Found 302 structures.
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1. Compound ID: 14376
|
LIP-(1-2)-+ LIP-(1-4)-+
| |
D-Diga-(1C-4)-/Variants 0/-b-D-Xylp-(1-4)-a-L-Rhap3Me-(1-3)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1-1)-a-D-Glcp
|
LIP-(1-6)-+
/Variants 0/ is:
a-Abep-(1-3)-
OR (exclusively)
a-D-Fucp-(1-3)- |
Show graphically |
Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_114701,IEDB_115015,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_142489,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_167188,IEDB_174332,IEDB_189517,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 5699
Wang L, Dong M, Lowary TL "Synthesis of unusual N-acylated aminosugar fragments of Mycobacterium marinum lipooligosaccharide IV" -
Journal of Organic Chemistry 80(5) (2015) 2767-2780
A convergent strategy was developed for the stereoselective synthesis of four unusual N-acylated monosaccharides (5-8), which are fragments of lipooligosaccharide IV (LOS-IV) from Mycobacterium marinum. A critical substrate-controlled asymmetric cyclization of an amino acid derived oxazolidine provided a key lactam intermediate 11, which was successfully converted to targets 5-7. The key step in the synthesis of 8 was a one-pot cascade oxidation-cyclization-oxidation reaction of a Boc-protected amino alcohol, prepared from 3-butynol, which led to the formation of lactam 15. The five-membered ring lactam intermediates in these synthetic routes were sensitive to elimination side reactions, but careful manipulation of the reaction sequence allowed for the stereoselective synthesis of the targets. This work represents the first synthesis of these unusual motifs, which have been shown to be essential to the bioactivity of LOS-IV
synthesis, lipooligosaccharide (LOS), Mycobacterium marinum
NCBI PubMed ID: 25642627Publication DOI: 10.1021/acs.joc.5b00064Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: tlowary@ualberta.ca
Institutions: Alberta Glycomics Centre and Department of Chemistry, University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada
Methods: 13C NMR, 1H NMR, chemical synthesis, optical rotation measurement, CC, HR-ESI-MS
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2. Compound ID: 14377
|
LIP-(1-2)-+ LIP-(1-4)-+
| |
D-Diga-(1C-4)-/Variants 1/-D-Diga-(1C-4)-/Variants 0/-b-D-Xylp-(1-4)-a-L-Rhap3Me-(1-3)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1-1)-a-D-Glcp
|
LIP-(1-6)-+
/Variants 0/ is:
a-Abep-(1-3)-
OR (exclusively)
a-D-Fucp-(1-3)-
/Variants 1/ is:
a-Abep-(1-3)-
OR (exclusively)
a-D-Fucp-(1-3)- |
Show graphically |
Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_114701,IEDB_115015,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_142489,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_167188,IEDB_174332,IEDB_189517,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 5699
Wang L, Dong M, Lowary TL "Synthesis of unusual N-acylated aminosugar fragments of Mycobacterium marinum lipooligosaccharide IV" -
Journal of Organic Chemistry 80(5) (2015) 2767-2780
A convergent strategy was developed for the stereoselective synthesis of four unusual N-acylated monosaccharides (5-8), which are fragments of lipooligosaccharide IV (LOS-IV) from Mycobacterium marinum. A critical substrate-controlled asymmetric cyclization of an amino acid derived oxazolidine provided a key lactam intermediate 11, which was successfully converted to targets 5-7. The key step in the synthesis of 8 was a one-pot cascade oxidation-cyclization-oxidation reaction of a Boc-protected amino alcohol, prepared from 3-butynol, which led to the formation of lactam 15. The five-membered ring lactam intermediates in these synthetic routes were sensitive to elimination side reactions, but careful manipulation of the reaction sequence allowed for the stereoselective synthesis of the targets. This work represents the first synthesis of these unusual motifs, which have been shown to be essential to the bioactivity of LOS-IV
synthesis, lipooligosaccharide (LOS), Mycobacterium marinum
NCBI PubMed ID: 25642627Publication DOI: 10.1021/acs.joc.5b00064Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: tlowary@ualberta.ca
Institutions: Alberta Glycomics Centre and Department of Chemistry, University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada
Methods: 13C NMR, 1H NMR, chemical synthesis, optical rotation measurement, CC, HR-ESI-MS
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3. Compound ID: 14378
|
LIP-(1-2)-+ LIP-(1-4)-+
| |
/Variants 2/-a-D-Fucp4N-(1-3)-D-Diga-(1C-4)-/Variants 1/-D-Diga-(1C-4)-/Variants 0/-b-D-Xylp-(1-4)-a-L-Rhap3Me-(1-3)-b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1-1)-a-D-Glcp
|
LIP-(1-6)-+
/Variants 0/ is:
a-Abep-(1-3)-
OR (exclusively)
a-D-Fucp-(1-3)-
/Variants 1/ is:
a-Abep-(1-3)-
OR (exclusively)
a-D-Fucp-(1-3)-
/Variants 2/ is:
Subst-(6-4)-
OR (exclusively)
Subst4-3Me-(6-4)-
OR (exclusively)
Subst3-3Me-(6-4)-
