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
[H][C@]12CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC[C@@]5(C)CCC(=C)[C@@H](C)[C@]25[H]
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
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 |
|---|---|---|
| [Constituents of the leaves of Holodiscus discolor (Pursh) Maxim]. | 2001 Nov |
|
| GC/MS analysis of some bioactive constituents from Carthamus lanatus L. | 2003 Sep-Oct |
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| Antioxidant Activity and Total Phenolic and Flavonoid Contents of Hieracium pilosella L. Extracts. | 2009 |
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| [Chemical constituents of Periploca forrestii]. | 2009 Dec |
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.
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DTXSID30909815
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C079988
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115250
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1059-14-9
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m10463
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Taraxasterol
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9401
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SUBSTANCE RECORD
