Cholesterol-5beta-hydroperoxide (BioDeep_00000425712)
代谢物信息卡片
3beta-hydroxy-5beta-cholest-6-ene-5-hydroperoxide
化学式: C27H46O3 (418.34467659999996)
中文名称:
谱图信息:
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分子结构信息
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InChI:
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代谢反应
0 个相关的代谢反应过程信息。
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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。
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文献列表
- Yoshiro Saito, Noriko Noguchi, Etsuo Niki. Cholesterol is more readily oxidized than phospholipid linoleates in cell membranes to produce cholesterol hydroperoxides.
Free radical biology & medicine.
2024 Feb; 211(?):89-95. doi:
10.1016/j.freeradbiomed.2023.12.011. [PMID: 38101585] - Pawel Pabisz, Jerzy Bazak, Michal Sabat, Albert W Girotti, Witold Korytowski. Cholesterol Hydroperoxide Co-trafficking in Testosterone-generating Leydig Cells: GPx4 Inhibition of Cytotoxic and Anti-steroidogenic Effects.
Cell biochemistry and biophysics.
2023 Nov; ?(?):. doi:
10.1007/s12013-023-01194-5. [PMID: 37995086] - Pawel Pabisz, Jerzy Bazak, Albert W Girotti, Witold Korytowski. Anti-steroidogenic effects of cholesterol hydroperoxide trafficking in MA-10 Leydig cells: Role of mitochondrial lipid peroxidation and inhibition thereof by selenoperoxidase GPx4.
Biochemical and biophysical research communications.
2022 02; 591(?):82-87. doi:
10.1016/j.bbrc.2021.12.117. [PMID: 34999258] - Albert W Girotti, Witold Korytowski. Pathophysiological potential of lipid hydroperoxide intermembrane translocation: Cholesterol hydroperoxide translocation as a special case.
Redox biology.
2021 10; 46(?):102096. doi:
10.1016/j.redox.2021.102096. [PMID: 34418596] - Sayuri Miyamoto, Rodrigo S Lima, Alex Inague, Lucas G Viviani. Electrophilic oxysterols: generation, measurement and protein modification.
Free radical research.
2021 Apr; 55(4):416-440. doi:
10.1080/10715762.2021.1879387. [PMID: 33494620] - Albert W Girotti, Witold Korytowski. Cholesterol Hydroperoxide Generation, Translocation, and Reductive Turnover in Biological Systems.
Cell biochemistry and biophysics.
2017 Dec; 75(3-4):413-419. doi:
10.1007/s12013-017-0799-0. [PMID: 28434137] - Witold Korytowski, Katarzyna Wawak, Pawel Pabisz, Jared C Schmitt, Alexandra C Chadwick, Daisy Sahoo, Albert W Girotti. Impairment of Macrophage Cholesterol Efflux by Cholesterol Hydroperoxide Trafficking: Implications for Atherogenesis Under Oxidative Stress.
Arteriosclerosis, thrombosis, and vascular biology.
2015 Oct; 35(10):2104-13. doi:
10.1161/atvbaha.115.306210. [PMID: 26315403] - Thiago C Genaro-Mattos, Raphael F Queiroz, Daniela Cunha, Patricia P Appolinario, Paolo Di Mascio, Iseli L Nantes, Ohara Augusto, Sayuri Miyamoto. Cytochrome c reacts with cholesterol hydroperoxides to produce lipid- and protein-derived radicals.
Biochemistry.
2015 May; 54(18):2841-50. doi:
10.1021/bi501409d. [PMID: 25865416] - Albert W Girotti, Tamas Kriska. Binding and cytotoxic trafficking of cholesterol hydroperoxides by sterol carrier protein-2.
Methods in molecular biology (Clifton, N.J.).
2015; 1208(?):421-35. doi:
10.1007/978-1-4939-1441-8_30. [PMID: 25323524] - Junji Terao. Cholesterol hydroperoxides and their degradation mechanism.
Sub-cellular biochemistry.