OR (exclusively)
Subst2-(6-4)-
Subst = SMILES CN1C(=O)C[C@@](C)(O)C1{6}C(N)=O;
Subst2 = SMILES CN1C(=O)C[C@@](C)(O)C1({6}C(N)=O)C(=O)O;
Subst3 = SMILES CN1C(=O){3}[C@H](O)[C@@](C)(O)C1({6}C(N)=O)C(=O)O;
Subst4 = SMILES CN1C(=O){3}[C@H](O)[C@@](C)(O)C1{6}C(N)=O |
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Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_114701,IEDB_115015,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_142489,IEDB_144998,IEDB_146664,IEDB_149135,IEDB_167188,IEDB_174332,IEDB_189517,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 5699
Wang L, Dong M, Lowary TL "Synthesis of unusual N-acylated aminosugar fragments of Mycobacterium marinum lipooligosaccharide IV" -
Journal of Organic Chemistry 80(5) (2015) 2767-2780
A convergent strategy was developed for the stereoselective synthesis of four unusual N-acylated monosaccharides (5-8), which are fragments of lipooligosaccharide IV (LOS-IV) from Mycobacterium marinum. A critical substrate-controlled asymmetric cyclization of an amino acid derived oxazolidine provided a key lactam intermediate 11, which was successfully converted to targets 5-7. The key step in the synthesis of 8 was a one-pot cascade oxidation-cyclization-oxidation reaction of a Boc-protected amino alcohol, prepared from 3-butynol, which led to the formation of lactam 15. The five-membered ring lactam intermediates in these synthetic routes were sensitive to elimination side reactions, but careful manipulation of the reaction sequence allowed for the stereoselective synthesis of the targets. This work represents the first synthesis of these unusual motifs, which have been shown to be essential to the bioactivity of LOS-IV
synthesis, lipooligosaccharide (LOS), Mycobacterium marinum
NCBI PubMed ID: 25642627Publication DOI: 10.1021/acs.joc.5b00064Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: tlowary@ualberta.ca
Institutions: Alberta Glycomics Centre and Department of Chemistry, University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada
Methods: 13C NMR, 1H NMR, chemical synthesis, optical rotation measurement, CC, HR-ESI-MS
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4. Compound ID: 22306
|
b-D-Digp-(1-4)-b-D-Digp-(1-4)-b-D-Digp-(1-3)-Subst
Subst = digoxigenin = SMILES O=C1OCC([C@H]2CC{14}[C@]3(O)[C@]4([H])CC[C@]5([H])C{3}[C@@H](O)CC[C@]5(C)[C@@]4([H])C{12}[C@@H](O)[C@]23C)=C1 |
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Structure type: oligomer
Trivial name: digoxin
Compound class: saponin glycoside, glycoside, triterpenoid glycoside, cardiac glycoside
The structure is contained in the following publication(s):
- Article ID: 9148
El-Sayed ER, Ahmed AS, Abdelhakim HK "A novel source of the cardiac glycoside digoxin from the endophytic fungus Epicoccum nigrum: isolation, characterization, production enhancement by gamma irradiation mutagenesis and anticancer activity evaluation" -
Journal of Applied Microbiology 128(3) (2020) 747-762
Different endophytic fungi were isolated and screened for their digoxin-producing ability. Strain improvement and different culture conditions were studied for more effective production of digoxin. Among the isolated fungi, an isolate produced digoxin in a concentration of 2.07 mg/l. The digoxin-producing fungal isolate was identified as Epicoccum nigrum Link according to the morphological features and phylogenetic analyses. The potentiality of the fungal strain for production enhancement of digoxin was performed by gamma radiation mutagenesis. Gamma irradiation dose of 1000 Gy intensified the digoxin yield by five-fold. Using this dose, a stable mutant strain with improved digoxin productivity was isolated and the stability for digoxin production was followed up across four successive generations. In the effort to increase digoxin magnitude, selection of the proper cultivation medium, addition of some elicitors to the most proper medium and several physical fermentation conditions were tested. Fermentation process carried out in malt extract autolysate medium (pH 6.5) supplemented by methyl jasmonate and inoculated with 2 ml of 6-day-old culture and incubated at 25°C for 10 days stimulated the highest production of digoxin to attain 50.14 mg/l. Moreover, cytotoxicity of digoxin separated from the fungal culture was tested against five different cancer cell lines. Based on the MTT assay, digoxin inhibited the proliferation of the five different cancer cell lines and the recorded 50% inhibitory concentration ranged from 10.76 to 35.14 μg/ml. This is the first report on the production and enhancement of digoxin using fungal fermentation as a new and alternate source with high productivity. These findings offer new and alternate sources with excellent biotechnological potential for digoxin production by fungal fermentation. Moreover, digoxin proved to be a promising anticancer agent whose anticancer potential should be assessed in prospective cancer therapy.
