Dihydroceramide (BioDeep_00000023381)

   

human metabolite Endogenous


代谢物信息卡片


N-[(2S,3R)-1,3-Dihydroxyoctadecan-2-yl]formamide

化学式: C19H39NO3 (329.29297840000004)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 0.16%

分子结构信息

SMILES: CCCCCCCCCCCCCCCC(C(CO)NC=O)O
InChI: InChI=1S/C19H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(23)18(16-21)20-17-22/h17-19,21,23H,2-16H2,1H3,(H,20,22)/t18-,19+/m0/s1

描述信息

Dihydroceramide is an intermediate in sphingolipid metabolism. Dihydroceramide is the third to last step in the synthesis of beta-D-Galactosyl-1,4-beta-D glucosylceramide and is converted from sphinganine via the enzyme acyl-CoA-dependent ceramide synthase (EC 2.3.1.24). It is then converted to N-acylsphingosine via the enzyme fatty acid desaturase (EC 1.14.-.-). [HMDB]
Dihydroceramide is an intermediate in sphingolipid metabolism. Dihydroceramide is the third to last step in the synthesis of beta-D-Galactosyl-1,4-beta-D glucosylceramide and is converted from sphinganine via the enzyme acyl-CoA-dependent ceramide synthase (EC 2.3.1.24). It is then converted to N-acylsphingosine via the enzyme fatty acid desaturase (EC 1.14.-.-).

同义名列表

4 个代谢物同义名

N-[(2S,3R)-1,3-Dihydroxyoctadecan-2-yl]formamide; N-(1,3-dihydroxyoctadecan-2-yl)formamide; N-Acylsphinganine; Dihydroceramide



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

36 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(10)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(22)

  • Sphingolipid Metabolism: Glucosylceramide (d18:1/18:0) + Water ⟶ Ceramide (d18:1/18:0) + D-Glucose
  • Gaucher Disease: Glucosylceramide (d18:1/18:0) + Water ⟶ Ceramide (d18:1/18:0) + D-Glucose
  • Globoid Cell Leukodystrophy: Glucosylceramide (d18:1/18:0) + Water ⟶ Ceramide (d18:1/18:0) + D-Glucose
  • Metachromatic Leukodystrophy (MLD): Glucosylceramide (d18:1/18:0) + Water ⟶ Ceramide (d18:1/18:0) + D-Glucose
  • Fabry Disease: Glucosylceramide (d18:1/18:0) + Water ⟶ Ceramide (d18:1/18:0) + D-Glucose
  • Krabbe Disease: Glucosylceramide (d18:1/18:0) + Water ⟶ Ceramide (d18:1/18:0) + D-Glucose
  • Sphingolipid Metabolism: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Gaucher Disease: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Globoid Cell Leukodystrophy: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Metachromatic Leukodystrophy (MLD): Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Fabry Disease: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Krabbe Disease: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Sphingolipid Metabolism: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Sphingolipid Metabolism: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Sphingolipid Metabolism: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Sphingolipid Metabolism: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Gaucher Disease: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Globoid Cell Leukodystrophy: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Metachromatic Leukodystrophy (MLD): Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Fabry Disease: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Krabbe Disease: Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate ⟶ 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
  • Sphingolipid Metabolism: L-Serine + Palmityl-CoA ⟶ 3-Dehydrosphinganine + Carbon dioxide

PharmGKB(0)

