Page last updated: 2024-11-12

oleandrin

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

Description

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

oleandrin : A steroid saponin that consists of oleandrigenin having a 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl residue attached to the oxygen function at position 3. [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]

Cross-References

ID SourceID
PubMed CID11541511
CHEMBL ID4285883
CHEBI ID59030
SCHEMBL ID25049
MeSH IDM0075525

Synonyms (56)

Synonym
(3beta,5beta,16beta)-16-acetoxy-3-[(2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
oleandrina
CHEBI:59030 ,
465-16-7
oleandrin
neriol
neriolin
corrigen
foliandrin
folinerin
neriostene
oleandrine
einecs 207-361-5
oleandrina [spanish]
(3beta,16beta)-16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-l-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide
hsdb 3518
16beta-acetoxy-3beta-(2,6-dideoxy-3-o-methyl-l-arabino-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide
nsc 692219
card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3-beta,5-beta,16-beta)-
card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta,16beta)-
16beta-(acetyloxy)-3beta-((2,6-dideoxy-3-o-methyl-l-arabino-hexopyranosyl)oxy)-14-hydroxycard-20-(22)-enolide
nsc-692219
ii95udu7i4 ,
unii-ii95udu7i4
C19987
oleandrin [who-dd]
card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-.alpha.-l-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3.beta.,5.beta.,16.beta.)-
oleandrin [mi]
anvirzel
S6918
SCHEMBL25049
(3 beta,16 beta)-16-(acetyloxy)-3-((2,6-dideoxy-3-o-methyl-l-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide
HY-13719
CS-5505
AKOS032430539
oleandrigenin oleandroside
folinevin
dtxcid401474666
(3beta,5beta,16beta)-16-acetoxy-3-((2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide
(3beta,5beta,16beta)-16-(acetyloxy)-3-
oleandrin, >=98% (hplc)
pbi-05204
pbi 05204
1315607-79-4
DB12843
[(3s,5r,8r,9s,10s,13r,14s,16s,17r)-14-hydroxy-3-[(2r,4s,5s,6s)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
[(3s,8r,9s,10s,13r,14s,16s,17r)-14-hydroxy-3-[(4s,5s,6s)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2h-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
Q411532
DTXSID40861950 ,
CHEMBL4285883
MS-30375
bdbm50465465
oleandrin (pbi-05204)
pbi-05204 (mixture of botanical compounds)
gtpl12618
pbi05204

Research Excerpts

Overview

Oleandrin is a monomeric compound extracted from leaves and seeds of Nerium oleander.

ExcerptReferenceRelevance
"Oleandrin is a cardiac glycoside obtained from of N."( Glycoside oleandrin downregulates toll-like receptor pathway genes and associated miRNAs in human melanoma cells.
Dodurga, Y; Elmas, L; Eroğlu Güneş, C; Kurar, E; Seçer Çelik, F; Seçme, M, 2022
)
1.85
"Oleandrin is a monomeric compound extracted from leaves and seeds of Nerium oleander. "( Oleandrin induces DNA damage responses in cancer cells by suppressing the expression of Rad51.
Bao, Z; Chen, Z; Feng, H; Li, W; Liang, Y; Shen, H; Tian, B; Wang, X; Ying, S, 2016
)
3.32

Treatment

Oleandrin treatment resulted in selective inhibition of human cancer cell growth but not rodent cell proliferation. Treatment also induced the phosphorylation of PERK and eIF2α.

ExcerptReferenceRelevance
"oleandrin treatment also induced the phosphorylation of PERK and eIF2α."( Oleandrin induces apoptosis via activating endoplasmic reticulum stress in breast cancer cells.
Jiang, YH; Li, XX; Meng, FD; Sui, CG; Sun, SL; Wang, DQ; Zheng, J, 2020
)
2.72
"Oleandrin treatment resulted in selective inhibition of human cancer cell growth but not rodent cell proliferation, which corresponded to the relative level of Na,K-ATPase alpha3 subunit protein expression."( Oleandrin-mediated inhibition of human tumor cell proliferation: importance of Na,K-ATPase alpha subunits as drug targets.
Cartwright, C; Chan, D; Dixon, S; Llansa, N; Mendoza, G; Menter, DG; Newman, RA; Suraokar, M; Yang, P, 2009
)
2.52
"Oleandrin-treated cells exhibited time- and concentration-dependent staining with acridine orange, a lysosomal stain."( Autophagic cell death of human pancreatic tumor cells mediated by oleandrin, a lipid-soluble cardiac glycoside.
Cartwright, C; Chan, D; Dixon, S; Johansen, M; Kondo, Y; Newman, RA; Yang, P; Yokoyama, T, 2007
)
1.3
"Treatment with oleandrin increased the number of apoptotic cells and led to nuclear pyknosis, fragmentation, and apoptotic body formation in breast cancer cells."( Oleandrin induces apoptosis via activating endoplasmic reticulum stress in breast cancer cells.
Jiang, YH; Li, XX; Meng, FD; Sui, CG; Sun, SL; Wang, DQ; Zheng, J, 2020
)
2.34
"Treatment with oleandrin facilitated nuclear translocation of FKHR in human, but not murine cells by dephosphorylating Akt."( Oleandrin induces apoptosis in human, but not in murine cells: dephosphorylation of Akt, expression of FasL, and alteration of membrane fluidity.
Manna, SK; Raghavendra, PB; Sreenivasan, Y, 2007
)
2.12

