13(S)-HPODE (BioDeep_00001868772)

Main id: BioDeep_00000003299

 

Volatile Flavor Compounds


代谢物信息卡片


13(S)-HPODE

化学式: C18H32O4 (312.2300472)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCC(C=CC=CCCCCCCCC(=O)O)OO
InChI: InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7-,15-12+/t17-/m0/s1

描述信息

D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides
The (S)-enantiomer of 13-HPODE

同义名列表

2 个代谢物同义名

13(S)-HPODE; (9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid



数据库引用编号

12 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

  • Ruriko Miyazaki, Shunji Kato, Yurika Otoki, Halida Rahmania, Masayoshi Sakaino, Shigeo Takeuchi, Toshiro Sato, Jun Imagi, Kiyotaka Nakagawa. Elucidation of decomposition pathways of linoleic acid hydroperoxide isomers by GC-MS and LC-MS/MS. Bioscience, biotechnology, and biochemistry. 2023 Jan; 87(2):179-190. doi: 10.1093/bbb/zbac189. [PMID: 36416801]
  • Michael Rohr, Chandrakala Aluganti Narasimhulu, Esra'a Keewan, Simran Hamid, Sampath Parthasarathy. The dietary peroxidized lipid, 13-HPODE, promotes intestinal inflammation by mediating granzyme B secretion from natural killer cells. Food & function. 2020 Nov; 11(11):9526-9534. doi: 10.1039/d0fo02328k. [PMID: 33089841]
  • Xiaojuan Wu, Fang Li, Wei Wu. Effects of oxidative modification by 13-hydroperoxyoctadecadienoic acid on the structure and functional properties of rice protein. Food research international (Ottawa, Ont.). 2020 06; 132(?):109096. doi: 10.1016/j.foodres.2020.109096. [PMID: 32331648]
  • Dillon Hershelman, Kirsten M Kahler, Morgan J Price, Iris Lu, Yuhan Fu, Patricia A Plumeri, Fred Karaisz, Natasha F Bassett, Peter M Findeis, Charles H Clapp. Oxygenation reactions catalyzed by the F557V mutant of soybean lipoxygenase-1: Evidence for two orientations of substrate binding. Archives of biochemistry and biophysics. 2019 10; 674(?):108082. doi: 10.1016/j.abb.2019.108082. [PMID: 31473191]
  • Christopher Wolff, Christian Zoschke, Suresh Kumar Kalangi, Pallu Reddanna, Monika Schäfer-Korting. Tumor microenvironment determines drug efficacy in vitro - apoptotic and anti-inflammatory effects of 15-lipoxygenase metabolite, 13-HpOTrE. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2019 Sep; 142(?):1-7. doi: 10.1016/j.ejpb.2019.06.003. [PMID: 31176725]
  • Yana Y Toporkova, Svetlana S Gorina, Elena K Bessolitsyna, Elena O Smirnova, Valeria S Fatykhova, Fredi Brühlmann, Tatiana M Ilyina, Lucia S Mukhtarova, Alexander N Grechkin. Double function hydroperoxide lyases/epoxyalcohol synthases (CYP74C) of higher plants: identification and conversion into allene oxide synthases by site-directed mutagenesis. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2018 Apr; 1863(4):369-378. doi: 10.1016/j.bbalip.2018.01.002. [PMID: 29325723]
  • Yana Y Toporkova, Valeria S Fatykhova, Yuri V Gogolev, Bulat I Khairutdinov, Lucia S Mukhtarova, Alexander N Grechkin. Epoxyalcohol synthase of Ectocarpus siliculosus. First CYP74-related enzyme of oxylipin biosynthesis in brown algae. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2017 Feb; 1862(2):167-175. doi: 10.1016/j.bbalip.2016.11.007. [PMID: 27863255]
  • Junya Ito, Kiyotaka Nakagawa, Shunji Kato, Takafumi Hirokawa, Shigefumi Kuwahara, Toshiharu Nagai, Teruo Miyazawa. A novel chiral stationary phase HPLC-MS/MS method to discriminate between enzymatic oxidation and auto-oxidation of phosphatidylcholine. Analytical and bioanalytical chemistry. 2016 Nov; 408(27):7785-7793. doi: 10.1007/s00216-016-9882-4. [PMID: 27549797]