1 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

  • Michele Dei Cas, Linda Montavoci, Claudia Pasini, Anna Caretti, Sara Penati, Carla Martinelli, Umberto Gianelli, Sara Casati, Francesca Nardecchia, Annalaura Torella, Nicola Brunetti-Pierri, Marco Trinchera. Loss of function and reduced levels of sphingolipid desaturase DEGS1 variants are both relevant in disease mechanism. Journal of lipid research. 2024 03; 65(3):100517. doi: 10.1016/j.jlr.2024.100517. [PMID: 38342436]
  • M John Chapman, Alexina Orsoni, Natalie A Mellett, Anh Nguyen, Paul Robillard, Jonathan E Shaw, Philippe Giral, Patrice Thérond, Debi Swertfeger, W Sean Davidson, Peter J Meikle. Pitavastatin treatment remodels the HDL subclass lipidome and proteome in hypertriglyceridemia. Journal of lipid research. 2024 02; 65(2):100494. doi: 10.1016/j.jlr.2023.100494. [PMID: 38160756]
  • Patricia Mingo-Casas, Javier Sanchez-Céspedes, Ana-Belén Blázquez, Josefina Casas, María Balsera-Manzanero, Laura Herrero, Ana Vázquez, Jerónimo Pachón, Manuela Aguilar-Guisado, José Miguel Cisneros, Juan-Carlos Saiz, Miguel A Martín-Acebes. Lipid signatures of West Nile virus infection unveil alterations of sphingolipid metabolism providing novel biomarkers. Emerging microbes & infections. 2023 Dec; 12(2):2231556. doi: 10.1080/22221751.2023.2231556. [PMID: 37377355]
  • Brian A Kleiboeker, Cheryl Frankfater, Mary E Davey, Fong-Fu Hsu. Lipidomic analysis of Porphyromonas gingivalis reveals novel glycerol bisphosphoceramide, phosphatidyl-, and phosphoglycerol dipeptide lipid families. Journal of lipid research. 2023 12; 64(12):100470. doi: 10.1016/j.jlr.2023.100470. [PMID: 37924978]
  • Ran Song, Aaron Fond, Xiaohong Li, Miao Tang, Xiaoming Zhan, Ruth Gordillo, Eva Marie Y Moresco, Bruce Beutler, Emre E Turer. The dual lipid desaturase/hydroxylase DEGS2 controls phytoceramide levels necessary to counter intestinal inflammation. Disease models & mechanisms. 2023 Aug; ?(?):. doi: 10.1242/dmm.050043. [PMID: 37589563]
  • Cheryl F Frankfater, Mariana G Sartorio, Ezequiel Valguarnera, Mario F Feldman, Fong-Fu Hsu. Lipidome of the Bacteroides Genus Containing New Peptidolipid and Sphingolipid Families Revealed by Multiple-Stage Mass Spectrometry. Biochemistry. 2023 Mar; ?(?):. doi: 10.1021/acs.biochem.2c00664. [PMID: 36880942]
  • Saskia Wedel, Lisa Hahnefeld, Mohamad Wessam Alnouri, Stefan Offermanns, Felix Hausch, Gerd Geisslinger, Marco Sisignano. The FKBP51 Inhibitor SAFit2 Restores the Pain-Relieving C16 Dihydroceramide after Nerve Injury. International journal of molecular sciences. 2022 Nov; 23(22):. doi: 10.3390/ijms232214274. [PMID: 36430751]
  • Xuantong Zhou, Furong Huang, Gang Ma, Wenqing Wei, Nan Wu, Zhihua Liu. Dysregulated ceramides metabolism by fatty acid 2-hydroxylase exposes a metabolic vulnerability to target cancer metastasis. Signal transduction and targeted therapy. 2022 10; 7(1):370. doi: 10.1038/s41392-022-01199-1. [PMID: 36274060]
  • Lisa Peters, Wolfgang M Kuebler, Szandor Simmons. Sphingolipids in Atherosclerosis: Chimeras in Structure and Function. International journal of molecular sciences. 2022 Oct; 23(19):. doi: 10.3390/ijms231911948. [PMID: 36233252]
  • Simona Zarini, Joseph T Brozinick, Karin A Zemski Berry, Amanda Garfield, Leigh Perreault, Anna Kerege, Hai Hoang Bui, Phil Sanders, Parker Siddall, Ming Shang Kuo, Bryan C Bergman. Serum dihydroceramides correlate with insulin sensitivity in humans and decrease insulin sensitivity in vitro. Journal of lipid research. 2022 10; 63(10):100270. doi: 10.1016/j.jlr.2022.100270. [PMID: 36030929]
  • Mario Ruiz, Marcus Henricsson, Jan Borén, Marc Pilon. Palmitic acid causes increased dihydroceramide levels when desaturase expression is directly silenced or indirectly lowered by silencing AdipoR2. Lipids in health and disease. 2021 Nov; 20(1):173. doi: 10.1186/s12944-021-01600-y. [PMID: 34839823]
  • Alberto Canfrán-Duque, Óscar Pastor, David García-Seisdedos, Yessenia L Molina, Bohdan Babiy, Milagros Lerma, Carmen Sánchez-Castellano, Javier Martínez-Botas, Diego Gómez-Coronado, Miguel A Lasunción, Alfonso J Cruz-Jentoft, Rebeca Busto. The Antipsychotic Risperidone Alters Dihydroceramide and Ceramide Composition and Plasma Membrane Function in Leukocytes In Vitro and In Vivo. International journal of molecular sciences. 2021 Apr; 22(8):. doi: 10.3390/ijms22083919. [PMID: 33920193]
