Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C30H50O |
| Molecular Weight | 426.7174 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1[C@@H]2[C@H]3CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C)CCC1=C
InChI
InChIKey=XWMMEBCFHUKHEX-ZJJHUPNDSA-N
InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22+,23-,24+,25-,27-,28+,29-,30-/m1/s1
| Molecular Formula | C30H50O |
| Molecular Weight | 426.7174 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Taraxasterol is a pentacyclic-triterpene and one of the main active components isolated from Taraxacum officinale. It has been reported to have potent anti-inflammatory properties. The anti-inflammatory effects of taraxasterol against LPS-induced acute lung injury may be due to its ability of inhibition of the NF-κB and MAPK signaling. In addition, taraxasterol protected human chondrocytes by inhibiting MMPs, NO and PGE2 production and therefore could be a useful agent for prevention and treatment of osteoarthritis.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Analgesic compounds from Scorzonera latifolia (Fisch. and Mey.) DC. | 2010-08-19 |
|
| Triterpenoids with acetylcholinesterase inhibition from Chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae). | 2010-04 |
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| Triterpene alcohol and fatty acid composition of shea nuts from seven African countries. | 2010 |
|
| [Chemical constituents of Periploca forrestii]. | 2009-12 |
|
| Fruit-surface flavonoid accumulation in tomato is controlled by a SlMYB12-regulated transcriptional network. | 2009-12 |
|
| Free Radical Scavenging Activity of Calotropis gigantea on Streptozotocin-Induced Diabetic Rats. | 2009-11 |
|
| The identification of ingested dandelion juice in gastric contents of a deceased person by direct sequencing and GC-MS methods. | 2009-05 |
|
| Antioxidant Activity and Total Phenolic and Flavonoid Contents of Hieracium pilosella L. Extracts. | 2009 |
|
| Ethnophytotherapeutical research in the high Molise region (Central-Southern Italy). | 2008-03-11 |
|
| [Study on triterpenes from of Ligularia xanthotricha]. | 2008-02 |
|
| Ethnobotanical remarks on Central and Southern Italy. | 2007-05-30 |
|
| Identification and determination of triterpenoids in Hieracium pilosella L. | 2007-03 |
|
| Taraxasterol and beta-sitosterol: new naturally compounds with chemoprotective/chemopreventive effects. | 2004 |
|
| GC/MS analysis of some bioactive constituents from Carthamus lanatus L. | 2003-10-28 |
|
| [Constituents of the leaves of Holodiscus discolor (Pursh) Maxim]. | 2001-11 |
|
| [Studies on chemical constituents from Chinese medicinal plant Hemistepta lyrata Bunge]. | 2001-06 |
Patents
Sample Use Guides
in mice: Mice were treated with 2.5, 5 and 10 mg/kg of taraxasterol prior to a lethal dose of lipopolysaccharide (LPS) challenge
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: In order to provide a scientific basis for the applicability of taraxasterol in osteoarthritis (OA), the anti-inflammatory effects of taraxasterol on IL-1β-stimulated osteoarthritic chondrocytes were investigated. Chondrocytes were pretreated with taraxasterol 1h before IL-1β treatment. The productions of MMP-1, MMP3, MMP13, PGE2 and NO were measured by ELISA and Griess reaction. The expression of COX-2, iNOS, and NF-κB was detected by western blot analysis. It was shown that taraxasterol dose-dependently suppressed MMP-1, MMP3, MMP13, PGE2 and NO production induced by IL-1β. The expression of COX-2 and iNOS was also inhibited by taraxasterol. Western blot analysis showed that taraxasterol suppressed IL-1β-induced NF-κB activation in a dose-dependent manner. Taken together, was found that taraxasterol protected human chondrocytes by inhibiting MMPs, NO and PGE2 production.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:12:31 GMT 2025
by
admin
on
Mon Mar 31 19:12:31 GMT 2025
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| Record UNII |
64SK2ERN9P
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| Record Status |
Validated (UNII)
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| Record Version |
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C079988
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m10463
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Taraxasterol
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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