Page last updated: 2024-12-07

taraxerone

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

Description

Taraxerone is a naturally occurring triterpene compound found in the roots of dandelion (Taraxacum officinale). It exhibits diverse biological activities, including anti-inflammatory, antioxidant, and anticancer properties. The compound's synthesis is usually achieved through extraction from dandelion roots or through chemical modification of other triterpenes. Its unique structural features, particularly the presence of a cyclopropane ring, contribute to its potent bioactivity. Taraxerone is of growing interest in scientific research due to its potential therapeutic applications. Studies have shown that taraxerone can inhibit the production of pro-inflammatory cytokines, reduce oxidative stress, and induce apoptosis in cancer cells. Further research is ongoing to explore its potential in treating various diseases, such as inflammatory bowel disease, arthritis, and cancer.'

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

Cross-References

ID SourceID
PubMed CID92785
CHEMBL ID519077
CHEBI ID67826
SCHEMBL ID3155249
MeSH IDM0054023

Synonyms (29)

Synonym
taraxerone
514-07-8
bdbm50275506
chebi:67826 ,
CHEMBL519077 ,
(4ar,6ar,6as,8ar,12ar,14ar,14br)-4,4,6a,6a,8a,11,11,14b-octamethyl-2,4a,5,6,8,9,10,12,12a,13,14,14a-dodecahydro-1h-picen-3-one
unii-vc7u2m012z
d-friedoolean-14-en-3-one
vc7u2m012z ,
3(2h)-picenone, 1,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-octadecahydro-4,4,6a,8a,11,11,12b,14b-octamethyl-, (4ar-(4a.alpha.,6a.beta.,8a.beta.,12a.beta.,12b.alpha.,14a.alpha.,14b.beta.))-
3(2h)-picenone, 1,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-octadecahydro-4,4,6a,8a,11,11,12b,14b-octamethyl-, (4ar,6ar,8ar,12ar,12bs,14ar,14br)-
taraxer-3-one
taraxer-14-en-3-one
skimmione
.delta.14-taraxen-3-one
27-norolean-14-en-3-one, 13-methyl-, (13.alpha.)-
taraxeron
SCHEMBL3155249
AKOS037515402
Q27136302
HY-N1177
4,4,6a,8a,11,11,12b,14b-octamethyl-1,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-octadecahydropicen-3(2h)-one
DTXSID60965707
CS-0016468
MS-27476
(4as,6as,6ar,8ar,12as,14as,14bs)-4,4,6a,6a,8a,11,11,14b-octamethyl-2,4 a,5,6,8,9,10,12,12a,13,14,14a-dodecahydro-1h-picen-3-one
3(2h)-picenone, 1,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-octadecahydro-4,4,6a,8a,11,11,12b,14b-octamethyl-, (4ar-(4aalpha,6abeta,8abeta,12abeta,12balpha,14aalpha,14bbeta))-
delta14-taraxen-3-one
27-norolean-14-en-3-one, 13-methyl-, (13alpha)-

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Treatment of taraxerone with m-chloroperoxybenzoic acid gave 14,15-epoxy lactones, which underwent the taraxerane-oleanane rearrangement leading to new seco-oleanane triterpenoids."( Application of the taraxerane-oleanane rearrangement to the synthesis of seco-oleanane triterpenoids from taraxerone.
Giang, PM; Matsunami, K; Minh Trang, V; Son, PT, 2015
)
0.98
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role 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]

Drug Classes (1)

ClassDescription
scalarane sesterterpenoidA class of sesterterpenoids based on the structure of the hypothetical sesterterpene scalarane.
[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)
Nitric oxide synthase, inducibleMus musculus (house mouse)IC50 (µMol)46.50000.00103.39119.6000AID344829
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1356061Antiproliferative activity against human A549 cells after 72 hrs by SRB assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita.
AID1356064Antiproliferative activity against human KB cells after 72 hrs by SRB assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita.
AID597077Antiparasitic activity against Trypanosoma brucei rhodesiense STIB 900 bloodstream form after 72 hrs by microplate fluorimetry2011Journal of natural products, Apr-25, Volume: 74, Issue:4
Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense.
AID1356062Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by SRB assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita.
AID1356063Antiproliferative activity against human MCF7 cells after 72 hrs by SRB assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita.
AID597078Cytotoxicity against rat L6 cells after 72 hrs by microplate fluorimetry2011Journal of natural products, Apr-25, Volume: 74, Issue:4
Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense.
AID344829Inhibition of iNOS-mediated NO production in LPS-induced mouse BV2 cells2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
New diterpenoids and the bioactivity of Erythrophleum fordii.
AID344828Inhibition of NADPH oxidase in LPS-induced mouse BV2 cells assessed as NOX-dependent ROS production at 50 uM2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
New diterpenoids and the bioactivity of Erythrophleum fordii.
AID1356065Antiproliferative activity against human KBVIN cells after 72 hrs by SRB assay2018Journal of natural products, 07-27, Volume: 81, Issue:7
Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita.
AID597076Antiplasmodial activity against chloroquine- and pyrimethamine-resistant Plasmodium falciparum K1 infected in human red blood cells assessed as [3H]hypoxanthine incorporation after 48 hrs by liquid scintillation counting2011Journal of natural products, Apr-25, Volume: 74, Issue:4
Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (9.09)18.7374
1990's4 (18.18)18.2507
2000's5 (22.73)29.6817
2010's10 (45.45)24.3611
2020's1 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.20

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

MetricThis Compound (vs All)
Research Demand Index25.20 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]