various pro-apoptotic chemicals. Biochemical pharmacology. 2002 Aug; 64(3):527-41. doi: 10.1016/s0006-2952(02)01110-3. [PMID: 12147305]
  • L Iuliano, F Micheletta, M Maranghi, G Frati, U Diczfalusy, F Violi. Bioavailability of vitamin E as function of food intake in healthy subjects: effects on plasma peroxide-scavenging activity and cholesterol-oxidation products. Arteriosclerosis, thrombosis, and vascular biology. 2001 Oct; 21(10):E34-7. doi: 10.1161/hq1001.098465. [PMID: 11597949]
  • M Del Puppo, M Galli Kienle, A Crosignani, M L Petroni, B Amati, M Zuin, M Podda. Cholesterol metabolism in primary biliary cirrhosis during simvastatin and UDCA administration. Journal of lipid research. 2001 Mar; 42(3):437-41. doi: . [PMID: 11254756]
  • S Meaney, M Hassan, A Sakinis, D Lütjohann, K von Bergmann, A Wennmalm , U Diczfalusy, I Björkhem. Evidence that the major oxysterols in human circulation originate from distinct pools of cholesterol: a stable isotope study. Journal of lipid research. 2001 Jan; 42(1):70-8. doi: 10.1016/s0022-2275(20)32337-3. [PMID: 11160367]
  • N M O'Brien, J A Woods, S A Aherne, Y C O'Callaghan. Cytotoxicity, genotoxicity and oxidative reactions in cell-culture models: modulatory effects of phytochemicals. Biochemical Society transactions. 2000 Feb; 28(2):22-6. doi: 10.1042/bst0280022. [PMID: 10816093]
  • S Garcia-Cruset, K L Carpenter, F Guardiola, M J Mitchinson. Oxysterols in cap and core of human advanced atherosclerotic lesions. Free radical research. 1999 May; 30(5):341-50. doi: 10.1080/10715769900300391. [PMID: 10342328]
  • B Ziedén, A Kaminskas, M Kristenson, Z Kucinskienê, B Vessby, A G Olsson, U Diczfalusy. Increased plasma 7 beta-hydroxycholesterol concentrations in a population with a high risk for cardiovascular disease. Arteriosclerosis, thrombosis, and vascular biology. 1999 Apr; 19(4):967-71. doi: 10.1161/01.atv.19.4.967. [PMID: 10195924]
  • K Müller, K L Carpenter, M A Freeman, M J Mitchinson. Antioxidant BO-653 and human macrophage-mediated LDL oxidation. Free radical research. 1999 Jan; 30(1):59-71. doi: 10.1080/10715769900300071. [PMID: 10193574]
  • M Del Puppo, M G Kienle, M L Petroni, A Crosignani, M Podda. Serum 27-hydroxycholesterol in patients with primary biliary cirrhosis suggests alteration of cholesterol catabolism to bile acids via the acidic pathway. Journal of lipid research. 1998 Dec; 39(12):2477-82. doi: . [PMID: 9831637]
  • D F Vine, C L Mamo, L J Beilin, T A Mori, K D Croft. Dietary oxysterols are incorporated in plasma triglyceride-rich lipoproteins, increase their susceptibility to oxidation and increase aortic cholesterol concentration of rabbits. Journal of lipid research. 1998 Oct; 39(10):1995-2004. doi: 10.1016/s0022-2275(20)32498-6. [PMID: 9788246]
  • Y V Yuan, D D Kitts, D V Godin. Interactive effects of increased intake of saturated fat and cholesterol on atherosclerosis in the Japanese quail (Coturnix japonica). The British journal of nutrition. 1998 Jul; 80(1):89-100. doi: 10.1017/s0007114598001810. [PMID: 9797648]
  • D Stengel, M Antonucci, W Gaoua, C Dachet, P Lesnik, D Hourton, E Ninio, M J Chapman, S Griglio. Inhibition of LPL expression in human monocyte-derived macrophages is dependent on LDL oxidation state: a key role for lysophosphatidylcholine. Arteriosclerosis, thrombosis, and vascular biology. 1998 Jul; 18(7):1172-80. doi: 10.1161/01.atv.18.7.1172. [PMID: 9672079]
  • A E Wakefield, S Y Ho, X G Li, J S D'Arrigo, R H Simon. The use of lipid-coated microbubbles as a delivery agent of 7beta-hydroxycholesterol in a radiofrequency lesion in the rat brain. Neurosurgery. 1998 Mar; 42(3):592-8. doi: 10.1097/00006123-199803000-00029. [PMID: 9526993]
  • J Nilsson, B Dahlgren, M Ares, J Westman, A Hultgårdh Nilsson, B Cercek, P K Shah. Lipoprotein-like phospholipid particles inhibit the smooth muscle cell cytotoxicity of lysophosphatidylcholine and platelet-activating factor. Arteriosclerosis, thrombosis, and vascular biology. 1998 Jan; 18(1):13-9. doi: 10.1161/01.atv.18.1.13. [PMID: 9445250]
  • H Matsui, K Okumura, H Mukawa, M Hibino, Y Toki, T Ito. Increased oxysterol contents in diabetic rat hearts: their involvement in diabetic cardiomyopathy. The Canadian journal of cardiology. 1997 Apr; 13(4):373-9. doi: NULL. [PMID: 9141969]
  • J T Salonen, K Nyyssönen, R Salonen, E Porkkala-Sarataho, T P Tuomainen, U Diczfalusy, I Björkhem. Lipoprotein oxidation and progression of carotid atherosclerosis. Circulation. 1997 Feb; 95(4):840-5. doi: 10.1161/01.cir.95.4.840. [PMID: 9054740]