  • Barbara Soldo, Matilda Šprung, Gloria Mušac, Maja Pavela-Vrančić, Ivica Ljubenkov. Evaluation of Olive Fruit Lipoxygenase Extraction Protocols on 9- and 13-Z,E-HPODE Formation. Molecules (Basel, Switzerland). 2016 Apr; 21(4):506. doi: 10.3390/molecules21040506. [PMID: 27104512]
  • Svetlana S Gorina, Yana Y Toporkova, Lucia S Mukhtarova, Elena O Smirnova, Ivan R Chechetkin, Bulat I Khairutdinov, Yuri V Gogolev, Alexander N Grechkin. Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Molecular cloning and identification of divinyl ether synthases CYP74M1 and CYP74M3. Biochimica et biophysica acta. 2016 Apr; 1861(4):301-9. doi: 10.1016/j.bbalip.2016.01.001. [PMID: 26776054]
  • Valerie E Ryman, Nandakumar Packiriswamy, Lorraine M Sordillo. Apoptosis of Endothelial Cells by 13-HPODE Contributes to Impairment of Endothelial Barrier Integrity. Mediators of inflammation. 2016; 2016(?):9867138. doi: 10.1155/2016/9867138. [PMID: 27818578]
  • Ryo Takahashi, Takaaki Goto, Tomoyuki Oe, Seon Hwa Lee. Angiotensin II modification by decomposition products of linoleic acid-derived lipid hydroperoxide. Chemico-biological interactions. 2015 Sep; 239(?):87-99. doi: 10.1016/j.cbi.2015.06.029. [PMID: 26111765]
  • Chun-Hua Huang, Fu-Rong Ren, Guo-Qiang Shan, Hao Qin, Li Mao, Ben-Zhan Zhu. Molecular mechanism of metal-independent decomposition of organic hydroperoxides by halogenated quinoid carcinogens and the potential biological implications. Chemical research in toxicology. 2015 May; 28(5):831-7. doi: 10.1021/tx500486z. [PMID: 25789984]
  • Kiyotaka Nakagawa, Shunji Kato, Teruo Miyazawa. Determination of Phosphatidylcholine Hydroperoxide (PCOOH) as a Marker of Membrane Lipid Peroxidation. Journal of nutritional science and vitaminology. 2015; 61 Suppl(?):S78-80. doi: 10.3177/jnsv.61.s78. [PMID: 26598897]
  • Josefin Zschaler, Juergen Arnhold. The hydroperoxide moiety of aliphatic lipid hydroperoxides is not affected by hypochlorous acid. Chemistry and physics of lipids. 2014 Dec; 184(?):42-51. doi: 10.1016/j.chemphyslip.2014.09.005. [PMID: 25260666]
  • Danilo Meyer, Cornelia Herrfurth, Florian Brodhun, Ivo Feussner. Degradation of lipoxygenase-derived oxylipins by glyoxysomes from sunflower and cucumber cotyledons. BMC plant biology. 2013 Nov; 13(?):177. doi: 10.1186/1471-2229-13-177. [PMID: 24207097]
  • Xu-Hua Wan, Shu-Xia Chen, Cong-Ying Wang, Ran-Ran Zhang, Si-Qiong Cheng, Huan-Wen Meng, Xiao-Qing Shen. Isolation, expression, and characterization of a hydroperoxide lyase gene from cucumber. International journal of molecular sciences. 2013 Nov; 14(11):22082-101. doi: 10.3390/ijms141122082. [PMID: 24213607]
  • Hao Qin, Chun-Hua Huang, Li Mao, Hai-Ying Xia, Balaraman Kalyanaraman, Jie Shao, Guo-Qiang Shan, Ben-Zhan Zhu. Molecular mechanism of metal-independent decomposition of lipid hydroperoxide 13-HPODE by halogenated quinoid carcinogens. Free radical biology & medicine. 2013 Oct; 63(?):459-66. doi: 10.1016/j.freeradbiomed.2013.05.008. [PMID: 23680403]
  • Eric K Hoobler, Charles Holz, Theodore R Holman. Pseudoperoxidase investigations of hydroperoxides and inhibitors with human lipoxygenases. Bioorganic & medicinal chemistry. 2013 Jul; 21(13):3894-9. doi: 10.1016/j.bmc.2013.04.016. [PMID: 23669189]
