2-Amino-3-hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate (BioDeep_00000897489)
代谢物信息卡片
2-Amino-3-hydroxyoctadec-4-en-1-yl 2-(trimethylazaniumyl)ethyl phosphate
化学式: C23H50N2O5P+ (465.34571600000004)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCCCCCCCCC=CC(C(COP(=O)([O-])OCC[N+](C)(C)C)[NH3+])O
InChI: InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/p+1/b18-17+/t22-,23+/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
- Yujuan Yao, Jinrun Zhou, Chenchen Lu, Wenjing Sun, Weihua Kong, Jing Zhao. MicroRNA-155-5p/EPAS1/interleukin 6 pathway participated in the protection function of sphingosylphosphorylcholine to ischemic cardiomyocytes.
Life sciences.
2021 Jan; 264(?):118692. doi:
10.1016/j.lfs.2020.118692. [PMID: 33130081] - Ha Young Lee, Kwang Min Cho, Min Kyung Kim, Mingyu Lee, Hun Kim, Cheol Yong Choi, Kyeong Kyu Kim, Joon Seong Park, Hong-Hee Kim, Yoe-Sik Bae. Sphingosylphosphorylcholine blocks ovariectomy-induced bone loss by suppressing Ca2+ /calmodulin-mediated osteoclast differentiation.
Journal of cellular and molecular medicine.
2021 01; 25(1):473-483. doi:
10.1111/jcmm.16101. [PMID: 33230972] - Ying Li, Qi Qi, Wan-Cheng Yang, Tian-Liang Zhang, Chen-Chen Lu, Yu-Juan Yao, Wei-Hua Kong, Jing Zhao. Sphingosylphosphorylcholine alleviates hypoxia-caused apoptosis in cardiac myofibroblasts via CaM/p38/STAT3 pathway.
Apoptosis : an international journal on programmed cell death.
2020 12; 25(11-12):853-863. doi:
10.1007/s10495-020-01639-9. [PMID: 33068199] - Iskren Menkovic, Michel Boutin, Abdulfatah Alayoubi, François E Mercier, Georges-Étienne Rivard, Christiane Auray-Blais. Identification of a Reliable Biomarker Profile for the Diagnosis of Gaucher Disease Type 1 Patients Using a Mass Spectrometry-Based Metabolomic Approach.
International journal of molecular sciences.
2020 Oct; 21(21):. doi:
10.3390/ijms21217869. [PMID: 33114153] - Anna Iwahori, Masamitsu Maekawa, Aya Narita, Akie Kato, Toshihiro Sato, Jiro Ogura, Yu Sato, Masafumi Kikuchi, Atsuko Noguchi, Katsumi Higaki, Torayuki Okuyama, Tsutomu Takahashi, Yoshikatsu Eto, Nariyasu Mano. Development of a Diagnostic Screening Strategy for Niemann-Pick Diseases Based on Simultaneous Liquid Chromatography-Tandem Mass Spectrometry Analyses of N-Palmitoyl-O-phosphocholine-serine and Sphingosylphosphorylcholine.
Biological & pharmaceutical bulletin.
2020 Sep; 43(9):1398-1406. doi:
10.1248/bpb.b20-00400. [PMID: 32581190] - Di Ge, Jia Gao, Lina Han, Ying Li, Hong-Hong Liu, Wan-Cheng Yang, Fen Chang, Jing Liu, Mei Yu, Jing Zhao. Novel effects of sphingosylphosphorylcholine on the apoptosis of breast cancer via autophagy/AKT/p38 and JNK signaling.
Journal of cellular physiology.
2019 07; 234(7):11451-11462. doi:
10.1002/jcp.27802. [PMID: 30488428] - Di Ge, Hong-Wei Yue, Hong-Hong Liu, Jing Zhao. Emerging roles of sphingosylphosphorylcholine in modulating cardiovascular functions and diseases.
Acta pharmacologica Sinica.
2018 Dec; 39(12):1830-1836. doi:
10.1038/s41401-018-0036-4. [PMID: 30050085] - Melissa P Wasserstein, George A Diaz, Robin H Lachmann, Marie-Hélène Jouvin, Indrani Nandy, Allena J Ji, Ana Cristina Puga. Olipudase alfa for treatment of acid sphingomyelinase deficiency (ASMD): safety and efficacy in adults treated for 30 months.
Journal of inherited metabolic disease.
2018 09; 41(5):829-838. doi:
10.1007/s10545-017-0123-6. [PMID: 29305734] - Bing Peng, Sascha Geue, Cristina Coman, Patrick Münzer, Dominik Kopczynski, Canan Has, Nils Hoffmann, Mailin-Christin Manke, Florian Lang, Albert Sickmann, Meinrad Gawaz, Oliver Borst, Robert Ahrends. Identification of key lipids critical for platelet activation by comprehensive analysis of the platelet lipidome.
Blood.
2018 08; 132(5):e1-e12. doi:
10.1182/blood-2017-12-822890. [PMID: 29784642] - L Kuchar, J Sikora, M E Gulinello, H Poupetova, A Lugowska, V Malinova, H Jahnova, B Asfaw, J Ledvinova. Quantitation of plasmatic lysosphingomyelin and lysosphingomyelin-509 for differential screening of Niemann-Pick A/B and C diseases.
