Digitonin (BioDeep_00000230831)
Secondary id: BioDeep_00000003838, BioDeep_00000171735
natural product PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C56H92O29 (1228.5724)
中文名称: 毛地黃皂苷, 毛地黄皂苷, 洋地黄皂苷
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1[C@@]2([H])[C@@](C)([C@@]3([H])CC[C@]4(C)[C@H]5[C@@H]([C@]6(OC[C@@H](CC6)C)O[C@H]5[C@@H](O)[C@@]4([H])[C@]3([H])CC2)C)C[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@H]2[C@H](O[C@H]3[C@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)[C@@H](O)[C@@H](CO)O3)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)CO3)[C@H](O)[C@@H](CO)O2)[C@@H](CO)O1
InChI: InChI=1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36-,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1
描述信息
A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D004071 - Digitalis Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents
Annotation level-1
Crystals or white powder. (NTP, 1992)
Digitin is a natural product found in Digitalis ciliata, Digitalis ferruginea, and other organisms with data available.
A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.
Digitonin, a glycoside obtained from Digitalis purpurea, could increase cell permeability by binding to cholesterol molecules and reduce tumor growth[1]. Digitonin is an natural detergent[2].
Digitonin, a glycoside obtained from Digitalis purpurea, could increase cell permeability by binding to cholesterol molecules and reduce tumor growth[1]. Digitonin is an natural detergent[2].
同义名列表
22 个代谢物同义名
Digitonin; (25R)-2alpha,15beta-dihydroxy-5alpha-spirostan-3beta-yl beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside; beta-D-Galactopyranoside, (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl O-beta-D-glucopyranosyl-(1.fwdarw.3)-O-beta-D-galactopyranosyl-(1.fwdarw.2)-O-(beta-D-xylopyranosyl-(1.fwdarw.3))-O-beta-D-glucopyranosyl-(1.fwdarw.4)-; (2.Alpha.,3.beta.,5.alpha.,15.beta.,16.beta.,25R)-2,15-Dihydroxyspirostan-3-yl .beta.-D-glucopyranosyl-(1->3)-.beta.-D-galactopyranosyl-(1->2)-[.beta.-D-xylopyranosyl-(1->3)]-.beta.-D-glucopyranosyl-(1->4)-.beta.-D-galactopyranoside; (25R)-2beta,15alpha-dihydroxy-5beta,8alpha,10alpha,14beta,17beta-spirostan-3alpha-yl beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside; beta-D-Galactopyranoside, (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl O-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->2)-O-(beta-D-xylopyranosyl-(1->3))-O-beta-D-glucopyranosyl-(1->4)-; beta-D-Galactopyranoside, (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl O-beta-D-glucopyranosyl-(1-3)-O-beta-D-galactopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-; 3-O-(Glcb1-3Galb1-2-(Xylb1-3)-Glcb1-4Galb)-(25R)-5alpha-spirostan-2alpha,3beta,15beta-triol; 5-19-03-00603 (Beilstein Handbook Reference); Digitonin - stable clear, water-soluble; Digitonin, Used as non-ionic detergent; Digitonin - water-insoluble; Digitonin - water-soluble; Digitonin, ~50\\% (TLC); Digitogenin, glycoside; UNII-KOO5CM684H; DIGITONIN [MI]; KOO5CM684H; Digitonine; AI3-44893; Digitin; Digitonin
数据库引用编号
67 个数据库交叉引用编号
- ChEBI: CHEBI:27729
- PubChem: 6537502
- PubChem: 6474107
- PubChem: 13124865
- ChEMBL: CHEMBL509531
- Wikipedia: Digitonin
- LipidMAPS: LMST01080003
- MeSH: Digitonin
- ChemIDplus: 0011024241
- chemspider: 4976216
- CAS: 11024-24-1
- MoNA: PR310422
- MoNA: PR308723
- MoNA: PR308722
- MoNA: RIKENPlaSMA008600
- MoNA: RIKENPlaSMA008599
