4-Hydroxysphinganine (BioDeep_00000002939)

 

Secondary id: BioDeep_00000405994

human metabolite Endogenous PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


[2S-(2R*,3R*,4S*)]-2-amino-1,3,4-octadecanetriol

化学式: C18H39NO3 (317.2929784)
中文名称: N-[12-[(7-硝基-2-1,3-苯并恶二唑-4-基)氨基]十二烷酰基]-植物鞘氨醇, 植物鞘氨醇, 糖脂, 4-羟基鞘氨醇
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.31%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

4-Hydroxysphinganine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/phytosphingosine (retrieved 2024-11-21) (BioDeep RN: BioDeep_00000002939). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCCCCCCCCCCC(C(C(CO)N)O)O
InChI: InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3

描述信息

Phytosphingosine is a phospholipid. Phospholipids are a class of lipids and a major component of all biological membranes; sphingolipid metabolites, such as sphingosine and ceramide, are highly bioactive compounds and are involved in diverse cell processes, including cell-cell interaction, cell proliferation, differentiation, and apoptosis. Phytosphingosine is also one of the most widely distributed natural sphingoid bases, which is abundant in fungi and plants, and also found in animals including humans. Phytosphingosine is structurally similar to sphingosine; phytosphingosine possesses a hydroxyl group at C-4 of the sphingoid long-chain base. The physiological roles of phytosphingosine are largely unknown. Phytosphingosine induces apoptosis in human T-cell lymphoma and non-small cell lung cancer cells, and induces caspase-independent cytochrome c release from mitochondria. In the presence of caspase inhibitors, phytosphingosine-induced apoptosis is almost completely suppressed, suggesting that phytosphingosine-induced apoptosis is largely dependent on caspase activities. (PMID: 12576463, 12531554, 8046331, 8048941,8706124) [HMDB]
Phytosphingosine is a phospholipid. Phospholipids are a class of lipids and a major component of all biological membranes; sphingolipid metabolites, such as sphingosine and ceramide, are highly bioactive compounds and are involved in diverse cell processes, including cell-cell interaction, cell proliferation, differentiation, and apoptosis. Phytosphingosine is also one of the most widely distributed natural sphingoid bases, which is abundant in fungi and plants, and also found in animals including humans. Phytosphingosine is structurally similar to sphingosine; phytosphingosine possesses a hydroxyl group at C-4 of the sphingoid long-chain base. The physiological roles of phytosphingosine are largely unknown. Phytosphingosine induces apoptosis in human T-cell lymphoma and non-small cell lung cancer cells, and induces caspase-independent cytochrome c release from mitochondria. In the presence of caspase inhibitors, phytosphingosine-induced apoptosis is almost completely suppressed, suggesting that phytosphingosine-induced apoptosis is largely dependent on caspase activities. (PMID: 12576463, 12531554, 8046331, 8048941,8706124).
Phytosphingosine is a?phospholipid and has anti-cancer activities. Phytosphingosine induces cell apoptosis via caspase 8 activation and Bax translocation in cancer cells[1].

同义名列表

23 个代谢物同义名

[2S-(2R*,3R*,4S*)]-2-amino-1,3,4-octadecanetriol; 4-hydroxysphinganine (SaccharoMyces Cerevisiae); (2S,3S,4R)-2-Amino-1,3,4-trihydroxyoctadecane; D-Ribo-1,3,4-trihydroxy-2-aminooctadecane; (2S,3S,4R)-2-Amino-1,3,4-octadecanetriol; (2S,3S,4R)-2-aminooctadecane-1,3,4-triol; D-Ribo-2-amino-1,3,4-octadecanetriol; 4-R-Hydroxyoctadecasphinganine; 2-Amino-1,3,4-octadecanetriol; 2-aminooctadecane-1,3,4-triol; 8-(Z-e)-C18-Phytosphingenine; (+)-D-Ribo-phytosphingosine; D-Ribo-phytosphingosine; 4-D-Hydroxy-sphinganine; 4-D-Hydroxysphinganine; 4R-hydroxysphinganine; 4D-Hydroxysphinganine; C18-Phytosphingosine; 4-Hydroxysphinganine; Phytosphingosine; SPB 18:0;O3; SP(t18:0); Phytosphingosine



数据库引用编号

24 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

21 个相关的代谢反应过程信息。

Reactome(12)