2014; 77(?):83-91. doi:
10.1007/978-94-007-7920-4_7. [PMID: 24374920] - Toshiyuki Nakamura, Ayako Noma, Sachiko Shimada, Nanase Ishii, Noriko Bando, Yoshichika Kawai, Junji Terao. Non-selective distribution of isomeric cholesterol hydroperoxides to microdomains in cell membranes and activation of matrix metalloproteinase activity in a model of dermal cells.
Chemistry and physics of lipids.
2013 Sep; 174(?):17-23. doi:
10.1016/j.chemphyslip.2013.05.004. [PMID: 23751409] - Soo-Ho Choi, Huiyong Yin, Amir Ravandi, Aaron Armando, Darren Dumlao, Jungsu Kim, Felicidad Almazan, Angela M Taylor, Coleen A McNamara, Sotirios Tsimikas, Edward A Dennis, Joseph L Witztum, Yury I Miller. Polyoxygenated cholesterol ester hydroperoxide activates TLR4 and SYK dependent signaling in macrophages.
PloS one.
2013; 8(12):e83145. doi:
10.1371/journal.pone.0083145. [PMID: 24376657] - Miriam Uemi, Graziella E Ronsein, Fernanda M Prado, Flávia D Motta, Sayuri Miyamoto, Marisa H G Medeiros, Paolo Di Mascio. Cholesterol hydroperoxides generate singlet molecular oxygen [O(2) ((1)Δ(g))]: near-IR emission, (18)O-labeled hydroperoxides, and mass spectrometry.
Chemical research in toxicology.
2011 Jun; 24(6):887-95. doi:
10.1021/tx200079d. [PMID: 21510702] - Agnieszka Broniec, Radoslaw Klosinski, Anna Pawlak, Marta Wrona-Krol, David Thompson, Tadeusz Sarna. Interactions of plasmalogens and their diacyl analogs with singlet oxygen in selected model systems.
Free radical biology & medicine.
2011 Apr; 50(7):892-8. doi:
10.1016/j.freeradbiomed.2011.01.002. [PMID: 21236336] - Graziella E Ronsein, Mauricio Cesar Bof de Oliveira, Marisa H G Medeiros, Sayuri Miyamoto, Paolo Di Mascio. DNA strand breaks and base modifications induced by cholesterol hydroperoxides.
Free radical research.
2011 Mar; 45(3):266-75. doi:
10.3109/10715762.2010.524215. [PMID: 20942561] - Tamas Kriska, Anna Pilat, Jared C Schmitt, Albert W Girotti. Sterol carrier protein-2 (SCP-2) involvement in cholesterol hydroperoxide cytotoxicity as revealed by SCP-2 inhibitor effects.
Journal of lipid research.
2010 Nov; 51(11):3174-84. doi:
10.1194/jlr.m008342. [PMID: 20656919] - Yuko Minami, Kyuichi Kawabata, Yoshiaki Kubo, Seiji Arase, Katsuya Hirasaka, Takeshi Nikawa, Noriko Bando, Yoshichika Kawai, Junji Terao. Peroxidized cholesterol-induced matrix metalloproteinase-9 activation and its suppression by dietary beta-carotene in photoaging of hairless mouse skin.
The Journal of nutritional biochemistry.
2009 May; 20(5):389-98. doi:
10.1016/j.jnutbio.2008.04.010. [PMID: 18656335] - Migiwa Asano, Hideyuki Nushida, Junko Adachi, Yasushi Nagasaki, Kanako Nakagawa, Azumi Kuse, Yasuhiro Ueno. Lipid hydroperoxides in human plasma after ethanol consumption.
Legal medicine (Tokyo, Japan).
2009 Apr; 11 Suppl 1(?):S223-5. doi:
10.1016/j.legalmed.2009.01.054. [PMID: 19261511] - Yuko Minami, Sayuri Yokoi, Mari Setoyama, Noriko Bando, Sayaka Takeda, Yoshichika Kawai, Junji Terao. Combination of TLC blotting and gas chromatography-mass spectrometry for analysis of peroxidized cholesterol.
Lipids.