Analytical biochemistry.
2017 May; 525(?):73-77. doi:
10.1016/j.ab.2017.02.019. [PMID: 28259515] - Christiane Wirrig, Jenny S McKean, Heather M Wilson, Graeme F Nixon. Sphingosylphosphorylcholine inhibits macrophage adhesion to vascular smooth muscle cells.
Biochemical pharmacology.
2016 09; 115(?):43-50. doi:
10.1016/j.bcp.2016.07.004. [PMID: 27402344] - Marie T Vanier, Paul Gissen, Peter Bauer, Maria J Coll, Alberto Burlina, Christian J Hendriksz, Philippe Latour, Cyril Goizet, Richard W D Welford, Thorsten Marquardt, Stefan A Kolb. Diagnostic tests for Niemann-Pick disease type C (NP-C): A critical review.
Molecular genetics and metabolism.
2016 08; 118(4):244-54. doi:
10.1016/j.ymgme.2016.06.004. [PMID: 27339554] - Feyza Aksu, Burhan Aksu, Nermin Unlu, Turan Karaca, Suleyman Ayvaz, Hayriye Erman, Hafize Uzun, Nursen Keles, Sule Bulur, Ercument Unlu. Antioxidant and renoprotective effects of sphingosylphosphorylcholine on contrast-induced nephropathy in rats.
Renal failure.
2016 Aug; 38(7):1089-98. doi:
10.1080/0886022x.2016.1194142. [PMID: 27309733] - Wenjing Li, Honghong Liu, Pingping Liu, Deling Yin, Shangli Zhang, Jing Zhao. Sphingosylphosphorylcholine promotes the differentiation of resident Sca-1 positive cardiac stem cells to cardiomyocytes through lipid raft/JNK/STAT3 and β-catenin signaling pathways.
Biochimica et biophysica acta.
2016 Jul; 1863(7 Pt A):1579-88. doi:
10.1016/j.bbamcr.2016.04.006. [PMID: 27066979] - Keiji Yokota, Toshio Ogino. Phase separation in lipid bilayer membranes induced by intermixing at a boundary of two phases with different components.
Chemistry and physics of lipids.
2015 Oct; 191(?):147-52. doi:
10.1016/j.chemphyslip.2015.09.001. [PMID: 26363303] - Hong-Wei Yue, Jing Liu, Ping-Ping Liu, Wen-Jing Li, Fen Chang, Jun-Ying Miao, Jing Zhao. Sphingosylphosphorylcholine protects cardiomyocytes against ischemic apoptosis via lipid raft/PTEN/Akt1/mTOR mediated autophagy.
Biochimica et biophysica acta.
2015 Sep; 1851(9):1186-93. doi:
10.1016/j.bbalip.2015.04.001. [PMID: 25871970] - Satoshi Shirao, Hiroshi Yoneda, Mizuya Shinoyama, Kazutaka Sugimoto, Hiroyasu Koizumi, Hideyuki Ishihara, Fumiaki Oka, Hirokazu Sadahiro, Sadahiro Nomura, Masami Fujii, Masakatsu Tamechika, Yoshiteru Kagawa, Yuji Owada, Michiyasu Suzuki. A novel trigger for cholesterol-dependent smooth muscle contraction mediated by the sphingosylphosphorylcholine-Rho-kinase pathway in the rat basilar artery: a mechanistic role for lipid rafts.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism.
2015 May; 35(5):835-42. doi:
10.1038/jcbfm.2014.260. [PMID: 25605290] - Nahed El-Najjar, Evelyn Orsó, Stefan Wallner, Gerhard Liebisch, Gerd Schmitz. Increased Levels of Sphingosylphosphorylcholine (SPC) in Plasma of Metabolic Syndrome Patients.
PloS one.
2015; 10(10):e0140683. doi:
10.1371/journal.pone.0140683. [PMID: 26466367] - Hongwei Yue, Wenjing Li, Pingping Liu, Jia Gao, Junying Miao, Jing Zhao. Inhibition of autophagy promoted sphingosylphosphorylcholine induced cell death in non-small cell lung cancer cells.
Biochemical and biophysical research communications.
2014 Oct; 453(3):502-7. doi:
10.1016/j.bbrc.2014.09.120. [PMID: 25285628] - Wei-Lien Chuang, Joshua Pacheco, Samantha Cooper, Margaret M McGovern, Gerald F Cox, Joan Keutzer, X Kate Zhang. Lyso-sphingomyelin is elevated in dried blood spots of Niemann-Pick B patients.
Molecular genetics and metabolism.
2014 Feb; 111(2):209-11. doi:
10.1016/j.ymgme.2013.11.012. [PMID: 24418695] - Richard W D Welford, Marco Garzotti, Charles Marques Lourenço, Eugen Mengel, Thorsten Marquardt, Janine Reunert, Yasmina Amraoui, Stefan A Kolb, Olivier Morand, Peter Groenen. Plasma lysosphingomyelin demonstrates great potential as a diagnostic biomarker for Niemann-Pick disease type C in a retrospective study.
PloS one.