endophytic, Anticancer, Epicoccum nigrum, cardiac glycosides, digoxin, gamma radiation
NCBI PubMed ID: 31710165Publication DOI: 10.1111/jam.14510Journal NLM ID: 9706280Publisher: Oxford: Blackwell Publishing for the Society for Applied Bacteriology
Correspondence: sayed_zahran2000@yahoo.com
Institutions: Plant Research Department, Nuclear Research Center, Atomic Energy Authority, Cairo, Egypt, Biochemistry Lab, Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt
Methods: PCR, TLC, HPLC, UV, extraction, cell growth, RNA sequencing, mutagenesis, anticancer activity assay, cell viability assay, cytotoxicity assay, DNA extraction, evaporation, MTT, filtration, BLAST
- Article ID: 10555
Aulabaugh AE, Crouch RC, Martin GE, Ragouzeos A, Shockcor JP, Spitzer TD, Farrant RD, Hudson BD, Lindon JC "The conformational behaviour of the cardiac glycoside digoxin as indicated by NMR spectroscopy and molecular dynamics calculations" -
Carbohydrate Research 230 (1992) 201-212
The 1H- and 13C-NMR spectra of digoxin in solution in Me2SO-d6 have been assigned completely. Measurement of the 3JC,H values has enabled estimation of the torsional angles involving the bonds linking the digitoxose residues, between the inner digitoxose and the genin unit, and for the unsaturated γ-lactone ring. These values have been supplemented by 1H-1H NOE data. In general, there is good agreement between the conformations in solution (NMR data) and the solid state (X-ray data), and that derived from theoretical modelling which shows evidence of conformational flexibility. The major difference occurs for the torsion between the genin and the innermost digitoxose residue where molecular dynamics predict the presence of two conformations, one similar to that seen by NMR and the other similar to the X-ray structure.
NCBI PubMed ID: 1394296Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Organic Chemistry Department, Burroughs Wellcome Co., Research Triangle Park, North Carolina 27709
Methods: 13C NMR, 1H NMR, X-ray
- Article ID: 11379
Kudo K, Tachikawa E, Kashimoto T, Takahashi E "Properties of ginseng saponin inhibition of catecholamine secretion in bovine adrenal chromaffin cells" -
European Journal of Pharmacology 341(2-3) (1998) 139-144
To investigate the relationship between the inhibitory effects of ginseng saponins (ginsenosides) on acetylcholine-evoked secretion of catecholamines and the structures of ginsenosides, we examined the effects of ginsenoside-Rg3 and -Rh2, which are panaxadiol saponins, 20(R)- and 20(S)-ginsenoside-Rg2, which are epimers involving the hydroxyl group at C-20 of sapogenin, and other plant saponins on the acetylcholine-evoked secretion of catecholamines from cultured bovine adrenal chromaffin cells. The ginsenoside-Rg3 (1-100 microM) and -Rh2 (10-100 microM) greatly reduced the acetylcholine-evoked secretion in a concentration-dependent manner comparable to that of ginsenoside-Rg2, a panaxatriol saponin, which was the most potent inhibitor in our previous study. 20(R)- and 20(S)-ginsenoside-Rg2 (1-100 microM) similarly reduced the acetylcholine-evoked secretion. In contrast, saikosaponin-a, glycyrrhizin and the cardiac glycosides (100 nM-100 microM), digitoxin and digoxin, had no significant inhibitory effect on catecholamine secretion. Saikosaponin-c (10-100 microM), however, had an inhibitory effect, which was less than that of ginsenoside-Rg2 and -Rg3. These results strongly suggest that the inhibitory effects of ginsenosides on the acetylcholine-evoked secretion of catecholamines from bovine adrenal chromaffin cells are a unique property of ginseng. Further, the relationship between the inhibitory effects and the structures of ginsenosides is discussed.
ginsenoside, Ginseng saponin, catecholamine, chromaffin cell, acetylcholine
NCBI PubMed ID: 9543231Publication DOI: 10.1016/s0014-2999(97)01350-2Journal NLM ID: 1254354Publisher: Amsterdam: Elsevier
Correspondence: Tachikawa E
Institutions: Department of Pharmacology, School of Medicine, Iwate Medical UniÍersity, Morioka, Japan, Department of Medicine, School of Dentistry, Iwate Medical UniÍersity, Morioka, Japan
Methods: biological assays
- Article ID: 12150
Eddleston M, Rajapakse S, Rajakanthan, Jayalath S, Sjöström L, Santharaj W, Thenabadu PN, Sheriff MHR, Warrell DA "Anti-digoxin Fab fragments in cardiotoxicity induced by ingestion of yellow oleander: a randomised controlled trial" -
Lancet 355(9208) (2000) 967-972
Severe cardiac glycoside cardiotoxicity after ingestion of yellow oleander seeds is an important problem in rural areas of Sri Lanka. Currently, patients must be transferred to the capital for temporary cardiac pacing. We did a randomised controlled trial to investigate whether anti-digoxin Fab could reverse serious oleander-induced arrhythmias. After a preliminary dose-finding study, 66 patients who presented to hospital with a serious cardiac arrhythmia were randomised to receive either 1200 mg of anti-digoxin Fab or a saline placebo. A 12-lead electrocardiogram, 3 min rhythm strip, and blood sample for measurement of electrolytes and cardiac glycosides were taken before treatment and at 12 timepoints thereafter. 34 patients received anti-digoxin Fab and 32 received placebo. The presenting arrhythmia had resolved completely after 2 h in 15 antibody-treated patients and two controls (p<0.001); 24 and five patients, respectively, were in sinus rhythm at 8 h (p<0.001). Kaplan-Meier analysis of time to first reversal showed a significant response to anti-digoxin Fab. The heart rate increased in cases, from 49.1 per min at baseline to 66.8 at 2 h, but not in controls (50.6 per min at baseline to 51.5; p<0.001). Mean serum potassium concentrations decreased from 4.9 mmol/L to 4.1 mmol/L at 2 h in cases; no such decrease occurred in controls. Anti-digoxin Fab fragments are a safe and effective treatment for serious cardiac arrhythmias induced by yellow oleander. Their use in small rural hospitals in Sri Lanka should minimise costly transfer of patients and reduce the numbers of deaths; however, further study will be required to confirm this reduction.