  • Fumika Mi-Ichi, Kazutaka Ikeda, Hiroshi Tsugawa, Sharmina Deloer, Hiroki Yoshida, Makoto Arita. Stage-Specific De Novo Synthesis of Very-Long-Chain Dihydroceramides Confers Dormancy to Entamoeba Parasites. mSphere. 2021 03; 6(2):. doi: 10.1128/msphere.00174-21. [PMID: 33731470]
  • Qianyang Huang, Shiying Hao, Xiaoming Yao, Jin You, Xiao Li, Donghai Lai, Chunle Han, James Schilling, Kuo Yuan Hwa, Sheeno Thyparambil, John Whitin, Harvey J Cohen, Henry Chubb, Scott R Ceresnak, Doff B McElhinney, Ronald J Wong, Gary M Shaw, David K Stevenson, Karl G Sylvester, Xuefeng B Ling. High-throughput quantitation of serological ceramides/dihydroceramides by LC/MS/MS: Pregnancy baseline biomarkers and potential metabolic messengers. Journal of pharmaceutical and biomedical analysis. 2021 Jan; 192(?):113639. doi: 10.1016/j.jpba.2020.113639. [PMID: 33017796]
  • Floriane Lachkar, Pascal Ferré, Fabienne Foufelle, Alexandra Papaioannou. Dihydroceramides: their emerging physiological roles and functions in cancer and metabolic diseases. American journal of physiology. Endocrinology and metabolism. 2021 01; 320(1):E122-E130. doi: 10.1152/ajpendo.00330.2020. [PMID: 33135459]
  • Aurélie Carlier, Franck Phan, Anaïs Szpigel, Eric Hajduch, Joe-Elie Salem, Jérémie Gautheron, Wilfried Le Goff, Maryse Guérin, Floriane Lachkar, Vlad Ratziu, Agnès Hartemann, Pascal Ferré, Fabienne Foufelle, Olivier Bourron. Dihydroceramides in Triglyceride-Enriched VLDL Are Associated with Nonalcoholic Fatty Liver Disease Severity in Type 2 Diabetes. Cell reports. Medicine. 2020 12; 1(9):100154. doi: 10.1016/j.xcrm.2020.100154. [PMID: 33377125]
  • Maria Apostolopoulou, Ruth Gordillo, Sofiya Gancheva, Klaus Strassburger, Christian Herder, Irene Esposito, Matthias Schlensak, Philipp E Scherer, Michael Roden. Role of ceramide-to-dihydroceramide ratios for insulin resistance and non-alcoholic fatty liver disease in humans. BMJ open diabetes research & care. 2020 11; 8(2):. doi: 10.1136/bmjdrc-2020-001860. [PMID: 33219119]
  • Mengzhen Sun, Qiya Wang, Maomao Zhang, Guohua Zhang, Tao Wu, Rui Liu, Wenjie Sui, Jiaojiao Zhang, Jinjin Yin, Min Zhang. Leuconostoc pseudomesenteroides improves microbiota dysbiosis and liver metabolism imbalance and ameliorates the correlation between dihydroceramide and strains of Firmicutes and Proteobacteria in high fat diet obese mice. Food & function. 2020 Aug; 11(8):6855-6865. doi: 10.1039/d0fo01009j. [PMID: 32666978]
  • F Fumeron, A Nicolas, J-P Bastard, S Fellahi, L Wigger, M Ibberson, C Cruciani-Guglielmacci, H Le Stunff, G Velho, C Magnan, M Marre, B Balkau, R Roussel. Dairy consumption is associated with lower plasma dihydroceramides in women from the D.E.S.I.R. cohort. Diabetes & metabolism. 2020 04; 46(2):144-149. doi: 10.1016/j.diabet.2019.06.002. [PMID: 31212089]
  • Katja Jakobi, Sandra Beyer, Alexander Koch, Dominique Thomas, Stephanie Schwalm, Stefan Zeuzem, Josef Pfeilschifter, Georgios Grammatikos. Sorafenib Treatment and Modulation of the Sphingolipid Pathway Affect Proliferation and Viability of Hepatocellular Carcinoma In Vitro. International journal of molecular sciences. 2020 Mar; 21(7):. doi: 10.3390/ijms21072409. [PMID: 32244391]
  • Fang-Fang Li, Ning Liu, Wei Liu, Mei Li, Fan Zhang, Zhen Dong, Jin-Lan Zhang, Hua Sun. Role of dihydroceramides in the progression of acute-on-chronic liver failure in rats. Chinese medical journal. 2020 Jan; 133(2):198-204. doi: 10.1097/cm9.0000000000000601. [PMID: 31880746]
  • Chiaki Yamada, Juliet Akkaoui, Anny Ho, Carolina Duarte, Richard Deth, Toshihisa Kawai, Frank Nichols, Madepalli K Lakshmana, Alexandru Movila. Potential Role of Phosphoglycerol Dihydroceramide Produced by Periodontal Pathogen Porphyromonas gingivalis in the Pathogenesis of Alzheimer's Disease. Frontiers in immunology. 2020; 11(?):591571. doi: 10.3389/fimmu.2020.591571. [PMID: 33329577]
  • Vadim Dolgin, Rachel Straussberg, Ruijuan Xu, Izolda Mileva, Yuval Yogev, Raed Khoury, Osnat Konen, Yael Barhum, Alex Zvulunov, Cungui Mao, Ohad S Birk. DEGS1 variant causes neurological disorder. European journal of human genetics : EJHG. 2019 11; 27(11):1668-1676. doi: 10.1038/s41431-019-0444-z. [PMID: 31186544]
  • A Galih Haribowo, J Thomas Hannich, Agnès H Michel, Márton Megyeri, Maya Schuldiner, Benoît Kornmann, Howard Riezman. Cytotoxicity of 1-deoxysphingolipid unraveled by genome-wide genetic screens and lipidomics in Saccharomyces cerevisiae. Molecular biology of the cell. 2019 10; 30(22):2814-2826. doi: 10.1091/mbc.e19-07-0364. [PMID: 31509475]
  • Emanuele La Corte, Michele Dei Cas, Alberto Raggi, Monica Patanè, Morgan Broggi, Silvia Schiavolin, Chiara Calatozzolo, Bianca Pollo, Carlotta Pipolo, Maria Grazia Bruzzone, Giuseppe Campisi, Rita Paroni, Riccardo Ghidoni, Paolo Ferroli. Long and Very-Long-Chain Ceramides Correlate with A More Aggressive Behavior in Skull Base Chordoma Patients. International journal of molecular sciences. 2019 Sep; 20(18):. doi: 10.3390/ijms20184480. [PMID: 31514293]
  • Nicholas B Blackburn, Laura F Michael, Peter J Meikle, Juan M Peralta, Marian Mosior, Scott McAhren, Hai H Bui, Melissa A Bellinger, Corey Giles, Satish Kumar, Ana C Leandro, Marcio Almeida, Jacquelyn M Weir, Michael C Mahaney, Thomas D Dyer, Laura Almasy, John L VandeBerg, Sarah Williams-Blangero, David C Glahn, Ravindranath Duggirala, Mark Kowala, John Blangero, Joanne E Curran. Rare DEGS1 variant significantly alters de novo ceramide synthesis pathway. Journal of lipid research. 2019 09; 60(9):1630-1639. doi: 10.1194/jlr.p094433. [PMID: 31227640]
  • Bhagirath Chaurasia, Trevor S Tippetts, Rafael Mayoral Monibas, Jinqi Liu, Ying Li, Liping Wang, Joseph L Wilkerson, C Rufus Sweeney, Renato Felipe Pereira, Doris Hissako Sumida, J Alan Maschek, James E Cox, Vincent Kaddai, Graeme Iain Lancaster, Monowarul Mobin Siddique, Annelise Poss, Mackenzie Pearson, Santhosh Satapati, Heather Zhou, David G McLaren, Stephen F Previs, Ying Chen, Ying Qian, Aleksandr Petrov, Margaret Wu, Xiaolan Shen, Jun Yao, Christian N Nunes, Andrew D Howard, Liangsu Wang, Mark D Erion, Jared Rutter, William L Holland, David E Kelley, Scott A Summers. Targeting a ceramide double bond improves insulin resistance and hepatic steatosis. Science (New York, N.Y.). 2019 07; 365(6451):386-392. doi: 10.1126/science.aav3722. [PMID: 31273070]
  • Nunya Chotiwan, Barbara G Andre, Irma Sanchez-Vargas, M Nurul Islam, Jeffrey M Grabowski, Amber Hopf-Jannasch, Erik Gough, Ernesto Nakayasu, Carol D Blair, John T Belisle, Catherine A Hill, Richard J Kuhn, Rushika Perera. Dynamic remodeling of lipids coincides with dengue virus replication in the midgut of Aedes aegypti mosquitoes. PLoS pathogens. 2018 02; 14(2):e1006853. doi: 10.1371/journal.ppat.1006853. [PMID: 29447265]
  • Andrej Kováčik, Petra Pullmannová, Jaroslav Maixner, Kateřina Vávrová. Effects of Ceramide and Dihydroceramide Stereochemistry at C-3 on the Phase Behavior and Permeability of Skin Lipid Membranes. Langmuir : the ACS journal of surfaces and colloids. 2018 01; 34(1):521-529. doi: 10.1021/acs.langmuir.7b03448. [PMID: 29228775]
  • Ah Young Lee, Jae Won Lee, Ji-Eun Kim, Hyuck Jun Mock, Sungjin Park, Sanghwa Kim, Seong-Ho Hong, Ji-Young Kim, Eun-Jung Park, Kyung-Sun Kang, Kwang Pyo Kim, Myung-Haing Cho. Dihydroceramide is a key metabolite that regulates autophagy and promotes fibrosis in hepatic steatosis model. Biochemical and biophysical research communications. 2017 12; 494(3-4):460-469. doi: 10.1016/j.bbrc.2017.10.110. [PMID: 29066349]
  • Valeria de Mello-Coelho, Roy G Cutler, Allyson Bunbury, Anita Tammara, Mark P Mattson, Dennis D Taub. Age-associated alterations in the levels of cytotoxic lipid molecular species and oxidative stress in the murine thymus are reduced by growth hormone treatment. Mechanisms of ageing and development. 2017 10; 167(?):46-55. doi: 10.1016/j.mad.2017.08.015. [PMID: 28865931]
  • Wei-Hung Jung, Chung-Chih Liu, Yu-Lian Yu, Yu-Chin Chang, Wen-Yu Lien, Hsi-Chun Chao, Shu-Yi Huang, Ching-Hua Kuo, Han-Chen Ho, Chih-Chiang Chan. Lipophagy prevents activity-dependent neurodegeneration due to dihydroceramide accumulation in vivo. EMBO reports. 2017 07; 18(7):1150-1165. doi: 10.15252/embr.201643480. [PMID: 28507162]
  • Nina Eikelis, Elisabeth A Lambert, Sarah Phillips, Carolina Ika Sari, Piyushkumar A Mundra, Jacquelyn M Weir, Kevin Huynh, Mariee T Grima, Nora E Straznicky, John B Dixon, Markus P Schlaich, Peter J Meikle, Gavin W Lambert. Muscle Sympathetic Nerve Activity Is Associated With Elements of the Plasma Lipidomic Profile in Young Asian Adults. The Journal of clinical endocrinology and metabolism. 2017 06; 102(6):2059-2068. doi: 10.1210/jc.2016-3738. [PMID: 28323975]
  • Hiroyuki Kanzaki, Alexandru Movila, Rayyan Kayal, Marcelo H Napimoga, Kenji Egashira, Floyd Dewhirst, Hajime Sasaki, Mohammed Howait, Ayman Al-Dharrab, Abdulghani Mira, Xiaozhe Han, Martin A Taubman, Frank C Nichols, Toshihisa Kawai. Phosphoglycerol dihydroceramide, a distinctive ceramide produced by Porphyromonas gingivalis, promotes RANKL-induced osteoclastogenesis by acting on non-muscle myosin II-A (Myh9), an osteoclast cell fusion regulatory factor. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2017 May; 1862(5):452-462. doi: 10.1016/j.bbalip.2017.01.008. [PMID: 28153611]
  • Leonore Wigger, Céline Cruciani-Guglielmacci, Anthony Nicolas, Jessica Denom, Neïké Fernandez, Frédéric Fumeron, Pedro Marques-Vidal, Alain Ktorza, Werner Kramer, Anke Schulte, Hervé Le Stunff, Robin Liechti, Ioannis Xenarios, Peter Vollenweider, Gérard Waeber, Ingo Uphues, Ronan Roussel, Christophe Magnan, Mark Ibberson, Bernard Thorens. Plasma Dihydroceramides Are Diabetes Susceptibility Biomarker Candidates in Mice and Humans. Cell reports. 2017 02; 18(9):2269-2279. doi: 10.1016/j.celrep.2017.02.019. [PMID: 28249170]
  • Simon Edvardson, Jae Kyo Yi, Chaim Jalas, Ruijuan Xu, Bryn D Webb, Justin Snider, Anastasia Fedick, Elisheva Kleinman, Nathan R Treff, Cungui Mao, Orly Elpeleg. Deficiency of the alkaline ceramidase ACER3 manifests in early childhood by progressive leukodystrophy. Journal of medical genetics. 2016 06; 53(6):389-96. doi: 10.1136/jmedgenet-2015-103457. [PMID: 26792856]
  • Heather Venant, Mehrdad Rahmaniyan, E Ellen Jones, Ping Lu, Michael B Lilly, Elizabeth Garrett-Mayer, Richard R Drake, Jacqueline M Kraveka, Charles D Smith, Christina Voelkel-Johnson. The Sphingosine Kinase 2 Inhibitor ABC294640 Reduces the Growth of Prostate Cancer Cells and Results in Accumulation of Dihydroceramides In Vitro and In Vivo. Molecular cancer therapeutics. 2015 Dec; 14(12):2744-52. doi: 10.1158/1535-7163.mct-15-0279. [PMID: 26494858]
  • Melissa E Hansen, Kurtis J Simmons, Trevor S Tippetts, Mikayla O Thatcher, Rex R Saito, Sheryl T Hubbard, Annie M Trumbull, Brian A Parker, Oliver J Taylor, Benjamin T Bikman. Lipopolysaccharide Disrupts Mitochondrial Physiology in Skeletal Muscle via Disparate Effects on Sphingolipid Metabolism. Shock (Augusta, Ga.). 2015 Dec; 44(6):585-92. doi: 10.1097/shk.0000000000000468. [PMID: 26529656]
  • Michelle M Mielke, Veera Venkata Ratnam Bandaru, Dingfen Han, Yang An, Susan M Resnick, Luigi Ferrucci, Norman J Haughey. Demographic and clinical variables affecting mid- to late-life trajectories of plasma ceramide and dihydroceramide species. Aging cell. 2015 Dec; 14(6):1014-23. doi: 10.1111/acel.12369. [PMID: 26193443]
  • B Lee Peterlin, Michelle M Mielke, Alex M Dickens, Subroto Chatterjee, Paul Dash, Guillermo Alexander, Rebeca V A Vieira, Veera Venkata Ratnam Bandaru, Joelle M Dorskind, Gretchen E Tietjen, Norman H Haughey. Interictal, circulating sphingolipids in women with episodic migraine: A case-control study. Neurology. 2015 Oct; 85(14):1214-23. doi: 10.1212/wnl.0000000000002004. [PMID: 26354990]
  • Jeremy T Warshauer, Ximena Lopez, Ruth Gordillo, Jessica Hicks, William L Holland, Estelle Anuwe, Martin B Blankfard, Philipp E Scherer, Ildiko Lingvay. Effect of pioglitazone on plasma ceramides in adults with metabolic syndrome. Diabetes/metabolism research and reviews. 2015 Oct; 31(7):734-44. doi: 10.1002/dmrr.2662. [PMID: 25959529]
  • Fernando D Testai, Hao-Liang Xu, John Kilkus, Vidyani Suryadevara, Irina Gorshkova, Evgeny Berdyshev, Dale A Pelligrino, Glyn Dawson. Changes in the metabolism of sphingolipids after subarachnoid hemorrhage. Journal of neuroscience research. 2015 May; 93(5):796-805. doi: 10.1002/jnr.23542. [PMID: 25597763]
  • Nuria Barbarroja, Sergio Rodriguez-Cuenca, Heli Nygren, Antonio Camargo, Ana Pirraco, Joana Relat, Irene Cuadrado, Vanessa Pellegrinelli, Gema Medina-Gomez, Chary Lopez-Pedrera, Francisco J Tinahones, J David Symons, Scott A Summers, Matej Oresic, Antonio Vidal-Puig. Increased dihydroceramide/ceramide ratio mediated by defective expression of degs1 impairs adipocyte differentiation and function. Diabetes. 2015 Apr; 64(4):1180-92. doi: 10.2337/db14-0359. [PMID: 25352638]
  • Christopher S Mirucki, Mehran Abedi, Jin Jiang, Qiang Zhu, Yu-Hsiung Wang, Kamran E Safavi, Robert B Clark, Frank C Nichols. Biologic activity of porphyromonas endodontalis complex lipids. Journal of endodontics. 2014 Sep; 40(9):1342-8. doi: 10.1016/j.joen.2014.02.017. [PMID: 25146013]
  • Georgios Grammatikos, Christiane Mühle, Nerea Ferreiros, Sirkka Schroeter, Dimitra Bogdanou, Stephanie Schwalm, Gudrun Hintereder, Johannes Kornhuber, Stefan Zeuzem, Christoph Sarrazin, Josef Pfeilschifter. Serum acid sphingomyelinase is upregulated in chronic hepatitis C infection and non alcoholic fatty liver disease. Biochimica et biophysica acta. 2014 Jul; 1841(7):1012-20. doi: 10.1016/j.bbalip.2014.04.007. [PMID: 24769340]
  • Barbora Skolová, Kateřina Jandovská, Petra Pullmannová, Ondřej Tesař, Jaroslav Roh, Alexandr Hrabálek, Kateřina Vávrová. The role of the trans double bond in skin barrier sphingolipids: permeability and infrared spectroscopic study of model ceramide and dihydroceramide membranes. Langmuir : the ACS journal of surfaces and colloids. 2014 May; 30(19):5527-35. doi: 10.1021/la500622f. [PMID: 24779554]
  • Manju Mamtani, Peter J Meikle, Hemant Kulkarni, Jacquelyn M Weir, Christopher K Barlow, Jeremy B Jowett, Claire Bellis, Thomas D Dyer, Laura Almasy, Michael C Mahaney, Ravindranath Duggirala, Anthony G Comuzzie, John Blangero, Joanne E Curran. Plasma dihydroceramide species associate with waist circumference in Mexican American families. Obesity (Silver Spring, Md.). 2014 Mar; 22(3):950-6. doi: 10.1002/oby.20598. [PMID: 23929697]
  • David J Montefusco, Lujia Chen, Nabil Matmati, Songjian Lu, Benjamin Newcomb, Gregory F Cooper, Yusuf A Hannun, Xinghua Lu. Distinct signaling roles of ceramide species in yeast revealed through systematic perturbation and systems biology analyses. Science signaling. 2013 Oct; 6(299):rs14. doi: 10.1126/scisignal.2004515. [PMID: 24170935]
  • Alejandro Garanto, Nawajes A Mandal, Meritxell Egido-Gabás, Gemma Marfany, Gemma Fabriàs, Robert E Anderson, Josefina Casas, Roser Gonzàlez-Duarte. Specific sphingolipid content decrease in Cerkl knockdown mouse retinas. Experimental eye research. 2013 May; 110(?):96-106. doi: 10.1016/j.exer.2013.03.003. [PMID: 23501591]
  • Alexandra Woodacre, Museer A Lone, Daniel Jablonowski, Roger Schneiter, Flaviano Giorgini, Raffael Schaffrath. A novel Sit4 phosphatase complex is involved in the response to ceramide stress in yeast. Oxidative medicine and cellular longevity. 2013; 2013(?):129645. doi: 10.1155/2013/129645. [PMID: 24082981]
  • Stefka D Spassieva, Mehrdad Rahmaniyan, Jacek Bielawski, Christopher J Clarke, Jacqueline M Kraveka, Lina M Obeid. Cell density-dependent reduction of dihydroceramide desaturase activity in neuroblastoma cells. Journal of lipid research. 2012 May; 53(5):918-928. doi: 10.1194/jlr.m019075. [PMID: 22377532]
  • Hai H Bui, Jennifer K Leohr, Ming-Shang Kuo. Analysis of sphingolipids in extracted human plasma using liquid chromatography electrospray ionization tandem mass spectrometry. Analytical biochemistry. 2012 Apr; 423(2):187-94. doi: 10.1016/j.ab.2012.01.027. [PMID: 22369892]
  • Aintzane Apraiz, Jolanta Idkowiak-Baldys, Naiara Nieto-Rementería, María Dolores Boyano, Yusuf A Hannun, Aintzane Asumendi. Dihydroceramide accumulation and reactive oxygen species are distinct and nonessential events in 4-HPR-mediated leukemia cell death. Biochemistry and cell biology = Biochimie et biologie cellulaire. 2012 Apr; 90(2):209-23. doi: 10.1139/o2012-001. [PMID: 22428532]