2014; 9(12):e114669. doi:
10.1371/journal.pone.0114669. [PMID: 25479233] - X Q Wang, L J Mao, Q H Fang, T Kobayashi, H J Kim, H Sugiura, S Kawasaki, S Togo, K Kamio, X Liu, S I Rennard. Sphingosylphosphorylcholine induces α-smooth muscle actin expression in human lung fibroblasts and fibroblast-mediated gel contraction via S1P2 receptor and Rho/Rho-kinase pathway.
Prostaglandins & other lipid mediators.
2014 Jan; 108(?):23-30. doi:
10.1016/j.prostaglandins.2014.02.002. [PMID: 24614064] - Seiichi Sakamoto, Hiromichi Nakahara, Takuhiro Uto, Yukihiro Shoyama, Osamu Shibata. Investigation of interfacial behavior of glycyrrhizin with a lipid raft model via a Langmuir monolayer study.
Biochimica et biophysica acta.
2013 Apr; 1828(4):1271-83. doi:
10.1016/j.bbamem.2013.01.006. [PMID: 23333324] - Tobias Busch, Milena Armacki, Tim Eiseler, Golsa Joodi, Claudia Temme, Julia Jansen, Götz von Wichert, M Bishr Omary, Joachim Spatz, Thomas Seufferlein. Keratin 8 phosphorylation regulates keratin reorganization and migration of epithelial tumor cells.
Journal of cell science.
2012 May; 125(Pt 9):2148-59. doi:
10.1242/jcs.080127. [PMID: 22344252] - Cai-Rong Yang, Yanchang Wei, Shu-Tao Qi, Lei Chen, Qing-Hua Zhang, Jun-Yu Ma, Yi-Bo Luo, Ya-Peng Wang, Yi Hou, Heide Schatten, Zhong-Hua Liu, Qing-Yuan Sun. The G protein coupled receptor 3 is involved in cAMP and cGMP signaling and maintenance of meiotic arrest in porcine oocytes.
PloS one.
2012; 7(6):e38807. doi:
10.1371/journal.pone.0038807. [PMID: 22685609] - Di Ge, Qingchuan Jing, Ning Meng, Le Su, Yun Zhang, Shangli Zhang, Junying Miao, Jing Zhao. Regulation of apoptosis and autophagy by sphingosylphosphorylcholine in vascular endothelial cells.
Journal of cellular physiology.
2011 Nov; 226(11):2827-33. doi:
10.1002/jcp.22632. [PMID: 21302284] - Hyo-Soon Jeong, Seung Hoon Lee, Hye-Young Yun, Kwang Jin Baek, Nyoun Soo Kwon, Kyoung-Chan Park, Dong-Seok Kim. Involvement of mTOR signaling in sphingosylphosphorylcholine-induced hypopigmentation effects.
Journal of biomedical science.
2011 Aug; 18(?):55. doi:
10.1186/1423-0127-18-55. [PMID: 21838918] - Christiane Wirrig, Irene Hunter, Fiona A Mathieson, Graeme F Nixon. Sphingosylphosphorylcholine is a proinflammatory mediator in cerebral arteries.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism.
2011 Jan; 31(1):212-21. doi:
10.1038/jcbfm.2010.79. [PMID: 20551970] - Erika Kovacs, Le Xu, Daniel A Pasek, Karoly Liliom, Gerhard Meissner. Regulation of ryanodine receptors by sphingosylphosphorylcholine: involvement of both calmodulin-dependent and -independent mechanisms.
Biochemical and biophysical research communications.
2010 Oct; 401(2):281-6. doi:
10.1016/j.bbrc.2010.09.050. [PMID: 20851108] - Dong-Seok Kim, Seo-Hyoung Park, Sun-Bang Kwon, Nyoun Soo Kwon, Kyoung-Chan Park. Sphingosylphosphorylcholine inhibits melanin synthesis via pertussis toxin-sensitive MITF degradation.
The Journal of pharmacy and pharmacology.
2010 Feb; 62(2):181-7. doi:
10.1211/jpp.62.02.0005. [PMID: 20487197] - Erika Kovacs, Judit Tóth, Beáta G Vértessy, Károly Liliom. Dissociation of calmodulin-target peptide complexes by the lipid mediator sphingosylphosphorylcholine: implications in calcium signaling.
The Journal of biological chemistry.
2010 Jan; 285(3):1799-808. doi:
10.1074/jbc.m109.053116. [PMID: 19910470] - Maria Sundh, Sofia Svedhem, Duncan S Sutherland. Influence of phase separating lipids on supported lipid bilayer formation at SiO2 surfaces.
Physical chemistry chemical physics : PCCP.
2010 Jan; 12(2):453-60. doi:
10.1039/b912598a. [PMID: 20023823] - Hyoung-June Kim, Kwang-Mi Kim, Jae-Young Koh, Min-Soo Noh, Mi-Kyung Park, Hye-Ja Lee, Soo-Youl Kim, Chang-Hoon Lee. Sphingosylphosphorylcholine induces degranulation of mast cells in the skin and plasma exudation in the ears of mice.
Journal of dermatological science.
2010 Jan; 57(1):57-9. doi:
10.1016/j.jdermsci.2009.09.007. [PMID: 19889516] - Andrea Huwiler, Josef Pfeilschifter. Lipids as targets for novel anti-inflammatory therapies.
Pharmacology & therapeutics.