digoxin, cardiotoxicity, yellow oleander, anti-digoxin Fab, arrhythmia
NCBI PubMed ID: 10768435Publication DOI: 10.1016/s0140-6736(00)90014-xJournal NLM ID: 2985213RPublisher: London: Elsevier
Correspondence: david.warrell@ndm.ox.ac.uk
Institutions: Centre for Tropical Medicine, Nuffield Department of Clinical Medicine, University of Oxford, Oxford, UK, Department for Clinical Medicine, University of Colombo, Colombo, Sri Lanka, Institute of Cardiology, National Hospital of Sri Lanka, Colombo, Sri Lanka, Protherics, London
Methods: biological assays
- Article ID: 12151
Eddleston M, Ariaratnam CA, Sjöström L, Jayalath S, Rajakanthan K, Rajapakse S, Colbert D, Meyer WP, Perera G, Attapattu S, Kularatne SAM, Sheriff MR, Warrell DA "Acute yellow oleander (Thevetia peruviana) poisoning: cardiac arrhythmias, electrolyte disturbances, and serum cardiac glycoside concentrations on presentation to hospital" -
Heart 83(3) (2000) 301-306
Objective was to describe the cardiac arrhythmias, electrolyte disturbances, and serum cardiac glycoside levels seen in patients presenting to hospital with acute yellow oleander (Thevetia peruviana) poisoning and to compare these with published reports of digitalis poisoning. Most symptomatic patients had conduction defects affecting the sinus node, the atrioventricular (AV) node, or both. Patients showing cardiac arrhythmias that required transfer for specialised management had significantly higher mean serum cardiac glycoside and potassium but not magnesium concentrations. Although there was considerable overlap between groups, those with conduction defects affecting both sinus and AV nodes had significantly higher mean serum cardiac glycoside levels. Most of these young previously healthy patients had conduction defects affecting the sinus or AV nodes. Relatively few had the atrial or ventricular tachyarrhythmias or ventricular ectopic beats that are typical of digoxin poisoning. Serious yellow oleander induced arrhythmias were associated with higher serum cardiac glycoside concentrations and hyperkalaemia but not with disturbances of magnesium.
digoxin, cardiotoxicity, yellow oleander, anti-digoxin Fab, arrhythmia
NCBI PubMed ID: 10677410Publication DOI: 10.1136/heart.83.3.301Journal NLM ID: 9602087Publisher: London: BMJ Pub. Group
Correspondence: david.warrell@ndm.ox.ac.uk
Institutions: Centre for Tropical Medicine, Nuffield Department of Clinical Medicine, University of Oxford, Oxford, UK, Department for Clinical Medicine, University of Colombo, Colombo, Sri Lanka, Therapeutic Antibodies Inc, Medical College of St. Bartholomew’s Hospital, London, UK, Department of Chemical Pathology, Homerton Hospital, London, UK, Anuradhapura General Hospital, Anuradhapura, Sri Lanka
Methods: biological assays
- Article ID: 12470
Melero CP, Medarde M, San Feliciano A "A short review on cardiotonic steroids and their aminoguanidine analogues" -
Molecules 5(1) (2000) 51-81
A short review on cardiotonic steroids and their analogues is presented. The natural, semisynthetic and synthetic derivatives, as well as their mechanism of action and structure-activity relationships are shown, with a special reference to aminoguanidine derivatives.