2007 Nov; 42(11):1055-63. doi:
10.1007/s11745-007-3099-4. [PMID: 17701239] - Tamas Kriska, Vladislav V Levchenko, Witold Korytowski, Barbara P Atshaves, Friedhelm Schroeder, Albert W Girotti. Intracellular dissemination of peroxidative stress. Internalization, transport, and lethal targeting of a cholesterol hydroperoxide species by sterol carrier protein-2-overexpressing hepatoma cells.
The Journal of biological chemistry.
2006 Aug; 281(33):23643-51. doi:
10.1074/jbc.m600744200. [PMID: 16772292] - Tamas Kriska, Albert W Girotti. A thin layer chromatographic method for determining the enzymatic activity of peroxidases catalyzing the two-electron reduction of lipid hydroperoxides.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2005 Nov; 827(1):58-64. doi:
10.1016/j.jchromb.2005.03.045. [PMID: 15899595] - Shu-Ping Hui, Tsuyoshi Murai, Teruki Yoshimura, Hitoshi Chiba, Hironori Nagasaka, Takao Kurosawa. Improved HPLC assay for lipid peroxides in human plasma using the internal standard of hydroperoxide.
Lipids.
2005 May; 40(5):515-22. doi:
10.1007/s11745-005-1412-2. [PMID: 16094862] - Jung Suh, Ben-Zhan Zhu, Balz Frei. Ascorbate does not act as a pro-oxidant towards lipids and proteins in human plasma exposed to redox-active transition metal ions and hydrogen peroxide.
Free radical biology & medicine.
2003 May; 34(10):1306-14. doi:
10.1016/s0891-5849(03)00147-3. [PMID: 12726918] - Andrew Vila, Witold Korytowski, Albert W Girotti. Spontaneous transfer of phospholipid and cholesterol hydroperoxides between cell membranes and low-density lipoprotein: assessment of reaction kinetics and prooxidant effects.
Biochemistry.
2002 Nov; 41(46):13705-16. doi:
10.1021/bi026467z. [PMID: 12427033] - Victor R Preedy, Junko Adachi, Migiwa Asano, Michael Koll, David Mantle, Onni Niemela, Seppo Parkkila, Alistair G Paice, Timothy Peters, Rajkumar Rajendram, Helmut Seitz, Yasuhiro Ueno, Simon Worrall. Free radicals in alcoholic myopathy: indices of damage and preventive studies.
Free radical biology & medicine.
2002 Apr; 32(8):683-7. doi:
10.1016/s0891-5849(01)00794-8. [PMID: 11937294] - A Vila, W Korytowski, A W Girotti. Spontaneous intermembrane transfer of various cholesterol-derived hydroperoxide species: kinetic studies with model membranes and cells.
Biochemistry.
2001 Dec; 40(48):14715-26. doi:
10.1021/bi011408r. [PMID: 11724586] - R Hurst, W Korytowski, T Kriska, R S Esworthy, F F Chu, A W Girotti. Hyperresistance to cholesterol hydroperoxide-induced peroxidative injury and apoptotic death in a tumor cell line that overexpresses glutathione peroxidase isotype-4.
Free radical biology & medicine.
2001 Nov; 31(9):1051-65. doi:
10.1016/s0891-5849(01)00685-2. [PMID: 11677038] - S Tahara, M Matsuo, T Kaneko. Age-related changes in oxidative damage to lipids and DNA in rat skin.
Mechanisms of ageing and development.
2001 Apr; 122(4):415-26. doi:
10.1016/s0047-6374(00)00257-8. [PMID: 11240163] - A Vila, W Korytowski, A W Girotti. Dissemination of peroxidative stress via intermembrane transfer of lipid hydroperoxides: model studies with cholesterol hydroperoxides.
Archives of biochemistry and biophysics.
2000 Aug; 380(1):208-18. doi:
10.1006/abbi.2000.1928. [PMID: 10900151] - W Korytowski, M Zareba, A W Girotti. Nitric oxide inhibition of free radical-mediated cholesterol peroxidation in liposomal membranes.
Biochemistry.
2000 Jun; 39(23):6918-28. doi:
10.1021/bi000393e. [PMID: 10841773] - J Adachi, M Asano, Y Ueno, M Reilly, D Mantle, T J Peters, V R Preedy. 7alpha- and 7beta-hydroperoxycholest-5-en-3beta-ol in muscle as indices of oxidative stress: response to ethanol dosage in rats.