2009 Oct; 124(1):96-112. doi:
10.1016/j.pharmthera.2009.06.008. [PMID: 19576246] - Lisa M Fox, Daryl G Cox, Jennifer L Lockridge, Xiaohua Wang, Xiuxu Chen, Louise Scharf, David L Trott, Rachel M Ndonye, Natacha Veerapen, Gurdyal S Besra, Amy R Howell, Mark E Cook, Erin J Adams, William H Hildebrand, Jenny E Gumperz. Recognition of lyso-phospholipids by human natural killer T lymphocytes.
PLoS biology.
2009 Oct; 7(10):e1000228. doi:
10.1371/journal.pbio.1000228. [PMID: 19859526] - Soo-Kyoung Choi, Duck-Sun Ahn, Young-Ho Lee. Comparison of contractile mechanisms of sphingosylphosphorylcholine and sphingosine-1-phosphate in rabbit coronary artery.
Cardiovascular research.
2009 May; 82(2):324-32. doi:
10.1093/cvr/cvp054. [PMID: 19218288] - Burhan Aksu, Hasan Umit, Mehmet Kanter, Ahmet Guzel, Mustafa Inan, Sabiha Civelek, Cevat Aktas, Hafize Uzun. Effects of sphingosylphosphorylcholine against cholestatic oxidative stress and liver damage in the common bile duct ligated rats.
Journal of pediatric surgery.
2009 Apr; 44(4):702-10. doi:
10.1016/j.jpedsurg.2008.09.016. [PMID: 19361629] - Vladimir A Snetkov, Gavin D Thomas, Bonnie Teague, Richard M Leach, Yasin Shaifta, Greg A Knock, Philip I Aaronson, Jeremy P T Ward. Low concentrations of sphingosylphosphorylcholine enhance pulmonary artery vasoreactivity: the role of protein kinase C delta and Ca2+ entry.
Hypertension (Dallas, Tex. : 1979).
2008 Feb; 51(2):239-45. doi:
10.1161/hypertensionaha.107.104802. [PMID: 18158336] - Graeme F Nixon, Fiona A Mathieson, Irene Hunter. The multi-functional role of sphingosylphosphorylcholine.
Progress in lipid research.
2008 Jan; 47(1):62-75. doi:
10.1016/j.plipres.2007.11.001. [PMID: 18042469] - Mijin Han, Yu-Lee Kim, Santosh J Sacket, Kyeok Kim, Hyo-Lim Kim, Ji-Yeong Jo, Nam-Chul Ha, Dong-Soon Im. Effect of direct albumin binding to sphingosylphosphorylcholine in Jurkat T cells.
Prostaglandins & other lipid mediators.
2007 Nov; 84(3-4):174-83. doi:
10.1016/j.prostaglandins.2007.08.003. [PMID: 17991619] - Cuiyan Xin, Shuyu Ren, Wolfgang Eberhardt, Josef Pfeilschifter, Andrea Huwiler. Sphingosylphosphorylcholine acts in an anti-inflammatory manner in renal mesangial cells by reducing interleukin-1beta-induced prostaglandin E2 formation.
Journal of lipid research.
2007 Sep; 48(9):1985-96. doi:
10.1194/jlr.m700077-jlr200. [PMID: 17592175] - Masayuki Tobo, Hideaki Tomura, Chihiro Mogi, Ju-Qiang Wang, Jin-Peng Liu, Mayumi Komachi, Alatangaole Damirin, Takao Kimura, Naoya Murata, Hitoshi Kurose, Koichi Sato, Fumikazu Okajima. Previously postulated "ligand-independent" signaling of GPR4 is mediated through proton-sensing mechanisms.
Cellular signalling.
2007 Aug; 19(8):1745-53. doi:
10.1016/j.cellsig.2007.03.009. [PMID: 17462861] - Hiroyuki Kinoshita, Naoyuki Matsuda, Yoshiki Kimoto, Setsuko Tohyama, Keiko Hama, Katsutoshi Nakahata, Yoshio Hatano. Sevoflurane, but not propofol, prevents Rho kinase-dependent contraction induced by sphingosylphosphorylcholine in the porcine coronary artery.
Anesthesia and analgesia.
2007 Aug; 105(2):325-9. doi:
10.1213/01.ane.0000270207.84083.ba. [PMID: 17646484] - Yoo Bin Kwon, Young-Sook Lee, Kyung-Cheol Sohn, Yong-Jun Piao, Seung Ju Back, Young-Joon Seo, Ki-Beom Suhr, Jang-Kyu Park, Chang Deok Kim, Jeung-Hoon Lee. Sphingosylphosphorylcholine-induced interleukin-6 production is mediated by protein kinase C and p42/44 extracellular signal-regulated kinase in human dermal fibroblasts.
Journal of dermatological science.
2007 May; 46(2):91-9. doi:
10.1016/j.jdermsci.2007.01.007. [PMID: 17321112] - Viral V Brahmbhatt, Fong-Fu Hsu, Jeff L-F Kao, Erin C Frank, David A Ford. Novel carbonyl and nitrile products from reactive chlorinating species attack of lysosphingolipid.
Chemistry and physics of lipids.