  • Y Miyashita, K Shirai, Y Ito, J Watanabe, Y Urano, T Murano, H Tomioka. Cytotoxicity of some oxysterols on human vascular smooth muscle cells was mediated by apoptosis. Journal of atherosclerosis and thrombosis. 1997; 4(2):73-8. doi: 10.5551/jat1994.4.73. [PMID: 9638517]
  • R P Patel, U Diczfalusy, S Dzeletovic, M T Wilson, V M Darley-Usmar. Formation of oxysterols during oxidation of low density lipoprotein by peroxynitrite, myoglobin, and copper. Journal of lipid research. 1996 Nov; 37(11):2361-71. doi: . [PMID: 8978488]
  • T Ito, S Kawata, Y Imai, H Kakimoto, J M Trzaskos, Y Matsuzawa. Hepatic cholesterol metabolism in patients with cholesterol gallstones: enhanced intracellular transport of cholesterol. Gastroenterology. 1996 May; 110(5):1619-27. doi: 10.1053/gast.1996.v110.pm8613070. [PMID: 8613070]
  • J R Guyton, M L Lenz, B Mathews, H Hughes, D Karsan, E Selinger, C V Smith. Toxicity of oxidized low density lipoproteins for vascular smooth muscle cells and partial protection by antioxidants. Atherosclerosis. 1995 Dec; 118(2):237-49. doi: 10.1016/0021-9150(95)05610-6. [PMID: 8770318]
  • C Hahn, C Reichel, K von Bergmann. Serum concentration of 7 alpha-hydroxycholesterol as an indicator of bile acid synthesis in humans. Journal of lipid research. 1995 Sep; 36(9):2059-66. doi: . [PMID: 8558093]
  • K L Carpenter, S E Taylor, C van der Veen, B K Williamson, J A Ballantine, M J Mitchinson. Lipids and oxidised lipids in human atherosclerotic lesions at different stages of development. Biochimica et biophysica acta. 1995 May; 1256(2):141-50. doi: 10.1016/0005-2760(94)00247-v. [PMID: 7766691]
  • J Reisch, F Pera, M Cramer. Detection and localization of autofluorescent substances in thymus tissue of sheep. Annals of anatomy = Anatomischer Anzeiger : official organ of the Anatomische Gesellschaft. 1994 Dec; 176(6):555-7. doi: 10.1016/s0940-9602(11)80395-x. [PMID: 7832288]
  • A Kupferberg, G Cremel, P Behr, A Van Dorsselaer, B Luu, M Mersel. Differential sensitivity of astrocyte primary cultures and derived spontaneous transformed cell lines to 7 beta-hydroxycholesterol: effect on plasma membrane lipid composition and fluidity, and on cell surface protein expression. Molecular and cellular biochemistry. 1991 Feb; 101(1):11-22. doi: 10.1007/bf00238433. [PMID: 2011116]
  • K L Carpenter, J A Ballantine, B Fussell, J H Enright, M J Mitchinson. Oxidation of cholesteryl linoleate by human monocyte-macrophages in vitro. Atherosclerosis. 1990 Aug; 83(2-3):217-29. doi: 10.1016/0021-9150(90)90167-h. [PMID: 2122906]
  • I Lelong, B Luu, M Mersel, S Rottem. Effect of 7 beta-hydroxycholesterol on growth and membrane composition of Mycoplasma capricolum. FEBS letters. 1988 May; 232(2):354-8. doi: 10.1016/0014-5793(88)80768-3. [PMID: 3378626]
  • I Björkhem, E Reihnér, B Angelin, S Ewerth, J E Akerlund, K Einarsson. On the possible use of the serum level of 7 alpha-hydroxycholesterol as a marker for increased activity of the cholesterol 7 alpha-hydroxylase in humans. Journal of lipid research. 1987 Aug; 28(8):889-94. doi: . [PMID: 3668387]
  • M W Rooney, S Yachnin, O Kucuk, L J Lis, J W Kauffman. Oxygenated cholesterols synergistically immobilize acyl chains and enhance protein helical structure in human erythrocyte membranes. Biochimica et biophysica acta. 1985 Oct; 820(1):33-9. doi: 10.1016/0005-2736(85)90212-3. [PMID: 4052416]
  • H Seltman, W Diven, M Rizk, B J Noland, R Chanderbhan, T J Scallen, G Vahouny, A Sanghvi. Regulation of bile-acid synthesis. Role of sterol carrier protein 2 in the biosynthesis of 7 alpha-hydroxycholesterol. The Biochemical journal. 1985 Aug; 230(1):19-24. doi: 10.1042/bj2300019. [PMID: 4052036]
  • A Sanghvi, E Grassi, C Bartman, R Lester, M Galli Kienle, G Galli. Measurement of cholesterol 7 alpha-hydroxylase activity with selected ion monitoring. Journal of lipid research. 1981 May; 22(4):720-4. doi: 10.1016/s0022-2275(20)37385-5. [PMID: 7276747]
  • H Oftebro, I Björkhem, F C Størmer, J I Pedersen. Cerebrotendinous xanthomatosis: defective liver mitochondrial hydroxylation of chenodeoxycholic acid precursors. Journal of lipid research. 1981 May; 22(4):632-40. doi: . [PMID: 6792308]
  • I Björkhem, H Oftebro, S Skrede, J I Pedersen. Assay of intermediates in bile acid biosynthesis using isotope dilution--mass spectrometry: hepatic levels in the normal state and in cerebrotendinous xanthomatosis. Journal of lipid research. 1981 Feb; 22(2):191-200. doi: . [PMID: 7017048]
  • Z B Tokarskaia, V I Tel'nov. [Determination of serum lipid levels in normal subjects]. Laboratornoe delo. 1981; ?(4):202-6. doi: NULL. [PMID: 6164850]