structure-activity relationships, digitalis glycosides analogues, inotropic activity, Na+, K+-ATPase, aminoguanidine analogues
Publication DOI: 10.3390/50100051Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: medarde@gugu.usal.es
Institutions: Departamento de Química Farmacéutica, Facultad de Farmacia, Salamanca, Spain
- Article ID: 12623
Rose AM, Qazzaz HM, Zolotarjova N, Mellett BJ, Martin AW, Valdes R Jr "Sodium pump isoforms in xenotransplantation: importance of biochemical compatibility" -
Clinical Chemistry 46(2) (2000) 234-241
Xenotransplantation of pig hearts to humans could be hampered by the reportedly reduced affinity for digoxin of pig heart. We examined the hypothesis that expression of the individual α-subunit isoforms of the sodium pump [Na+,K+-ATPase (NKA)], the receptor for the plant-derived cardiac glycosides, may be responsible for this difference. We used a NKA-inhibition assay in combination with Western analysis, immunohistochemistry, and phosphorylation of the NKA α subunit to identify the distribution and expression of α isoforms in four chambers of porcine and human hearts. We confirmed that tissue from porcine heart is less sensitive to digitalis (IC50 = 1740 nmol/L) when compared with human heart (IC50 = 840 nmol/L), whereas porcine cerebral cortex-mix had an affinity comparable to that of human heart (IC50 = 910 nmol/L). Our data show that porcine cerebral cortex-mix and human heart contain all three α isoforms, whereas porcine heart expresses only the α1 isoform. The different expressions of sodium pump isoforms in human vs porcine cardiac tissues suggests that porcine hearts may not be pharmacologically or endocrinologically compatible when used in humans. Studies of both pharmacologic and endocrinologic tissue compatibility are needed prior to selection of organs for xenotransplantation.
NCBI PubMed ID: 10657379Publication DOI: 10.1093/clinchem/46.2.234Journal NLM ID: 9421549Publisher: Oxford: Oxford University Press
Correspondence: rvaldes@louisville.edu
Institutions: Department of Pathology and Laboratory Medicine, University of Louisville, School of Medicine, Louisville, USA, Department of Biochemistry and Molecular Biology, University of Louisville, School of Medicine, Louisville, USA
Methods: biological assays
- Article ID: 12912
Eder M, Mehnert W "Solubility and dissolution rate of digoxin from Digitalis lanata dry extracts" -
Die Pharmazie 55(12) (2000) 928-933
The influence on solubility and dissolution rate was investigated for digoxin as a model drug with a very low solubility in water. The investigations were carried out with different fractions of extracts from leaves of Digitalis lanata. These fractions differ in the composition of concomitant compounds. The solubility of digoxin from the extract fractions is increased up to 42 times, with considerable differences between the fractions. The solubility depends on the weight of the extract fraction; a limit of solubility exists. Even after separation of the solved extract components the solubility of digoxin in the residues is larger than that of the pure digoxin. The dissolution rate of digoxin of "Vorgereinigter Gesamtglykosidextrakt (VE)" and the glycosid fraction G 1 is influenced significantly, whereas digoxin in the glycosid fraction G 4 has such a degree of purity that the solubility properties are not influenced by the small amount of concomitant compounds. After 10 min already 50.4% of the digoxin in the extract fraction G 1 are dissolved, while only 21.7% of the pure digoxin are dissolved in that interval. The extract fractions exhibit different wettability properties, so that the increased dissolution rate could be attributed to improved wettability of the extract fractions. Physical mixtures of crystal-line digoxin and compounds of the extracts of the almost digoxin free fraction G 2 did not exert an influence on the dissolution behavior. Different batches of the extract fractions showed different solubility in spite of comparable digoxin content.
NCBI PubMed ID: 11189870Journal NLM ID: 9800766Publisher: Eschborn: Govi-Verlag Pharmazautischer Verlag
Institutions: Fachbereich Biologie, Chemie, Pharmazie-Institute für Pharmazie-der Freien Universität Berlin, Germany
Methods: HPLC, extraction
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5. Compound ID: 22345
|
b-D-Digp-(1-3)-Subst
Subst = strophanthidin = SMILES C[C@]12CC[C@H]3[C@@H](CC{5}[C@@]4(O)[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: monomer
; 534.60
C29H42O9
Trivial name: helveticoside
Compound class: saponin glycoside, glycoside
The structure is contained in the following publication(s):
- Article ID: 9164
Lau MF, Chua KH, Sabaratnam V, Kuppusamy UR "In vitro and in silico anticancer evaluation of a medicinal mushroom, Ganoderma neo-japonicum Imazeki, against human colonic carcinoma cells" -
Biotechnology and Applied Biochemistry 2020 (2020) ID 2013
Ganoderma neo-japonicum is a well-known medicinal mushroom in Asian countries. However, scientific validations on its curative activities are confined to cirrhosis and diabetes. In this study, the anticancer properties of G. neo-japonicum were evaluated using cellular and computational models. The ethanolic extract (EtOH) with a promising inhibitory effect was fractionated into four different fractions: hexane (Hex), chloroform (Chl), butanol (Btn), and aqueous (Aq). The active fractions were then subjected to cell apoptosis assessment and phytochemical profiling. Molecular docking was conducted to elucidate the affinity of selected constituents towards antiapoptotic Bcl-2 protein. The butanol fraction showed the highest antioxidant activities as well as total phenolic content. Both hexane and chloroform fractions exerted a potent cytotoxic effect on colonic carcinoma cells through the induction of apoptosis. Phytochemical analysis revealed that the chloroform fraction is terpenoid enriched whereas the hexane fraction comprises predominantly sterol constituents. Stellasterol and 1,25-dihydroxyvitamin D3 3-glycoside were demonstrated to have a high affinity towards Bcl-2 protein. Overall, G. neo-japonicum can be considered as a compelling therapeutic candidate for cancer treatment.