2007 Feb; 145(2):72-84. doi:
10.1016/j.chemphyslip.2006.10.006. [PMID: 17126823] - Alexander Kleger, Tobias Busch, Stefan Liebau, Katja Prelle, Stephan Paschke, Michael Beil, Alexandra Rolletschek, Anna Wobus, Eckhard Wolf, Guido Adler, Thomas Seufferlein. The bioactive lipid sphingosylphosphorylcholine induces differentiation of mouse embryonic stem cells and human promyelocytic leukaemia cells.
Cellular signalling.
2007 Feb; 19(2):367-77. doi:
10.1016/j.cellsig.2006.07.015. [PMID: 16978842] - Eun Su Jeon, Hyun Jung Moon, Mi Jeong Lee, Hae Young Song, Young Mi Kim, Yong Chan Bae, Jin Sup Jung, Jae Ho Kim. Sphingosylphosphorylcholine induces differentiation of human mesenchymal stem cells into smooth-muscle-like cells through a TGF-beta-dependent mechanism.
Journal of cell science.
2006 Dec; 119(Pt 23):4994-5005. doi:
10.1242/jcs.03281. [PMID: 17105765] - Noriyasu Morikage, Hiroko Kishi, Masafumi Sato, Fengling Guo, Satoshi Shirao, Takashi Yano, Masaaki Soma, Kimikazu Hamano, Kensuke Esato, Sei Kobayashi. Cholesterol primes vascular smooth muscle to induce Ca2 sensitization mediated by a sphingosylphosphorylcholine-Rho-kinase pathway: possible role for membrane raft.
Circulation research.
2006 Aug; 99(3):299-306. doi:
10.1161/01.res.0000235877.33682.e9. [PMID: 16825579] - Dong-Seok Kim, Seo-Hyoung Park, Sun-Bang Kwon, Eun-Sang Park, Chang-Hun Huh, Sang-Woong Youn, Kyoung-Chan Park. Sphingosylphosphorylcholine-induced ERK activation inhibits melanin synthesis in human melanocytes.
Pigment cell research.
2006 Apr; 19(2):146-53. doi:
10.1111/j.1600-0749.2005.00287.x. [PMID: 16524430] - Claudia Czyborra, Angela Bischoff, Martin C Michel. Indomethacin differentiates the renal effects of sphingosine-1-phosphate and sphingosylphosphorylcholine.
Naunyn-Schmiedeberg's archives of pharmacology.
2006 Apr; 373(1):37-44. doi:
10.1007/s00210-006-0037-6. [PMID: 16521006] - Eun Su Jeon, Hae Young Song, Mi Ra Kim, Hyun Jung Moon, Yong Chan Bae, Jin Sup Jung, Jae Ho Kim. Sphingosylphosphorylcholine induces proliferation of human adipose tissue-derived mesenchymal stem cells via activation of JNK.
Journal of lipid research.
2006 Mar; 47(3):653-64. doi:
10.1194/jlr.m500508-jlr200. [PMID: 16339111] - Gavin D Thomas, Vladimir A Snetkov, Rupal Patel, Richard M Leach, Philip I Aaronson, Jeremy P T Ward. Sphingosylphosphorylcholine-induced vasoconstriction of pulmonary artery: activation of non-store-operated Ca2+ entry.
Cardiovascular research.
2005 Oct; 68(1):56-64. doi:
10.1016/j.cardiores.2005.05.013. [PMID: 15950201] - Yixin Jin, Bassam B Damaj, Azzam A Maghazachi. Human resting CD16-, CD16+ and IL-2-, IL-12-, IL-15- or IFN-alpha-activated natural killer cells differentially respond to sphingosylphosphorylcholine, lysophosphatidylcholine and platelet-activating factor.
European journal of immunology.
2005 Sep; 35(9):2699-708. doi:
10.1002/eji.200526129. [PMID: 16078278] - Hideki Sakagami, Junken Aoki, Yumiko Natori, Kiyotaka Nishikawa, Yoshiyuki Kakehi, Yasuhiro Natori, Hiroyuki Arai. Biochemical and molecular characterization of a novel choline-specific glycerophosphodiester phosphodiesterase belonging to the nucleotide pyrophosphatase/phosphodiesterase family.
The Journal of biological chemistry.
2005 Jun; 280(24):23084-93. doi:
10.1074/jbc.m413438200. [PMID: 15788404] - Xuequan Lu, Robert Bittman. Synthesis of a photoactivatable (2S,3R)-sphingosylphosphorylcholine analogue.
The Journal of organic chemistry.
2005 Jun; 70(12):4746-50. doi:
10.1021/jo050513u. [PMID: 15932314] - Eun Su Jeon, Yong Jung Kang, Hae Young Song, Dong-Soon Im, Hyeon Soo Kim, Sung Ho Ryu, Yong Keun Kim, Jae Ho Kim. Sphingosylphosphorylcholine generates reactive oxygen species through calcium-, protein kinase Cdelta- and phospholipase D-dependent pathways.
Cellular signalling.
2005 Jun; 17(6):777-87. doi:
10.1016/j.cellsig.2004.11.004. [PMID: 15722202] - Kwan-Sik Kim, Juan Ren, Ying Jiang, Quteba Ebrahem, Russell Tipps, Kelly Cristina, Yi-jin Xiao, Jing Qiao, Kevin L Taylor, Hazel Lum, Bela Anand-Apte, Yan Xu. GPR4 plays a critical role in endothelial cell function and mediates the effects of sphingosylphosphorylcholine.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2005 May; 19(7):819-21. doi:
10.1096/fj.04-2988fje. [PMID: 15857892] - Eun Su Jeon, Yong Jung Kang, Hae Young Song, Jae Suk Woo, Jin Sup Jung, Yong Keun Kim, Jae Ho Kim. Role of MEK-ERK pathway in sphingosylphosphorylcholine-induced cell death in human adipose tissue-derived mesenchymal stem cells.
Biochimica et biophysica acta.
2005 May; 1734(1):25-33. doi:
10.1016/j.bbalip.2005.01.005. [PMID: 15866480] - V S Kamanna, B V Bassa, S H Ganji, D D Roh. Bioactive lysophospholipids and mesangial cell intracellular signaling pathways: role in the pathobiology of kidney disease.
Histology and histopathology.
2005 04; 20(2):603-13. doi:
10.14670/hh-20.603. [PMID: 15736064] - S Suresh, J Spatz, J P Mills, A Micoulet, M Dao, C T Lim, M Beil, T Seufferlein. Connections between single-cell biomechanics and human disease states: gastrointestinal cancer and malaria.
Acta biomaterialia.
2005 Jan; 1(1):15-30. doi:
10.1016/j.actbio.2004.09.001. [PMID: 16701777] - Evi Kostenis. Novel clusters of receptors for sphingosine-1-phosphate, sphingosylphosphorylcholine, and (lyso)-phosphatidic acid: new receptors for "old" ligands.
Journal of cellular biochemistry.
2004 Aug; 92(5):923-36. doi:
10.1002/jcb.20092. [PMID: 15258916] - Hiroshi Deguchi, Subramanian Yegneswaran, John H Griffin. Sphingolipids as bioactive regulators of thrombin generation.
The Journal of biological chemistry.
2004 Mar; 279(13):12036-42. doi:
10.1074/jbc.m302531200. [PMID: 14722105] - Yukiko Miura, Eriko Gotoh, Futoshi Nara, Masahiro Nishijima, Kentaro Hanada. Hydrolysis of sphingosylphosphocholine by neutral sphingomyelinases.
FEBS letters.
2004 Jan; 557(1-3):288-92. doi:
10.1016/s0014-5793(03)01523-0. [PMID: 14741383] - Michael Beil, Alexandre Micoulet, Götz von Wichert, Stephan Paschke, Paul Walther, M Bishr Omary, Paul P Van Veldhoven, Ulrike Gern, Elke Wolff-Hieber, Juliane Eggermann, Johannes Waltenberger, Guido Adler, Joachim Spatz, Thomas Seufferlein. Sphingosylphosphorylcholine regulates keratin network architecture and visco-elastic properties of human cancer cells.
Nature cell biology.
2003 Sep; 5(9):803-11. doi:
10.1038/ncb1037. [PMID: 12942086] - Timothy Clair, Junken Aoki, Eunjin Koh, Russell W Bandle, Suk Woo Nam, Malgorzata M Ptaszynska, Gordon B Mills, Elliott Schiffmann, Lance A Liotta, Mary L Stracke. Autotaxin hydrolyzes sphingosylphosphorylcholine to produce the regulator of migration, sphingosine-1-phosphate.
Cancer research.
2003 Sep; 63(17):5446-53. doi:
. [PMID: 14500380] - Eugen Brailoiu, Nae J Dun. Extra- and intracellular sphingosylphosphorylcholine promote spontaneous transmitter release from frog motor nerve endings.
Molecular pharmacology.
2003 Jun; 63(6):1430-6. doi:
10.1124/mol.63.6.1430. [PMID: 12761354] - Midori Yasukochi, Akira Uehara, Sei Kobayashi, Joshua R Berlin. Ca2+ and voltage dependence of cardiac ryanodine receptor channel block by sphingosylphosphorylcholine.
Pflugers Archiv : European journal of physiology.
2003 Mar; 445(6):665-73. doi:
10.1007/s00424-002-0945-3. [PMID: 12632186] - Christoph Altmann, Dagmar Meyer Zu Heringdorf, Dilek Böyükbas, Michael Haude, Karl H Jakobs, Martin C Michel. Sphingosylphosphorylcholine, a naturally occurring lipid mediator, inhibits human platelet function.
British journal of pharmacology.
2003 Feb; 138(3):435-44. doi:
10.1038/sj.bjp.0705063. [PMID: 12569068] - Reiko Okamoto, Junko Arikawa, Mutsumi Ishibashi, Makoto Kawashima, Yutaka Takagi, Genji Imokawa. Sphingosylphosphorylcholine is upregulated in the stratum corneum of patients with atopic dermatitis.
Journal of lipid research.
2003 Jan; 44(1):93-102. doi:
10.1194/jlr.m200225-jlr200. [PMID: 12518027] - Dagmar Meyer zu Heringdorf, Herbert M Himmel, Karl H Jakobs. Sphingosylphosphorylcholine-biological functions and mechanisms of action.
Biochimica et biophysica acta.
