P0020

Pristimerin

• Synonym(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
• Empirical Formula (Hill Notation): C₃₀H₄₀O₄
• CAS Number: 1258-84-0
• Molecular Weight: 464.64
• MDL number: MFCD01711331
• UNSPSC Code: 12352200
• PubChem Substance ID: 329819975
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• storage condition: protect from light
• color: orange
• solubility: DMSO: ≥5 mg/mL
• storage temp.: −20°C
• SMILES string: 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
• InChI key: JFACETXYABVHFD-WXPPGMDDSA-N

Description

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).

Biochem/physiol Actions

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.

Features and Benefits

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable