Cholesteryl glucoside (BioDeep_00000005333)

 

Secondary id: BioDeep_00000177448, BioDeep_00000636789

natural product


代谢物信息卡片


cholest-5-en-3beta-yl beta-D-glucopyranoside

化学式: C33H56O6 (548.4077)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 33.54%

分子结构信息

SMILES: C1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)CC2=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@@]([H])(CCCC(C)C)C)[C@@]4(C)CC[C@]3([H])[C@@]2(C)C1
InChI: InChI=1S/C33H56O6/c1-19(2)7-6-8-20(3)24-11-12-25-23-10-9-21-17-22(13-15-32(21,4)26(23)14-16-33(24,25)5)38-31-30(37)29(36)28(35)27(18-34)39-31/h9,19-20,22-31,34-37H,6-8,10-18H2,1-5H3/t20-,22+,23+,24-,25+,26+,27-,28-,29+,30-,31+,32+,33-/m1/s1

描述信息

同义名列表

11 个代谢物同义名

cholesteryl beta-D-glucoside; Cholesteryl glucoside; (3beta)-cholest-5-en-3-yl D-glucopyranoside; Cholest-5-en-3?-yl ?-D-glucopyranoside; cholesteryl-alpha-D-glucopyranside; Cholesteryl-alpha-D-glucoside; Cholesterol glucoside; ST 27:1;O;Hex; cholest-5-en-3beta-yl beta-D-glucopyranoside; Cholesteryl-beta-D-glucoside; SCHEMBL12928640



数据库引用编号

16 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)

11 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

  • Lih-Lih Ong, Hau-Ming Jan, Hong-Hanh Thi Le, Tsai-Chen Yang, Chou-Yu Kuo, Ai-Feng Feng, Kwok-Kong Tony Mong, Chun-Hung Lin. Membrane lipid remodeling eradicates Helicobacter pylori by manipulating the cholesteryl 6'-acylglucoside biosynthesis. Journal of biomedical science. 2024 Apr; 31(1):44. doi: 10.1186/s12929-024-01031-8. [PMID: 38685037]
  • Sasikala Muthusamy, Hau-Ming Jan, Ming-Yen Hsieh, Soumik Mondal, Wen-Chun Liu, Yi-An Ko, Wei-Yuan Yang, Kwok-Kong Tony Mong, Guang-Chao Chen, Chun-Hung Lin. Enhanced enzymatic production of cholesteryl 6'-acylglucoside impairs lysosomal degradation for the intracellular survival of Helicobacter pylori. Journal of biomedical science. 2021 Oct; 28(1):72. doi: 10.1186/s12929-021-00768-w. [PMID: 34706729]
  • Michio Shimamura. Structure, metabolism and biological functions of steryl glycosides in mammals. The Biochemical journal. 2020 11; 477(21):4243-4261. doi: 10.1042/bcj20200532. [PMID: 33186452]
  • Hau-Ming Jan, Yi-Chi Chen, Tsai-Chen Yang, Lih-Lih Ong, Chia-Chen Chang, Sasikala Muthusamy, Andualem Bahiru Abera, Ming-Shiang Wu, Jacquelyn Gervay-Hague, Kwok-Kong Tony Mong, Chun-Hung Lin. Cholesteryl α-D-glucoside 6-acyltransferase enhances the adhesion of Helicobacter pylori to gastric epithelium. Communications biology. 2020 03; 3(1):120. doi: 10.1038/s42003-020-0855-y. [PMID: 32170208]
  • Majjid A Qaria, Naveen Kumar, Arif Hussain, Shamsul Qumar, Sankara N Doddam, Ludovico P Sepe, Niyaz Ahmed. Roles of Cholesteryl-α-Glucoside Transferase and Cholesteryl Glucosides in Maintenance of Helicobacter pylori Morphology, Cell Wall Integrity, and Resistance to Antibiotics. mBio. 2018 11; 9(6):. doi: 10.1128/mbio.01523-18. [PMID: 30482827]
  • Shin-Yi Du, Hung-Jung Wang, Hsin-Hung Cheng, Sheng-De Chen, Lily Hui-Ching Wang, Wen-Ching Wang. Cholesterol glucosylation by Helicobacter pylori delays internalization and arrests phagosome maturation in macrophages. Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi. 2016 Oct; 49(5):636-645. doi: 10.1016/j.jmii.2014.05.011. [PMID: 25070282]
  • Michio Shimamura. Immunological functions of steryl glycosides. Archivum immunologiae et therapiae experimentalis. 2012 Oct; 60(5):351-9. doi: 10.1007/s00005-012-0190-1. [PMID: 22936327]
  • M Shimamura, H Hidaka. Therapeutic potential of cholesteryl O-acyl α-glucoside found in Helicobacter pylori. Current medicinal chemistry. 2012; 19(28):4869-74. doi: 10.2174/092986712803341502. [PMID: 22934809]
  • Hisako Akiyama, Narie Sasaki, Shuwa Hanazawa, Mari Gotoh, Susumu Kobayashi, Yoshio Hirabayashi, Kimiko Murakami-Murofushi. Novel sterol glucosyltransferase in the animal tissue and cultured cells: evidence that glucosylceramide as glucose donor. Biochimica et biophysica acta. 2011 May; 1811(5):314-22. doi: 10.1016/j.bbalip.2011.02.005. [PMID: 21397038]
  • Imre Gombos, Tim Crul, Stefano Piotto, Burcin Güngör, Zsolt Török, Gábor Balogh, Mária Péter, J Peter Slotte, Federica Campana, Ana-Maria Pilbat, Akos Hunya, Noémi Tóth, Zsuzsanna Literati-Nagy, László Vígh, Attila Glatz, Mario Brameshuber, Gerhard J Schütz, Andrea Hevener, Mark A Febbraio, Ibolya Horváth, László Vígh. Membrane-lipid therapy in operation: the HSP co-inducer BGP-15 activates stress signal transduction pathways by remodeling plasma membrane rafts. PloS one. 2011; 6(12):e28818. doi: 10.1371/journal.pone.0028818. [PMID: 22174906]
  • Mikhail A Maslov, Nina G Morozova, Evgeniya I Chizhik, Dmitriy A Rapoport, Elena I Ryabchikova, Marina A Zenkova, Galina A Serebrennikova. Synthesis and delivery activity of new cationic cholesteryl glucosides. Carbohydrate research. 2010 Nov; 345(17):2438-49. doi: 10.1016/j.carres.2010.09.012. [PMID: 20943217]
  • Yunbao Liu, Muraleedharan G Nair. An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. Journal of natural products. 2010 Jul; 73(7):1193-5. doi: 10.1021/np1000945. [PMID: 20565070]
