NCBI Taxonomy: 285815

Digitalis ciliata (ncbi_taxid: 285815)

found 60 associated metabolites at species taxonomy rank level.

Ancestor: Digitalis

Child Taxonomies: none taxonomy data.

Digitoxin

3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

C41H64O13 (764.4346694)


Digitoxin appears as odorless white or pale buff microcrystalline powder. Used as a cardiotonic drug. (EPA, 1998) Digitoxin is a cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain. It has a role as an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is functionally related to a digitoxigenin. It is a conjugate acid of a digitoxin(1-). A cardiac glycoside sometimes used in place of digoxin. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665) Digitoxin is a natural product found in Digitalis obscura, Digitalis parviflora, and other organisms with data available. Digitoxin is a lipid soluble cardiac glycoside that inhibits the plasma membrane sodium potassium ATPase, leading to increased intracellular sodium and calcium levels and decreased intracellular potassium levels. In studies increased intracellular calcium precedes cell death and decreased intracellular potassium increase caspase activation and DNA fragmentation, causing apoptosis and inhibition of cancer cell growth. (NCI) Digitoxin is only found in individuals that have used or taken this drug. It is a cardiac glycoside sometimes used in place of digoxin. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665)Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digitoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential. A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665) See also: Acetyldigitoxin (is active moiety of). Digitoxin, also known as crystodigin or digitoxoside, belongs to cardenolide glycosides and derivatives class of compounds. Those are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. Thus, digitoxin is considered to be a sterol lipid molecule. Digitoxin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Digitoxin can be synthesized from digitoxigenin. Digitoxin can also be synthesized into 3-O-acetyldigitoxin. Digitoxin can be found in common bean, which makes digitoxin a potential biomarker for the consumption of this food product. Digitoxin can be found primarily in blood and urine. Digitoxin is a non-carcinogenic (not listed by IARC) potentially toxic compound. Digitoxin is a drug which is used for the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure. Digitoxin is a cardiac glycoside. It is a phytosteroid and is similar in structure and effects to digoxin (though the effects are longer-lasting). Unlike digoxin (which is eliminated from the body via the kidneys), it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current Western medical practice. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective . Digitoxin exhibits similar toxic effects to the more-commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhoea, confusion, visual disturbances, and cardiac arrhythmias (DrugBank). Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digitoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential (T3DB). Digitoxin is a cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain. It has a role as an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It derives from a digitoxigenin. It is a conjugate acid of a digitoxin(1-). Digitoxin appears as odorless white or pale buff microcrystalline powder. It is a cardiac glycoside sometimes used in place of digoxin. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digitoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential. C - Cardiovascular system > C01 - Cardiac therapy > C01A - Cardiac glycosides > C01AA - Digitalis glycosides D020011 - Protective Agents > D002316 - Cardiotonic Agents > D004071 - Digitalis Glycosides D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides C78274 - Agent Affecting Cardiovascular System > C78322 - Cardiotonic Agent D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D004791 - Enzyme Inhibitors C471 - Enzyme Inhibitor Digitoxin is a potent Na+/K+-ATPase inhibitor with an EC50 value of 0.78 μM. Digitoxin is a potent Na+/K+-ATPase inhibitor with an EC50 value of 0.78 μM.

   

Luteolin

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

C15H10O6 (286.047736)


Luteolin is a naturally occurring flavonoid. (PMID:17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445). Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate. Luteolin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis. 5,7,3,4-tetrahydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. Flavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Annes Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 361; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 48 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

   

Apigenin

5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

C15H10O5 (270.052821)


Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (A7924). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (A7925). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (A7926). 5,7,4-trihydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565). Flavone found in a wide variety of foodstuffs; buckwheat, cabbage, celeriac, celery, lettuce, oregano, parsley, peppermint, perilla, pummelo juice, thyme, sweet potatoes, green tea and wild carrot [DFC] A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB002_Apigenin_pos_10eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_40eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_20eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_30eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_50eV_CB000005.txt [Raw Data] CB002_Apigenin_neg_40eV_000005.txt [Raw Data] CB002_Apigenin_neg_20eV_000005.txt [Raw Data] CB002_Apigenin_neg_10eV_000005.txt [Raw Data] CB002_Apigenin_neg_50eV_000005.txt CONFIDENCE standard compound; INTERNAL_ID 151 [Raw Data] CB002_Apigenin_neg_30eV_000005.txt CONFIDENCE standard compound; ML_ID 26 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

Digitonin

2-({2-[(2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{5,7,9,13-tetramethyl-5-oxaspiro[oxane-2,6-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-3,15-dioloxy}oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-3-yl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C56H92O29 (1228.5723982)


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 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].