Alcoholism, clinical and experimental research.
2000 May; 24(5):675-81. doi:
". [PMID: 10832909] - S Yamazaki, N Ozawa, A Hiratsuka, T Watabe. Photogeneration of 3beta-hydroxy-5alpha-cholest-6-ene-5-hydroperoxide in rat skin: evidence for occurrence of singlet oxygen in vivo.
Free radical biology & medicine.
1999 Aug; 27(3-4):301-8. doi:
10.1016/s0891-5849(99)00047-7. [PMID: 10468202] - J Adachi, M Asano, T Naito, Y Ueno, H Imamichi, Y Tatsuno. Cholesterol hydroperoxides in erythrocyte membranes of alcoholic patients.
Alcoholism, clinical and experimental research.
1999 Apr; 23(4 Suppl):96S-100S. doi:
10.1111/j.1530-0277.1999.tb04543.x. [PMID: 10235288] - D Armstrong, R W Browne. Synthesis of lipid and cholesterol hydroperoxide standards.
Methods in molecular biology (Clifton, N.J.).
1998; 108(?):139-45. doi:
10.1385/0-89603-472-0:139. [PMID: 9921524] - P G Geiger, W Korytowski, F Lin, A W Girotti. Lipid peroxidation in photodynamically stressed mammalian cells: use of cholesterol hydroperoxides as mechanistic reporters.
Free radical biology & medicine.
1997; 23(1):57-68. doi:
10.1016/s0891-5849(96)00587-4. [PMID: 9165297] - W Korytowski, P G Geiger, A W Girotti. Enzymatic reducibility in relation to cytotoxicity for various cholesterol hydroperoxides.
Biochemistry.
1996 Jul; 35(26):8670-9. doi:
10.1021/bi960522k. [PMID: 8679629] - L Tang, V P Smith, K Gounaris, M E Selkirk. Brugia pahangi: the cuticular glutathione peroxidase (gp29) protects heterologous membranes from lipid peroxidation.
Experimental parasitology.
1996 Apr; 82(3):329-32. doi:
10.1006/expr.1996.0041. [PMID: 8631385] - D Caruso, M F Rasetti, L De Angelis, G Galli. Identification of 3 beta-hydroxy-5 alpha-cholest-6-ene-5-hydroperoxide in human oxidized LDL.
Chemistry and physics of lipids.
1996 Mar; 79(2):181-6. doi:
10.1016/0009-3084(95)02519-7. [PMID: 8640903] - M D Coffey, R A Cole, S M Colles, G M Chisolm. In vitro cell injury by oxidized low density lipoprotein involves lipid hydroperoxide-induced formation of alkoxyl, lipid, and peroxyl radicals.
The Journal of clinical investigation.
1995 Oct; 96(4):1866-73. doi:
10.1172/jci118232. [PMID: 7560078] - P G Geiger, W Korytowski, A W Girotti. Photodynamically generated 3-beta-hydroxy-5 alpha-cholest-6-ene-5- hydroperoxide: toxic reactivity in membranes and susceptibility to enzymatic detoxification.
Photochemistry and photobiology.
1995 Sep; 62(3):580-7. doi:
10.1111/j.1751-1097.1995.tb02388.x. [PMID: 8570716] - J Christison, H Sies, R Stocker. Human blood cells support the reduction of low-density-lipoprotein-associated cholesteryl ester hydroperoxides by albumin-bound ebselen.
The Biochemical journal.
1994 Dec; 304 ( Pt 2)(?):341-5. doi:
10.1042/bj3040341. [PMID: 7998966] - A Sevanian, R Seraglia, P Traldi, P Rossato, F Ursini, H Hodis. Analysis of plasma cholesterol oxidation products using gas- and high-performance liquid chromatography/mass spectrometry.
Free radical biology & medicine.
1994 Nov; 17(5):397-409. doi:
10.1016/0891-5849(94)90166-x. [PMID: 7835746] - G J Bachowski, W Korytowski, A W Girotti. Characterization of lipid hydroperoxides generated by photodynamic treatment of leukemia cells.