  • Reynier Suardíaz, Laura Masgrau, José M Lluch, Angels González-Lafont. An insight into the regiospecificity of linoleic acid peroxidation catalyzed by mammalian 15-lipoxygenases. The journal of physical chemistry. B. 2013 Apr; 117(14):3747-54. doi: 10.1021/jp312747q. [PMID: 23496802]
  • Natsuki Otaki, Miho Chikazawa, Ritsuko Nagae, Yuki Shimozu, Takahiro Shibata, Sohei Ito, Yoshinari Takasaki, Junichi Fujii, Koji Uchida. Identification of a lipid peroxidation product as the source of oxidation-specific epitopes recognized by anti-DNA autoantibodies. The Journal of biological chemistry. 2010 Oct; 285(44):33834-42. doi: 10.1074/jbc.m110.165175. [PMID: 20736172]
  • Satoshi Imaizumi, Victor Grijalva, Mohamad Navab, Brian J Van Lenten, Alan C Wagner, G M Anantharamiah, Alan M Fogelman, Srinivasa T Reddy. L-4F differentially alters plasma levels of oxidized fatty acids resulting in more anti-inflammatory HDL in mice. Drug metabolism letters. 2010 Aug; 4(3):139-48. doi: 10.2174/187231210791698438. [PMID: 20642447]
  • Peter G Slade, Michelle V Williams, Viral Brahmbhatt, Ajit Dash, John S Wishnok, Steven R Tannenbaum. Proteins modified by the lipid peroxidation aldehyde 9,12-dioxo-10(E)-dodecenoic acid in MCF7 breast cancer cells. Chemical research in toxicology. 2010 Mar; 23(3):557-67. doi: 10.1021/tx9002808. [PMID: 20131800]
  • Keiichi Ishihara, Kenji Amano, Eiichi Takaki, Abdul Shukkur Ebrahim, Atsushi Shimohata, Noriko Shibazaki, Ikuyo Inoue, Mayuko Takaki, Yuto Ueda, Haruhiko Sago, Charles J Epstein, Kazuhiro Yamakawa. Increased lipid peroxidation in Down's syndrome mouse models. Journal of neurochemistry. 2009 Sep; 110(6):1965-76. doi: 10.1111/j.1471-4159.2009.06294.x. [PMID: 19645748]
  • Aaron T Wecksler, Cyril Jacquot, Wilfred A van der Donk, Theodore R Holman. Mechanistic investigations of human reticulocyte 15- and platelet 12-lipoxygenases with arachidonic acid. Biochemistry. 2009 Jul; 48(26):6259-67. doi: 10.1021/bi802332j. [PMID: 19469483]
  • Achuthan Raghavamenon, Mahdi Garelnabi, Sainath Babu, Alex Aldrich, Dmitry Litvinov, Sampath Parthasarathy. Alpha-tocopherol is ineffective in preventing the decomposition of preformed lipid peroxides and may promote the accumulation of toxic aldehydes: a potential explanation for the failure of antioxidants to affect human atherosclerosis. Antioxidants & redox signaling. 2009 Jun; 11(6):1237-48. doi: 10.1089/ars.2008.2248. [PMID: 19186999]
  • Ryosuke Iijima, Takatsugu Ichikawa, Masatoshi Yamazaki. Sialic acid attenuates the cytotoxicity of the lipid hydroperoxides HpODE and HpETE. Carbohydrate research. 2009 May; 344(7):933-5. doi: 10.1016/j.carres.2009.02.025. [PMID: 19329108]
  • Yo Omata, Yoshiro Saito, Katsuhide Fujita, Yoko Ogawa, Keiko Nishio, Yasukazu Yoshida, Etsuo Niki. Induction of adaptive response and enhancement of PC12 cell tolerance by lipopolysaccharide primarily through the upregulation of glutathione S-transferase A3 via Nrf2 activation. Free radical biology & medicine. 2008 Nov; 45(10):1437-45. doi: 10.1016/j.freeradbiomed.2008.08.018. [PMID: 18793714]
  • Sonia Patui, Carlo Peresson, Enrico Braidot, Franco Tubaro, Alessio Colussi, Bernd Bonnländer, Francesco Macrì, Angelo Vianello. Lipoxygenase distribution in coffee (Coffea arabica L.) berries. Journal of agricultural and food chemistry. 2007 Oct; 55(20):8223-30. doi: 10.1021/jf070982s. [PMID: 17848084]
  • Michelle V Williams, John S Wishnok, Steven R Tannenbaum. Covalent adducts arising from the decomposition products of lipid hydroperoxides in the presence of cytochrome c. Chemical research in toxicology. 2007 May; 20(5):767-75. doi: 10.1021/tx600289r. [PMID: 17407328]