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(6)

PharmGKB(0)

8 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

  • Andreea Nădăban, Gerrit S Gooris, Charlotte M Beddoes, Robert M Dalgliesh, Marc Malfois, Bruno Demé, Joke A Bouwstra. The molecular arrangement of ceramides in the unit cell of the long periodicity phase of stratum corneum models shows a high adaptability to different ceramide head group structures. Biochimica et biophysica acta. Biomembranes. 2024 Jun; 1866(5):184324. doi: 10.1016/j.bbamem.2024.184324. [PMID: 38688405]
  • F J Bikker. [Phytosphingosine, a new ingredient for oral care products?]. Nederlands tijdschrift voor tandheelkunde. 2024 04; 131(4):163-166. doi: 10.5177/ntvt.2024.04.23102. [PMID: 38591120]
  • Andreea Nădăban, Jannik Rousel, Dounia El Yachioui, Gerrit S Gooris, Charlotte M Beddoes, Robert M Dalgliesh, Marc Malfois, Robert Rissmann, Joke A Bouwstra. Effect of sphingosine and phytosphingosine ceramide ratio on lipid arrangement and barrier function in skin lipid models. Journal of lipid research. 2023 Jun; ?(?):100400. doi: 10.1016/j.jlr.2023.100400. [PMID: 37301511]
  • Nina Hartrampf, Samuel M Leitao, Nils Winter, Henry Toombs-Ruane, James A Frank, Petra Schwille, Dirk Trauner, Henri G Franquelim. Structural Diversity of Photoswitchable Sphingolipids for Optodynamic Control of Lipid Microdomains. Biophysical journal. 2023 Mar; ?(?):. doi: 10.1016/j.bpj.2023.02.029. [PMID: 36869591]
  • Andreea Nădăban, Gerrit S Gooris, Charlotte M Beddoes, Robert M Dalgliesh, Joke A Bouwstra. Phytosphingosine ceramide mainly localizes in the central layer of the unique lamellar phase of skin lipid model systems. Journal of lipid research. 2022 09; 63(9):100258. doi: 10.1016/j.jlr.2022.100258. [PMID: 35931203]
  • Keiko Nakashima, Yukie Hirahara, Taro Koike, Susumu Tanaka, Keizo Gamo, Souichi Oe, Shinichi Hayashi, Ryohei Seki-Omura, Yousuke Nakano, Chisato Ohe, Takashi Yoshida, Yosky Kataoka, Masayuki Tsuda, Tatsuyuki Yamashita, Koichi Honke, Masaaki Kitada. Sulfatide with ceramide composed of phytosphingosine (t18:0) and 2-hydroxy FAs in renal intercalated cells. Journal of lipid research. 2022 06; 63(6):100210. doi: 10.1016/j.jlr.2022.100210. [PMID: 35439525]
  • Jieying Luo, Junaid Ahmed Shaikh, Lei Huang, Lei Zhang, Shahid Iqbal, Yu Wang, Bojiang Liu, Quan Zhou, Aisha Ajmal, Maryam Rizvi, Maryam Ajmal, Yingwu Liu. Human Plasma Metabolomics Identify 9-cis-retinoic Acid and Dehydrophytosphingosine Levels as Novel biomarkers for Early Ventricular Fibrillation after ST-elevated Myocardial Infarction. Bioengineered. 2022 02; 13(2):3334-3350. doi: 10.1080/21655979.2022.2027067. [PMID: 35094641]
  • René Glenz, Agnes Kaiping, Delia Göpfert, Hannah Weber, Benjamin Lambour, Marvin Sylvester, Christian Fröschel, Martin J Mueller, Mohamed Osman, Frank Waller. The major plant sphingolipid long chain base phytosphingosine inhibits growth of bacterial and fungal plant pathogens. Scientific reports. 2022 01; 12(1):1081. doi: 10.1038/s41598-022-05083-4. [PMID: 35058538]
  • Fabio Strati, Joana S L Oliveira, Lukas Opalka, Tetiana Mukhina, Bodo Dobner, Reinhard H H Neubert, Gerald Brezesinski. Two- and Three-Dimensional Physical-Chemical Characterization of CER[AP]: A Study of Stereochemistry and Chain Symmetry. The journal of physical chemistry. B. 2021 09; 125(35):9960-9969. doi: 10.1021/acs.jpcb.1c05572. [PMID: 34463098]
  • Andrej Kováčik, Petra Pullmannová, Lukáš Opálka, Michaela Šilarová, Jaroslav Maixner, Kateřina Vávrová. Effects of (R)- and (S)-α-Hydroxylation of Acyl Chains in Sphingosine, Dihydrosphingosine, and Phytosphingosine Ceramides on Phase Behavior and Permeability of Skin Lipid Models. International journal of molecular sciences. 2021 Jul; 22(14):. doi: 10.3390/ijms22147468. [PMID: 34299088]
  • Lucía Guevara, María Ángeles Domínguez-Anaya, Alba Ortigosa, Salvador González-Gordo, Caridad Díaz, Francisca Vicente, Francisco J Corpas, José Pérez Del Palacio, José M Palma. Identification of Compounds with Potential Therapeutic Uses from Sweet Pepper (Capsicum annuum L.) Fruits and Their Modulation by Nitric Oxide (NO). International journal of molecular sciences. 2021 Apr; 22(9):. doi: 10.3390/ijms22094476. [PMID: 33922964]
  • Li Wang, Xiaodong Suo, Yujie Liu, Chen Liu, Ming Luo. Sphingosine Promotes Embryo Biomass in Upland Cotton: A Biochemical and Transcriptomic Analysis. Biomolecules. 2021 04; 11(4):. doi: 10.3390/biom11040525. [PMID: 33915924]
  • Nathaniel L Hepowit, Jessica K A Macedo, Lyndsay E A Young, Ke Liu, Ramon C Sun, Jason A MacGurn, Robert C Dickson. Enhancing lifespan of budding yeast by pharmacological lowering of amino acid pools. Aging. 2021 03; 13(6):7846-7871. doi: 10.18632/aging.202849. [PMID: 33744865]
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  • Xiaolei Ma, Lulu Lu, Zheng Zhao, Mingru Cai, Na Gao, Gangwen Han. Lipidomics profiling of skin surface lipids in senile pruritus. Lipids in health and disease. 2020 Jul; 19(1):171. doi: 10.1186/s12944-020-01347-y. [PMID: 32677954]
  • Priya Gupta, Shweta Roy, Ashis Kumar Nandi. MEDEA-interacting protein LONG-CHAIN BASE KINASE 1 promotes pattern-triggered immunity in Arabidopsis thaliana. Plant molecular biology. 2020 May; 103(1-2):173-184. doi: 10.1007/s11103-020-00982-4. [PMID: 32100164]
  • Ning-Jing Liu, Tao Zhang, Zhao-Hui Liu, Xin Chen, Hui-Shan Guo, Bai-Hang Ju, Yuan-Yuan Zhang, Guo-Zhu Li, Qiang-Hui Zhou, Yong-Mei Qin, Yu-Xian Zhu. Phytosphinganine Affects Plasmodesmata Permeability via Facilitating PDLP5-Stimulated Callose Accumulation in Arabidopsis. Molecular plant. 2020 01; 13(1):128-143. doi: 10.1016/j.molp.2019.10.013. [PMID: 31698047]
  • L E Uche, G S Gooris, C M Beddoes, J A Bouwstra. New insight into phase behavior and permeability of skin lipid models based on sphingosine and phytosphingosine ceramides. Biochimica et biophysica acta. Biomembranes. 2019 07; 1861(7):1317-1328. doi: 10.1016/j.bbamem.2019.04.005. [PMID: 30991016]
  • Shruthi Satish, Cristina Jiménez-Ortigosa, Yanan Zhao, Min Hee Lee, Enriko Dolgov, Thomas Krüger, Steven Park, David W Denning, Olaf Kniemeyer, Axel A Brakhage, David S Perlin. Stress-Induced Changes in the Lipid Microenvironment of β-(1,3)-d-Glucan Synthase Cause Clinically Important Echinocandin Resistance in Aspergillus fumigatus. mBio. 2019 06; 10(3):. doi: 10.1128/mbio.00779-19. [PMID: 31164462]
  • Barbora Amélie Čuříková-Kindlová, Olivier Diat, František Štěpánek, Kateřina Vávrová, Jarmila Zbytovská. Probing the interactions among sphingosine and phytosphingosine ceramides with non- and alpha-hydroxylated acyl chains in skin lipid model membranes. International journal of pharmaceutics. 2019 May; 563(?):384-394. doi: 10.1016/j.ijpharm.2019.04.010. [PMID: 30959237]
  • Renï Glenz, Dorette Schmalhaus, Markus Krischke, Martin J Mueller, Frank Waller. Elevated Levels of Phosphorylated Sphingobases Do Not Antagonize Sphingobase- or Fumonisin B1-Induced Plant Cell Death. Plant & cell physiology. 2019 May; 60(5):1109-1119. doi: 10.1093/pcp/pcz033. [PMID: 30796453]
  • Mariko Takahashi, Kumi Izawa, Makoto Urai, Yoshinori Yamanishi, Akie Maehara, Masamichi Isobe, Toshihiro Matsukawa, Ayako Kaitani, Ayako Takamori, Shino Uchida, Hiromichi Yamada, Masakazu Nagamine, Tomoaki Ando, Toshiaki Shimizu, Hideoki Ogawa, Ko Okumura, Yuki Kinjo, Toshio Kitamura, Jiro Kitaura. The phytosphingosine-CD300b interaction promotes zymosan-induced, nitric oxide-dependent neutrophil recruitment. Science signaling. 2019 01; 12(564):. doi: 10.1126/scisignal.aar5514. [PMID: 30647146]
  • Lili Sun, Hongmei Jia, Liyan Ma, Meng Yu, Yong Yang, Yang Liu, Hongwu Zhang, Zhongmei Zou. Metabolic profiling of hypoxia/reoxygenation injury in H9c2 cells reveals the accumulation of phytosphingosine and the vital role of Dan-Shen in Xin-Ke-Shu. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Oct; 49(?):83-94. doi: 10.1016/j.phymed.2018.06.026. [PMID: 30217265]
  • Tomotaka Nagasawa, Hikaru Nakamichi, Yoichiro Hama, Shigeki Higashiyama, Yasuyuki Igarashi, Susumu Mitsutake. Phytosphingosine is a novel activator of GPR120. Journal of biochemistry. 2018 Jul; 164(1):27-32. doi: 10.1093/jb/mvy017. [PMID: 29373685]
  • Daiki Yanagawa, Toshiki Ishikawa, Hiroyuki Imai. Synthesis and degradation of long-chain base phosphates affect fumonisin B1-induced cell death in Arabidopsis thaliana. Journal of plant research. 2017 May; 130(3):571-585. doi: 10.1007/s10265-017-0923-7. [PMID: 28303405]
  • Barbora Školová, Andrej Kováčik, Ondřej Tesař, Lukáš Opálka, Kateřina Vávrová. Phytosphingosine, sphingosine and dihydrosphingosine ceramides in model skin lipid membranes: permeability and biophysics. Biochimica et biophysica acta. Biomembranes. 2017 May; 1859(5):824-834. doi: 10.1016/j.bbamem.2017.01.019. [PMID: 28109750]
  • Nuria Cubells-Baeza, Cristina Gómez-Casado, Leticia Tordesillas, Carmen Ramírez-Castillejo, María Garrido-Arandia, Pablo González-Melendi, María Herrero, Luis F Pacios, Araceli Díaz-Perales. Identification of the ligand of Pru p 3, a peach LTP. Plant molecular biology. 2017 May; 94(1-2):33-44. doi: 10.1007/s11103-017-0590-z. [PMID: 28299506]
  • Guangguo Tan, Haibo Wang, Jianlin Yuan, Weijun Qin, Xin Dong, Hong Wu, Ping Meng. Three serum metabolite signatures for diagnosing low-grade and high-grade bladder cancer. Scientific reports. 2017 04; 7(?):46176. doi: 10.1038/srep46176. [PMID: 28382976]
  • Christin Fischer, Sven Klockmann, Hauke Wessels, Tim Hünniger, Jil Schrader, Angelika Paschke-Kratzin, Markus Fischer. Aptamer-based trapping of phytosphingosine in urine samples. Journal of biotechnology. 2016 Nov; 238(?):30-34. doi: 10.1016/j.jbiotec.2016.09.005. [PMID: 27637314]
  • Fernando Martínez-Montañés, Museer A Lone, Fong-Fu Hsu, Roger Schneiter. Accumulation of long-chain bases in yeast promotes their conversion to a long-chain base vinyl ether. Journal of lipid research. 2016 11; 57(11):2040-2050. doi: 10.1194/jlr.m070748. [PMID: 27561298]