apoptosis, Antioxidant, molecular docking, Anticancer, Ganoderma neo-japonicum
NCBI PubMed ID: 32856730Publication DOI: 10.1002/bab.2013Journal NLM ID: 8609465Correspondence: Kuppusamy UR
Institutions: Mushroom Research Centre, University of Malaya, Kuala Lumpur, Malaysia, Department of Biomedical Science, Faculty of Medicine, University of Malaya, Kuala Lumpur, Malaysia, Institute of Biological Science, Faculty of Science, University of Malaya, Kuala Lumpur, Malaysia
Methods: GC-MS, extraction, LC-MS, cell growth, antioxidant activities, cell viability assay, radical scavenging assay, evaporation, MTT, filtration, apoptosis assay, binding assay, Folin phenol reagent method
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6. Compound ID: 22348
|
b-D-Digp-(1-3)-Subst
Subst = strophanthidin = SMILES C[C@]12CC[C@H]3[C@@H](CC{5}[C@@]4(O)[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: monomer
; 535 [M+H]+
Trivial name: helveticoside
Compound class: saponin glycoside, glycoside
The structure is contained in the following publication(s):
- Article ID: 9166
Kopp B, Krenn L, Kubelka E, Kubelka W "Cardenolides from Adonis aestivalis" -
Phytochemistry 31(9) (1992) 3195-3198
Four cardenolides were isolated for the first time from the aerial parts of Adonis aestivalis. The compounds were identified by spectrometry and for 3-epi-periplogenin, helveticoside also by comparison with authentic substances. Two new cardenolides were structurally elucidated: strophanthidin-3-O-β-D-digitoxosido-α-L-cymarosido-β-D-glucoside and strophanthidin-3-O-β-D-digitoxosido-β-D-digoxoside-β-D-diginosido-β-D-glucoside.
cardiac glycosides, Adonis aestivalis, Ranunculaceae, cardenolides, strophanthidin, 3-epi-periplogenin, helveticoside, strophanthidin-3-O-β-D-digitoxosido-α-L-cymarosido-β-D-glucoside, strophanthidin-3-O-β-D-digitoxosido-β-D-digoxoside-β-D-diginosido-β-D-glucoside
NCBI PubMed ID: 1368415Publication DOI: 10.1016/0031-9422(92)83473-cJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Institute of Pharmacognosy, University of Vienna, Vienna, Austria
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, GC-MS, TLC, acid hydrolysis, GLC, HPLC, extraction, CC, derivatization
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7. Compound ID: 22349
|
b-D-Glcp-(1-4)-a-L-Digp3Me-(1-4)-b-D-Digp-(1-3)-Subst
Subst = strophanthidin = SMILES C[C@]12CC[C@H]3[C@@H](CC{5}[C@@]4(O)[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
; 841 [M+H]+
Compound class: saponin glycoside, glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9166
Kopp B, Krenn L, Kubelka E, Kubelka W "Cardenolides from Adonis aestivalis" -
Phytochemistry 31(9) (1992) 3195-3198
Four cardenolides were isolated for the first time from the aerial parts of Adonis aestivalis. The compounds were identified by spectrometry and for 3-epi-periplogenin, helveticoside also by comparison with authentic substances. Two new cardenolides were structurally elucidated: strophanthidin-3-O-β-D-digitoxosido-α-L-cymarosido-β-D-glucoside and strophanthidin-3-O-β-D-digitoxosido-β-D-digoxoside-β-D-diginosido-β-D-glucoside.
cardiac glycosides, Adonis aestivalis, Ranunculaceae, cardenolides, strophanthidin, 3-epi-periplogenin, helveticoside, strophanthidin-3-O-β-D-digitoxosido-α-L-cymarosido-β-D-glucoside, strophanthidin-3-O-β-D-digitoxosido-β-D-digoxoside-β-D-diginosido-β-D-glucoside
NCBI PubMed ID: 1368415Publication DOI: 10.1016/0031-9422(92)83473-cJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Institute of Pharmacognosy, University of Vienna, Vienna, Austria
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, GC-MS, TLC, acid hydrolysis, GLC, HPLC, extraction, CC, derivatization
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8. Compound ID: 22350
|
b-D-Glcp-(1-4)-b-D-2,6dlyxHexp3Me-(1-4)-b-D-Digp-(1-4)-b-D-Digp-(1-3)-Subst
Subst = strophanthidin = SMILES C[C@]12CC[C@H]3[C@@H](CC{5}[C@@]4(O)[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
; 971 [M+H]+
Compound class: saponin glycoside, glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9166
Kopp B, Krenn L, Kubelka E, Kubelka W "Cardenolides from Adonis aestivalis" -
Phytochemistry 31(9) (1992) 3195-3198
Four cardenolides were isolated for the first time from the aerial parts of Adonis aestivalis. The compounds were identified by spectrometry and for 3-epi-periplogenin, helveticoside also by comparison with authentic substances. Two new cardenolides were structurally elucidated: strophanthidin-3-O-β-D-digitoxosido-α-L-cymarosido-β-D-glucoside and strophanthidin-3-O-β-D-digitoxosido-β-D-digoxoside-β-D-diginosido-β-D-glucoside.