- MoNA: RIKENPlaSMA008594
- MoNA: RIKENPlaSMA008593
- MoNA: RIKENPlaSMA008587
- MoNA: RIKENPlaSMA008586
- MoNA: RIKENPlaSMA008581
- MoNA: RIKENPlaSMA008580
- MoNA: RIKENPlaSMA008574
- MoNA: RIKENPlaSMA008568
- MoNA: RIKENPlaSMA008567
- MoNA: RIKENPlaSMA008562
- MoNA: RIKENPlaSMA008561
- MoNA: RIKENPlaSMA008555
- MoNA: RIKENPlaSMA008554
- MoNA: RIKENPlaSMA008548
- MoNA: RIKENPlaSMA008547
- MoNA: RIKENPlaSMA008543
- MoNA: RIKENPlaSMA008542
- MoNA: RIKENPlaSMA008538
- MoNA: RIKENPlaSMA008537
- MoNA: RIKENPlaSMA008531
- MoNA: RIKENPlaSMA008530
- MoNA: RIKENPlaSMA004416
- MoNA: RIKENPlaSMA004415
- MoNA: RIKENPlaSMA004414
- MoNA: RIKENPlaSMA004413
- MoNA: RIKENPlaSMA004412
- MoNA: RIKENPlaSMA004411
- MoNA: RIKENPlaSMA004410
- MoNA: RIKENPlaSMA004409
- MoNA: RIKENPlaSMA004408
- MoNA: RIKENPlaSMA004407
- MoNA: RIKENPlaSMA004406
- MoNA: VF-NPL-LTQ007338
- MoNA: VF-NPL-LTQ007337
- MoNA: VF-NPL-QEHF014973
- MoNA: VF-NPL-QEHF014972
- MoNA: VF-NPL-QEHF014971
- MoNA: VF-NPL-QEHF014970
- MoNA: VF-NPL-QEHF014969
- MoNA: VF-NPL-QEHF014968
- MoNA: VF-NPL-QEHF014967
- MoNA: VF-NPL-QEHF014966
- MoNA: VF-NPL-QEHF014965
- medchemexpress: HY-N4000
- PMhub: MS000172568
- MetaboLights: MTBLC27729
- KEGG: C00765
- PubChem: 4027
- KNApSAcK: 27729
- LOTUS: LTS0080570
- LOTUS: LTS0165386
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)
38 个相关的物种来源信息
- 6656 - Arthropoda: LTS0080570
- 6656 - Arthropoda: LTS0165386
- 30102 - Cicadellidae: LTS0080570
- 30102 - Cicadellidae: LTS0165386
- 4163 - Digitalis: LTS0080570
- 4163 - Digitalis: LTS0165386
- 285815 - Digitalis ciliata: 10.1007/BF00630673
- 285815 - Digitalis ciliata: LTS0080570
- 285817 - Digitalis ferruginea: 10.1007/BF00630673
- 285817 - Digitalis ferruginea: LTS0080570
- 49450 - Digitalis lanata: 10.1002/ARDP.19362740710
- 49450 - Digitalis lanata: 10.1055/S-0028-1097375
- 49450 - Digitalis lanata: LTS0080570
- 49450 - Digitalis lanata: LTS0165386
- 4164 - Digitalis purpurea: 10.1002/ANGE.19630751458
- 4164 - Digitalis purpurea: 10.1007/BF00630673
- 4164 - Digitalis purpurea: 10.1248/CPB.12.1250
- 4164 - Digitalis purpurea: 10.1248/YAKUSHI1947.75.1_25
- 4164 - Digitalis purpurea: LTS0080570
- 4164 - Digitalis purpurea: LTS0165386
- 2759 - Eukaryota: LTS0080570
- 2759 - Eukaryota: LTS0165386
- 50557 - Insecta: LTS0080570
- 50557 - Insecta: LTS0165386
- 3398 - Magnoliopsida: LTS0080570
- 3398 - Magnoliopsida: LTS0165386
- 33208 - Metazoa: LTS0080570
- 33208 - Metazoa: LTS0165386
- 156152 - Plantaginaceae: LTS0080570
- 156152 - Plantaginaceae: LTS0165386
- 33090 - Plants: -
- 35493 - Streptophyta: LTS0080570
- 35493 - Streptophyta: LTS0165386
- 58023 - Tracheophyta: LTS0080570
- 58023 - Tracheophyta: LTS0165386
- 33090 - Viridiplantae: LTS0080570
- 33090 - Viridiplantae: LTS0165386
- 33090 - 毛地黄: -
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。
亚细胞结构定位 | 关联基因列表 |
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文献列表
- Daria V Grigorieva, Irina V Gorudko, Natalia A Grudinina, Oleg M Panasenko, Igor V Semak, Alexey V Sokolov, Alexander V Timoshenko. Lactoferrin modified by hypohalous acids: Partial loss in activation of human neutrophils.
International journal of biological macromolecules.
2022 Jan; 195(?):30-40. doi:
10.1016/j.ijbiomac.2021.11.165
. [PMID: 34863835] - André T Graça, Michael Hall, Karina Persson, Wolfgang P Schröder. High-resolution model of Arabidopsis Photosystem II reveals the structural consequences of digitonin-extraction.