   

Digitoxigenin

4-{5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-2,5-dihydrofuran-2-one

C23H34O4 (374.24569640000004)


   

Digitonin

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)-

C56H92O29 (1228.5723982)


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].

   

Apigenin

5,7,4-Trihydroxyflavone

C15H10O5 (270.052821)


Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.061 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.062 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.058 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.059 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

Luteolin

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- (9CI)

C15H10O6 (286.047736)


Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.976 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.975 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.968 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.971 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

   

Lanatoside A

Card-20(22)-enolide,3-[(O-b-D-glucopyranosyl-(1®4)-O-3-O-acetyl-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1®4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1®4)-2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-

C49H76O19 (968.4980545999999)


D020011 - Protective Agents > D002316 - Cardiotonic Agents > D004071 - Digitalis Glycosides D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides

   

Digitoxin

Digitoxin

C41H64O13 (764.4346694)


relative retention time with respect to 9-anthracene Carboxylic Acid is 1.470 Digitoxin is a potent Na+/K+-ATPase inhibitor with an EC50 value of 0.78 μM. Digitoxin is a potent Na+/K+-ATPase inhibitor with an EC50 value of 0.78 μM.

   

Digitoxigenin

4-(3,14-DIHYDROXY-10,13-DIMETHYL-HEXADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-17-YL)-5H-FURAN-2-ONE

C23H34O4 (374.24569640000004)


D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 23

   

luteolin 3-glucoside

luteolin 3-glucoside

C21H20O11 (448.100557)


   

gitaloxin

gitaloxin

C42H64O15 (808.4244994)


A cardenolide glycoside that is gitoxin in which the 16beta-hydroxy group has been formylated. D020011 - Protective Agents > D002316 - Cardiotonic Agents > D004071 - Digitalis Glycosides D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides

   

Versulin

4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)- (9CI)

C15H10O5 (270.052821)


Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

Digitoxigenin

4-{5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-2,5-dihydrofuran-2-one

C23H34O4 (374.24569640000004)


   

(2r,3r,4s,6s)-6-{[(2r,3s,4s,6s)-6-{[(2r,3s,4s,6r)-6-{[(1r,3as,3br,5as,7s,9as,9br,11ar)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-2-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate

(2r,3r,4s,6s)-6-{[(2r,3s,4s,6s)-6-{[(2r,3s,4s,6r)-6-{[(1r,3as,3br,5as,7s,9as,9br,11ar)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-2-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate

C49H76O19 (968.4980545999999)


   

4-[(1r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-5-{[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-{[(2r,4s,5r,6r)-5-hydroxy-6-methyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one

4-[(1r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-5-{[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-{[(2r,4s,5r,6r)-5-hydroxy-6-methyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one

C47H74O18 (926.4874904000001)


   

(3r,4s,6s)-6-{[(2r,3s,4s,6s)-6-{[(2r,3s,4s,6r)-6-{[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-2-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate

(3r,4s,6s)-6-{[(2r,3s,4s,6s)-6-{[(2r,3s,4s,6r)-6-{[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-2-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate

C49H76O19 (968.4980545999999)


   

4-[(1s,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,4s,5s,6r)-5-{[(2s,4s,5s,6r)-5-{[(2s,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one

4-[(1s,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,4s,5s,6r)-5-{[(2s,4s,5s,6r)-5-{[(2s,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one

C41H64O13 (764.4346694)


   

luteolin 3'-glucoside

luteolin 3'-glucoside

C21H20O11 (448.100557)


   

(2s,3s,4r,5r,6r)-2-{[(2r,3s,4r,5s,6s)-2-{[(2r,3r,4s,5r,6s)-2-{[(2r,3r,4r,5r,6r)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1's,2s,2'r,3's,4's,5r,7'r,8's,9'r,12's,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-3',15'-dioloxy]oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3s,4r,5r,6r)-2-{[(2r,3s,4r,5s,6s)-2-{[(2r,3r,4s,5r,6s)-2-{[(2r,3r,4r,5r,6r)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1's,2s,2'r,3's,4's,5r,7'r,8's,9'r,12's,13's,15's,16's,18'r)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-3',15'-dioloxy]oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2s,3r,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C56H92O29 (1228.5723982)