Compounds > oleanderolide
Page last updated: 2024-11-12

oleanderolide

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Description

oleanderolide: oleanane-type triterpene from Nerium oleander; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
NeriumgenusA plant genus of the family APOCYNACEAE. It is a very poisonous plant that contains cardioactive agents.[MeSH]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]

Cross-References

ID SourceID
PubMed CID11113483
CHEMBL ID498230
MeSH IDM0482517

Synonyms (3)

Synonym
oleanderolide
CHEMBL498230
(1s,4s,5r,8r,10s,13r,14r,16s,17s,18r)-10,16-dihydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-23-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID1066408Induction of apoptosis in human A2780 cells assessed as DNA ladder formation at 30 uM after 24 hrs by electrophoresis2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1915606Inhibition of human carboxylesterase using 4-benzoyl-N-butyl-1,8-naphthalimide as substrate by fluorescence based assay2021European journal of medicinal chemistry, Jan-15, Volume: 210Recent research progress of Uncaria spp. based on alkaloids: phytochemistry, pharmacology and structural chemistry.
AID1066417Cytotoxicity against human A549 cells after 96 hrs by SRB assay2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID545993Inhibition of recombinant PTP1B expressed in Escherichia coli BL21 after 30 mins by spectrophotometry2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B.
AID1066414Cell cycle arrest in human A2780 cells assessed as accumulation at G1 phase at 30 uM by propidium iodide staining-based FACS analysis (Rvb = 51.839 %)2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID744761Inhibition of PTP1B (unknown origin) expressed in Escherichia coli expression system using p-nitrophenyl phosphate as substrate assessed as release of p-nitrophenol at 10 ug/mL incubated for 10 mins prior to substrate addition measured after 30 mins relat2013European journal of medicinal chemistry, May, Volume: 63Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors.
AID1066418Cytotoxicity against human HT-29 cells after 96 hrs by SRB assay2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID744758Insulin sensitizing activity in mouse 3T3L1 cells assessed as increase in glucose uptake at 10 ug/mL after 50 hrs by ELISA relative to control2013European journal of medicinal chemistry, May, Volume: 63Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors.
AID1066415Cytotoxicity against mouse NIH/3T3 cells after 96 hrs by SRB assay2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID377096Cytotoxicity against human WI 38 cells after 48 hrs by WST-8 assay2005Journal of natural products, Feb, Volume: 68, Issue:2
Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
AID1061259Inhibition of topoisomerase 1 (unknown origin)-mediated relaxation of supercoiled plasmid DNA assessed as intensity of supercoiled DNA after 30 mins by agarose gel electrophoresis relative to camptothecin2014Bioorganic & medicinal chemistry, Jan-01, Volume: 22, Issue:1
Rational design and synthesis of topoisomerase I and II inhibitors based on oleanolic acid moiety for new anti-cancer drugs.
AID1061262Inhibition of topoisomerase 2 (unknown origin)-mediated kinetoplast DNA decatenation at 100 uM after 30 mins by agarose gel electrophoresis2014Bioorganic & medicinal chemistry, Jan-01, Volume: 22, Issue:1
Rational design and synthesis of topoisomerase I and II inhibitors based on oleanolic acid moiety for new anti-cancer drugs.
AID1061258Inhibition of topoisomerase 2 (unknown origin)-mediated kinetoplast DNA decatenation assessed as intensity of supercoiled DNA after 30 mins by agarose gel electrophoresis relative to etoposide2014Bioorganic & medicinal chemistry, Jan-01, Volume: 22, Issue:1
Rational design and synthesis of topoisomerase I and II inhibitors based on oleanolic acid moiety for new anti-cancer drugs.
AID1066404Induction of apoptosis in human A2780 cells assessed as vital cells at 30 uM after 24 hrs by annexin V/propidium iodide staining-based FACS analysis (Rvb = 82.15%)2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1066419Cytotoxicity against human A2780 cells after 96 hrs by SRB assay2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1066413Cell cycle arrest in human A2780 cells assessed as accumulation at G2 phase at 30 uM by propidium iodide staining-based FACS analysis (Rvb = 15.721 %)2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID377097Cytotoxicity against human VA13 cells after 48 hrs by WST-8 assay2005Journal of natural products, Feb, Volume: 68, Issue:2
Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
AID1066406Induction of apoptosis in human A2780 cells assessed as necrotic cells at 30 uM after 24 hrs by annexin V/propidium iodide staining-based FACS analysis (Rvb = 1.78%)2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1066409Cell cycle arrest in human A2780 cells assessed as reduction of G2/M phase at 30 uM by propidium iodide staining-based FACS analysis2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1066403Induction of apoptosis in human A2780 cells assessed as necrotic cells at 30 uM after 24 hrs by annexin V/propidium iodide staining-based FACS analysis (Rvb = 6.37%)2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1066405Induction of apoptosis in human A2780 cells assessed as secondary necrotic cells at 30 uM after 24 hrs by annexin V/propidium iodide staining-based FACS analysis (Rvb = 9.71%)2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1066420Cytotoxicity against human 8505C cells after 96 hrs by SRB assay2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1066416Cytotoxicity against human MCF7 cells after 96 hrs by SRB assay2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID377098Cytotoxicity against human Hep G2 cells after 48 hrs by WST-8 assay2005Journal of natural products, Feb, Volume: 68, Issue:2
Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
AID545992Inhibition of recombinant PTP1B expressed in Escherichia coli BL21 up to 5 ug/ml after 30 mins by spectrophotometry2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B.
AID1066412Cell cycle arrest in human A2780 cells assessed as accumulation at S phase at 30 uM by propidium iodide staining-based FACS analysis (Rvb = 32.439 %)2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID1066421Cytotoxicity against human 518A2 cells after 96 hrs by SRB assay2014European journal of medicinal chemistry, Jan-24, Volume: 72The chemical and biological potential of C ring modified triterpenoids.
AID744759Inhibition of PTP1B (unknown origin) expressed in Escherichia coli expression system using p-nitrophenyl phosphate as substrate assessed as release of p-nitrophenol incubated for 10 mins prior to substrate addition measured after 30 mins2013European journal of medicinal chemistry, May, Volume: 63Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (12.50)29.6817
2010's5 (62.50)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.66