2002 May; 1582(1-3):178-89. doi:
10.1016/s1388-1981(02)00154-3. [PMID: 12069827] - Luca M Neri, Roberta Bortul, Paola Borgatti, Giovanna Tabellini, Giovanna Baldini, Silvano Capitani, Alberto M Martelli. Proliferating or differentiating stimuli act on different lipid-dependent signaling pathways in nuclei of human leukemia cells.
Molecular biology of the cell.
2002 Mar; 13(3):947-64. doi:
10.1091/mbc.01-02-0086. [PMID: 11907274] - K Zhu, L M Baudhuin, G Hong, F S Williams, K L Cristina, J H Kabarowski, O N Witte, Y Xu. Sphingosylphosphorylcholine and lysophosphatidylcholine are ligands for the G protein-coupled receptor GPR4.
The Journal of biological chemistry.
2001 Nov; 276(44):41325-35. doi:
10.1074/jbc.m008057200. [PMID: 11535583] - J M Lyons, N J Karin. A role for G protein-coupled lysophospholipid receptors in sphingolipid-induced Ca2+ signaling in MC3T3-E1 osteoblastic cells.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research.
2001 Nov; 16(11):2035-42. doi:
10.1359/jbmr.2001.16.11.2035. [PMID: 11697799] - K Higuchi, M Kawashima, Y Takagi, H Kondo, Y Yada, Y Ichikawa, G Imokawa. Sphingosylphosphorylcholine is an activator of transglutaminase activity in human keratinocytes.
Journal of lipid research.
2001 Oct; 42(10):1562-70. doi:
. [PMID: 11590211] - J R Nofer, B Levkau, I Wolinska, R Junker, M Fobker, A von Eckardstein, U Seedorf, G Assmann. Suppression of endothelial cell apoptosis by high density lipoproteins (HDL) and HDL-associated lysosphingolipids.
The Journal of biological chemistry.
2001 Sep; 276(37):34480-5. doi:
10.1074/jbc.m103782200. [PMID: 11432865] - J H Kabarowski, K Zhu, L Q Le, O N Witte, Y Xu. Lysophosphatidylcholine as a ligand for the immunoregulatory receptor G2A.
Science (New York, N.Y.).
2001 Jul; 293(5530):702-5. doi:
10.1126/science.1061781. [PMID: 11474113] - K Liliom, G Sun, M Bünemann, T Virág, N Nusser, D L Baker, D A Wang, M J Fabian, B Brandts, K Bender, A Eickel, K U Malik, D D Miller, D M Desiderio, G Tigyi, L Pott. Sphingosylphosphocholine is a naturally occurring lipid mediator in blood plasma: a possible role in regulating cardiac function via sphingolipid receptors.
The Biochemical journal.
2001 Apr; 355(Pt 1):189-97. doi:
10.1042/0264-6021:3550189. [PMID: 11256963] - K R Lynch, T L Macdonald. Structure activity relationships of lysophospholipid mediators.
Prostaglandins & other lipid mediators.
2001 Apr; 64(1-4):33-45. doi:
10.1016/s0090-6980(01)00106-x. [PMID: 11324706] - D Meyer zu Heringdorf, H Lass, I Kuchar, M Lipinski, R Alemany, U Rümenapp, K H Jakobs. Stimulation of intracellular sphingosine-1-phosphate production by G-protein-coupled sphingosine-1-phosphate receptors.
European journal of pharmacology.
2001 Mar; 414(2-3):145-54. doi:
10.1016/s0014-2999(01)00789-0. [PMID: 11239914] - J R Nofer, M Fobker, G Höbbel, R Voss, I Wolinska, M Tepel, W Zidek, R Junker, U Seedorf, A von Eckardstein, G Assmann, M Walter. Activation of phosphatidylinositol-specific phospholipase C by HDL-associated lysosphingolipid. Involvement in mitogenesis but not in cholesterol efflux.
Biochemistry.
2000 Dec; 39(49):15199-207. doi:
10.1021/bi001162a. [PMID: 11106499] - R Bittman, C A Verbicky. Methanolysis of sphingomyelin. Toward an epimerization-free methodology for the preparation of D-erythro-sphingosylphosphocholine.
Journal of lipid research.
2000 Dec; 41(12):2089-93. doi:
". [PMID: 11108743] - A Bischoff, P Czyborra, D Meyer Zu Heringdorf, K H Jakobs, M C Michel. Sphingosine-1-phosphate reduces rat renal and mesenteric blood flow in vivo in a pertussis toxin-sensitive manner.
British journal of pharmacology.
2000 Aug; 130(8):1878-83. doi:
10.1038/sj.bjp.0703516. [PMID: 10952678] - N Murata, K Sato, J Kon, H Tomura, F Okajima. Quantitative measurement of sphingosine 1-phosphate by radioreceptor-binding assay.
Analytical biochemistry.
2000 Jun; 282(1):115-20. doi:
10.1006/abio.2000.4580. [PMID: 10860507] - T Kanazawa, S Nakamura, M Momoi, T Yamaji, H Takematsu, H Yano, H Sabe, A Yamamoto, T Kawasaki, Y Kozutsumi. Inhibition of cytokinesis by a lipid metabolite, psychosine.
The Journal of cell biology.