Toxicity

ExcerptReferenceRelevance
"Nerium oleander (No), is a toxic plant."( Cytotoxic effects of leaf, stem and root extracts of Nerium oleander on leukemia cell lines and role of the p-glycoprotein in this effect.
Akgün-Dar, K; Atasever, B; Carin, M; Kiliçaslan-Ayna, T; Kuruca, SE; Meriçli, F; Seyhan, VG; Turan, N, 2006
)
0.33
" Grade ≥ 3 treatment-emergent adverse events occurred in 63."( A Phase II, Single-Arm, Open-Label, Bayesian Adaptive Efficacy and Safety Study of PBI-05204 in Patients with Stage IV Metastatic Pancreatic Adenocarcinoma.
Berlin, J; Borazanci, EH; Cardin, DB; Newman, RA; Picozzi, VJ; Rosemury, A; Roth, MT; Steinbach, M; Wadlow, RC, 2020
)
0.56

Pharmacokinetics

ExcerptReferenceRelevance
" Oleandrin was rapidly absorbed after oral dosing (Cmax at 20 min) although the elimination half-life was longer (2."( Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander.
Felix, E; Ho, DH; Johansen, M; Madden, TL; Newman, RA; Ni, D,
)
1.31

Compound-Compound Interactions

ExcerptReferenceRelevance
" Selected cardiac glycosides were tested in combination with four clinically relevant cytotoxic drugs (5-fluorouracil, oxaliplatin, cisplatin, irinotecan)."( Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.
Bohlin, L; Felth, J; Fryknäs, M; Gullbo, J; Lindskog, M; Rickardson, L; Rosén, J; Wickström, M, 2009
)
0.35
"In the majority of the cell lines tested, lower concentrations of Anvirzel™ induced a synergistic effect when combined with low concentrations of Cisplatin after an incubation period of 48 to 72 h."( Anvirzel™ in combination with cisplatin in breast, colon, lung, prostate, melanoma and pancreatic cancer cell lines.
Apostolou, P; Chatziioannou, M; Ioannou, E; Knocke, DR; Komiotis, D; Nester, J; Papasotiriou, I; Toloudi, M, 2013
)
0.39

Bioavailability

ExcerptReferenceRelevance
"h/ml), respectively, resulting in an oral bioavailability of approximately 30%."( Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander.
Felix, E; Ho, DH; Johansen, M; Madden, TL; Newman, RA; Ni, D,
)
0.4

Dosage Studied

Oleandrin, ouabain, and digoxin in the used dosage do not present therapeutic potential for the treatment of congestive heart failure.