  • Sebastian Luci, Anja Bettzieche, Corinna Brandsch, Klaus Eder. Research paper effects of 13-HPODE on expression of genes involved in thyroid hormone synthesis, iodide uptake and formation of hydrogen peroxide in porcine thyrocytes. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2006 Nov; 76(6):398-406. doi: 10.1024/0300-9831.76.6.398. [PMID: 17607960]
  • Mutsuko Shirai, Yoshichika Kawai, Rintaro Yamanishi, Takashi Kinoshita, Hiroshi Chuman, Junji Terao. Effect of a conjugated quercetin metabolite, quercetin 3-glucuronide, on lipid hydroperoxide-dependent formation of reactive oxygen species in differentiated PC-12 cells. Free radical research. 2006 Oct; 40(10):1047-53. doi: 10.1080/10715760600794287. [PMID: 17015249]
  • Stacy K Seeley, Julie A Poposki, John Maksimchuk, Jill Tebbe, Jon Gaudreau, Bengt Mannervik, Arthur W Bull. Metabolism of oxidized linoleic acid by glutathione transferases: peroxidase activity toward 13-hydroperoxyoctadecadienoic acid. Biochimica et biophysica acta. 2006 Jul; 1760(7):1064-70. doi: 10.1016/j.bbagen.2006.02.020. [PMID: 16624487]
  • Su Duy Nguyen, Tae-Sook Jeong, Dai-Eun Sok. Apolipoprotein A-I-mimetic peptides with antioxidant actions. Archives of biochemistry and biophysics. 2006 Jul; 451(1):34-42. doi: 10.1016/j.abb.2006.04.010. [PMID: 16759634]
  • Bettina König, Klaus Eder. Differential action of 13-HPODE on PPARalpha downstream genes in rat Fao and human HepG2 hepatoma cell lines. The Journal of nutritional biochemistry. 2006 Jun; 17(6):410-8. doi: 10.1016/j.jnutbio.2005.08.011. [PMID: 16216487]
  • Satoru Sakuma, Kumiko Usa, Yohko Fujimoto. The regulation of formation of prostaglandins and arachidonoyl-CoA from arachidonic acid in rabbit kidney medulla microsomes by linoleic acid hydroperoxide. Prostaglandins & other lipid mediators. 2006 May; 79(3-4):271-7. doi: 10.1016/j.prostaglandins.2006.02.005. [PMID: 16647640]
  • Sae Iimura, Hideo Iwahashi. Enhancement by cigarette smoke extract of the radical formation in a reaction mixture of 13-hydroperoxide octadecadienoic acid and ferric ions. Journal of biochemistry. 2006 Apr; 139(4):671-6. doi: 10.1093/jb/mvj082. [PMID: 16672267]
  • Shinichi Iwai, Ahmad Aljada, Akira Higa, Takako Nakanishi-Ueda, Shohei Fukuda, Maki Kamegawa, Shigehiro Iwabuchi, Toshihiko Ueda, Sergio Caballero, Richard Browne, Aqeela Afzal, Maria Grant, Hajime Yasuhara, Ryohei Koide, Katsuji Oguchi, Paresh Dandona, Donald Armstrong. Activation of AP-1 and increased synthesis of MMP-9 in the rabbit retina induced by lipid hydroperoxide. Current eye research. 2006 Apr; 31(4):337-46. doi: 10.1080/02713680600577780. [PMID: 16603467]
  • Isabelle Durot, Lisa Devillard, Cindy Tissier, David Vandroux, Sophie Voisin, Sabir Jaquir, Luc Rochette, Pierre Athias. Dependence on the phospholipid polyunsaturated fatty acids of the oxidative injury of isolated cardiomyocytes. Free radical research. 2006 Mar; 40(3):251-61. doi: 10.1080/10715760500509165. [PMID: 16484041]
  • Leif-Alexander Garbe, Roberto Barbosa de Almeida, Renate Nagel, Karl Wackerbauer, Roland Tressl. Dual positional and stereospecificity of lipoxygenase isoenzymes from germinating barley (green malt): biotransformation of free and esterified linoleic acid. Journal of agricultural and food chemistry. 2006 Feb; 54(3):946-55. doi: 10.1021/jf051993t. [PMID: 16448207]