Lipids.
1994 Jul; 29(7):449-59. doi:
10.1007/bf02578241. [PMID: 7968265] - K Akasaka, H Ohrui, H Meguro. Simultaneous determination of hydroperoxides of phosphatidylcholine, cholesterol esters and triacylglycerols by column-switching high-performance liquid chromatography with a post-column detection system.
Journal of chromatography.
1993 Dec; 622(2):153-9. doi:
10.1016/0378-4347(93)80261-2. [PMID: 8150864] - W Korytowski, G J Bachowski, A W Girotti. Analysis of cholesterol and phospholipid hydroperoxides by high-performance liquid chromatography with mercury drop electrochemical detection.
Analytical biochemistry.
1993 Aug; 213(1):111-9. doi:
10.1006/abio.1993.1393. [PMID: 8238862] - H Kamido, A Kuksis, L Marai, J J Myher. Identification of core aldehydes among in vitro peroxidation products of cholesteryl esters.
Lipids.
1993 Apr; 28(4):331-6. doi:
10.1007/bf02536319. [PMID: 8487625] - B U Meyer, W Schneider, E F Elstner. Peroxide-dependent amino acid oxidation and chemiluminescence catalysed by magnesium-pyridoxal phosphate-glutamate complex.
Biochemical pharmacology.
1992 Aug; 44(3):505-8. doi:
10.1016/0006-2952(92)90442-l. [PMID: 1510700] - M Maiorino, A Roveri, F Ursini. Antioxidant effect of Ebselen (PZ 51): peroxidase mimetic activity on phospholipid and cholesterol hydroperoxides vs free radical scavenger activity.
Archives of biochemistry and biophysics.
1992 Jun; 295(2):404-9. doi:
10.1016/0003-9861(92)90534-4. [PMID: 1586168] - H Fujita, I Matsuo. Type I lipid photo-oxidation by the nonsteroidal anti-inflammatory drug suprofen: a possible key to its photosensitivity.
Photodermatology, photoimmunology & photomedicine.
1992 199; 9(5):203-8. doi:
". [PMID: 1342189] - C L Tipton, M Shih, W J Magat. Isolation and characterization of calmodulin-inactivating cholesterol hydroperoxides.
Journal of lipid research.
1991 Sep; 32(9):1403-8. doi:
". [PMID: 1753210] - W Korytowski, G J Bachowski, A W Girotti. Chromatographic separation and electrochemical determination of cholesterol hydroperoxides generated by photodynamic action.
Analytical biochemistry.
1991 Aug; 197(1):149-56. doi:
10.1016/0003-2697(91)90371-y. [PMID: 1952058] - J G Coghlan, W D Flitter, A E Holley, M Norell, A G Mitchell, C D Ilsley, T F Slater. Detection of free radicals and cholesterol hydroperoxides in blood taken from the coronary sinus of man during percutaneous transluminal coronary angioplasty.
Free radical research communications.
1991; 14(5-6):409-17. doi:
10.3109/10715769109093429. [PMID: 1663908] - J P Thomas, M Maiorino, F Ursini, A W Girotti. Protective action of phospholipid hydroperoxide glutathione peroxidase against membrane-damaging lipid peroxidation. In situ reduction of phospholipid and cholesterol hydroperoxides.
The Journal of biological chemistry.
1990 Jan; 265(1):454-61. doi:
10.1016/s0021-9258(19)40252-4. [PMID: 2294113] - C L Tipton, P C Leung, J S Johnson, R J Brooks, D C Beitz. Cholesterol hydroperoxides inhibit calmodulin and suppress atherogenesis in rabbits.
Biochemical and biophysical research communications.
1987 Aug; 146(3):1166-72. doi:
10.1016/0006-291x(87)90770-4. [PMID: 3619923] - N M Made Gowda, L L Smith. On reaction of sterol hydroperoxides with superoxide.
Journal of steroid biochemistry.
1984 Apr; 20(4A):917-22. doi:
10.1016/0022-4731(84)90406-0. [PMID: 6323884]