  • Gunthard Stübs, Bernd Rupp, Ralf R Schumann, Nicolas W J Schröder, Jörg Rademann. Chemoenzymatic synthesis of a glycolipid library and elucidation of the antigenic epitope for construction of a vaccine against Lyme disease. Chemistry (Weinheim an der Bergstrasse, Germany). 2010 Mar; 16(11):3536-44. doi: 10.1002/chem.200902205. [PMID: 20143357]
  • Ellen Hildebrandt, David J McGee. Helicobacter pylori lipopolysaccharide modification, Lewis antigen expression, and gastric colonization are cholesterol-dependent. BMC microbiology. 2009 Dec; 9(?):258. doi: 10.1186/1471-2180-9-258. [PMID: 20003432]
  • Anna Potocka, Jan Zimowski. Metabolism of conjugated sterols in eggplant. Part 1. UDP-glucose : sterol glucosyltransferase. Acta biochimica Polonica. 2008; 55(1):127-34. doi: . [PMID: 18196184]
  • Anna Potocka, Jan Zimowski. Metabolism of conjugated sterols in eggplant. Part 2. Phospholipid : steryl glucoside acyltransferase. Acta biochimica Polonica. 2008; 55(1):135-40. doi: . [PMID: 18196183]
  • Anne-Helene Lebrun, Christian Wunder, Janosch Hildebrand, Yuri Churin, Ulrich Zähringer, Buko Lindner, Thomas F Meyer, Ernst Heinz, Dirk Warnecke. Cloning of a cholesterol-alpha-glucosyltransferase from Helicobacter pylori. The Journal of biological chemistry. 2006 Sep; 281(38):27765-72. doi: 10.1074/jbc.m603345200. [PMID: 16844692]
  • J D Schulz, E L Hawkes, C A Shaw. Cycad toxins, Helicobacter pylori and parkinsonism: cholesterol glucosides as the common denomenator. Medical hypotheses. 2006; 66(6):1222-6. doi: 10.1016/j.mehy.2004.12.033. [PMID: 16488551]
  • Hirofumi Shimomura, Shunji Hayashi, Kenji Yokota, Keiji Oguma, Yoshikazu Hirai. Alteration in the composition of cholesteryl glucosides and other lipids in Helicobacter pylori undergoing morphological change from spiral to coccoid form. FEMS microbiology letters. 2004 Aug; 237(2):407-13. doi: 10.1016/j.femsle.2004.07.004. [PMID: 15321690]
  • Shohko Kunimoto, Wataru Murofushi, Isao Yamatsu, Yukie Hasegawa, Narie Sasaki, Susumu Kobayashi, Tetsuyuki Kobayashi, Hiromu Murofushi, Kimiko Murakami-Murofushi. Cholesteryl glucoside-induced protection against gastric ulcer. Cell structure and function. 2003 Jun; 28(3):179-86. doi: 10.1247/csf.28.179. [PMID: 12951438]
  • Shohko Kunimoto, Wataru Murofushi, Hirofumi Kai, Yoko Ishida, Ayako Uchiyama, Tetsuyuki Kobayashi, Susumu Kobayashi, Hiromu Murofushi, Kimiko Murakami-Murofushi. Steryl glucoside is a lipid mediator in stress-responsive signal transduction. Cell structure and function. 2002 Jun; 27(3):157-62. doi: 10.1247/csf.27.157. [PMID: 12207046]
  • S Kunimoto, T Kobayashi, S Kobayashi, K Murakami-Murofushi. Expression of cholesteryl glucoside by heat shock in human fibroblasts. Cell stress & chaperones. 2000 Jan; 5(1):3-7. doi: . [PMID: 10701833]
  • M Haque, Y Hirai, K Yokota, N Mori, I Jahan, H Ito, H Hotta, I Yano, Y Kanemasa, K Oguma. Lipid profile of Helicobacter spp.: presence of cholesteryl glucoside as a characteristic feature. Journal of bacteriology. 1996 Apr; 178(7):2065-70. doi: 10.1128/jb.178.7.2065-2070.1996. [PMID: 8606185]
  • Y Hirai, M Haque, T Yoshida, K Yokota, T Yasuda, K Oguma. Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis. Journal of bacteriology. 1995 Sep; 177(18):5327-33. doi: 10.1128/jb.177.18.5327-5333.1995. [PMID: 7665522]
  • M Haque, Y Hirai, K Yokota, K Oguma. Steryl glycosides: a characteristic feature of the Helicobacter spp.?. Journal of bacteriology. 1995 Sep; 177(18):5334-7. doi: 10.1128/jb.177.18.5334-5337.1995. [PMID: 7665523]
  • W Abraham, P W Wertz, R R Burken, D T Downing. Glucosylsterol and acylglucosylsterol of snake epidermis: structure determination. Journal of lipid research. 1987 Apr; 28(4):446-9. doi: 10.1016/s0022-2275(20)38695-8. [PMID: 3585177]
  • G Deliconstantinos. Temperature effect of cholesterol association with synaptosomal plasma membranes of rabbit brain. The Biochemical journal. 1984 Sep; 222(3):825-8. doi: 10.1042/bj2220825. [PMID: 6487274]
  • S G Alivisatos, G Deliconstantinos, A Papaphilis, G P Theodosiadis. Cooperative nature of the binding of cholesterol on to synaptosomal plasma membranes of dog brain. Biochimica et biophysica acta. 1981 May; 643(3):642-9. doi: 10.1016/0005-2736(81)90360-6. [PMID: 7248291]