  • Frank C Nichols, Bekim Bajrami, Robert B Clark, William Housley, Xudong Yao. Free lipid A isolated from Porphyromonas gingivalis lipopolysaccharide is contaminated with phosphorylated dihydroceramide lipids: recovery in diseased dental samples. Infection and immunity. 2012 Feb; 80(2):860-74. doi: 10.1128/iai.06180-11. [PMID: 22144487]
  • Frank C Nichols, Xudong Yao, Bekim Bajrami, Julia Downes, Sydney M Finegold, Erica Knee, James J Gallagher, William J Housley, Robert B Clark. Phosphorylated dihydroceramides from common human bacteria are recovered in human tissues. PloS one. 2011 Feb; 6(2):e16771. doi: 10.1371/journal.pone.0016771. [PMID: 21347306]
  • Hiroyuki Fukami, Hideki Tachimoto, Mikiya Kishi, Takayuki Kaga, Hatsue Waki, Machiko Iwamoto, Yasukazu Tanaka. Preparation of (13)C-labeled ceramide by acetic acid bacteria and its incorporation in mice. Journal of lipid research. 2010 Nov; 51(11):3389-95. doi: 10.1194/jlr.d009191. [PMID: 20656918]
  • Yu-Hsiung Wang, Jin Jiang, Qiang Zhu, Amer Z AlAnezi, Robert B Clark, Xi Jiang, David W Rowe, Frank C Nichols. Porphyromonas gingivalis lipids inhibit osteoblastic differentiation and function. Infection and immunity. 2010 Sep; 78(9):3726-35. doi: 10.1128/iai.00225-10. [PMID: 20584977]
  • Jolanta Idkowiak-Baldys, Aintzane Apraiz, Li Li, Mehrdad Rahmaniyan, Christopher J Clarke, Jacqueline M Kraveka, Aintzane Asumendi, Yusuf A Hannun. Dihydroceramide desaturase activity is modulated by oxidative stress. The Biochemical journal. 2010 Mar; 427(2):265-74. doi: 10.1042/bj20091589. [PMID: 20105137]
  • Hyejung Park, Christopher A Haynes, Alison V Nairn, Michael Kulik, Stephen Dalton, Kelley Moremen, Alfred H Merrill. Transcript profiling and lipidomic analysis of ceramide subspecies in mouse embryonic stem cells and embryoid bodies. Journal of lipid research. 2010 Mar; 51(3):480-9. doi: 10.1194/jlr.m000984. [PMID: 19786568]
  • Youn-Sun Lee, Kyeong-Mi Choi, Mi-Hwa Choi, So-Young Ji, Jae-Myung Yoo, Yong-Moon Lee, Jin-Tae Hong, Yeo-Pyo Yun, Hwan-Soo Yoo. Simultaneous HPLC analysis of ceramide and dihydroceramide in human hairs. Archives of pharmacal research. 2009 Dec; 32(12):1795-801. doi: 10.1007/s12272-009-2219-5. [PMID: 20162410]
  • Antje Pohl, Iván López-Montero, Florent Rouvière, Fabrice Giusti, Philippe F Devaux. Rapid transmembrane diffusion of ceramide and dihydroceramide spin-labelled analogues in the liquid ordered phase. Molecular membrane biology. 2009 Apr; 26(3):194-204. doi: 10.1080/09687680902733815. [PMID: 19247845]
  • Christine Graf, Barbara Zemann, Philipp Rovina, Nicole Urtz, Andrea Schanzer, Roland Reuschel, Diana Mechtcheriakova, Matthias Müller, Evelin Fischer, Claudia Reichel, Susanna Huber, Janet Dawson, Josef G Meingassner, Andreas Billich, Satoru Niwa, Rudolf Badegruber, Paul P Van Veldhoven, Bernd Kinzel, Thomas Baumruker, Frédéric Bornancin. Neutropenia with impaired immune response to Streptococcus pneumoniae in ceramide kinase-deficient mice. Journal of immunology (Baltimore, Md. : 1950). 2008 Mar; 180(5):3457-66. doi: 10.4049/jimmunol.180.5.3457. [PMID: 18292572]
  • F C Nichols, K Rojanasomsith. Porphyromonas gingivalis lipids and diseased dental tissues. Oral microbiology and immunology. 2006 Apr; 21(2):84-92. doi: 10.1111/j.1399-302x.2006.00264.x. [PMID: 16476017]
  • F-Xabier Contreras, Gorka Basañez, Alicia Alonso, Andreas Herrmann, Félix M Goñi. Asymmetric addition of ceramides but not dihydroceramides promotes transbilayer (flip-flop) lipid motion in membranes. Biophysical journal. 2005 Jan; 88(1):348-59. doi: 10.1529/biophysj.104.050690. [PMID: 15465865]
  • Frank C Nichols, Birgit Riep, JiYoung Mun, Martha D Morton, Mike T Bojarski, Floyd E Dewhirst, Michael B Smith. Structures and biological activity of phosphorylated dihydroceramides of Porphyromonas gingivalis. Journal of lipid research. 2004 Dec; 45(12):2317-30. doi: 10.1194/jlr.m400278-jlr200. [PMID: 15466368]
  • Fumio Omae, Masao Miyazaki, Ayako Enomoto, Minoru Suzuki, Yusuke Suzuki, Akemi Suzuki. DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine. The Biochemical journal. 2004 May; 379(Pt 3):687-95. doi: 10.1042/bj20031425. [PMID: 14731113]