Scientific reports.
2021 07; 11(1):15534. doi:
10.1038/s41598-021-94914-x
. [PMID: 34330992] - Lindsey R Hayes, Lauren Duan, Svetlana Vidensky, Petr Kalab. Nuclear Transport Assays in Permeabilized Mouse Cortical Neurons.
Journal of visualized experiments : JoVE.
2021 07; ?(173):. doi:
10.3791/62710
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Journal of immunological methods.
2021 02; 489(?):112943. doi:
10.1016/j.jim.2020.112943
. [PMID: 33333059] - Raymond Malabed, Shinya Hanashima, Michio Murata, Kaori Sakurai. Interactions of OSW-1 with Lipid Bilayers in Comparison with Digitonin and Soyasaponin.
Langmuir : the ACS journal of surfaces and colloids.
2020 04; 36(13):3600-3610. doi:
10.1021/acs.langmuir.9b03957
. [PMID: 32160747] - Stine Lauritzen Sønder, Theresa Louise Boye, Regine Tölle, Jörn Dengjel, Kenji Maeda, Marja Jäättelä, Adam Cohen Simonsen, Jyoti K Jaiswal, Jesper Nylandsted. Annexin A7 is required for ESCRT III-mediated plasma membrane repair.
Scientific reports.
2019 04; 9(1):6726. doi:
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. [PMID: 31040365] - Acidália Carine Vieira Santos, Francianne Oliveira Santos, Hélimar Gonçalves Lima, Gisele Dias Da Silva, Rosangela Soares Uzêda, Êuder Reis Dias, Alexsandro Branco, Klauber Viana Cardoso, Jorge Mauricio David, Mariana Borges Botura, Silvia Lima Costa, Maria José Moreira Batatinha. In vitro ovicidal and larvicidal activities of some saponins and flavonoids against parasitic nematodes of goats.
Parasitology.
2018 12; 145(14):1884-1889. doi:
10.1017/s0031182018000689
. [PMID: 29781423] - Jonas M la Cour, Pernille Winding Gojkovic, Sophie E B Ambjørner, Jonas Bagge, Simone M Jensen, Svetlana Panina, Martin W Berchtold. ALG-2 participates in recovery of cells after plasma membrane damage by electroporation and digitonin treatment.
PloS one.
2018; 13(9):e0204520. doi:
10.1371/journal.pone.0204520
. [PMID: 30240438] - Raymond Malabed, Shinya Hanashima, Michio Murata, Kaori Sakurai. Sterol-recognition ability and membrane-disrupting activity of Ornithogalum saponin OSW-1 and usual 3-O-glycosyl saponins.
Biochimica et biophysica acta. Biomembranes.
2017 Dec; 1859(12):2516-2525. doi:
10.1016/j.bbamem.2017.09.019
. [PMID: 28947142] - Helen Y Fan, Heiko Heerklotz. Digitonin does not flip across cholesterol-poor membranes.
Journal of colloid and interface science.
2017 Oct; 504(?):283-293. doi:
10.1016/j.jcis.2017.05.034
. [PMID: 28551523] - M Orczyk, K Wojciechowski, G Brezesinski. Disordering Effects of Digitonin on Phospholipid Monolayers.
Langmuir : the ACS journal of surfaces and colloids.
2017 04; 33(15):3871-3881. doi:
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PloS one.
2017; 12(10):e0185691. doi:
10.1371/journal.pone.0185691
. [PMID: 28977033] - Kamil Wojciechowski, Marta Orczyk, Thomas Gutberlet, Gerald Brezesinski, Thomas Geue, Philippe Fontaine. On the Interaction between Digitonin and Cholesterol in Langmuir Monolayers.
Langmuir : the ACS journal of surfaces and colloids.
2016 09; 32(35):9064-73. doi:
10.1021/acs.langmuir.6b01737
. [PMID: 27518122] - Kyoko Shinzawa-Itoh, Harunobu Shimomura, Sachiko Yanagisawa, Satoru Shimada, Ryoko Takahashi, Marika Oosaki, Takashi Ogura, Tomitake Tsukihara. Purification of Active Respiratory Supercomplex from Bovine Heart Mitochondria Enables Functional Studies.
The Journal of biological chemistry.
2016 Feb; 291(8):4178-84. doi:
10.1074/jbc.m115.680553
. [PMID: 26698328] - Stephen A Adam. Nuclear Protein Transport in Digitonin Permeabilized Cells.
Methods in molecular biology (Clifton, N.J.).