cardiac glycosides, Adonis aestivalis, Ranunculaceae, cardenolides, strophanthidin, 3-epi-periplogenin, helveticoside, strophanthidin-3-O-β-D-digitoxosido-α-L-cymarosido-β-D-glucoside, strophanthidin-3-O-β-D-digitoxosido-β-D-digoxoside-β-D-diginosido-β-D-glucoside
NCBI PubMed ID: 1368415Publication DOI: 10.1016/0031-9422(92)83473-cJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Institute of Pharmacognosy, University of Vienna, Vienna, Austria
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, GC-MS, TLC, acid hydrolysis, GLC, HPLC, extraction, CC, derivatization
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9. Compound ID: 23723
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b-D-Fucp3Me-(1-4)-b-D-Digp3Me-(1-3)-+
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b-D-Glcp-(1-6)-b-D-Glcp-(1-2)-b-D-Fucp3Me-(1-20)-Subst
Subst = pregn-5-en-3β,20α-diol = SMILES C{20}[C@H](O)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_241101,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 9749
Kawanishi S, Sakuma S, Shoji J "Constituents of the Chinese crude drug 'Wujiapi'. V. Structure of glycoside H1 of Bei-Wujiapi" -
Chemical and Pharmaceutical Bulletin 20 (1972) 469-475
Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
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10. Compound ID: 23773
Structure type: oligomer
Contained glycoepitopes: IEDB_142489,IEDB_149135,SB_86
The structure is contained in the following publication(s):
- Article ID: 9762
Kawanishi S, Kasai R, Sakuma S, Shoji J "Constituents of Chinese crude drug 'Wujiapi.' VIII. On the structures of new oligosaccharides C1, D2, F1 and F2 of Bei-Wujiapi" -
Chemical and Pharmaceutical Bulletin 25 (1977) 2055-2060
Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
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11. Compound ID: 23787
|
b-D-Fucp3Me-(1-4)-b-D-Digp3Me-(1-3)-+
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b-D-Glcp-(1-6)-b-D-Glcp-(1-2)-b-D-Fucp3Me-(1-20)-Subst
Subst = pregn-5-en-3β,16α,20S-triol = SMILES C{20}[C@H](O)[C@H]1{16}[C@H](O)C[C@@]2([H])[C@]3([H])CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_241101,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 9767
Sakuma S, Kawanishi S, Shoji J "Constituents of the Chinese crude drug 'wujiapi'. IX. Structure of glycoside H2, a potentiator of NGF-mediated nerve fiber outgrowth" -
Chemical and Pharmaceutical Bulletin 28 (1980) 163-168
Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
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12. Compound ID: 24201
Structure type: oligomer
Trivial name: neocondurangotriose wilforibiose
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9972
Hayashi K, Nakagawa T, Wada K, Yoshimura S, Tsukamoto S, Narita H, Mitsuhashi H "Studies on the constituents of Asclepiadaceae plants. The oligosaccharides and the 13C NMR of Asclepiadaceae glycosides" -
Proceedings of Tennen Yuki Kagobutsu Toronkai Koen Yoshishu = Symposium on the Chemistry of Natural Products [Japanese] (26th : 1983 : Kyoto) (1983) Vol. 26, 204-211
During the course of our studies on the biologically active asclepiadaceous glycosides, several oligosaccharides were isolated from hydrolysate of the glycoside which showed positive Keller-Kiliani reaction due to 2-deoxysugar contained. Four new oligosaccharides: neocondurangotriose from Condurango Cortex, dregeatriose from Dregea volubilis, glaucobiose from Cynanchum glaucescens, and wilforibiose from C. wilfordi were elucidated to have the structures (14), (15), (11), and (12) respectively on the bases of chemical and spectroscopic data. Characteristic glycosidation shifts were observed among the 2,6-dideoxysugars and the related oligosaccharides and glycosides. These shifts seemed to be separated into two categories which are ascribed to the orientation of the substitution of the ProR(β)carbon in Fig. 6.