  • Mutsuko Shirai, Yoshichika Kawai, Rintaro Yamanishi, Junji Terao. Approach to novel functional foods for stress control 5. Antioxidant activity profiles of antidepressant herbs and their active components. The journal of medical investigation : JMI. 2005 Nov; 52 Suppl(?):249-51. doi: 10.2152/jmi.52.249. [PMID: 16366510]
  • Dimitrios I Tsitsigiannis, Susan Kunze, David K Willis, Ivo Feussner, Nancy P Keller. Aspergillus infection inhibits the expression of peanut 13S-HPODE-forming seed lipoxygenases. Molecular plant-microbe interactions : MPMI. 2005 Oct; 18(10):1081-9. doi: 10.1094/mpmi-18-1081. [PMID: 16255247]
  • Manuela Pérez-Gilabert, Isabel Sánchez-Felipe, Asunción Morte, Francisco García-Carmona. Kinetic properties of lipoxygenase from desert truffle (Terfezia claveryi Chatin) ascocarps: effect of inhibitors and activators. Journal of agricultural and food chemistry. 2005 Jul; 53(15):6140-5. doi: 10.1021/jf050521b. [PMID: 16029008]
  • Seon Hwa Lee, Tomoyuki Oe, Jasbir S Arora, Ian A Blair. Analysis of FeII-mediated decomposition of a linoleic acid-derived lipid hydroperoxide by liquid chromatography/mass spectrometry. Journal of mass spectrometry : JMS. 2005 May; 40(5):661-8. doi: 10.1002/jms.838. [PMID: 15739161]
  • Igor Ivanov, Jan Saam, Hartmut Kuhn, Hermann-Georg Holzhütter. Dual role of oxygen during lipoxygenase reactions. The FEBS journal. 2005 May; 272(10):2523-35. doi: 10.1111/j.1742-4658.2005.04673.x. [PMID: 15885101]
  • Bernt Gerhardt, Kerstin Fischer, Thomas J Balkenhohl, Georg Pohnert, Hartmut Kühn, Claus Wasternack, Ivo Feussner. Lipoxygenase-mediated metabolism of storage lipids in germinating sunflower cotyledons and beta-oxidation of (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid by the cotyledonary glyoxysomes. Planta. 2005 Apr; 220(6):919-30. doi: 10.1007/s00425-004-1408-1. [PMID: 15526214]
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  • Ivan R Chechetkin, Natalia V Medvedeva, Alexander N Grechkin. The novel pathway for ketodiene oxylipin biosynthesis in Jerusalem artichoke (Helianthus tuberosus) tubers. Biochimica et biophysica acta. 2004 Nov; 1686(1-2):7-14. doi: 10.1016/j.bbalip.2004.07.001. [PMID: 15522817]
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  • Hideo Iwahashi, Kayo Akata, Atsuko Sunaga, Yoshiko Tone, Noriko Yamada, Keiko Iijima. The inhibitory effect of luteolin-7-O-glucoside on the formation of pentyl and 7-carboxyheptyl radicals from 13-hydroperoxy-9,11-octadecadienoic acid in the presence of iron(II) ions. Free radical research. 2004 Aug; 38(8):869-76. doi: 10.1080/10715760410001722033. [PMID: 15493461]
  • Michiharu Tanabe, Sadaharu Tabuchi, Masato Iwatsuki, Masamichi Kurosaki, Hideki Kamitani, Masayuki Yokota, Takashi Watanabe. Incorporation of arachidonic and linoleic acid hydroperoxides into cultured human umbilical vein endothelial cells. Prostaglandins, leukotrienes, and essential fatty acids. 2004 Jun; 70(6):485-9. doi: 10.1016/j.plefa.2003.10.003. [PMID: 15120710]
  • Roopashree S Dwarakanath, Saurabh Sahar, Marpadga A Reddy, Daniela Castanotto, John J Rossi, Rama Natarajan. Regulation of monocyte chemoattractant protein-1 by the oxidized lipid, 13-hydroperoxyoctadecadienoic acid, in vascular smooth muscle cells via nuclear factor-kappa B (NF-kappa B). Journal of molecular and cellular cardiology. 2004 Apr; 36(4):585-95. doi: 10.1016/j.yjmcc.2004.02.007. [PMID: 15081318]
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