  • Fong-Fu Hsu. Complete structural characterization of ceramides as [M-H]- ions by multiple-stage linear ion trap mass spectrometry. Biochimie. 2016 Nov; 130(?):63-75. doi: 10.1016/j.biochi.2016.07.012. [PMID: 27523779]
  • Huijuan Gao, Gaofu Qi, Rong Yin, Hongchun Zhang, Chenggang Li, Xiuyun Zhao. Bacillus cereus strain S2 shows high nematicidal activity against Meloidogyne incognita by producing sphingosine. Scientific reports. 2016 06; 6(?):28756. doi: 10.1038/srep28756. [PMID: 27338781]
  • Kyle D Luttgeharm, Edgar B Cahoon, Jonathan E Markham. Substrate specificity, kinetic properties and inhibition by fumonisin B1 of ceramide synthase isoforms from Arabidopsis. The Biochemical journal. 2016 Mar; 473(5):593-603. doi: 10.1042/bj20150824. [PMID: 26635357]
  • Sören Stahlberg, Stefan Lange, Bodo Dobner, Daniel Huster. Probing the Role of Ceramide Headgroup Polarity in Short-Chain Model Skin Barrier Lipid Mixtures by ²H Solid-State NMR Spectroscopy. Langmuir : the ACS journal of surfaces and colloids. 2016 Mar; 32(8):2023-31. doi: 10.1021/acs.langmuir.5b04173. [PMID: 26828109]
  • María José Gómez-Torres, Eva María García, Jaime Guerrero, Sonia Medina, María José Izquierdo-Rico, Ángel Gil-Izquierdo, Jesús Orduna, María Savirón, Leopoldo González-Brusi, Jorge Ten, Rafael Bernabeu, Manuel Avilés. Metabolites involved in cellular communication among human cumulus-oocyte-complex and sperm during in vitro fertilization. Reproductive biology and endocrinology : RB&E. 2015 Nov; 13(?):123. doi: 10.1186/s12958-015-0118-9. [PMID: 26553294]
  • Joaquim T Marquês, André M Cordeiro, Ana S Viana, Andreas Herrmann, H Susana Marinho, Rodrigo F M de Almeida. Formation and Properties of Membrane-Ordered Domains by Phytoceramide: Role of Sphingoid Base Hydroxylation. Langmuir : the ACS journal of surfaces and colloids. 2015 Sep; 31(34):9410-21. doi: 10.1021/acs.langmuir.5b02550. [PMID: 26262576]
  • Susanne Grether-Beck, Ingo Felsner, Tim Koehler, Mike Farwick, Peter Lersch, Anthony V Rawlings, Jean Krutmann. Topical ceramides neither enhance UVB-induced apoptosis in normal human keratinocytes nor affect viability in UVB-irradiated reconstructed human epidermis. Experimental dermatology. 2014 Nov; 23(11):853-5. doi: 10.1111/exd.12526. [PMID: 25078364]
  • D Pin, M Bekrich, O Fantini, G Noel, E Vidémont. An emulsion restores the skin barrier by decreasing the skin pH and inflammation in a canine experimental model. Journal of comparative pathology. 2014 Aug; 151(2-3):244-54. doi: 10.1016/j.jcpa.2014.04.009. [PMID: 24975893]
  • Erwin Swinnen, Tobias Wilms, Jolanta Idkowiak-Baldys, Bart Smets, Pepijn De Snijder, Sabina Accardo, Ruben Ghillebert, Karin Thevissen, Bruno Cammue, Dirk De Vos, Jacek Bielawski, Yusuf A Hannun, Joris Winderickx. The protein kinase Sch9 is a key regulator of sphingolipid metabolism in Saccharomyces cerevisiae. Molecular biology of the cell. 2014 Jan; 25(1):196-211. doi: 10.1091/mbc.e13-06-0340. [PMID: 24196832]
  • Alexander Sigruener, Victoria Tarabin, György Paragh, Gerhard Liebisch, Tim Koehler, Mike Farwick, Gerd Schmitz. Effects of sphingoid bases on the sphingolipidome in early keratinocyte differentiation. Experimental dermatology. 2013 Oct; 22(10):677-9. doi: 10.1111/exd.12231. [PMID: 24079743]
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