ExcerptRelevanceReference
" Oleandrin was rapidly absorbed after oral dosing (Cmax at 20 min) although the elimination half-life was longer (2."( Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander.
Felix, E; Ho, DH; Johansen, M; Madden, TL; Newman, RA; Ni, D,
)
1.31
" It is concluded that the glycosides oleandrin, ouabain, and digoxin in the used dosage do not present therapeutic potential for the treatment of congestive heart failure caused by doxorubicin."( Comparative Therapeutic Potential of Cardioactive Glycosides in Doxorubicin Model of Heart Failure.
Botelho, AFM; Canta, GN; da Cruz, JPO; da Silva Ferreira, R; Fernandes, PBU; Lempek, MR; Mantovani, MM; Melo, MM; Silva, FLA; Veado, JCC, 2022
)
0.99
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
cardenolide glycosideAny member of the class of cardenolides with glycosyl residues attached to position 3.
14beta-hydroxy steroidA 14-hydroxy steroid in which the hydroxy group has a beta-configuration.
steroid ester
steroid saponinAny saponin derived from a hydroxysteroid.
[compound class information is derived from 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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Neurogenic locus notch homolog protein 1Mus musculus (house mouse)IC50 (µMol)0.12000.12000.12000.1200AID1410576
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
Golgi membraneNeurogenic locus notch homolog protein 1Mus musculus (house mouse)
extracellular regionNeurogenic locus notch homolog protein 1Mus musculus (house mouse)
nucleoplasmNeurogenic locus notch homolog protein 1Mus musculus (house mouse)
endoplasmic reticulum membraneNeurogenic locus notch homolog protein 1Mus musculus (house mouse)
cytosolNeurogenic locus notch homolog protein 1Mus musculus (house mouse)
plasma membraneNeurogenic locus notch homolog protein 1Mus musculus (house mouse)
endosome membraneNeurogenic locus notch homolog protein 1Mus musculus (house mouse)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID1570107Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1570125Inhibition of porcine kidney Na+/K+-ATPase at 50 uM preincubated for 2 mins followed by ATP addition and measured after 6 mins by bagin-sky assay relative to Olean-drigenin
AID1410589Inhibition of doxycycline-induced recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) activation expressed in human LS174T cells assessed as reduction in NCID expression after 12 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410584Cytotoxicity against human HPBALL cells after 72 hrs by alamar blue dye based fluorescence assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410590Inhibition of doxycycline-induced recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) activation expressed in human LS174T cells assessed as reduction in NCID expression at 0.5 uM after 12 hrs in presence of proteasome inhibitor MG132 2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410577Effect on Notch1 mRNA expression in human HPBALL cells at 0.1 to 0.5 uM measured after 12 hrs2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410579Down regulation of Notch1 expression in human HPBALL cells at 0.5 uM after 12 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410585Down regulation of Notch1 expression in human HPBALL cells at 0.5 uM after 12 hrs in presence of proteasome inhibitor MG132 by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410578Inhibition of Notch1 in human HPBALL cells assessed as reduction in NICD expression at 0.5 uM after 12 hrs in presence of proteasome inhibitor MG132 by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410576Inhibition of recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) expressed in human LS174T cells assessed as reduction in doxycycline-induced NICD expression after 12 hrs by Bright-Glo luciferase reporter gene assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410582Inhibition of Notch1 in human HPBALL cells assessed as reduction in NICD expression after 72 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410580Inhibition of Notch1 in human HPBALL cells assessed as reduction in HES1 expression after 72 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1740504Cytotoxicity against human BJ cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay
AID1570110Antiproliferative activity against human Hep3B cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1410588Inhibition of doxycycline-induced Notch1 (1704 to 2531 residues) expression in human LS174T cells after 12 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1410587Inhibition of doxycycline-induced recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) activation expressed in human LS174T cells assessed as reduction in Hes5 level at 0.05 to 0.3 uM after 12 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1740503Cytotoxicity against human HeLa cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay
AID1410581Inhibition of Notch1 in human HPBALL cells assessed as reduction in NICD expression at 0.5 uM after 12 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1740501Cytotoxicity against human CEM cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay
AID1570112Inhibition of porcine kidney Na+/K+-ATPase assessed as residual activity at 50 uM preincubated for 2 mins followed by ATP addition and measured after 6 mins by bagin-sky assay relative to untreated control
AID1740502Cytotoxicity against human MCF7 cells assessed as reduction in cell viability incubated for 72 hrs by resazurin assay
AID1410583Cytotoxicity against HEK293 cells after 72 hrs by fluorescence assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1740505Inhibition of porcine kidney Na+/K+ ATPase at 50 uM assessed as enzyme residual activity using ATP as substrate incubated for 2 mins followed by substrate addition and measured after 6 mins (Rvb = 100 +/-3.16%)
AID1570109Antiproliferative activity against human A2780 cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1570111Cytotoxicity against human BJ cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1410586Inhibition of doxycycline-induced recombinant mouse N-terminal FLAG-tagged Notch1 (1704 to 2531 residues) activation expressed in human LS174T cells assessed as reduction in Hes1 level at 0.05 to 0.3 uM after 12 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
The Notch Inhibitors Isolated from Nerium indicum.
AID1570106Antiproliferative activity against human CEM cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1570108Antiproliferative activity against human HeLa cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (103)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (6.80)18.7374
1990's12 (11.65)18.2507
2000's35 (33.98)29.6817
2010's30 (29.13)24.3611
2020's19 (18.45)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 48.53

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index48.53 (24.57)
Research Supply Index4.71 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index74.96 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (48.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (2.80%)5.53%
Reviews5 (4.67%)6.00%
Case Studies17 (15.89%)4.05%
Observational0 (0.00%)0.25%
Other82 (76.64%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]