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.66 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.86 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
catechin
Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.		3.4110catechinantioxidant;
plant metabolite
oleanolic acid
[no description available]		4.4360hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.110delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.0210taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
etoposide
[no description available]		2.110beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
staurosporine
[no description available]		2.110indolocarbazole alkaloid;
organic heterooctacyclic compound		apoptosis inducer;
bacterial metabolite;
EC 2.7.11.13 (protein kinase C) inhibitor;
geroprotector
ursolic acid
[no description available]		3.5920hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite
betulinic acid
[no description available]		2.0210hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
betulin
betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.		2.0210diol;
pentacyclic triterpenoid		analgesic;
anti-inflammatory agent;
antineoplastic agent;
antiviral agent;
metabolite
beta-amyrin
beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.		3.4110pentacyclic triterpenoid;
secondary alcohol		Aspergillus metabolite;
plant metabolite
alpha-amyrin
alpha-amyrin: beta-amyrin is also available; a 5 ring triterpene derived from taraxasterol that differs from beta-amyrin in having the 29-carbon at the 19 position. alpha-amyrin : A pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group.		2.0210pentacyclic triterpenoid;
secondary alcohol
arjunolic acid
arjunolic acid: oleanane type; isol from Cochlospermum tinctorium (Bixaceae); structure given in first source; RN given refers to (2alpha,3beta,4alpha)-isomer; RN for cpd without isomeric designation not avail 12/89. arjunolic acid : A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities.		2.110hydroxy monocarboxylic acid;
pentacyclic triterpenoid		antibacterial agent;
antifungal agent;
antioxidant;
metabolite
maslinic acid
(2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria		2.520dihydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
plant metabolite
rosiglitazone
[no description available]		2.0810aminopyridine;
thiazolidinediones		EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
insulin-sensitizing drug
uvaol
uvaol: from Vauquelinia corymbosa (Rosaceae)		2.0210triterpenoidmetabolite
procyanidin b3
procyanidin B3 : A proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 8' in alpha-configuration. It can be found in red wine, in barley, in beer, in peach or in Jatropha macrantha, the Huanarpo Macho.		3.4110biflavonoid;
hydroxyflavan;
polyphenol;
proanthocyanidin		anti-inflammatory agent;
antioxidant;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
metabolite
meropenem
Meropenem: A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.. meropenem : A carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.		2.610alpha,beta-unsaturated monocarboxylic acid;
carbapenemcarboxylic acid;
organic sulfide;
pyrrolidinecarboxamide		antibacterial agent;
antibacterial drug;
drug allergen
methyl ursolate
methyl ursolate: structure in first source		2.4620
digitoxigenin
Digitoxigenin: 3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.. digitoxigenin : A 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22).		2.61014beta-hydroxy steroid;
3beta-hydroxy steroid
quercetin
[no description available]		2.1107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
oleanonic acid
oleanonic acid: structure in first source		2.0510
isoquercitrin
[no description available]		2.110
ConditionIndicatedRelationship StrengthStudiesTrials
Diabetes Mellitus
A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.		02.0510
Obesity
A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).		02.0510
Skin Aging
The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.		02.110