  • Christian Riebeling, Jeremy C Allegood, Elaine Wang, Alfred H Merrill, Anthony H Futerman. Two mammalian longevity assurance gene (LAG1) family members, trh1 and trh4, regulate dihydroceramide synthesis using different fatty acyl-CoA donors. The Journal of biological chemistry. 2003 Oct; 278(44):43452-9. doi: 10.1074/jbc.m307104200. [PMID: 12912983]
  • Mihaela Dragusin, Cristian Gurgui, Gunter Schwarzmann, Joerg Hoernschemeyer, Gerhild van Echten-Deckert. Metabolism of the unnatural anticancer lipid safingol, L-threo-dihydrosphingosine, in cultured cells. Journal of lipid research. 2003 Sep; 44(9):1772-9. doi: 10.1194/jlr.m300160-jlr200. [PMID: 12777464]
  • Arun Gidwani, H Alex Brown, David Holowka, Barbara Baird. Disruption of lipid order by short-chain ceramides correlates with inhibition of phospholipase D and downstream signaling by FcepsilonRI. Journal of cell science. 2003 Aug; 116(Pt 15):3177-87. doi: 10.1242/jcs.00621. [PMID: 12829737]
  • Evan L Riddle, Kristi S Rau, Matthew K Topham, Glen R Hanson, Annette E Fleckenstein. Ceramide-induced alterations in dopamine transporter function. European journal of pharmacology. 2003 Jan; 458(1-2):31-6. doi: 10.1016/s0014-2999(02)02727-9. [PMID: 12498904]
  • Benjamin J Pettus, Alicia Bielawska, Bart-Jan Kroesen, Peter D R Moeller, Zdzislaw M Szulc, Yusuf A Hannun, Mark Busman. Observation of different ceramide species from crude cellular extracts by normal-phase high-performance liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. Rapid communications in mass spectrometry : RCM. 2003; 17(11):1203-11. doi: 10.1002/rcm.1043. [PMID: 12772277]
  • Samer El Bawab, Julnar Usta, Patrick Roddy, Zdzislaw M Szulc, Alicja Bielawska, Yusuf A Hannun. Substrate specificity of rat brain ceramidase. Journal of lipid research. 2002 Jan; 43(1):141-8. doi: 10.1016/s0022-2275(20)30197-8. [PMID: 11792733]
  • T Kajimoto, S Ohmori, Y Shirai, N Sakai, N Saito. Subtype-specific translocation of the delta subtype of protein kinase C and its activation by tyrosine phosphorylation induced by ceramide in HeLa cells. Molecular and cellular biology. 2001 Mar; 21(5):1769-83. doi: 10.1128/mcb.21.5.1769-1783.2001. [PMID: 11238914]
  • P Navarro, A M Valverde, J L Rohn, M Benito, M Lorenzo. Akt mediates insulin rescue from apoptosis in brown adipocytes: effect of ceramide. Growth hormone & IGF research : official journal of the Growth Hormone Research Society and the International IGF Research Society. 2000 Oct; 10(5):256-66. doi: 10.1054/ghir.2000.0165. [PMID: 11042022]
  • R Charles, L Sandirasegarane, J Yun, N Bourbon, R Wilson, R P Rothstein, S W Levison, M Kester. Ceramide-coated balloon catheters limit neointimal hyperplasia after stretch injury in carotid arteries. Circulation research. 2000 Aug; 87(4):282-8. doi: 10.1161/01.res.87.4.282. [PMID: 10948061]
  • C G Freire-de-Lima, M P Nunes, S Corte-Real, M P Soares, J O Previato, L Mendonça-Previato, G A DosReis. Proapoptotic activity of a Trypanosoma cruzi ceramide-containing glycolipid turned on in host macrophages by IFN-gamma. Journal of immunology (Baltimore, Md. : 1950). 1998 Nov; 161(9):4909-16. doi: ". [PMID: 9794425]
  • M Yano, E Kishida, Y Muneyuki, Y Masuzawa. Quantitative analysis of ceramide molecular species by high performance liquid chromatography. Journal of lipid research. 1998 Oct; 39(10):2091-8. doi: 10.1016/s0022-2275(20)32508-6. [PMID: 9788256]
  • G van Echten-Deckert, A Klein, T Linke, T Heinemann, J Weisgerber, K Sandhoff. Turnover of endogenous ceramide in cultured normal and Farber fibroblasts. Journal of lipid research. 1997 Dec; 38(12):2569-79. doi: 10.1016/s0022-2275(20)30041-9. [PMID: 9458280]
  • G Lozanski, F Berthier, I Kushner. The sphingomyelin-ceramide pathway participates in cytokine regulation of C-reactive protein and serum amyloid A, but not alpha-fibrinogen. The Biochemical journal. 1997 Nov; 328 ( Pt 1)(?):271-5. doi: 10.1042/bj3280271. [PMID: 9359864]
  • . . . . doi: . [PMID: 37187315]
  • . . . . doi: . [PMID: 22200621]
  • . . . . doi: . [PMID: 20068046]