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P0020

Sigma-Aldrich

Pristimerin

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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:
Molecular Weight:
464.64
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
SML2432F131SML0343
Pristimerin

Sigma-Aldrich

P0020

Pristimerin

Ethyl rosmarinate ≥98% (HPLC)

Sigma-Aldrich

SML2432

Ethyl rosmarinate

FPL 64176 ≥98% (HPLC), powder

Sigma-Aldrich

F131

FPL 64176

Methylstat ≥98% (HPLC)

Sigma-Aldrich

SML0343

Methylstat

form

powder

form

powder

form

powder

form

powder

storage condition

protect from light

storage condition

desiccated, protect from light

storage condition

desiccated, protect from light

storage condition

-

color

orange

color

white to beige

color

white to beige

color

white to beige

solubility

DMSO: ≥5 mg/mL

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: >20 mg/mL (Solutions should be freshly prepared.), H2O: insoluble

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

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.

Storage Class Code

11 - Combustible Solids

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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
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
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
Yongwei Wang et al.
PloS one, 7(8), e43826-e43826 (2012-09-07)
Despite rapid advances in chemotherapy and surgical resection strategies, pancreatic cancer remains the fourth leading cause of cancer related deaths in the United States with a 5-year survival rate of less than 5%. Therefore, novel therapeutic agents for the prevention
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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