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digitonin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

Digitonin: 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. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

digitonin : 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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
DigitalisgenusA genus of toxic herbaceous Eurasian plants of the Plantaginaceae which yield cardiotonic DIGITALIS GLYCOSIDES. The most useful species are Digitalis lanata and D. purpurea.[MeSH]PlantaginaceaeA plant family of order Lamiales. The Plantago genus is best known. Lesser known members include Hippuris, Littorella and Callitriche.[MeSH]

Cross-References

ID SourceID
PubMed CID129316177
MeSH IDM0006380

Synonyms (1)

Synonym
digitonin

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" As an extension of this hypothesis, the relative resistance of some brain monoaminergic neurons to the toxic actions of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine may result from the subcellular sequestration of MPP+ in the storage vesicle."( Subcellular compartmentalization of 1-methyl-4-phenylpyridinium with catecholamines in adrenal medullary chromaffin vesicles may explain the lack of toxicity to adrenal chromaffin cells.
Daniels, AJ; Diliberto, EJ; Reinhard, JF; Viveros, OH, 1987
)
0.27
"65-fold more toxic in each cell line, respectively."( Digitonin synergistically enhances the cytotoxicity of plant secondary metabolites in cancer cells.
Eid, SY; El-Readi, MZ; Wink, M, 2012
)
0.38
"In vitro generated data on toxic potencies are generally based on nominal concentrations."( In vitro toxicity testing with microplate cell cultures: Impact of cell binding.
Gülden, M; Schreiner, J; Seibert, H, 2015
)
0.42

Compound-Compound Interactions

ExcerptReferenceRelevance
"We determined the ability of some phytochemicals, including alkaloids (glaucine, harmine, and sanguinarine), phenolics (EGCG and thymol), and terpenoids (menthol, aromadendrene, β-sitosterol-O-glucoside, and β-carotene), alone or in combination with the saponin digitonin to reverse the relative multi-drug resistance of Caco-2 and CEM/ADR5000 cells to the chemotherapeutical agent doxorubicin."( Synergism of three-drug combinations of sanguinarine and other plant secondary metabolites with digitonin and doxorubicin in multi-drug resistant cancer cells.
Eid, SY; El-Readi, MZ; Wink, M, 2012
)
0.38

Bioavailability

ExcerptReferenceRelevance
" Given the known hypocholesterolemic and antiatherosclerotic properties of some steroid glycosides, we synthesized a series of sterol derivatives by coupling some phytosterols known to interact with sterol absorption and also to be poorly absorbed to a cationic group."( Selection of cholesterol absorption inhibitors devoid of secondary intestinal effects.
Abou el Fadil, F; Boubia, B; Descroix-Vagne, M; Guffroy, C; Marquet, F; Pansu, D,
)
0.13
" To what extent cell binding affects the bioavailability depends on the BCF and the cell volume fraction."( In vitro toxicity testing with microplate cell cultures: Impact of cell binding.
Gülden, M; Schreiner, J; Seibert, H, 2015
)
0.42

Dosage Studied

A biphasic dose-response curve was observed for the unmasking of catalase activity by digitonin in latency studies. Either linear or sigmoid dose- response for release of the cytoplasmic marker lactate dehydrogenase and the granule markers lysozyme, beta-glucuronidase, lactoferrin, and myeloperoxidase was noted.

ExcerptRelevanceReference
" Under essentially identical conditions, the dose-response curve for IPR stimulation of AC activity in the absence of 3-isobutyl-1-methylxanthine was similar in trained and control rats."( Enhanced coupling of adenylate cyclase to lipolysis in permeabilized adipocytes from trained rats.
Izawa, T; Komabayashi, T; Mochizuki, T; Suda, K; Tsuboi, M, 1991
)
0.28
" The GDP analogue GDP-beta-S caused a 50% inhibition of the phosphorylation of 80K induced by a saturating concentration of vasopressin and shifted the vasopressin dose-response curve to the right."( Vasopressin rapidly stimulates protein kinase C in digitonin-permeabilized Swiss 3T3 cells: involvement of a pertussis toxin-insensitive guanine nucleotide binding protein.
Erusalimsky, JD; Rozengurt, E, 1989
)
0.28
" A biphasic dose-response curve was observed for the unmasking of catalase activity by digitonin in latency studies."( Studies on catalase compartmentation in digitonin-treated rat hepatocytes.
Flatmark, T; Fukami, MH, 1986
)
0.27
" Dose-response curves comparing 45Ca efflux and insulin secretion suggested that AA also stimulates hormone release by at least one other mechanism in addition to Ca2+ mobilization."( Exogenous arachidonic acid promotes insulin release from intact or permeabilized rat islets by dual mechanisms. Putative activation of Ca2+ mobilization and protein kinase C.
Metz, SA, 1988
)
0.27
" Analysis of thermal dose-response curves for cells exposed to between 10 and 100 microM DEM indicated that cell survival was unaffected by the addition of DEM until a critical concentration was surpassed."( Subcellular localization of glutathione and thermal sensitivity.
Freeman, ML; Meredith, MJ, 1988
)
0.27
" The DNA dsb dose-response shoulder could be restored by irradiating nuclei in the presence of sulphydryl compounds."( Use of 'nuclear monolayers' to identify factors influencing DNA double-strand breakage by X-rays.
Radford, IR, 1987
)
0.27
" On the basis of kinetic data, dose-response data, and failure of elevated cytosolic calcium levels to inhibit lipid secretion, it was concluded that disturbed intracellular calcium homeostasis probably is not important in CCl4-dependent inhibition of secretion of very low density lipoproteins."( Evidence against a role for disturbed hepatocellular calcium homeostasis in the fatty liver of carbon tetrachloride hepatotoxicity.
Brattin, WJ; Glende, EA; Pencil, SD; Recknagel, RO, 1984
)
0.27
" From these results and from dose-response curves of QO2 versus uncoupler concentrations, we conclude that 1 microM is an upper limit for free uncoupler concentration in the medium to avoid unwanted side effects during cell physiology studies that require total mitochondrial uncoupling."( Changes in interfacial potentials induced by carbonylcyanide phenylhydrazone uncouplers: possible role in inhibition of mitochondrial oxygen consumption and other transport processes.
Benos, DJ; Reyes, J, 1984
)
0.27
" The dose-response data correlated well with target cell viable count."( Real-time measurement of cell permeabilization with low-molecular-weight membranolytic agents.
Akerman, KE; Karp, MT; Oker-Blom, C; Saviranta, P; Virta, M, 1995
)
0.29
" The dose-response curves of these four compounds are indicative of multiple binding sites and/or modes of interaction with ABCR."( Retinal stimulates ATP hydrolysis by purified and reconstituted ABCR, the photoreceptor-specific ATP-binding cassette transporter responsible for Stargardt disease.
Molday, RS; Nathans, J; Sun, H, 1999
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,990)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901065 (53.52)18.7374
1990's533 (26.78)18.2507
2000's272 (13.67)29.6817
2010's103 (5.18)24.3611
2020's17 (0.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.05%)5.53%
Reviews17 (0.82%)6.00%
Case Studies5 (0.24%)4.05%
Observational0 (0.00%)0.25%
Other2,057 (98.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]