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P0020

Sigma-Aldrich

Pristimerin

Synonyme(s) :

(9b,13a,14b,20a)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26 -trinoroleana-1(10),3,5,7-tertraen-29-oic acid methyl ester, Celastrol methyl ester

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About This Item

Formule empirique (notation de Hill):
C30H40O4
Numéro CAS:
1258-84-0
Poids moléculaire :
464.64
Numéro MDL:
MFCD01711331
Code UNSPSC :
12352200
ID de substance PubChem :
329819975
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Couleur

orange

Solubilité

DMSO: ≥5 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

COC(=O)[C@]1(C)CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]3(C)C2C1

InChI

1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1

Clé InChI

JFACETXYABVHFD-WXPPGMDDSA-N

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Application

Pristimerin has been used as an anti-tumor agent to study its effects on conditionally reprogrammed patient-derived lung adenocarcinoma cells (CRLCs). It has also been used as an anti-tumor agent to study its effects on conditionally reprogrammed patient derived-primary hepatocellular carcinoma cells (CRHCs).

Actions biochimiques/physiologiques

More active than euphol against MGL, better activity with rat neurons, but less selective relative to similar enzymes. First MGL inhibitor to act reversibly, several others covalently bind to cysteine residues. Other studies involve multiply mylome, pristimerin inhibits NF-κB activation via inhibition of IKK-α or IKK-β. It is the methyl ester of celastrol (C0869).
Pristimerin is a quinone methide triterpenoid found abundantly in Celastraceae and Hippocrateaceae families. It shows anti-inflammatory, anti-malarial, anti-bacterial, and insecticidal properties. Pristimerin exhibits anti-cancer and anti-proliferative activity by affecting vasculogenesis, apoptosis, autophagy, migration, and invasion of tumor cells. It has been studied to exhibit therapeutic effects against leukemia, glioma, breast cancer, prostate cancer, oral cancer, and lung cancer.

Caractéristiques et avantages

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Code de la classe de stockage

11 - Combustible Solids

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Jia-Jun Li et al.
Frontiers in pharmacology, 10, 746-746 (2019-07-30)
As a quinonemethide triterpenoid extracted from species of the Celastraceae and Hippocrateaceae, pristimerin has been shown potent anti-cancer effects. Specifically, it was found that pristimerin can affect many tumor-related processes, such as apoptosis, autophagy, migration and invasion, vasculogenesis, and drug
Tsugiya Murayama et al.
Antiviral chemistry & chemotherapy, 18(3), 133-139 (2007-07-14)
We examined the anticytomegalovirus properties of four compounds: pristimerin, the pristimerin analogue, lupeol and 2-acetylphenol-1-beta-D-glucopyranosyl (1 --> 6)-beta-D-xylpyranoside (acetophenol glycoside), isolated from Maytenus heterophylla, a Kenyan medicinal plant. The effects were studied on human cytomegalovirus (HCMV) replication in the human
Jin Sun Lee et al.
Biological & pharmaceutical bulletin, 36(2), 316-325 (2013-02-02)
Pristimerin is a naturally occurring triterpenoid that causes cytotoxicity in several cancer cell lines. However, the mechanism of action for the cytotoxic effect of pristimerin has not been unexplored. The purpose of this study was to investigate the effect of
V M Dirsch et al.
European journal of pharmacology, 336(2-3), 211-217 (1998-01-24)
Inducible nitric oxide synthase dependent production of nitric oxide (NO) plays an important role in inflammation. We investigated whether pristimerin ((20alpha)-3-hydroxy-2-oxo-24-nor-friedela-1(10),3,5,7-te traen-carboxylic acid-(29)-methylester), an antitumoral, antimicrobial as well as anti-inflammatory plant compound, has an effect on the inducible NO synthase
Du-Qiang Luo et al.
Pest management science, 61(1), 85-90 (2004-12-14)
Pristimerin and celastrol isolated from the roots of Celastrus hypoleucus (Oliv) Warb f argutior Loes exhibited inhibitory effects against diverse phytopathogenic fungi. Pristimerin and celastrol were found to inhibit the mycelial growth of Rhizoctonia solani Kuhn and Glomerella cingulata (Stonem)
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