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Hokkaido, Japan
Methods: 13C NMR
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13. Compound ID: 24248
|
b-D-Glcp-(1-6)-b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = Δ16-digitoxigenin = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC[C@]4(C)C(C(CO5)=CC5=O)=CC{14}[C@]4(O)[C@]3([H])CC[C@@]([H])2C1 |
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Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9996
Yamauchi T, Abe F "Cardiac glycosides and pregnanes from Adenium obesum (studies on the constituents of Adenium. I)" -
Chemical and Pharmaceutical Bulletin 38(3) (1990) 669-672
Cardiac glycosides and pregnanes from the roots and the stems of Adenium obesum ROEM. et SCHULT. were investigated. Among 30 cardiac glycosides including 15 known glycosides and 15 new combinations of the known aglycones and sugars, the structures of 11 glycosides were elucidated. Oleandrigenin β-gentiobiosyl-β-thevetoside was the main glycoside. Neridienone A and 16,17-dihydroneridienone A, common pregnanes in Apocynaceae, were also isolated.
Adenium obesum, Apocynaceae, cardiac glycoside, D-thevetoside, obeside, obebioside, obetrioside, pregnane, neridienone A
NCBI PubMed ID: 2347008Publication DOI: 10.1248/cpb.38.669Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003628395Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Fukuoka University, Japan
Methods: 13C NMR, 1H NMR, gel filtration, FAB-MS, TLC, HPLC, melting point measurement
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14. Compound ID: 24249
|
b-D-Digp3Me-(1-3)-Subst
Subst = digitoxigenin = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H](C(CO5)=CC5=O)CC{14}[C@]4(O)[C@]3([H])CC[C@@]([H])2C1 |
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Structure type: oligomer
Trivial name: somalin
Compound class: saponin glycoside
The structure is contained in the following publication(s):
- Article ID: 9996
Yamauchi T, Abe F "Cardiac glycosides and pregnanes from Adenium obesum (studies on the constituents of Adenium. I)" -
Chemical and Pharmaceutical Bulletin 38(3) (1990) 669-672
Cardiac glycosides and pregnanes from the roots and the stems of Adenium obesum ROEM. et SCHULT. were investigated. Among 30 cardiac glycosides including 15 known glycosides and 15 new combinations of the known aglycones and sugars, the structures of 11 glycosides were elucidated. Oleandrigenin β-gentiobiosyl-β-thevetoside was the main glycoside. Neridienone A and 16,17-dihydroneridienone A, common pregnanes in Apocynaceae, were also isolated.
Adenium obesum, Apocynaceae, cardiac glycoside, D-thevetoside, obeside, obebioside, obetrioside, pregnane, neridienone A
NCBI PubMed ID: 2347008Publication DOI: 10.1248/cpb.38.669Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003628395Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Fukuoka University, Japan
Methods: 13C NMR, 1H NMR, gel filtration, FAB-MS, TLC, HPLC, melting point measurement
- Article ID: 10247
Cabrera GM, Deluca ME, Seldes AM, Gros EG, Oberti JC, Crockett J, Gross ML "Cardenolide glycosides from the roots of Mandevilla pentlandiana" -
Phytochemistry 32 (1993) 1253-1259
From the roots of Mandevilla pentlandiana 13 cardenolide-type compounds were isolated. Besides free aglycones digitoxigenin and oleandrigenin, the structures of mono-, tri-, tetra- and pentaglycosides of both genins were characterized by means of chromatographic and spectroscopic methods.
cardenolides, roots, Apocynaceae, Mandevilla pentlandiana, cardiotonic glycosides
Publication DOI: 10.1016/S0031-9422(00)95101-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, Argentina, Department of Chemistry, University of Nebraska, Lincoln, NE, U.S.A.
Methods: 13C NMR, 1H NMR, EI-MS, gel filtration, FAB-MS, partial acid hydrolysis, TLC, acid hydrolysis, HPLC, acetylation analysis
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15. Compound ID: 24250
|
b-D-Digp3Me-(1-3)-Subst
Subst = oleandrigenin = SMILES O{3}[C@H]1CC[C@@]2(C)[C@@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C){14}[C@]3(O)C[C@H](OC(C)=O)[C@@H]4C(CO5)=CC5=O)([H])C1 |
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Structure type: oligomer
Compound class: saponin glycoside
The structure is contained in the following publication(s):
- Article ID: 9996
Yamauchi T, Abe F "Cardiac glycosides and pregnanes from Adenium obesum (studies on the constituents of Adenium. I)" -
Chemical and Pharmaceutical Bulletin 38(3) (1990) 669-672
Cardiac glycosides and pregnanes from the roots and the stems of Adenium obesum ROEM. et SCHULT. were investigated. Among 30 cardiac glycosides including 15 known glycosides and 15 new combinations of the known aglycones and sugars, the structures of 11 glycosides were elucidated. Oleandrigenin β-gentiobiosyl-β-thevetoside was the main glycoside. Neridienone A and 16,17-dihydroneridienone A, common pregnanes in Apocynaceae, were also isolated.
Adenium obesum, Apocynaceae, cardiac glycoside, D-thevetoside, obeside, obebioside, obetrioside, pregnane, neridienone A
NCBI PubMed ID: 2347008Publication DOI: 10.1248/cpb.38.669Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003628395Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Fukuoka University, Japan
Methods: 13C NMR, 1H NMR, gel filtration, FAB-MS, TLC, HPLC, melting point measurement
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