2000 May; 149(4):943-50. doi:
10.1083/jcb.149.4.943. [PMID: 10811833] - Y Xu, K Zhu, G Hong, W Wu, L M Baudhuin, Y Xiao, D S Damron. Sphingosylphosphorylcholine is a ligand for ovarian cancer G-protein-coupled receptor 1.
Nature cell biology.
2000 May; 2(5):261-7. doi:
10.1038/35010529. [PMID: 10806476] - A Uehara, M Yasukochi, I Imanaga, J R Berlin. Effect of sphingosylphosphorylcholine on the single channel gating properties of the cardiac ryanodine receptor.
FEBS letters.
1999 Nov; 460(3):467-71. doi:
10.1016/s0014-5793(99)01385-x. [PMID: 10556518] - C Rodriguez-Lafrasse, M T Vanier. Sphingosylphosphorylcholine in Niemann-Pick disease brain: accumulation in type A but not in type B.
Neurochemical research.
1999 Feb; 24(2):199-205. doi:
10.1023/a:1022501702403. [PMID: 9972865] - P F Chen, T Y Chin, S H Chueh. Ca2+ signaling induced by sphingosylphosphorylcholine and sphingosine 1-phosphate via distinct mechanisms in rat glomerular mesangial cells.
Kidney international.
1998 Nov; 54(5):1470-83. doi:
10.1046/j.1523-1755.1998.00162.x. [PMID: 9844123] - D Meyer zu Heringdorf, N Niederdräing, E Neumann, R Fröde, H Lass, C J Van Koppen, K H Jakobs. Discrimination between plasma membrane and intracellular target sites of sphingosylphosphorylcholine.
European journal of pharmacology.
1998 Jul; 354(1):113-22. doi:
10.1016/s0014-2999(98)00436-1. [PMID: 9726638] - H M Himmel, D Meyer zu Heringdorf, B Windorfer, C J van Koppen, U Ravens, K H Jakobs. Guanine nucleotide-sensitive inhibition of L-type Ca2+ current by lysosphingolipids in RINm5F insulinoma cells.
Molecular pharmacology.
1998 May; 53(5):862-9. doi:
NULL. [PMID: 9584212] - A Berger, C M Cultaro, S Segal, S Spiegel. The potent lipid mitogen sphingosylphosphocholine activates the DNA binding activity of upstream stimulating factor (USF), a basic helix-loop-helix-zipper protein.
Biochimica et biophysica acta.
1998 Feb; 1390(2):225-36. doi:
10.1016/s0005-2760(97)00180-x. [PMID: 9507145] - N Sueyoshi, H Izu, M Ito. Preparation of a naturally occurring D-erythro-(2S, 3R)-sphingosylphosphocholine using Shewanella alga NS-589.
Journal of lipid research.
1997 Sep; 38(9):1923-7. doi:
. [PMID: 9323602] - T S Lai, A Bielawska, K A Peoples, Y A Hannun, C S Greenberg. Sphingosylphosphocholine reduces the calcium ion requirement for activating tissue transglutaminase.
The Journal of biological chemistry.
1997 Jun; 272(26):16295-300. doi:
10.1074/jbc.272.26.16295. [PMID: 9195933] - T Yamada, F Okajima, S Ohwada, Y Kondo. Growth inhibition of human pancreatic cancer cells by sphingosylphosphorylcholine and influence of culture conditions.
Cellular and molecular life sciences : CMLS.
1997 May; 53(5):435-41. doi:
10.1007/s000180050052. [PMID: 9176562] - M Bünemann, K Liliom, B K Brandts, L Pott, J L Tseng, D M Desiderio, G Sun, D Miller, G Tigyi. A novel membrane receptor with high affinity for lysosphingomyelin and sphingosine 1-phosphate in atrial myocytes.
The EMBO journal.
1996 Oct; 15(20):5527-34. doi:
10.1002/j.1460-2075.1996.tb00937.x. [PMID: 8896446] - S Furuya, S Kurono, Y Hirabayashi. Lysosphingomyelin-elicited Ca2+ mobilization from rat brain microsomes.
Journal of lipid mediators and cell signalling.
1996 Sep; 14(1-3):303-11. doi:
10.1016/0929-7855(96)00539-1. [PMID: 8906576] - Y Murata, J Ogata, Y Higaki, M Kawashima, Y Yada, K Higuchi, T Tsuchiya, S Kawainami, G Imokawa. Abnormal expression of sphingomyelin acylase in atopic dermatitis: an etiologic factor for ceramide deficiency?.
The Journal of investigative dermatology.
1996 Jun; 106(6):1242-9. doi:
10.1111/1523-1747.ep12348937. [PMID: 8752664] - T Seufferlein, E Rozengurt. Sphingosylphosphorylcholine rapidly induces tyrosine phosphorylation of p125FAK and paxillin, rearrangement of the actin cytoskeleton and focal contact assembly. Requirement of p21rho in the signaling pathway.
The Journal of biological chemistry.
1995 Oct; 270(41):24343-51. doi:
10.1074/jbc.270.41.24343. [PMID: 7592646] - S Spiegel, S Milstien. Sphingolipid metabolites: members of a new class of lipid second messengers.
The Journal of membrane biology.
1995 Aug; 146(3):225-37. doi:
10.1007/bf00233943. [PMID: 8568838]