2016; 1411(?):479-87. doi:
10.1007/978-1-4939-3530-7_29
. [PMID: 27147060] - Ikhwan Resmala Sudji, Yamunadevi Subburaj, Nataliya Frenkel, Ana J García-Sáez, Michael Wink. Membrane Disintegration Caused by the Steroid Saponin Digitonin Is Related to the Presence of Cholesterol.
Molecules (Basel, Switzerland).
2015 Nov; 20(11):20146-60. doi:
10.3390/molecules201119682
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Cold Spring Harbor protocols.
2015 Nov; 2015(11):1017-23. doi:
10.1101/pdb.prot086165
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The Plant cell.
2015 Nov; 27(11):3213-27. doi:
10.1105/tpc.15.00443
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Journal of virology.
2015 Oct; 89(20):10442-52. doi:
10.1128/jvi.01588-15
. [PMID: 26246568] - Beata Korchowiec, Marcelina Gorczyca, Kamila Wojszko, Maria Janikowska, Max Henry, Ewa Rogalska. Impact of two different saponins on the organization of model lipid membranes.
Biochimica et biophysica acta.
2015 Oct; 1848(10 Pt A):1963-73. doi:
10.1016/j.bbamem.2015.06.007
. [PMID: 26055895] - Etienne Meunier, Petr Broz. Quantification of Cytosolic vs. Vacuolar Salmonella in Primary Macrophages by Differential Permeabilization.
Journal of visualized experiments : JoVE.
2015 Jul; ?(101):e52960. doi:
10.3791/52960
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Journal of visualized experiments : JoVE.
2015 Apr; ?(98):. doi:
10.3791/52509
. [PMID: 25939013] - Ana Joaquina Jimenez, Paolo Maiuri, Julie Lafaurie-Janvore, Séverine Divoux, Matthieu Piel, Franck Perez. ESCRT machinery is required for plasma membrane repair.
Science (New York, N.Y.).
2014 Feb; 343(6174):1247136. doi:
10.1126/science.1247136
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Nature protocols.
2014 Feb; 9(2):421-38. doi:
10.1038/nprot.2014.018
. [PMID: 24457333] - Safaa Yehia Eid, Mahmoud Zaki El-Readi, Essam Eldin Mohamed Nour Eldin, Sameer Hassan Fatani, Michael Wink. Influence of combinations of digitonin with selected phenolics, terpenoids, and alkaloids on the expression and activity of P-glycoprotein in leukaemia and colon cancer cells.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2013 Dec; 21(1):47-61. doi:
10.1016/j.phymed.2013.07.019
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The international journal of biochemistry & cell biology.
2013 Nov; 45(11):2585-95. doi:
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Methods in molecular biology (Clifton, N.J.).
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Journal of visualized experiments : JoVE.
2012 Dec; ?(70):e50066. doi:
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Biochimica et biophysica acta.
2012 Dec; 1818(12):3000-9. doi:
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. [PMID: 22842546] - Safaa Yehia Eid, Mahmoud Zaki El-Readi, Michael Wink. Synergism of three-drug combinations of sanguinarine and other plant secondary metabolites with digitonin and doxorubicin in multi-drug resistant cancer cells.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 Nov; 19(14):1288-97. doi:
10.1016/j.phymed.2012.08.010
. [PMID: 23146422] - Safaa Yehia Eid, Mahmoud Zaki El-Readi, Michael Wink. Digitonin synergistically enhances the cytotoxicity of plant secondary metabolites in cancer cells.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 Nov; 19(14):1307-14. doi:
10.1016/j.phymed.2012.09.002
. [PMID: 23062361] - Ellen De Geyter, Guy Smagghe, Yvan Rahbé, Danny Geelen. Triterpene saponins of Quillaja saponaria show strong aphicidal and deterrent activity against the pea aphid Acyrthosiphon pisum.
Pest management science.
2012 Feb; 68(2):164-9. doi:
10.1002/ps.2235
. [PMID: 21717567] - Florian Herrmann, Michael Wink. Synergistic interactions of saponins and monoterpenes in HeLa cells, Cos7 cells and in erythrocytes.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2011 Oct; 18(13):1191-6. doi:
10.1016/j.phymed.2011.08.070
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Analytical biochemistry.
2011 Sep; 416(2):218-27. doi:
10.1016/j.ab.2011.05.039
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Journal of medicinal chemistry.
2011 Jul; 54(13):4548-58. doi:
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Journal of pharmaceutical and biomedical analysis.
2011 Jan; 54(1):217-21. doi:
10.1016/j.jpba.2010.07.037
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Chemico-biological interactions.
2010 Dec; 188(3):386-92. doi:
10.1016/j.cbi.2010.08.004
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Cell death & disease.
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